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$1,150,000

Experience charming Rhinebeck Village in this post and beam Village home only blocks to fine dining, shops, farmer's market, etc. This 3 bedroom 2 1/2 bath home blends craftmanship with comfort. Radiant heat on the main level, spacious country kitchen and a large living room for gathering and or entertaining. Large primary bedroom with adjoining bath with skylights, shower and whirlpool tub, two vanities and double closet. Two comfortable bedrooms, each with closet, and full bath with laundry complete the upper level. Additional features include central air, propane heat, stainless steel appliances (French door refrigerator, DW, gas range, two ovens, microwave, wine frig), breakfast bar, natural wood finishes throughout. Generator. Attached heated two car garage with automatic door opener. Stone rear patio, attractively landscaped parcel with excellent screening.

3 Beds ⋅ 3 Baths ⋅ 1032296 MLS

Experience charming Rhinebeck Village in this post and beam Village home only blocks to fine dining, shops, farmer's market, etc. This 3 bedroom 2 1/2 bath home blends craftmanship with comfort. Radiant heat on the main level, spacious country kitchen and a large living room for gathering and or entertaining. Large primary bedroom with adjoining bath with skylights, shower and whirlpool tub, two vanities and double closet. Two comfortable bedrooms, each with closet, and full bath with laundry complete the upper level. Additional features include central air, propane heat, stainless steel appliances (French door refrigerator, DW, gas range, two ovens, microwave, wine frig), breakfast bar, natural wood finishes throughout. Generator. Attached heated two car garage with automatic door opener. Stone rear patio, attractively landscaped parcel with excellent screening.

5 Prospect Street, Rhinebeck

$995,000

Set along a quiet, tree-lined road in the heart of Rhinebeck Village, 7 Cramer Rd offers the best of Hudson Valley living—where a slower pace, scenic beauty, and a vibrant local culture come together effortlessly. Completely remodeled between 2020–2021, this home delivers true one-level living with a thoughtful, high-quality renovation throughout. Every detail has been carefully considered, creating a space that feels fresh, warm, and easy to live in. Inside, hardwood floors run throughout, complemented by two propane fireplaces that bring a cozy, modern feel to the main living spaces. The kitchen is both stylish and functional, featuring Thermador appliances, quartz countertops, Avante wine cooler with a wet bar is ideal for both everyday living and entertaining. Open floor plan flows seamlessly from one area to the next. The primary suite is privately situated and beautifully finished with a walk-in shower, double sink vanity, and a generous walk-in closet. Two additional bedrooms and a second full bath complete the main level, offering flexibility for guests, work-from-home needs, or creative space. Behind the scenes, major upgrades provide peace of mind, including a new septic system, propane generator, two Mitsubishi air handlers in the basement, and a 2-zone electric heat pump hot water heater known for its efficiency. The basement adds functionality with an egress window/fire escape hatch for safety and future possibilities. Outside, enjoy a Trex deck perfect for relaxing or hosting, stamped concrete walkways, a new driveway, and a one-car garage with space for two vehicles. Vinyl siding and excellent drainage make for easy, low-maintenance living year-round. Turnkey and move-in ready, this is a Rhinebeck home that blends modern comfort with the laid-back charm of the Hudson Valley—an ideal retreat or full-time residence just moments from it all.

3 Beds ⋅ 2 Baths ⋅ 1029262 MLS

Set along a quiet, tree-lined road in the heart of Rhinebeck Village, 7 Cramer Rd offers the best of Hudson Valley living—where a slower pace, scenic beauty, and a vibrant local culture come together effortlessly. Completely remodeled between 2020–2021, this home delivers true one-level living with a thoughtful, high-quality renovation throughout. Every detail has been carefully considered, creating a space that feels fresh, warm, and easy to live in. Inside, hardwood floors run throughout, complemented by two propane fireplaces that bring a cozy, modern feel to the main living spaces. The kitchen is both stylish and functional, featuring Thermador appliances, quartz countertops, Avante wine cooler with a wet bar is ideal for both everyday living and entertaining. Open floor plan flows seamlessly from one area to the next. The primary suite is privately situated and beautifully finished with a walk-in shower, double sink vanity, and a generous walk-in closet. Two additional bedrooms and a second full bath complete the main level, offering flexibility for guests, work-from-home needs, or creative space. Behind the scenes, major upgrades provide peace of mind, including a new septic system, propane generator, two Mitsubishi air handlers in the basement, and a 2-zone electric heat pump hot water heater known for its efficiency. The basement adds functionality with an egress window/fire escape hatch for safety and future possibilities. Outside, enjoy a Trex deck perfect for relaxing or hosting, stamped concrete walkways, a new driveway, and a one-car garage with space for two vehicles. Vinyl siding and excellent drainage make for easy, low-maintenance living year-round. Turnkey and move-in ready, this is a Rhinebeck home that blends modern comfort with the laid-back charm of the Hudson Valley—an ideal retreat or full-time residence just moments from it all.

7 Cramer Road, Rhinebeck

$3,250,000

A Victorian on one of Rhinebeck’s most walkable blocks, minutes on foot from the Village center. Deep green shingle-and-clapboard exterior, cream gingerbread trim, and a wraparound porch with scrollwork brackets set the house back from the street behind mature landscaping. The property is over 1/3 of an acre on a corner lot with an extraordinary side entrance and a wall of privacy fencing which hides the crown jewel of the property, a fully enclosed pool and entertainment space between the house and a rebuilt luxury garage/barn. Inside, the original main house retains many historic Victorian details: ceiling & trim detail, a built-in library wall, a wood burning fireplace and a carved dark-wood staircase with its original newel post. A chinoiserie-papered breakfast nook off the kitchen doubles as a game table. An early 2000’s addition to the home created a great room for dining and living on the main floor, and a generous primary suite above. Upstairs, original bedrooms carry the same period restraint — white walls, wood floors, and 3 bedrooms with 2 full baths, one on the hall and one ensuite. The second floor addition created a generous laundry room and an large primary suite with a black-glazed fireplace, a jetted soaking tub under five windows, a marble-tiled shower and an oversized walk through closet. Outside, a stone patio anchored by a full brick fireplace and pergola looks over an in-ground pool, bordered by mature plantings on all sides for privacy. A separate barn was rebuilt in 2016 offering an additional 960 finished square feet. Currently set up as a game room — ping pong, shuffleboard, foosball, corrugated-metal ceiling, it has its own heat and air, and a half bath upstairs and one downstairs with direct access from the pool. The garage can accommodate four cars and has solar panels to offset energy expenses. Less than 2 hours from NYC and 3 miles to the Amtrak Station at Rhinecliff.

4 Beds ⋅ 4 Baths ⋅ 1022134 MLS

A Victorian on one of Rhinebeck’s most walkable blocks, minutes on foot from the Village center. Deep green shingle-and-clapboard exterior, cream gingerbread trim, and a wraparound porch with scrollwork brackets set the house back from the street behind mature landscaping. The property is over 1/3 of an acre on a corner lot with an extraordinary side entrance and a wall of privacy fencing which hides the crown jewel of the property, a fully enclosed pool and entertainment space between the house and a rebuilt luxury garage/barn. Inside, the original main house retains many historic Victorian details: ceiling & trim detail, a built-in library wall, a wood burning fireplace and a carved dark-wood staircase with its original newel post. A chinoiserie-papered breakfast nook off the kitchen doubles as a game table. An early 2000’s addition to the home created a great room for dining and living on the main floor, and a generous primary suite above. Upstairs, original bedrooms carry the same period restraint — white walls, wood floors, and 3 bedrooms with 2 full baths, one on the hall and one ensuite. The second floor addition created a generous laundry room and an large primary suite with a black-glazed fireplace, a jetted soaking tub under five windows, a marble-tiled shower and an oversized walk through closet. Outside, a stone patio anchored by a full brick fireplace and pergola looks over an in-ground pool, bordered by mature plantings on all sides for privacy. A separate barn was rebuilt in 2016 offering an additional 960 finished square feet. Currently set up as a game room — ping pong, shuffleboard, foosball, corrugated-metal ceiling, it has its own heat and air, and a half bath upstairs and one downstairs with direct access from the pool. The garage can accommodate four cars and has solar panels to offset energy expenses. Less than 2 hours from NYC and 3 miles to the Amtrak Station at Rhinecliff.

62 Livingston Street, Rhinebeck

$595,000

Nestled in the heart of the Village of Rhinebeck, this beautifully renovated one-level ranch blends timeless charm with modern comfort. Offering 1,300 square feet of thoughtfully updated living space, the home features three bedrooms, two baths, and gleaming hardwood floors throughout. The renovated kitchen is designed to impress with stainless steel appliances, a premium Wolf range, and an effortless flow into the main living areas, making it ideal for both everyday living and entertaining. Just beyond, an expansive screened porch overlooks the backyard, creating the perfect space for morning coffee, summer dinners, or simply relaxing. Situated on a level 0.35-acre lot, the property also features a fire pit for enjoying evenings outdoors. Built in 1958 and tastefully updated, this move-in-ready home offers the convenience of one-level living just moments from Rhinebeck's renowned restaurants, boutiques, farmers market, and cultural attractions. A rare opportunity to own a turnkey home in one of the Hudson Valley's most sought-after villages.

3 Beds ⋅ 2 Baths ⋅ 1017343 MLS

Nestled in the heart of the Village of Rhinebeck, this beautifully renovated one-level ranch blends timeless charm with modern comfort. Offering 1,300 square feet of thoughtfully updated living space, the home features three bedrooms, two baths, and gleaming hardwood floors throughout. The renovated kitchen is designed to impress with stainless steel appliances, a premium Wolf range, and an effortless flow into the main living areas, making it ideal for both everyday living and entertaining. Just beyond, an expansive screened porch overlooks the backyard, creating the perfect space for morning coffee, summer dinners, or simply relaxing. Situated on a level 0.35-acre lot, the property also features a fire pit for enjoying evenings outdoors. Built in 1958 and tastefully updated, this move-in-ready home offers the convenience of one-level living just moments from Rhinebeck's renowned restaurants, boutiques, farmers market, and cultural attractions. A rare opportunity to own a turnkey home in one of the Hudson Valley's most sought-after villages.

5 Orchard Street, Rhinebeck

$779,000

Welcome to 19 Closs Drive, a beautiful, updated, move in ready 3 BR, 2 BTH ranch located within walking distance to Rhinebeck Village shops, restaurants, boutiques, schools and spas. The exterior of the house has been tastefully updated with new siding and stonework in 2020. A newer mission style front door & porch beckons you to enter into this home replete with gleaming hardwood floors in the living room & bedrooms. The bright living room, lit up by the morning sun, is a cozy gathering place. The fireplace warms you up on those chilly winter days. The heart of this home is a stunning kitchen featuring an island, granite countertops, tile floor & stainless-steel appliances. Ideal for entertaining, the kitchen is open to the dining area & is steps from the living room. The screened porch offers additional dining & entertaining area. An outdoor patio offers another place to relax with your morning coffee or evening glass of wine. The primary suite with updated bath, two additional bedrooms & updated hall bathroom completes the first-floor layout. The basement auxiliary recreation area features new carpet, ceiling tiles & lights and has separate zoned baseboard heat. Work bench located in basement utility room. There are 2 garages to help you stay dry when going to & from the car. Close by are many historic sites as well as colleges such as Bard College, Vassar College, Marist University & the Culinary Institute of America. There are many recreational opportunities in the area including the Walkway Over the Hudson, golf courses or water activities on the Hudson River & nearby lakes. The train station is about a 7-minute drive to travel for work or pleasure. There is much to see & do in Rhinebeck & the surrounding area. Low taxes, village amenities & easy commute to NYC via train, or Albany via NYS Thruway make this a reason to move to Rhinebeck!

3 Beds ⋅ 2 Baths ⋅ 1028512 MLS

Welcome to 19 Closs Drive, a beautiful, updated, move in ready 3 BR, 2 BTH ranch located within walking distance to Rhinebeck Village shops, restaurants, boutiques, schools and spas. The exterior of the house has been tastefully updated with new siding and stonework in 2020. A newer mission style front door & porch beckons you to enter into this home replete with gleaming hardwood floors in the living room & bedrooms. The bright living room, lit up by the morning sun, is a cozy gathering place. The fireplace warms you up on those chilly winter days. The heart of this home is a stunning kitchen featuring an island, granite countertops, tile floor & stainless-steel appliances. Ideal for entertaining, the kitchen is open to the dining area & is steps from the living room. The screened porch offers additional dining & entertaining area. An outdoor patio offers another place to relax with your morning coffee or evening glass of wine. The primary suite with updated bath, two additional bedrooms & updated hall bathroom completes the first-floor layout. The basement auxiliary recreation area features new carpet, ceiling tiles & lights and has separate zoned baseboard heat. Work bench located in basement utility room. There are 2 garages to help you stay dry when going to & from the car. Close by are many historic sites as well as colleges such as Bard College, Vassar College, Marist University & the Culinary Institute of America. There are many recreational opportunities in the area including the Walkway Over the Hudson, golf courses or water activities on the Hudson River & nearby lakes. The train station is about a 7-minute drive to travel for work or pleasure. There is much to see & do in Rhinebeck & the surrounding area. Low taxes, village amenities & easy commute to NYC via train, or Albany via NYS Thruway make this a reason to move to Rhinebeck!

19 Closs Drive, Rhinebeck

$455,000

Welcome to 32 North Loop, a well-maintained townhouse-style condominium in The Woods at Rhinebeck. Offering 1,194 square feet, this 1 bedroom, 1.5 bath home is ideally located just a short distance from the heart of Rhinebeck Village, where you'll enjoy easy access to shops, restaurants, and everyday conveniences. The inviting open-concept floor plan connects the living and dining areas, creating a comfortable space for everyday living and entertaining. An electric fireplace adds warmth and ambiance, while the kitchen features a center island with breakfast bar. A convenient first-floor powder room, laundry closet, and garage access complete the main level. Upstairs, the spacious primary bedroom offers a private ensuite bath with a double vanity. A generous den at the top of the stairs provides flexible space for a home office, additional living area, or guest accommodations. Large windows throughout the home fill the interior with abundant natural light. Additional highlights include a newer, energy-efficient heat pump for year-round heating and cooling, an attached one-car garage with extra storage, and low-maintenance condominium living. Residents of The Woods at Rhinebeck enjoy exceptional amenities, including a clubhouse, outdoor swimming pool, tennis court, picturesque ponds, and beautifully landscaped grounds with mature trees, creating a peaceful setting. Whether you're searching for a full-time residence or a weekend Hudson Valley retreat, 32 North Loop offers the perfect blend of comfort, convenience, and peaceful atmosphere in the Village of Rhinebeck.

1 Beds ⋅ 2 Baths ⋅ 1027738 MLS

Welcome to 32 North Loop, a well-maintained townhouse-style condominium in The Woods at Rhinebeck. Offering 1,194 square feet, this 1 bedroom, 1.5 bath home is ideally located just a short distance from the heart of Rhinebeck Village, where you'll enjoy easy access to shops, restaurants, and everyday conveniences. The inviting open-concept floor plan connects the living and dining areas, creating a comfortable space for everyday living and entertaining. An electric fireplace adds warmth and ambiance, while the kitchen features a center island with breakfast bar. A convenient first-floor powder room, laundry closet, and garage access complete the main level. Upstairs, the spacious primary bedroom offers a private ensuite bath with a double vanity. A generous den at the top of the stairs provides flexible space for a home office, additional living area, or guest accommodations. Large windows throughout the home fill the interior with abundant natural light. Additional highlights include a newer, energy-efficient heat pump for year-round heating and cooling, an attached one-car garage with extra storage, and low-maintenance condominium living. Residents of The Woods at Rhinebeck enjoy exceptional amenities, including a clubhouse, outdoor swimming pool, tennis court, picturesque ponds, and beautifully landscaped grounds with mature trees, creating a peaceful setting. Whether you're searching for a full-time residence or a weekend Hudson Valley retreat, 32 North Loop offers the perfect blend of comfort, convenience, and peaceful atmosphere in the Village of Rhinebeck.

32 North Loop, Rhinebeck

$725,000

Nestled within the sought-after lakeside community of Sepasco Village in the Town of Rhinebeck, this spacious and meticulously maintained 2,800-square-foot home offers an exceptional blend of comfort, flexibility, and Hudson Valley living. Featuring four bedrooms and three-and-one-half baths, the thoughtfully designed floor plan includes primary suites on both the main and second levels, making it ideal for a variety of living arrangements. Designed for today’s lifestyle, the home offers an abundance of versatile living space, including a kitchen, dining room, living room, den, family room, office, gym, media/game room, and four generously proportioned bedrooms. Whether working from home, entertaining guests, pursuing hobbies, or accommodating multi-generational living, this home easily adapts to your needs. Outdoor living is equally inviting, with an expansive deck that includes both open-air and beautifully screened-in areas, creating wonderful spaces for dining, relaxing, and entertaining. The fenced backyard is spacious and offers endless possibilities for recreation, gardening, and pets. Residents enjoy access to Lake Sepasco, a motor-free glacial lake that is not open to the public. Spend your days swimming, paddleboarding, kayaking, fishing, or enjoying lakeside picnics in this peaceful natural setting just minutes from the Village of Rhinebeck. Located within the Rhinebeck Central School District, the property is also convenient to highly regarded public and private schools, children’s camps, sporting and social clubs, and the region’s renowned equestrian facilities, riding trails, fox hunting, polo grounds, fly-fishing, hiking, skiing and more. Ideally situated in the heart of the Hudson Valley, the property is approximately 5 minutes to Rhinebeck, 7 minutes to Red Hook, 10 minutes to the Amtrak station in Rhinecliff, 30 minutes to Poughkeepsie and Metro-North trains to Grand Central Terminal, 20 minutes to Kingston, 25 minutes to Millbrook, 30 minutes to Hudson, and two hours from New York City by car. Don’t pass this one by. This is town and country living at its finest.

4 Beds ⋅ 4 Baths ⋅ 1025736 MLS

Nestled within the sought-after lakeside community of Sepasco Village in the Town of Rhinebeck, this spacious and meticulously maintained 2,800-square-foot home offers an exceptional blend of comfort, flexibility, and Hudson Valley living. Featuring four bedrooms and three-and-one-half baths, the thoughtfully designed floor plan includes primary suites on both the main and second levels, making it ideal for a variety of living arrangements. Designed for today’s lifestyle, the home offers an abundance of versatile living space, including a kitchen, dining room, living room, den, family room, office, gym, media/game room, and four generously proportioned bedrooms. Whether working from home, entertaining guests, pursuing hobbies, or accommodating multi-generational living, this home easily adapts to your needs. Outdoor living is equally inviting, with an expansive deck that includes both open-air and beautifully screened-in areas, creating wonderful spaces for dining, relaxing, and entertaining. The fenced backyard is spacious and offers endless possibilities for recreation, gardening, and pets. Residents enjoy access to Lake Sepasco, a motor-free glacial lake that is not open to the public. Spend your days swimming, paddleboarding, kayaking, fishing, or enjoying lakeside picnics in this peaceful natural setting just minutes from the Village of Rhinebeck. Located within the Rhinebeck Central School District, the property is also convenient to highly regarded public and private schools, children’s camps, sporting and social clubs, and the region’s renowned equestrian facilities, riding trails, fox hunting, polo grounds, fly-fishing, hiking, skiing and more. Ideally situated in the heart of the Hudson Valley, the property is approximately 5 minutes to Rhinebeck, 7 minutes to Red Hook, 10 minutes to the Amtrak station in Rhinecliff, 30 minutes to Poughkeepsie and Metro-North trains to Grand Central Terminal, 20 minutes to Kingston, 25 minutes to Millbrook, 30 minutes to Hudson, and two hours from New York City by car. Don’t pass this one by. This is town and country living at its finest.

404 Sepasco Center Street, Rhinebeck

$935,000

Experience refined Hudson Valley living in this stunning 5-bedroom, 3-bath Saltbox Colonial, extensively renovated since 2023. Soaring ceilings, a dramatic catwalk, and sleek contemporary finishes create a light-filled, sophisticated retreat. Designed with an open floor plan for effortless entertaining, the home features gleaming hardwood floors, a striking wood-burning fireplace, and beautifully updated living spaces throughout. At the heart of the home is a designer kitchen featuring waterfall granite countertops, state-of-the-art appliances, and seamless flow into the living and dining areas. The spacious primary suite offers a peaceful retreat, while a second bedroom features its own en-suite bath with a glass-enclosed shower, making it ideal for guests or multigenerational living. Three additional bedrooms are generously sized and filled with natural light, creating comfortable and inviting spaces for family, guests, or a home office. Every detail has been thoughtfully considered since the home's 2023 renovation. Recent improvements include a fully renovated kitchen, four beautifully renovated bathrooms, refinished hardwood floors, a new porch sliding door, new washer and dryer, an updated fireplace mantel, professionally cleaned and sanitized ductwork, extensive pool upgrades, and comprehensive well and water system improvements completed by AquaCare. Step outside to your private backyard oasis featuring a refreshing 18 x 36 in-ground pool with new liner, filter and bluestone coping, professionally maintained & perfect for summer entertaining or relaxing afternoons at home. Enjoy dining al fresco on the rear deck, unwind with your favorite book, or take advantage of the expansive yard with plenty of room for gardening, recreation, and enjoying the natural surroundings. The unfinished basement offers excellent potential for future finished living space or abundant storage, while the oversized two-car garage provides ample room for vehicles, tools, and outdoor equipment. Located in the sought-after Vanderburgh Cove community, you're just 2 minutes from the Hudson River, 4 minutes to the Village of Rhinebeck, only 8 minutes to the Rhinecliff Amtrak station, and just minutes from the future SoHo House Hudson Valley. Enjoy easy access to acclaimed restaurants, boutiques, art galleries, farmers' markets, scenic hiking trails, the Culinary Institute of America, the historic Hyde Park estates, and Bard College. Blending modern elegance with timeless Hudson Valley charm, this exceptional home offers sophisticated finishes, thoughtfully designed living spaces, and effortless indoor-outdoor living in one of the Hudson Valley's most desirable communities.

5 Beds ⋅ 4 Baths ⋅ 1025128 MLS

Experience refined Hudson Valley living in this stunning 5-bedroom, 3-bath Saltbox Colonial, extensively renovated since 2023. Soaring ceilings, a dramatic catwalk, and sleek contemporary finishes create a light-filled, sophisticated retreat. Designed with an open floor plan for effortless entertaining, the home features gleaming hardwood floors, a striking wood-burning fireplace, and beautifully updated living spaces throughout. At the heart of the home is a designer kitchen featuring waterfall granite countertops, state-of-the-art appliances, and seamless flow into the living and dining areas. The spacious primary suite offers a peaceful retreat, while a second bedroom features its own en-suite bath with a glass-enclosed shower, making it ideal for guests or multigenerational living. Three additional bedrooms are generously sized and filled with natural light, creating comfortable and inviting spaces for family, guests, or a home office. Every detail has been thoughtfully considered since the home's 2023 renovation. Recent improvements include a fully renovated kitchen, four beautifully renovated bathrooms, refinished hardwood floors, a new porch sliding door, new washer and dryer, an updated fireplace mantel, professionally cleaned and sanitized ductwork, extensive pool upgrades, and comprehensive well and water system improvements completed by AquaCare. Step outside to your private backyard oasis featuring a refreshing 18 x 36 in-ground pool with new liner, filter and bluestone coping, professionally maintained & perfect for summer entertaining or relaxing afternoons at home. Enjoy dining al fresco on the rear deck, unwind with your favorite book, or take advantage of the expansive yard with plenty of room for gardening, recreation, and enjoying the natural surroundings. The unfinished basement offers excellent potential for future finished living space or abundant storage, while the oversized two-car garage provides ample room for vehicles, tools, and outdoor equipment. Located in the sought-after Vanderburgh Cove community, you're just 2 minutes from the Hudson River, 4 minutes to the Village of Rhinebeck, only 8 minutes to the Rhinecliff Amtrak station, and just minutes from the future SoHo House Hudson Valley. Enjoy easy access to acclaimed restaurants, boutiques, art galleries, farmers' markets, scenic hiking trails, the Culinary Institute of America, the historic Hyde Park estates, and Bard College. Blending modern elegance with timeless Hudson Valley charm, this exceptional home offers sophisticated finishes, thoughtfully designed living spaces, and effortless indoor-outdoor living in one of the Hudson Valley's most desirable communities.

4 Cove Road, Rhinebeck

$2,950,000

Rarely does an offering of this magnitude become available in the Hudson Valley. Encompassing more than 137 acres across three parcels, this extraordinary farm compound presents a unique opportunity to restore and reimagine a legacy country estate in one of the region's most desirable locations. At the heart of the property is a classic 1910 Colonial residence offering over 4,000 square feet of living space. Rich with original character, the home showcases wide-board floors, original doors and hardware, and timeless architectural details throughout. The gracious floor plan includes a kitchen, den, formal dining room, living room, and sunroom, along with a ground-floor primary suite. Upstairs are three additional bedrooms, two full bathrooms, and an office. Three-zone heating and cooling provide year-round comfort. The grounds are equally impressive, featuring a 40' x 18' gunite pool, a tennis court, and a picturesque 2.5-acre pond complete with a fountain. Equestrian and agricultural amenities abound, including ten paddocks, an outdoor riding ring, and a machine shed. The South Barn offers exceptional flexibility, with a dramatic entertaining space of reclaimed post and beam timber, ideal for hosting on a grand scale, as well as potential use as a home theater, fitness facility, creative studio, or office. Amenities include a kitchenette and one-and-a-half baths. The lower level features an efficiency accommodation, garage space for two vehicles, and extensive storage. The North Barn is a fully equipped equestrian facility with 18 stalls, a rider's lounge with half bath, and a one-bedroom apartment complete with kitchen and full bath. Adjacent to the barn is an additional caretaker's cottage offering two bedrooms, a kitchen, and a full bathroom. Perfectly positioned just off the Taconic State Parkway and approximately 20 minutes from both Millbrook and Rhinebeck, the property offers convenient access to the Hudson Valley's renowned dining, cultural attractions, outdoor recreation, and charming villages. Offered in estate condition, this is a rare chance to create a truly exceptional Hudson Valley property with all infrastructure in place — a private farm and country compound of remarkable scale, beauty, and great potential for farming income and agricultural exemptions.

4 Beds ⋅ 5 Baths ⋅ 1021484 MLS

Rarely does an offering of this magnitude become available in the Hudson Valley. Encompassing more than 137 acres across three parcels, this extraordinary farm compound presents a unique opportunity to restore and reimagine a legacy country estate in one of the region's most desirable locations. At the heart of the property is a classic 1910 Colonial residence offering over 4,000 square feet of living space. Rich with original character, the home showcases wide-board floors, original doors and hardware, and timeless architectural details throughout. The gracious floor plan includes a kitchen, den, formal dining room, living room, and sunroom, along with a ground-floor primary suite. Upstairs are three additional bedrooms, two full bathrooms, and an office. Three-zone heating and cooling provide year-round comfort. The grounds are equally impressive, featuring a 40' x 18' gunite pool, a tennis court, and a picturesque 2.5-acre pond complete with a fountain. Equestrian and agricultural amenities abound, including ten paddocks, an outdoor riding ring, and a machine shed. The South Barn offers exceptional flexibility, with a dramatic entertaining space of reclaimed post and beam timber, ideal for hosting on a grand scale, as well as potential use as a home theater, fitness facility, creative studio, or office. Amenities include a kitchenette and one-and-a-half baths. The lower level features an efficiency accommodation, garage space for two vehicles, and extensive storage. The North Barn is a fully equipped equestrian facility with 18 stalls, a rider's lounge with half bath, and a one-bedroom apartment complete with kitchen and full bath. Adjacent to the barn is an additional caretaker's cottage offering two bedrooms, a kitchen, and a full bathroom. Perfectly positioned just off the Taconic State Parkway and approximately 20 minutes from both Millbrook and Rhinebeck, the property offers convenient access to the Hudson Valley's renowned dining, cultural attractions, outdoor recreation, and charming villages. Offered in estate condition, this is a rare chance to create a truly exceptional Hudson Valley property with all infrastructure in place — a private farm and country compound of remarkable scale, beauty, and great potential for farming income and agricultural exemptions.

1197 Bulls Head Road, Clinton Corners

$1,450,000

Tucked gracefully in a private, tree-lined setting, this timeless New England-inspired residence offers the rare combination of classic architecture, exceptional craftsmanship, and effortless everyday living. Sunlight pours in through expansive windows, framing views of mature trees and a rolling lawn in every season. Every detail reflects quality--from the substantial millwork and rich materials to the thoughtful balance of formal and casual spaces. The expansive living room is both inviting and refined. At the heart of the home, the spacious kitchen is designed for both everyday living and effortless entertaining. A generous center island provides abundant workspace, complemented by ample cabinetry and a well-appointed layout. Three generously proportioned bedrooms provide peaceful retreats, each filled with natural light and tranquil views of the surrounding landscape. Outdoors, the property transforms into a private retreat. A freeform pool anchors the backyard, surrounded by natural stone terraces and layered gardens that blend seamlessly into the landscape. Whether gathering around the fire pit or spending quiet afternoons poolside, the setting feels peaceful and secluded. Beautifully maintained and thoughtfully designed, this is a home that lives as well as it looks: elegant without feeling formal, spacious without excess, and timeless in every sense.

3 Beds ⋅ 3 Baths ⋅ 1019762 MLS

Tucked gracefully in a private, tree-lined setting, this timeless New England-inspired residence offers the rare combination of classic architecture, exceptional craftsmanship, and effortless everyday living. Sunlight pours in through expansive windows, framing views of mature trees and a rolling lawn in every season. Every detail reflects quality--from the substantial millwork and rich materials to the thoughtful balance of formal and casual spaces. The expansive living room is both inviting and refined. At the heart of the home, the spacious kitchen is designed for both everyday living and effortless entertaining. A generous center island provides abundant workspace, complemented by ample cabinetry and a well-appointed layout. Three generously proportioned bedrooms provide peaceful retreats, each filled with natural light and tranquil views of the surrounding landscape. Outdoors, the property transforms into a private retreat. A freeform pool anchors the backyard, surrounded by natural stone terraces and layered gardens that blend seamlessly into the landscape. Whether gathering around the fire pit or spending quiet afternoons poolside, the setting feels peaceful and secluded. Beautifully maintained and thoughtfully designed, this is a home that lives as well as it looks: elegant without feeling formal, spacious without excess, and timeless in every sense.

28 Crimson Hill Road, Rhinebeck

$690,000

Welcome to effortless living at The Gardens at Rhinebeck, a well-maintained community offering several ponds, walking trails, and a butterfly & bird sanctuary just minutes from the heart of Rhinebeck Village. This inviting condominium offers a peaceful setting with scenic views and is perfectly situated beside a tranquil pond. Step inside to discover updated flooring throughout the both levels. The main floor features a thoughtfully designed floor plan that blends comfort and functionality. The kitchen features stainless steel appliances, granite countertops, a classic tile backsplash, a center island with additional storage, and a charming windowed breakfast nook—an ideal spot to enjoy your morning coffee. Just off the kitchen are a convenient powder room, coat closet, and direct access to the attached one-car garage. The open living and dining area is filled with natural light and designed for both everyday living and entertaining. An electric fireplace creates a cozy focal point, while updated lighting enhances the home's welcoming atmosphere. Sliding glass doors open to a private patio overlooking the backyard and picturesque pond, creating the perfect setting for outdoor dining, relaxing, or simply taking in the peaceful surroundings. Upstairs, the primary suite serves as a comfortable retreat, offering generous closet space, serene pond views, and an en-suite bath with a double-sink vanity and walk-in shower. A second bedroom and full guest bath provide additional accommodations while the versatile loft area offers various possibilities as a home office, media room, or playroom. Residents of The Gardens enjoy a truly carefree lifestyle, with landscaping and snow removal included in the common charges, allowing more time to enjoy the community's amenities. The clubhouse - available for private events for a fee - features a fitness center with both cardio & weight machines and free weights, men's and women's locker rooms with showers, a full kitchen, and a spacious deck for gatherings. During the warmer months, residents also enjoy the swimming pool as well as the tennis/pickleball courts. Offering comfort, convenience, and a peaceful setting just minutes from the shops and restaurants of Rhinebeck Village and the Amtrak train station.

2 Beds ⋅ 3 Baths ⋅ 1020176 MLS

Welcome to effortless living at The Gardens at Rhinebeck, a well-maintained community offering several ponds, walking trails, and a butterfly & bird sanctuary just minutes from the heart of Rhinebeck Village. This inviting condominium offers a peaceful setting with scenic views and is perfectly situated beside a tranquil pond. Step inside to discover updated flooring throughout the both levels. The main floor features a thoughtfully designed floor plan that blends comfort and functionality. The kitchen features stainless steel appliances, granite countertops, a classic tile backsplash, a center island with additional storage, and a charming windowed breakfast nook—an ideal spot to enjoy your morning coffee. Just off the kitchen are a convenient powder room, coat closet, and direct access to the attached one-car garage. The open living and dining area is filled with natural light and designed for both everyday living and entertaining. An electric fireplace creates a cozy focal point, while updated lighting enhances the home's welcoming atmosphere. Sliding glass doors open to a private patio overlooking the backyard and picturesque pond, creating the perfect setting for outdoor dining, relaxing, or simply taking in the peaceful surroundings. Upstairs, the primary suite serves as a comfortable retreat, offering generous closet space, serene pond views, and an en-suite bath with a double-sink vanity and walk-in shower. A second bedroom and full guest bath provide additional accommodations while the versatile loft area offers various possibilities as a home office, media room, or playroom. Residents of The Gardens enjoy a truly carefree lifestyle, with landscaping and snow removal included in the common charges, allowing more time to enjoy the community's amenities. The clubhouse - available for private events for a fee - features a fitness center with both cardio & weight machines and free weights, men's and women's locker rooms with showers, a full kitchen, and a spacious deck for gatherings. During the warmer months, residents also enjoy the swimming pool as well as the tennis/pickleball courts. Offering comfort, convenience, and a peaceful setting just minutes from the shops and restaurants of Rhinebeck Village and the Amtrak train station.

364 Gardenia Drive, Rhinebeck

$849,000

Set perfectly on a peaceful country road just minutes from the heart of Rhinebeck, this recently renovated home offers the perfect balance of modern comfort and year-round retreat. Inside, thoughtful updates create a warm and welcoming atmosphere centered around the wood-burning fireplace - the heart of the home and the perfect place to gather on crisp Hudson Valley evenings. The interiors blend contemporary finishes with timeless character, creating spaces that feel both stylish and effortlessly livable. Designed for entertaining and relaxation, the home truly shines outdoors. A generous screened-in porch extends the living space into the surrounding landscape, offering the ideal setting for morning coffee, summer dinners, or quiet afternoons with a book. Two separate fire pit areas invite evenings under the stars, while the hot tub provides the perfect place to unwind after a day exploring everything the Hudson Valley has to offer. The fully finished lower level adds valuable living space, ideal for a media room, rec room, guest accommodations, or creative studio. The climate-controlled garage offers even more versatility, making an excellent office, workshop, fitness space, or additional recreation area. Just 90 minutes from the George Washington Bridge, this home offers an effortless escape to the heart of the Hudson Valley. Located just minutes from the Village of Rhinebeck, you'll enjoy easy access to beloved local favorites including Pretty to Think So, The Amsterdam, Le Petit Bistro, and The Shelter Wine Bar, along with charming boutiques, farmers markets, and year-round cultural attractions. The nearby Rhinecliff Amtrak station also offers a convenient direct connection to Manhattan, making weekend getaways and full-time living equally appealing.

3 Beds ⋅ 3 Baths ⋅ 1019924 MLS

Set perfectly on a peaceful country road just minutes from the heart of Rhinebeck, this recently renovated home offers the perfect balance of modern comfort and year-round retreat. Inside, thoughtful updates create a warm and welcoming atmosphere centered around the wood-burning fireplace - the heart of the home and the perfect place to gather on crisp Hudson Valley evenings. The interiors blend contemporary finishes with timeless character, creating spaces that feel both stylish and effortlessly livable. Designed for entertaining and relaxation, the home truly shines outdoors. A generous screened-in porch extends the living space into the surrounding landscape, offering the ideal setting for morning coffee, summer dinners, or quiet afternoons with a book. Two separate fire pit areas invite evenings under the stars, while the hot tub provides the perfect place to unwind after a day exploring everything the Hudson Valley has to offer. The fully finished lower level adds valuable living space, ideal for a media room, rec room, guest accommodations, or creative studio. The climate-controlled garage offers even more versatility, making an excellent office, workshop, fitness space, or additional recreation area. Just 90 minutes from the George Washington Bridge, this home offers an effortless escape to the heart of the Hudson Valley. Located just minutes from the Village of Rhinebeck, you'll enjoy easy access to beloved local favorites including Pretty to Think So, The Amsterdam, Le Petit Bistro, and The Shelter Wine Bar, along with charming boutiques, farmers markets, and year-round cultural attractions. The nearby Rhinecliff Amtrak station also offers a convenient direct connection to Manhattan, making weekend getaways and full-time living equally appealing.

438 White Schoolhouse Road, Rhinebeck

$1,375,000

RARE RHINEBECK VILLAGE OFFERING! Located on one of the village's most desirable streets, this combined property consists of TWO houses, each on their own separate lot and tax parcels, adjacent to each other. First there is a Cape-style home that is thoughtfully renovated with high end finishes. Upon entering, immediately your senses calm and you feel right at home. An open floor plan, but with designated spaces; a cozy sitting area, next to the wood burning fireplace. The large dining area that flows into the well-designed kitchen. Thermador appliances, a butcher-block island, plenty of cabinets, a large pantry and storage. At the end of the counter, a seating area for your guests to mingle and chat while you are preparing dinner. Another great spot is the rear lounging space, overlooking the bluestone patio with beautiful perennial plantings. Sip your morning coffee, open up the french doors and hear the birds sing. On the second floor, you have an amazing spa-like bathroom with a soaking tub overlooking the picture-perfect view, also there's a steam shower, and double vanities. Two additional rooms, one used as a bedroom, the other as a separate office. Central A/C, first floor laundry, another full bath, central vacuum, radiant floor heat, and on demand hot water are extra features. The attached garage has a workshop and additional storage. The next door home is delightfully charming with Original Arts and Craft woodwork throughout. It has two bedrooms, a kitchenette with dining area, and a renovated full bath. The serene living room adjoins the enclosed front porch. The potential for use of this property is many. Live in one, rent the other, use as a generational compound, your choice! Wonderful backyards with lush gardens for both houses, and privacy even though you are a short distance away from fun things to do in Rhinebeck Village. Enjoy a movie at Upstate Films, have dinner at yummy Cinnamon, or book a massage at Mirbeau Spa. Whether you are looking for a weekend retreat, full time living or an investment opportunity, this dual property offers all those possibilities.

3 Beds ⋅ 3 Baths ⋅ 1018441 MLS

RARE RHINEBECK VILLAGE OFFERING! Located on one of the village's most desirable streets, this combined property consists of TWO houses, each on their own separate lot and tax parcels, adjacent to each other. First there is a Cape-style home that is thoughtfully renovated with high end finishes. Upon entering, immediately your senses calm and you feel right at home. An open floor plan, but with designated spaces; a cozy sitting area, next to the wood burning fireplace. The large dining area that flows into the well-designed kitchen. Thermador appliances, a butcher-block island, plenty of cabinets, a large pantry and storage. At the end of the counter, a seating area for your guests to mingle and chat while you are preparing dinner. Another great spot is the rear lounging space, overlooking the bluestone patio with beautiful perennial plantings. Sip your morning coffee, open up the french doors and hear the birds sing. On the second floor, you have an amazing spa-like bathroom with a soaking tub overlooking the picture-perfect view, also there's a steam shower, and double vanities. Two additional rooms, one used as a bedroom, the other as a separate office. Central A/C, first floor laundry, another full bath, central vacuum, radiant floor heat, and on demand hot water are extra features. The attached garage has a workshop and additional storage. The next door home is delightfully charming with Original Arts and Craft woodwork throughout. It has two bedrooms, a kitchenette with dining area, and a renovated full bath. The serene living room adjoins the enclosed front porch. The potential for use of this property is many. Live in one, rent the other, use as a generational compound, your choice! Wonderful backyards with lush gardens for both houses, and privacy even though you are a short distance away from fun things to do in Rhinebeck Village. Enjoy a movie at Upstate Films, have dinner at yummy Cinnamon, or book a massage at Mirbeau Spa. Whether you are looking for a weekend retreat, full time living or an investment opportunity, this dual property offers all those possibilities.

43 & 45 South Street, Rhinebeck

$545,000

Bright, Stylish 2-Bedroom Condo in The Woods at Rhinebeck. This well maintained 2-bedroom, 2.5-bath condo offers effortless living in one of Rhinebeck’s most desirable communities. Light-filled and welcoming, the home features an open main level that flows seamlessly to a screened-in porch, perfect for morning coffee, summer dinners, or simply enjoying the peaceful wooded setting. Upstairs, both bedrooms are generously sized, with the den opening to a charming Juliet balcony that brings in soft natural light and fresh air. Each bedroom has its own full bath, complemented by a convenient half bath on the main floor. Residents of The Woods at Rhinebeck enjoy a resort-style lifestyle with access to a pool, clubhouse, and tennis court, all just moments from the heart of Rhinebeck Village. Restaurants, boutiques, parks, and the Amtrak station are minutes away, making this an ideal full-time home or weekend retreat. A serene, stylish, and wonderfully located condo—move-in ready and close to everything Rhinebeck has to offer.

2 Beds ⋅ 3 Baths ⋅ 1015633 MLS

Bright, Stylish 2-Bedroom Condo in The Woods at Rhinebeck. This well maintained 2-bedroom, 2.5-bath condo offers effortless living in one of Rhinebeck’s most desirable communities. Light-filled and welcoming, the home features an open main level that flows seamlessly to a screened-in porch, perfect for morning coffee, summer dinners, or simply enjoying the peaceful wooded setting. Upstairs, both bedrooms are generously sized, with the den opening to a charming Juliet balcony that brings in soft natural light and fresh air. Each bedroom has its own full bath, complemented by a convenient half bath on the main floor. Residents of The Woods at Rhinebeck enjoy a resort-style lifestyle with access to a pool, clubhouse, and tennis court, all just moments from the heart of Rhinebeck Village. Restaurants, boutiques, parks, and the Amtrak station are minutes away, making this an ideal full-time home or weekend retreat. A serene, stylish, and wonderfully located condo—move-in ready and close to everything Rhinebeck has to offer.

28 E Knoll, Rhinebeck

$1,385,000

Set on a quiet no-outlet cul-de-sac in desirable Staatsburg and within the Rhinebeck Central School District, this classic 3,600-square-foot Colonial offers timeless design, wonderful natural light, and picturesque Hudson River and Catskill Mountain views — all under 10 minutes to Rhinebeck Village. Thoughtfully positioned on the property with mature landscaping and expansive open lawn, the home welcomes you with spacious, light-filled interiors and a layout designed for both comfortable everyday living and effortless entertaining. The gracious front-to-back living room features a classic brick wood-burning fireplace and opens directly to a rear deck tucked beneath a beautiful shade tree — the perfect setting for outdoor dining, quiet mornings, or sunset gatherings overlooking the landscape beyond. At the center of the home is a generously sized kitchen with a substantial island bar, abundant workspace, and an informal dining area that flows seamlessly into a spectacular rear family room addition. Designed to maximize the extraordinary setting, this stunning space offers radiant heated floors, a wood-burning fireplace, and dramatic walls of windows framing beautiful Hudson River and Catskill Mountain vistas. The main level also includes a formal dining room with scenic views, a private office ideal for remote work or creative pursuits, a stylish full bath, and an inviting foyer that sets the tone upon arrival. Upstairs, all three bedrooms enjoy captivating river and mountain views. The gracious primary suite offers a peaceful retreat complete with a sitting area, exterior Juliet balcony, walk-in closet, and a beautifully appointed private bath. A spacious secondary bedroom includes its own dedicated bath, while the third bedroom is ideal for guests, a second office, or studio space with inspiring views. Additional features include hardwood, tile, and stone flooring throughout, central air conditioning, a two-bay attached garage, and a full unfinished basement offering abundant storage, space for a gym or other pursuits. Outside, the in-ground pool offers a peaceful setting for summer relaxation, entertaining, and enjoying the surrounding landscape and views. Beyond the pool, the open lawn provides ample space for gardening, recreation, or future solar installation. Blending classic Colonial character, beautiful natural surroundings, and a highly convenient location under 10 minutes to Rhinebeck Village, this property offers an exceptional opportunity to experience the very best of Hudson Valley living.

3 Beds ⋅ 4 Baths ⋅ 998036 MLS

Set on a quiet no-outlet cul-de-sac in desirable Staatsburg and within the Rhinebeck Central School District, this classic 3,600-square-foot Colonial offers timeless design, wonderful natural light, and picturesque Hudson River and Catskill Mountain views — all under 10 minutes to Rhinebeck Village. Thoughtfully positioned on the property with mature landscaping and expansive open lawn, the home welcomes you with spacious, light-filled interiors and a layout designed for both comfortable everyday living and effortless entertaining. The gracious front-to-back living room features a classic brick wood-burning fireplace and opens directly to a rear deck tucked beneath a beautiful shade tree — the perfect setting for outdoor dining, quiet mornings, or sunset gatherings overlooking the landscape beyond. At the center of the home is a generously sized kitchen with a substantial island bar, abundant workspace, and an informal dining area that flows seamlessly into a spectacular rear family room addition. Designed to maximize the extraordinary setting, this stunning space offers radiant heated floors, a wood-burning fireplace, and dramatic walls of windows framing beautiful Hudson River and Catskill Mountain vistas. The main level also includes a formal dining room with scenic views, a private office ideal for remote work or creative pursuits, a stylish full bath, and an inviting foyer that sets the tone upon arrival. Upstairs, all three bedrooms enjoy captivating river and mountain views. The gracious primary suite offers a peaceful retreat complete with a sitting area, exterior Juliet balcony, walk-in closet, and a beautifully appointed private bath. A spacious secondary bedroom includes its own dedicated bath, while the third bedroom is ideal for guests, a second office, or studio space with inspiring views. Additional features include hardwood, tile, and stone flooring throughout, central air conditioning, a two-bay attached garage, and a full unfinished basement offering abundant storage, space for a gym or other pursuits. Outside, the in-ground pool offers a peaceful setting for summer relaxation, entertaining, and enjoying the surrounding landscape and views. Beyond the pool, the open lawn provides ample space for gardening, recreation, or future solar installation. Blending classic Colonial character, beautiful natural surroundings, and a highly convenient location under 10 minutes to Rhinebeck Village, this property offers an exceptional opportunity to experience the very best of Hudson Valley living.

13 Spy Glass Lane, Staatsburg

$2,955,000

This is a rare opportunity to thoughtfully steward and restore one of Rhinebeck Village’s most architecturally compelling historic residences — a property defined by provenance, scale, and enduring beauty. Set on coveted Chestnut Street, this distinguished circa-1870 Italianate villa offers 4 bedrooms and 2.5 baths and is among the few remaining historic homes in the village to retain such remarkable original detail and integrity. Soaring ceilings, grand arched openings, oversized bay windows, marble fireplaces, original plaster medallions, plaster walls, crown moldings, decorative chandeliers, and beautifully preserved original windows speak to a level of craftsmanship rarely found today. The home’s exceptional acoustics — enhanced by the original plaster walls — create a quiet richness and warmth throughout the interiors that is immediately felt upon entering. Built for local attorney and town supervisor George Esselstyn, the residence unfolds across graciously proportioned rooms filled with natural light, including a richly atmospheric library anchored by an intact soft-coal heating stove and original glass-front bookcases. Outside, the property becomes even more extraordinary. An original two-bay carriage barn with a walk-up loft offers exceptional potential for studio, guest, or creative use. The residence sits on an oversized village parcel with 100 feet of road frontage, accompanied by an additional separately deeded adjoining lot with another 50 feet of frontage — a rarity within Rhinebeck Village and an offering that creates an estate-like setting of unusual scale, privacy, and presence. A truly exceptional offering for those who value architectural authenticity, history, and the rare privilege of bringing a significant home into its next chapter.

4 Beds ⋅ 3 Baths ⋅ 1006579 MLS

This is a rare opportunity to thoughtfully steward and restore one of Rhinebeck Village’s most architecturally compelling historic residences — a property defined by provenance, scale, and enduring beauty. Set on coveted Chestnut Street, this distinguished circa-1870 Italianate villa offers 4 bedrooms and 2.5 baths and is among the few remaining historic homes in the village to retain such remarkable original detail and integrity. Soaring ceilings, grand arched openings, oversized bay windows, marble fireplaces, original plaster medallions, plaster walls, crown moldings, decorative chandeliers, and beautifully preserved original windows speak to a level of craftsmanship rarely found today. The home’s exceptional acoustics — enhanced by the original plaster walls — create a quiet richness and warmth throughout the interiors that is immediately felt upon entering. Built for local attorney and town supervisor George Esselstyn, the residence unfolds across graciously proportioned rooms filled with natural light, including a richly atmospheric library anchored by an intact soft-coal heating stove and original glass-front bookcases. Outside, the property becomes even more extraordinary. An original two-bay carriage barn with a walk-up loft offers exceptional potential for studio, guest, or creative use. The residence sits on an oversized village parcel with 100 feet of road frontage, accompanied by an additional separately deeded adjoining lot with another 50 feet of frontage — a rarity within Rhinebeck Village and an offering that creates an estate-like setting of unusual scale, privacy, and presence. A truly exceptional offering for those who value architectural authenticity, history, and the rare privilege of bringing a significant home into its next chapter.

31 Chestnut Street, Rhinebeck

$3,850,000

WhistleWood Farm A rare multi-use estate set on just under 40 acres in the heart of Rhinebeck, NY. Currently operating as a successful bed-and-breakfast, event venue, and horse boarding facility, WhistleWood Farm offers exceptional flexibility for both residential and commercial buyers seeking a true Hudson Valley destination property. Comprised of three parcels totaling nearly 40 acres, the property is equally suited as a private compound, gentleman’s farm, equestrian retreat, boutique hospitality venture, or wellness-focused escape. Existing hospitality and equestrian infrastructure provide a strong foundation for continued or expanded use. The main residence spans approximately 4,500 square feet and features 5 bedrooms, 5 full baths, and 2 kitchens—offering remarkable flexibility for private living, guest accommodations, or hospitality operations. Complementing the main house is an beautifully appointed 1,500-square-foot carriage house with three bedrooms and three baths, rich in character and perfectly suited for guests, extended stays, or expanded event and hospitality use. Walking trails through the woods create a rare sense of privacy and connection to the landscape just moments from the heart of Rhinebeck Village—with its celebrated dining, farm-to-table restaurants, boutiques, and nearby Amtrak access. For the tennis enthusiast, premier tennis facilities conveniently located next door further enhance the property’s lifestyle appeal. Open meadows, mature trees, and a coveted Village-adjacent setting make WhistleWood Farm a truly rare offering—equally compelling as a private estate, hospitality investment, or legacy property in the Hudson Valley. Additional features include solar power, further enhancing the property’s efficiency and long-term sustainability.

7 Beds ⋅ 7 Baths ⋅ 1003365 MLS

WhistleWood Farm A rare multi-use estate set on just under 40 acres in the heart of Rhinebeck, NY. Currently operating as a successful bed-and-breakfast, event venue, and horse boarding facility, WhistleWood Farm offers exceptional flexibility for both residential and commercial buyers seeking a true Hudson Valley destination property. Comprised of three parcels totaling nearly 40 acres, the property is equally suited as a private compound, gentleman’s farm, equestrian retreat, boutique hospitality venture, or wellness-focused escape. Existing hospitality and equestrian infrastructure provide a strong foundation for continued or expanded use. The main residence spans approximately 4,500 square feet and features 5 bedrooms, 5 full baths, and 2 kitchens—offering remarkable flexibility for private living, guest accommodations, or hospitality operations. Complementing the main house is an beautifully appointed 1,500-square-foot carriage house with three bedrooms and three baths, rich in character and perfectly suited for guests, extended stays, or expanded event and hospitality use. Walking trails through the woods create a rare sense of privacy and connection to the landscape just moments from the heart of Rhinebeck Village—with its celebrated dining, farm-to-table restaurants, boutiques, and nearby Amtrak access. For the tennis enthusiast, premier tennis facilities conveniently located next door further enhance the property’s lifestyle appeal. Open meadows, mature trees, and a coveted Village-adjacent setting make WhistleWood Farm a truly rare offering—equally compelling as a private estate, hospitality investment, or legacy property in the Hudson Valley. Additional features include solar power, further enhancing the property’s efficiency and long-term sustainability.

52 Pells Road, Rhinebeck

$2,750,000

Milan Hall Farm circa 1750 Truly exceptional. Completely private. Set across 87 acres of open field and quiet forest, Milan Hall Farm unfolds as a rare Hudson Valley offering—where land, history, and thoughtful stewardship meet. A winding stream and natural waterfall trace the landscape, alongside a private 1.3-mile walking trail through the woods, all bordered by enduring stone walls that speak to the property's agricultural past. Protected under conservation easement with the Winnakee Land Trust and New York State forestry program, the land offers both privacy and permanence. The farmhouse, dating to the mid-18th century, has been carefully expanded to accommodate modern living while honoring its origins. Three bedrooms, each with en-suite baths, are complemented by a light-filled conservatory, a quiet library, and multiple gathering spaces anchored by wood-burning stoves. A broad porch overlooks the gardens, while bluestone patios extend living outdoors. The grounds are meticulously maintained, with layered gardens, mature plantings, and curated outdoor spaces throughout. A separate guest cottage, complete with a full kitchen, one bedroom, bath, sitting area, and wood-burning stove, provides a welcoming retreat for extended stays or visiting family and friends. Further enhancing the estate is a thoughtfully designated three-acre building envelope within the Conservation Easement, offering the rare opportunity to add complementary structures such as an accessory dwelling, swimming pool, pool house, studio, sheds, or other accessory buildings. Existing improvements also present opportunities for thoughtful expansion and adaptation, whether by enhancing the guest cottage, exploring the potential for additional space above the existing two-car garage (subject to approvals), reimagining the historic barn, or creating additional living, work, or wellness spaces. Together, these possibilities allow the estate to evolve over time while preserving its extraordinary privacy and the integrity of the surrounding landscape. The beautifully preserved 1853 post-and-beam barn, equipped with electric and water, presents endless possibilities as a studio, workshop, or future living space. Additional outbuildings, including a two-car garage, support both function and form. Modern amenities—including solar power, central air, and a whole-house generator—blend seamlessly with the home's historic character, bringing comfort and efficiency to everyday living. Just minutes from Rhinebeck Village, Amtrak, and some of the Hudson Valley's most celebrated restaurants, boutiques, and cultural destinations, Milan Hall Farm feels worlds away while remaining remarkably convenient.

3 Beds ⋅ 4 Baths ⋅ 987569 MLS

Milan Hall Farm circa 1750 Truly exceptional. Completely private. Set across 87 acres of open field and quiet forest, Milan Hall Farm unfolds as a rare Hudson Valley offering—where land, history, and thoughtful stewardship meet. A winding stream and natural waterfall trace the landscape, alongside a private 1.3-mile walking trail through the woods, all bordered by enduring stone walls that speak to the property's agricultural past. Protected under conservation easement with the Winnakee Land Trust and New York State forestry program, the land offers both privacy and permanence. The farmhouse, dating to the mid-18th century, has been carefully expanded to accommodate modern living while honoring its origins. Three bedrooms, each with en-suite baths, are complemented by a light-filled conservatory, a quiet library, and multiple gathering spaces anchored by wood-burning stoves. A broad porch overlooks the gardens, while bluestone patios extend living outdoors. The grounds are meticulously maintained, with layered gardens, mature plantings, and curated outdoor spaces throughout. A separate guest cottage, complete with a full kitchen, one bedroom, bath, sitting area, and wood-burning stove, provides a welcoming retreat for extended stays or visiting family and friends. Further enhancing the estate is a thoughtfully designated three-acre building envelope within the Conservation Easement, offering the rare opportunity to add complementary structures such as an accessory dwelling, swimming pool, pool house, studio, sheds, or other accessory buildings. Existing improvements also present opportunities for thoughtful expansion and adaptation, whether by enhancing the guest cottage, exploring the potential for additional space above the existing two-car garage (subject to approvals), reimagining the historic barn, or creating additional living, work, or wellness spaces. Together, these possibilities allow the estate to evolve over time while preserving its extraordinary privacy and the integrity of the surrounding landscape. The beautifully preserved 1853 post-and-beam barn, equipped with electric and water, presents endless possibilities as a studio, workshop, or future living space. Additional outbuildings, including a two-car garage, support both function and form. Modern amenities—including solar power, central air, and a whole-house generator—blend seamlessly with the home's historic character, bringing comfort and efficiency to everyday living. Just minutes from Rhinebeck Village, Amtrak, and some of the Hudson Valley's most celebrated restaurants, boutiques, and cultural destinations, Milan Hall Farm feels worlds away while remaining remarkably convenient.

457 Round Lake Road, Rhinebeck

$459,000

Wonderful 3 bedroom ranch located on a quiet road in Rhinebeck! Amenities include; hardwood floors, brick fireplace, bright eat-in kitchen, formal dining room, ceramic tiled bathroom, covered porch, and level yard! Minutes to the Village of Rhinebeck, parks, medical facilities, shopping, restaurants, Rhinecliff train station, and so much more!

3 Beds ⋅ 1 Baths ⋅ 987299 MLS

Wonderful 3 bedroom ranch located on a quiet road in Rhinebeck! Amenities include; hardwood floors, brick fireplace, bright eat-in kitchen, formal dining room, ceramic tiled bathroom, covered porch, and level yard! Minutes to the Village of Rhinebeck, parks, medical facilities, shopping, restaurants, Rhinecliff train station, and so much more!

8 King Road, Rhinebeck

$625,000

"Set on 12 generous acres in one of Rhinebeck’s most appealing country settings, this updated property offers space, privacy, and exceptional flexibility just minutes from Rhinebeck Village and the Taconic Parkway. The home features a remodeled kitchen, generous natural light, and inviting living spaces with strong potential for redesign or further customization. Recent upgrades include 200 amp electric service, well pump, boiler, heat pump and oak flooring. A restored barn adds valuable additional space, ideal for a studio, office, guest area, creative workspace, or recreation along a two-car garage with EV charging. With expansive acreage and multiple usable spaces, the property offers the rare opportunity to create a highly personal Hudson Valley retreat whether as a full-time residence, weekend home, or live/work environment. Close to Rhinebeck’s downtown restaurants, shops, cultural destinations, and Amtrak access, this property combines country privacy with convenient access to the best of the Hudson Valley."

3 Beds ⋅ 1 Baths ⋅ 984293 MLS

"Set on 12 generous acres in one of Rhinebeck’s most appealing country settings, this updated property offers space, privacy, and exceptional flexibility just minutes from Rhinebeck Village and the Taconic Parkway. The home features a remodeled kitchen, generous natural light, and inviting living spaces with strong potential for redesign or further customization. Recent upgrades include 200 amp electric service, well pump, boiler, heat pump and oak flooring. A restored barn adds valuable additional space, ideal for a studio, office, guest area, creative workspace, or recreation along a two-car garage with EV charging. With expansive acreage and multiple usable spaces, the property offers the rare opportunity to create a highly personal Hudson Valley retreat whether as a full-time residence, weekend home, or live/work environment. Close to Rhinebeck’s downtown restaurants, shops, cultural destinations, and Amtrak access, this property combines country privacy with convenient access to the best of the Hudson Valley."

461 White Schoolhouse, Rhinebeck

$990,000

Incredible multi-lot opportunity perfectly positioned between Rhinebeck and Red Hook, offering three separate lots included in one price. Lot 1 encompasses 3.899 acres and features a fully renovated 2005 duplex with two vacant, turn-key units ready for immediate income or occupancy. Apartment A is a beautifully updated 1-bedroom, 1-bathroom unit, while Apartment B is nearly double the size, featuring 1 bedroom, 1 bathroom, and two large bonus/flex rooms perfect for a home office, gym, or creative space. The building also boasts a massive, oversized garage with 10-foot ceilings, providing the ultimate setup for a premium workshop or contractor machine storage. Tucked privately at the back of the property atop a scenic hill sits Lot 2a is a Board of Health approved (BOHA) 4.11-acre home site offering privacy and sweeping views. Lot 2 provides another 3.046 BOHA acres with excellent road frontage on Round Lake Road for additional development potential. This exceptionally versatile property is just 11 minutes to Red Hook, 12 minutes to Rhinebeck Village, and only 15 minutes to the Rhinecliff Train Station, making it an absolute dream for investors, builders, or anyone looking to create a premium Hudson Valley compound.

2 Beds ⋅ 2 Baths ⋅ 927774 MLS

Incredible multi-lot opportunity perfectly positioned between Rhinebeck and Red Hook, offering three separate lots included in one price. Lot 1 encompasses 3.899 acres and features a fully renovated 2005 duplex with two vacant, turn-key units ready for immediate income or occupancy. Apartment A is a beautifully updated 1-bedroom, 1-bathroom unit, while Apartment B is nearly double the size, featuring 1 bedroom, 1 bathroom, and two large bonus/flex rooms perfect for a home office, gym, or creative space. The building also boasts a massive, oversized garage with 10-foot ceilings, providing the ultimate setup for a premium workshop or contractor machine storage. Tucked privately at the back of the property atop a scenic hill sits Lot 2a is a Board of Health approved (BOHA) 4.11-acre home site offering privacy and sweeping views. Lot 2 provides another 3.046 BOHA acres with excellent road frontage on Round Lake Road for additional development potential. This exceptionally versatile property is just 11 minutes to Red Hook, 12 minutes to Rhinebeck Village, and only 15 minutes to the Rhinecliff Train Station, making it an absolute dream for investors, builders, or anyone looking to create a premium Hudson Valley compound.

400 Round Lake Road, Rhinebeck