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$1,895,000

Feast your eyes on this gorgeous contemporary sited on 8 private acres between the Villages of Rhinebeck and Red Hook, offering 4 bedrooms and 3.5 baths in a total of 3200 finished square feet. The distinctive exterior is wrapped with redwood siding and a standing seam metal roof. Corner windows flood the home with light while capturing the natural beauty of the setting. The 15 x 40 infinity propane heated saltwater pool spills into the forest, flanked by a hot tub, a cedar pavilion with integrated speakers, lighting, and a ceiling fan on one side, and an alfresco dining area with a retractable awning on the other. The heart of the home is a dream kitchen designed for easy everyday living and entertaining complete with a 6-burner Viking gas range, Miele wall oven, microwave and steam oven, an additional electric cooktop and a dedicated coffee bar area. The expansive living area is centered around a propane fireplace with spectacular views of the pool and deep forest that lays beyond it. The first-floor primary suite is positioned on one side of the main level of the home, separate from the two additional bedrooms on the same floor. One of the bedrooms is equipped with a murphy-bed/book case unit for multi-purpose use as a home office or art studio. The finished lower level expands the home’s versatility with a guest suite and full ensuite bath, as well as a delightful media/game room. This level also features an office area, additional coffee station, and two huge walk-in closets. Additional highlights include radiant heat throughout the home, an oversized 4 car garage with workshop space, hardwood floors, whole house generator, exterior lighting, blue stone and river stone patio. Perfectly positioned to easily take advantage of the many farm markets, restaurants, cultural and recreational destinations offered in the Hudson Valley.

4 Beds ⋅ 4 Baths ⋅ 1048583 MLS

Feast your eyes on this gorgeous contemporary sited on 8 private acres between the Villages of Rhinebeck and Red Hook, offering 4 bedrooms and 3.5 baths in a total of 3200 finished square feet. The distinctive exterior is wrapped with redwood siding and a standing seam metal roof. Corner windows flood the home with light while capturing the natural beauty of the setting. The 15 x 40 infinity propane heated saltwater pool spills into the forest, flanked by a hot tub, a cedar pavilion with integrated speakers, lighting, and a ceiling fan on one side, and an alfresco dining area with a retractable awning on the other. The heart of the home is a dream kitchen designed for easy everyday living and entertaining complete with a 6-burner Viking gas range, Miele wall oven, microwave and steam oven, an additional electric cooktop and a dedicated coffee bar area. The expansive living area is centered around a propane fireplace with spectacular views of the pool and deep forest that lays beyond it. The first-floor primary suite is positioned on one side of the main level of the home, separate from the two additional bedrooms on the same floor. One of the bedrooms is equipped with a murphy-bed/book case unit for multi-purpose use as a home office or art studio. The finished lower level expands the home’s versatility with a guest suite and full ensuite bath, as well as a delightful media/game room. This level also features an office area, additional coffee station, and two huge walk-in closets. Additional highlights include radiant heat throughout the home, an oversized 4 car garage with workshop space, hardwood floors, whole house generator, exterior lighting, blue stone and river stone patio. Perfectly positioned to easily take advantage of the many farm markets, restaurants, cultural and recreational destinations offered in the Hudson Valley.

8 Sarah Court, Rhinebeck

$535,000

Welcome to lakeside living in Sepasco Village, located in the Town of Rhinebeck and within the Rhinebeck Central School District. This charming 1,534 sqft ranch offers comfortable single-level living with 2 bedrooms, 1.5 baths, and an inviting layout. The spacious living room features a double-sided wood-burning fireplace shared with the eat-in kitchen, creating a warm and welcoming focal point. French doors open from the living room to a large screened-in porch, an ideal setting for morning coffee, outdoor dining, or relaxing and enjoying the peaceful surroundings. The eat-in kitchen offers ample space for a dining table and convenient access to a powder room with stackable laundry. Just off the kitchen, a small office provides a dedicated space for working from home, hobbies, or household organization. Outside, enjoy a large, fully fenced backyard with plenty of room for recreation, gardening, pets, or simply relaxing outdoors. A one-car garage adds convenient parking and storage. The home features all-electric mechanicals and an oversized septic tank appropriately sized for a three-bedroom home. The property's location in Sepasco Village is ideal, positioned a short distance across from the community picnic area and close to lake access. Enjoy the recreational opportunities and relaxed atmosphere of a lakeside community, with convenient access to all that Rhinebeck and the surrounding Hudson Valley have to offer.

2 Beds ⋅ 2 Baths ⋅ 1048580 MLS

Welcome to lakeside living in Sepasco Village, located in the Town of Rhinebeck and within the Rhinebeck Central School District. This charming 1,534 sqft ranch offers comfortable single-level living with 2 bedrooms, 1.5 baths, and an inviting layout. The spacious living room features a double-sided wood-burning fireplace shared with the eat-in kitchen, creating a warm and welcoming focal point. French doors open from the living room to a large screened-in porch, an ideal setting for morning coffee, outdoor dining, or relaxing and enjoying the peaceful surroundings. The eat-in kitchen offers ample space for a dining table and convenient access to a powder room with stackable laundry. Just off the kitchen, a small office provides a dedicated space for working from home, hobbies, or household organization. Outside, enjoy a large, fully fenced backyard with plenty of room for recreation, gardening, pets, or simply relaxing outdoors. A one-car garage adds convenient parking and storage. The home features all-electric mechanicals and an oversized septic tank appropriately sized for a three-bedroom home. The property's location in Sepasco Village is ideal, positioned a short distance across from the community picnic area and close to lake access. Enjoy the recreational opportunities and relaxed atmosphere of a lakeside community, with convenient access to all that Rhinebeck and the surrounding Hudson Valley have to offer.

303 Sepasco Lake Drive, Rhinebeck

$546,000

56 Pond Drive East is a one-story end unit in "The Woods" in Rhinebeck Village. This unit offers a quiet setting overlooking the pond. The amenities include a swimming pool, tennis courts and a club house. Some of this unit's features are a new heat pump (2026), new windows and patio door (2024), new garage interior and door (2026). A pleasant walk into the Village where you will find shops, restaurants, a movie theater, spas, etc. All this just 10 minutes to Amtrak. Final offers due Monday, September 14th at noon.

2 Beds ⋅ 2 Baths ⋅ 1048507 MLS

56 Pond Drive East is a one-story end unit in "The Woods" in Rhinebeck Village. This unit offers a quiet setting overlooking the pond. The amenities include a swimming pool, tennis courts and a club house. Some of this unit's features are a new heat pump (2026), new windows and patio door (2024), new garage interior and door (2026). A pleasant walk into the Village where you will find shops, restaurants, a movie theater, spas, etc. All this just 10 minutes to Amtrak. Final offers due Monday, September 14th at noon.

56 Pond Drive E, Rhinebeck

$1,125,000

This exceptional log home offers a tranquil retreat on 8.8 acres, featuring a private pond and a park-like setting. The property emphasizes privacy and includes an inground pool with a deck for outdoor enjoyment. Additionally, it boasts a substantial workshop with a one-bedroom guest quarters located above it, providing versatile extra space. Another run-in shed offers further utility storage. The location is highly desirable, offering the serenity of a private estate while remaining just minutes from the charming Rhinebeck village and convenient access to the Taconic Parkway.

4 Beds ⋅ 3 Baths ⋅ 1044719 MLS

This exceptional log home offers a tranquil retreat on 8.8 acres, featuring a private pond and a park-like setting. The property emphasizes privacy and includes an inground pool with a deck for outdoor enjoyment. Additionally, it boasts a substantial workshop with a one-bedroom guest quarters located above it, providing versatile extra space. Another run-in shed offers further utility storage. The location is highly desirable, offering the serenity of a private estate while remaining just minutes from the charming Rhinebeck village and convenient access to the Taconic Parkway.

331 Mountain View Road Unit #325, Rhinebeck

$925,000

Set back from a quiet country road on 2.12 private acres, this fully renovated mid-century ranch offers an effortless blend of modern design, comfort, and Hudson Valley living. The chic, light-filled, single-level interior features an open floor plan, hardwood and ceramic tile floors, three bedrooms, and two baths, including a cozy primary suite with ensuite bath. The eat-in kitchen opens to a patio just off the back, creating seamless entertaining options including a deck for sunning and relaxation. Outside, a saline in-ground pool is privately sited within a fenced yard, framed by expansive lawn and wooded views. An enclosed raised-bed garden provides a dedicated space for growing vegetables, herbs, or flowers. The attached two-car garage offers the potential for additional living space, studio, gym, or office, while the property has room for a pool house or detached garage. Minutes to Rhinebeck Village and Amtrak, the Taconic Parkway and under two hours to NYC, this is an ideal country retreat or full-time home. Rhinebeck Schools.

3 Beds ⋅ 2 Baths ⋅ 1047657 MLS

Set back from a quiet country road on 2.12 private acres, this fully renovated mid-century ranch offers an effortless blend of modern design, comfort, and Hudson Valley living. The chic, light-filled, single-level interior features an open floor plan, hardwood and ceramic tile floors, three bedrooms, and two baths, including a cozy primary suite with ensuite bath. The eat-in kitchen opens to a patio just off the back, creating seamless entertaining options including a deck for sunning and relaxation. Outside, a saline in-ground pool is privately sited within a fenced yard, framed by expansive lawn and wooded views. An enclosed raised-bed garden provides a dedicated space for growing vegetables, herbs, or flowers. The attached two-car garage offers the potential for additional living space, studio, gym, or office, while the property has room for a pool house or detached garage. Minutes to Rhinebeck Village and Amtrak, the Taconic Parkway and under two hours to NYC, this is an ideal country retreat or full-time home. Rhinebeck Schools.

62 Frost Road, Rhinebeck

$719,000

Ready to make the move to Rhinebeck in the beautiful Hudson Valley? Welcome to 19 Closs Drive, where timeless charm meets modern comfort in this beautifully updated, move-in-ready 3-bedroom, 2-bath ranch, ideally located just a short stroll from the heart of Rhinebeck Village. Enjoy easy access to restaurants, charming boutiques, cafes, schools, spas in this sought-after Hudson Valley community. You will appreciate the home's exceptional curb appeal. New siding & attractive stonework (2020), along with a welcoming Mission-style front porch and entry door, create a warm first impression. Inside, gleaming hardwood floors flow throughout the living room and bedrooms. Abundant natural light fills the living room, where a cozy fireplace makes the perfect gathering place during every season. The beautifully renovated kitchen is the centerpiece of the home, featuring granite countertops, a center island, stainless steel appliances, & tile flooring. Open to the dining area, this thoughtfully designed space is ideal for everyday living & effortless entertaining. A spacious screened porch extends your living space, offering the perfect setting for outdoor dining, relaxing with friends, or enjoying peaceful summer evenings. A charming patio provides another private retreat for morning coffee or an evening glass of wine. The comfortable primary suite includes an updated en-suite bath, while two additional bedrooms & a stylishly renovated full hall bath complete the main level. The finished lower level adds valuable flexible living space with new carpeting, ceiling tiles, updated lighting, separate zoned baseboard heat, and endless possibilities for a family room, media room, home office, fitness area, or playroom. A utility room with a workbench provides excellent storage and workspace. An attached two-car garage offers everyday convenience & protection from the elements. Situated in the heart of the Hudson Valley, this home is just minutes from renowned destinations including Bard College, Vassar College, Marist University, & the Culinary Institute of America. Enjoy weekends exploring the Walkway Over the Hudson, the Hudson River, nearby lakes, golf courses, hiking trails, historic estates, farmers markets, and wineries. Rhinecliff Amtrak Station is approximately seven minutes away, making travel to New York City or Albany simple & convenient. 19 Closs Drive presents a rare opportunity to enjoy the very best of Rhinebeck living, whether you are looking for a full time residence or weekend retreat, This turnkey home seamlessly combines comfort, style, and convenience in one of the Hudson Valley's most desirable communities. Whether you're looking for a full-time residence or a weekend escape, you'll love everything this exceptional home & Rhinebeck have to offer.

3 Beds ⋅ 2 Baths ⋅ 1047112 MLS

Ready to make the move to Rhinebeck in the beautiful Hudson Valley? Welcome to 19 Closs Drive, where timeless charm meets modern comfort in this beautifully updated, move-in-ready 3-bedroom, 2-bath ranch, ideally located just a short stroll from the heart of Rhinebeck Village. Enjoy easy access to restaurants, charming boutiques, cafes, schools, spas in this sought-after Hudson Valley community. You will appreciate the home's exceptional curb appeal. New siding & attractive stonework (2020), along with a welcoming Mission-style front porch and entry door, create a warm first impression. Inside, gleaming hardwood floors flow throughout the living room and bedrooms. Abundant natural light fills the living room, where a cozy fireplace makes the perfect gathering place during every season. The beautifully renovated kitchen is the centerpiece of the home, featuring granite countertops, a center island, stainless steel appliances, & tile flooring. Open to the dining area, this thoughtfully designed space is ideal for everyday living & effortless entertaining. A spacious screened porch extends your living space, offering the perfect setting for outdoor dining, relaxing with friends, or enjoying peaceful summer evenings. A charming patio provides another private retreat for morning coffee or an evening glass of wine. The comfortable primary suite includes an updated en-suite bath, while two additional bedrooms & a stylishly renovated full hall bath complete the main level. The finished lower level adds valuable flexible living space with new carpeting, ceiling tiles, updated lighting, separate zoned baseboard heat, and endless possibilities for a family room, media room, home office, fitness area, or playroom. A utility room with a workbench provides excellent storage and workspace. An attached two-car garage offers everyday convenience & protection from the elements. Situated in the heart of the Hudson Valley, this home is just minutes from renowned destinations including Bard College, Vassar College, Marist University, & the Culinary Institute of America. Enjoy weekends exploring the Walkway Over the Hudson, the Hudson River, nearby lakes, golf courses, hiking trails, historic estates, farmers markets, and wineries. Rhinecliff Amtrak Station is approximately seven minutes away, making travel to New York City or Albany simple & convenient. 19 Closs Drive presents a rare opportunity to enjoy the very best of Rhinebeck living, whether you are looking for a full time residence or weekend retreat, This turnkey home seamlessly combines comfort, style, and convenience in one of the Hudson Valley's most desirable communities. Whether you're looking for a full-time residence or a weekend escape, you'll love everything this exceptional home & Rhinebeck have to offer.

19 Closs Drive, Rhinebeck

$2,395,000

A classic, modern farmhouse on five acres with a pond, perennial gardens, and a beautiful, sprawling backyard all on a dead end road. Newly constructed in 2022, the immaculate 4,000+ square foot home is perfectly executed. The interiors feel luxurious with wideboard white oak floors throughout and a vaulted 17ft ceiling in the main, open living space. There is a gas fireplace anchoring the room and the open kitchen features an extra large Liebherr refrigerator, a double oven and coffee station. There is a spacious pantry with additional storage and a wine fridge. You’ll find a home office and formal dining room. The primary suite is on the main floor, large with sliding doors out to a private balcony and hot tub. The bath is ensuite with double vanities, radiant heated floors and a soaking tub and there are two walk-in closets. You'll find two additional bedrooms on the main level, both well sized and connected by a jack-and-jill bath. Upstairs is a large sitting area currently used as a play room, an additional bedroom and a full bath, as well as a flex space which the current owners use as sleeping quarters. The 2,500+ square foot basement has fabulous high ceilings making it super usable, it’s set up as a home gym. A large screened in porch overlooks the backyard and the woods beyond, and there are raised garden beds ready for when the weather turns. An irrigation system has been installed which keep the gardens very low maintenance. There is an attached two car garage and the home sits in a neighborhood setting amongst other homes of a cohesive aesthetic. 11 Crimson Hill is a wonderful turnkey option just minutes to Rhinebeck village and Amtrak. Located in the Rhinebeck School District it is perfect for year round or weekend living.

4 Beds ⋅ 4 Baths ⋅ 1045717 MLS

A classic, modern farmhouse on five acres with a pond, perennial gardens, and a beautiful, sprawling backyard all on a dead end road. Newly constructed in 2022, the immaculate 4,000+ square foot home is perfectly executed. The interiors feel luxurious with wideboard white oak floors throughout and a vaulted 17ft ceiling in the main, open living space. There is a gas fireplace anchoring the room and the open kitchen features an extra large Liebherr refrigerator, a double oven and coffee station. There is a spacious pantry with additional storage and a wine fridge. You’ll find a home office and formal dining room. The primary suite is on the main floor, large with sliding doors out to a private balcony and hot tub. The bath is ensuite with double vanities, radiant heated floors and a soaking tub and there are two walk-in closets. You'll find two additional bedrooms on the main level, both well sized and connected by a jack-and-jill bath. Upstairs is a large sitting area currently used as a play room, an additional bedroom and a full bath, as well as a flex space which the current owners use as sleeping quarters. The 2,500+ square foot basement has fabulous high ceilings making it super usable, it’s set up as a home gym. A large screened in porch overlooks the backyard and the woods beyond, and there are raised garden beds ready for when the weather turns. An irrigation system has been installed which keep the gardens very low maintenance. There is an attached two car garage and the home sits in a neighborhood setting amongst other homes of a cohesive aesthetic. 11 Crimson Hill is a wonderful turnkey option just minutes to Rhinebeck village and Amtrak. Located in the Rhinebeck School District it is perfect for year round or weekend living.

11 Crimson Hill, Rhinebeck

$699,500

Welcome to The Gardens at Rhinebeck II, an upscale community of beautifully maintained homes. This 2-bedroom, 2.5-bath, 1,495-square-foot condo is stylish and move-in ready, with 9-foot ceilings, central air, and a bright, airy main floor that feels instantly welcoming. The main floor features a thoughtfully designed floor plan that blends comfort and functionality. The kitchen features stainless steel GE appliances, granite countertops, an elegant backsplash, a center island with additional storage and room for barstools for entertaining, and a charming, windowed breakfast nook, perfect for your morning coffee. Just off the kitchen is a wallpapered powder room, coat closet, pantry, and direct access to an attached garage with additional storage room. The open living and dining area is filled with natural light and designed for both everyday living and entertaining. An electric fireplace adds a warm and beautiful focal point. The windows and sliding glass doors open to a private patio, perfect for dining, relaxing, and taking in the tranquil surroundings. Upstairs, the primary bedroom offers a private balcony with pond and sunset views, ample closets, and an en-suite bath with a double vanity and walk-in shower. The second bedroom with full guest bath provides additional accommodation, while the loft offers a possible media room, home office, den, playroom, or additional sleeping space. This floor also has a linen closet plus washer and dryer for convenience, all with new carpeting. New water heater 2024. New faucet 2026. New paint and carpeting. Residents of the Gardens enjoy a carefree lifestyle, with landscaping, snow removal, and trash pickup included in the common charges, allowing more time to enjoy the community’s amenities. The Clubhouse has a full kitchen with dining and deck space available for private events, as well as a large living room for Canasta, Bridge, book clubs, and Mah Jongg. The fitness center has both cardio and weight machines plus free weights, and the men’s and women’s locker rooms have showers. These amenities are complemented by the newly expanded swimming pool, as well as two tennis/pickleball courts, ponds, and walking trails. This unbeatable Rhinebeck location is just minutes from Historic Rhinebeck Village, close to restaurants, vibrant shopping, farmers’ market, theater, parks, cultural attractions, Bard’s renowned Fisher Center, schools, and the Amtrak Station. The best of Hudson Valley living!

2 Beds ⋅ 3 Baths ⋅ 1041074 MLS

Welcome to The Gardens at Rhinebeck II, an upscale community of beautifully maintained homes. This 2-bedroom, 2.5-bath, 1,495-square-foot condo is stylish and move-in ready, with 9-foot ceilings, central air, and a bright, airy main floor that feels instantly welcoming. The main floor features a thoughtfully designed floor plan that blends comfort and functionality. The kitchen features stainless steel GE appliances, granite countertops, an elegant backsplash, a center island with additional storage and room for barstools for entertaining, and a charming, windowed breakfast nook, perfect for your morning coffee. Just off the kitchen is a wallpapered powder room, coat closet, pantry, and direct access to an attached garage with additional storage room. The open living and dining area is filled with natural light and designed for both everyday living and entertaining. An electric fireplace adds a warm and beautiful focal point. The windows and sliding glass doors open to a private patio, perfect for dining, relaxing, and taking in the tranquil surroundings. Upstairs, the primary bedroom offers a private balcony with pond and sunset views, ample closets, and an en-suite bath with a double vanity and walk-in shower. The second bedroom with full guest bath provides additional accommodation, while the loft offers a possible media room, home office, den, playroom, or additional sleeping space. This floor also has a linen closet plus washer and dryer for convenience, all with new carpeting. New water heater 2024. New faucet 2026. New paint and carpeting. Residents of the Gardens enjoy a carefree lifestyle, with landscaping, snow removal, and trash pickup included in the common charges, allowing more time to enjoy the community’s amenities. The Clubhouse has a full kitchen with dining and deck space available for private events, as well as a large living room for Canasta, Bridge, book clubs, and Mah Jongg. The fitness center has both cardio and weight machines plus free weights, and the men’s and women’s locker rooms have showers. These amenities are complemented by the newly expanded swimming pool, as well as two tennis/pickleball courts, ponds, and walking trails. This unbeatable Rhinebeck location is just minutes from Historic Rhinebeck Village, close to restaurants, vibrant shopping, farmers’ market, theater, parks, cultural attractions, Bard’s renowned Fisher Center, schools, and the Amtrak Station. The best of Hudson Valley living!

415 Gardenia Drive, Rhinebeck

$449,000

Attention Contractors and Investors: INCREDIBLE MARKET FIX and SELL opportunity in the village of Rhinebeck. NEW LOWER PRICE. This house also offers great potential for Buyers looking to renovate and make it their own. Village ranch, nice layout and built to last. 3 good sized bedrooms, one full bath and new half bath, kitchen with newer appliances, breakfast area, dining room, and inviting living room with a fireplace (new pellet stove). Hard wood floors throughout. Large, dry, walk-out, unfinished basement with high ceilings and larger windows. 2 car garage. New water heater and expansion tank new oil tank, oil burner from 2007. House needs some work/renovation and upgrades. Get to supermarket, library, town recreation area, and Amtrak in less than 5 minutes. Sidewalks into the village and hospital. Easy access to Route 9 and Kingston/Rhinecliff Bridge. Endless possibilities here. This property is being sold "As Is".

3 Beds ⋅ 2 Baths ⋅ 1025066 MLS

Attention Contractors and Investors: INCREDIBLE MARKET FIX and SELL opportunity in the village of Rhinebeck. NEW LOWER PRICE. This house also offers great potential for Buyers looking to renovate and make it their own. Village ranch, nice layout and built to last. 3 good sized bedrooms, one full bath and new half bath, kitchen with newer appliances, breakfast area, dining room, and inviting living room with a fireplace (new pellet stove). Hard wood floors throughout. Large, dry, walk-out, unfinished basement with high ceilings and larger windows. 2 car garage. New water heater and expansion tank new oil tank, oil burner from 2007. House needs some work/renovation and upgrades. Get to supermarket, library, town recreation area, and Amtrak in less than 5 minutes. Sidewalks into the village and hospital. Easy access to Route 9 and Kingston/Rhinecliff Bridge. Endless possibilities here. This property is being sold "As Is".

110 Montgomery Street, Rhinebeck

$545,000

Fully Available! A bright, pondside 2-Bedroom Condo in The Woods at Rhinebeck. This 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 porch overlooking two ponds, 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 ⋅ 1042293 MLS

Fully Available! A bright, pondside 2-Bedroom Condo in The Woods at Rhinebeck. This 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 porch overlooking two ponds, 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.

50 Pond Drive E, Rhinebeck

$849,000

Set on 3.7 private acres at the end of a quiet dead-end road, 17 Molland Drive feels tucked away from the world. Surrounded by mature trees and established landscape, the property has a peaceful, private quality, with plenty of room to wander, garden, gather outdoors, or simply enjoy the quiet. Built in the 1970s, the spacious home has a relaxed, rambling character and unfolds across two generous levels. Oversized windows bring in abundant natural light and keep the surrounding landscape present throughout the house. The main floor moves easily between a bright sunroom, expansive living and dining spaces, an updated kitchen, and well-proportioned bedrooms. Distinct rooms give the house warmth and definition without sacrificing its sense of openness. The home has seen substantial improvements in recent years, including a new roof and skylights, updated heating and plumbing, refinished floors, refreshed walls, and a new kitchen. A rebuilt deck extends the living space into the trees, while a stone patio below offers another quiet place for outdoor dining and entertaining. In the living room, a new chimney is ready for the addition of a wood stove. The finished lower level adds another dimension to the house, with direct access to the patio, backyard, and surrounding landscape. Its flexible spaces lend themselves easily to a media room, studio, home office, gym, guest quarters, or a comfortable setup for extended family. An attached two-car garage is unusually bright, with multiple windows, new garage doors, a new floor, and a center drain. The driveway has also been redone recently with improved drainage and a fresh stone surface. Outside, considerable work has gone into restoring the land and opening it back up to its natural surroundings. The grounds have been cleared and thoughtfully landscaped, trees selectively removed, garden areas improved, and a garden shed added. Sections of old wood fencing lend a bit of country character, while a trail behind the property winds into the woods and offers another way to experience the land. Despite its sense of seclusion, the property is approximately seven miles from the heart of Rhinebeck Village and within the Rhinebeck Central School District. Restaurants, shops, farmers’ markets, and the cultural life of the Village are close at hand, yet coming home to Molland Drive feels distinctly removed from it all. Substantial yet unpretentious, 17 Molland Drive offers something increasingly hard to find: space, privacy, quiet, and nature, with the conveniences of Rhinebeck just a short drive away.

4 Beds ⋅ 3 Baths ⋅ 1042046 MLS

Set on 3.7 private acres at the end of a quiet dead-end road, 17 Molland Drive feels tucked away from the world. Surrounded by mature trees and established landscape, the property has a peaceful, private quality, with plenty of room to wander, garden, gather outdoors, or simply enjoy the quiet. Built in the 1970s, the spacious home has a relaxed, rambling character and unfolds across two generous levels. Oversized windows bring in abundant natural light and keep the surrounding landscape present throughout the house. The main floor moves easily between a bright sunroom, expansive living and dining spaces, an updated kitchen, and well-proportioned bedrooms. Distinct rooms give the house warmth and definition without sacrificing its sense of openness. The home has seen substantial improvements in recent years, including a new roof and skylights, updated heating and plumbing, refinished floors, refreshed walls, and a new kitchen. A rebuilt deck extends the living space into the trees, while a stone patio below offers another quiet place for outdoor dining and entertaining. In the living room, a new chimney is ready for the addition of a wood stove. The finished lower level adds another dimension to the house, with direct access to the patio, backyard, and surrounding landscape. Its flexible spaces lend themselves easily to a media room, studio, home office, gym, guest quarters, or a comfortable setup for extended family. An attached two-car garage is unusually bright, with multiple windows, new garage doors, a new floor, and a center drain. The driveway has also been redone recently with improved drainage and a fresh stone surface. Outside, considerable work has gone into restoring the land and opening it back up to its natural surroundings. The grounds have been cleared and thoughtfully landscaped, trees selectively removed, garden areas improved, and a garden shed added. Sections of old wood fencing lend a bit of country character, while a trail behind the property winds into the woods and offers another way to experience the land. Despite its sense of seclusion, the property is approximately seven miles from the heart of Rhinebeck Village and within the Rhinebeck Central School District. Restaurants, shops, farmers’ markets, and the cultural life of the Village are close at hand, yet coming home to Molland Drive feels distinctly removed from it all. Substantial yet unpretentious, 17 Molland Drive offers something increasingly hard to find: space, privacy, quiet, and nature, with the conveniences of Rhinebeck just a short drive away.

17 Molland Drive, Rhinebeck

$299,000

Over the Hudson River, and through the Ferncliff Forest Woods lies 532 River Road! Ideally situated in one of the Hudson Valley’s most desirable areas, this inviting property offers a wonderful opportunity to enjoy the beauty, character, and lifestyle that make Rhinebeck so special for an incredible value. With 3 bedrooms and 2 baths this sweet vintage home is spacious and all one level! Additional Two Car Garage for storage and more. Set on almost half an acre, the property is set back from the road and backs up to the Astor Forest 1000 acre woods. A short bike ride to the Village, or walk to Miglorelli Farm Stand every night for Hudson Valley Provisions. Convenient location puts you close to Rhinebeck Village, restaurants, shops, farms, Kingston Rhinecliff Bridge and the Hudson River. A wonderful opportunity to invest in the Rhinebeck market with a beautiful piece of land in an incredible location.

3 Beds ⋅ 2 Baths ⋅ 1038233 MLS

Over the Hudson River, and through the Ferncliff Forest Woods lies 532 River Road! Ideally situated in one of the Hudson Valley’s most desirable areas, this inviting property offers a wonderful opportunity to enjoy the beauty, character, and lifestyle that make Rhinebeck so special for an incredible value. With 3 bedrooms and 2 baths this sweet vintage home is spacious and all one level! Additional Two Car Garage for storage and more. Set on almost half an acre, the property is set back from the road and backs up to the Astor Forest 1000 acre woods. A short bike ride to the Village, or walk to Miglorelli Farm Stand every night for Hudson Valley Provisions. Convenient location puts you close to Rhinebeck Village, restaurants, shops, farms, Kingston Rhinecliff Bridge and the Hudson River. A wonderful opportunity to invest in the Rhinebeck market with a beautiful piece of land in an incredible location.

532 River Road, Rhinebeck

$799,000

Tucked into a peaceful hillside setting on four private acres, 133 White Schoolhouse Lane offers a quiet Rhinebeck retreat surrounded by the natural beauty of the Hudson Valley. Thoughtfully designed for privacy and comfort, the home balances open, connected living spaces with more traditional rooms that create warmth, separation, and flexibility. The layout feels both inviting and practical, with generous natural light, beautiful hardwood floors, and an easy flow between living and gathering spaces. A three-season sunroom creates a seamless connection to the outdoors and offers the perfect place to relax and take in the surrounding landscape from spring through fall. The attached two-car garage adds everyday convenience and ample storage, while the expansive acreage provides plenty of room to garden, entertain, explore, or simply enjoy the tranquility of nature. Recent upgrades include central air conditioning and a whole-house generator, bringing modern comfort and added peace of mind throughout the seasons. Private yet accessible, 133 White Schoolhouse Lane offers the best of Hudson Valley living—a comfortable, flexible home surrounded by nature, just a short drive from the shops, restaurants, and charm of Rhinebeck. Just 90 minutes from the George Washington Bridge, 133 White Schoolhouse Lane offers an easy escape to the heart of the Hudson Valley. The property is only minutes from the Village of Rhinebeck, where favorite spots like Pretty to Think So, The Little Goat, Le Petit Bistro, and RhineCellar are joined by independent shops, farmers markets, and year-round cultural offerings. For added convenience, the nearby Rhinecliff Amtrak station provides direct service to Manhattan, making the home equally well suited for weekend retreats or full-time Hudson Valley living.

4 Beds ⋅ 2 Baths ⋅ 1037254 MLS

Tucked into a peaceful hillside setting on four private acres, 133 White Schoolhouse Lane offers a quiet Rhinebeck retreat surrounded by the natural beauty of the Hudson Valley. Thoughtfully designed for privacy and comfort, the home balances open, connected living spaces with more traditional rooms that create warmth, separation, and flexibility. The layout feels both inviting and practical, with generous natural light, beautiful hardwood floors, and an easy flow between living and gathering spaces. A three-season sunroom creates a seamless connection to the outdoors and offers the perfect place to relax and take in the surrounding landscape from spring through fall. The attached two-car garage adds everyday convenience and ample storage, while the expansive acreage provides plenty of room to garden, entertain, explore, or simply enjoy the tranquility of nature. Recent upgrades include central air conditioning and a whole-house generator, bringing modern comfort and added peace of mind throughout the seasons. Private yet accessible, 133 White Schoolhouse Lane offers the best of Hudson Valley living—a comfortable, flexible home surrounded by nature, just a short drive from the shops, restaurants, and charm of Rhinebeck. Just 90 minutes from the George Washington Bridge, 133 White Schoolhouse Lane offers an easy escape to the heart of the Hudson Valley. The property is only minutes from the Village of Rhinebeck, where favorite spots like Pretty to Think So, The Little Goat, Le Petit Bistro, and RhineCellar are joined by independent shops, farmers markets, and year-round cultural offerings. For added convenience, the nearby Rhinecliff Amtrak station provides direct service to Manhattan, making the home equally well suited for weekend retreats or full-time Hudson Valley living.

133 White Schoolhouse Road, Rhinebeck

$699,000

*Re-introdusing *this storybook Ranch style home . Tucked away on a quiet dead end road in Clinton and offering an incredible blend of privacy , beauty and flexible living in an unbeatable location . This sundrenched home boast 2557 sq sf with 3 bedrooms, 3 full baths on 2.47 acres of parklike property , mature trees and nature all around as well as exclusive rights to private Long Pond -famed for its pristine waters. A sunlight eat-in kitchen that flows effortlessly to the dining area and opens directly onto the expansive back deck- ideal for summer gatherings or quiet mornings overlooking the beautiful back yard escape. The primary suite offers plently of light with an ensuite bath. Two additional bedrooms and full bath offer versatile space for guest/family. The finished lower level significantly expands your living options with a large rec room / other , full bath , dedicated office /den and laundry room. This level has dual egress points and direct access to a 2 car garage. Outside three large sheds( two equipped w electricity) offer endless potential as creative spaces. Located in the sought after Rhinebeck school district, just 10 min to the Taconic State Parkway and under 20 min to the shops, dining and culture of both Rhinebeck and Millbrook.

3 Beds ⋅ 3 Baths ⋅ 987969 MLS

*Re-introdusing *this storybook Ranch style home . Tucked away on a quiet dead end road in Clinton and offering an incredible blend of privacy , beauty and flexible living in an unbeatable location . This sundrenched home boast 2557 sq sf with 3 bedrooms, 3 full baths on 2.47 acres of parklike property , mature trees and nature all around as well as exclusive rights to private Long Pond -famed for its pristine waters. A sunlight eat-in kitchen that flows effortlessly to the dining area and opens directly onto the expansive back deck- ideal for summer gatherings or quiet mornings overlooking the beautiful back yard escape. The primary suite offers plently of light with an ensuite bath. Two additional bedrooms and full bath offer versatile space for guest/family. The finished lower level significantly expands your living options with a large rec room / other , full bath , dedicated office /den and laundry room. This level has dual egress points and direct access to a 2 car garage. Outside three large sheds( two equipped w electricity) offer endless potential as creative spaces. Located in the sought after Rhinebeck school district, just 10 min to the Taconic State Parkway and under 20 min to the shops, dining and culture of both Rhinebeck and Millbrook.

60 Camp Drive, Rhinebeck

$699,000

Tucked away on a quiet cul-de-sac in the heart of charming Rhinebeck Village, this newly renovated modern ranch offers the perfect blend of style, comfort, and convenience. Privately set on an easy-to-maintain .32-acre lot, this move-in ready home features 3 bedrooms and 3 full bathrooms with beautifully updated finishes throughout. Step inside to discover new hardwood floors flowing throughout the main level, creating a warm and contemporary feel. The bright, spacious eat-in kitchen is designed for both everyday living and entertaining, featuring new stainless-steel appliances, granite countertops, and sliding glass doors leading to the deck for effortless indoor-outdoor living. All bathrooms have been thoughtfully renovated with elegant new tile finishes. The desirable main-level primary suite offers a walk-in closet and private sliding doors opening to its own secluded deck, creating a peaceful retreat. The finished lower level expands the living space with endless possibilities for a recreation room, home office, guest quarters, or media room, and includes a full bathroom for added flexibility. Enjoy the rare combination of a quiet setting and exceptional convenience, just moments from Rhinebeck Village shops, restaurants, parks, and amenities. A paved driveway, attached garage, and carport complete this beautifully updated home in one of the Hudson Valley’s most sought-after locations.

3 Beds ⋅ 3 Baths ⋅ 1033820 MLS

Tucked away on a quiet cul-de-sac in the heart of charming Rhinebeck Village, this newly renovated modern ranch offers the perfect blend of style, comfort, and convenience. Privately set on an easy-to-maintain .32-acre lot, this move-in ready home features 3 bedrooms and 3 full bathrooms with beautifully updated finishes throughout. Step inside to discover new hardwood floors flowing throughout the main level, creating a warm and contemporary feel. The bright, spacious eat-in kitchen is designed for both everyday living and entertaining, featuring new stainless-steel appliances, granite countertops, and sliding glass doors leading to the deck for effortless indoor-outdoor living. All bathrooms have been thoughtfully renovated with elegant new tile finishes. The desirable main-level primary suite offers a walk-in closet and private sliding doors opening to its own secluded deck, creating a peaceful retreat. The finished lower level expands the living space with endless possibilities for a recreation room, home office, guest quarters, or media room, and includes a full bathroom for added flexibility. Enjoy the rare combination of a quiet setting and exceptional convenience, just moments from Rhinebeck Village shops, restaurants, parks, and amenities. A paved driveway, attached garage, and carport complete this beautifully updated home in one of the Hudson Valley’s most sought-after locations.

16 Trinity Place, Rhinebeck

$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

$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

$1,350,000

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

$1,375,000

Properties of this caliber are seldom available in the Village of Rhinebeck. Ideally situated on one of its most desirable streets, this tastefully renovated Cape-style home blends timeless character with modern comfort and exceptional craftsmanship. From the moment you enter, a sense of calm and comfort welcomes you. Elegantly designed living spaces, high-end finishes, and an effortless indoor-outdoor flow create an inviting retreat just a short stroll from the village’s acclaimed restaurants, boutiques, farmers market, schools, and cultural attractions. An open floor plan offers defined yet connected living spaces, including a cozy sitting area beside the wood-burning fireplace, a spacious dining area, and a modern kitchen featuring premium Thermador appliances, with induction cooktop, quartz counters, and abundant cabinetry. A seating area at the end of the counter invites guests to gather while meals are prepared. The rear lounging area overlooks the bluestone patio and perennial gardens—an ideal place to enjoy your morning coffee with the French doors open to the sound of birds. Upstairs, the spa-inspired bath features a soaking tub with picturesque views, a steam shower, and double vanities. Two additional finished rooms provide exceptional flexibility; one currently used as a bedroom and the other as a home office. Additional amenities include central air conditioning, a Miele washer and dryer, a second full bath, central vacuum, radiant floor heat, on-demand hot water, sound system and an attached garage with workshop and additional storage. Included in the sale is a delightful adjacent one level cottage on its own separately deeded parcel. Rich natural wood finishes and abundant natural light create a bright, welcoming atmosphere while showcasing the home’s original craftsmanship. A generously sized living room opens to the enclosed front porch, creating an inviting space to relax. An updated bath, kitchenette, two bedrooms, and private outdoor spaces make it ideal for visiting guests, a home office, artist’s studio, wellness retreat, multigenerational living, or an income-producing rental. Together, the two separately deeded homes provide exceptional flexibility, offering a rare combination of privacy, convenience, and versatility. Enjoy a movie at Upstate Films, dinner at Little Goat, or a relaxing afternoon at Mirbeau Spa—all just a short stroll away. Whether you’re looking for a weekend retreat, full-time residence, multigenerational living, rental income, or an investment, this remarkable property offers many options. Opportunities like this are seldom available in the Village of Rhinebeck.

3 Beds ⋅ 3 Baths ⋅ 1018441 MLS

Properties of this caliber are seldom available in the Village of Rhinebeck. Ideally situated on one of its most desirable streets, this tastefully renovated Cape-style home blends timeless character with modern comfort and exceptional craftsmanship. From the moment you enter, a sense of calm and comfort welcomes you. Elegantly designed living spaces, high-end finishes, and an effortless indoor-outdoor flow create an inviting retreat just a short stroll from the village’s acclaimed restaurants, boutiques, farmers market, schools, and cultural attractions. An open floor plan offers defined yet connected living spaces, including a cozy sitting area beside the wood-burning fireplace, a spacious dining area, and a modern kitchen featuring premium Thermador appliances, with induction cooktop, quartz counters, and abundant cabinetry. A seating area at the end of the counter invites guests to gather while meals are prepared. The rear lounging area overlooks the bluestone patio and perennial gardens—an ideal place to enjoy your morning coffee with the French doors open to the sound of birds. Upstairs, the spa-inspired bath features a soaking tub with picturesque views, a steam shower, and double vanities. Two additional finished rooms provide exceptional flexibility; one currently used as a bedroom and the other as a home office. Additional amenities include central air conditioning, a Miele washer and dryer, a second full bath, central vacuum, radiant floor heat, on-demand hot water, sound system and an attached garage with workshop and additional storage. Included in the sale is a delightful adjacent one level cottage on its own separately deeded parcel. Rich natural wood finishes and abundant natural light create a bright, welcoming atmosphere while showcasing the home’s original craftsmanship. A generously sized living room opens to the enclosed front porch, creating an inviting space to relax. An updated bath, kitchenette, two bedrooms, and private outdoor spaces make it ideal for visiting guests, a home office, artist’s studio, wellness retreat, multigenerational living, or an income-producing rental. Together, the two separately deeded homes provide exceptional flexibility, offering a rare combination of privacy, convenience, and versatility. Enjoy a movie at Upstate Films, dinner at Little Goat, or a relaxing afternoon at Mirbeau Spa—all just a short stroll away. Whether you’re looking for a weekend retreat, full-time residence, multigenerational living, rental income, or an investment, this remarkable property offers many options. Opportunities like this are seldom available in the Village of Rhinebeck.

43 & 45 South 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. HOME FEATURES: • Approx. 4,600-square-foot main residence • Five bedrooms • Multiple gathering and entertaining spaces • Apartment within the main house • Two kitchens • Beamed and cathedral ceilings • Fireplaces • Separate 1,500-square-foot carriage house • Two-bedroom, two-bath carriage house • Additional apartment above the barn • Country views from many rooms • Flexible layout for private residential • Minutes to Rhinebeck Village and Rhinecliff Amtrak LOT FEATURES: • Nearly 40 acres in Rhinebeck, New York • Original stone walls throughout the property • Seven fenced pastures and one paddock • Two ponds • Over two miles of walking and riding trails • Keep Safe fencing throughout • Grass riding ring • Riding arena with TravelRight footing • Mature trees and open meadows • Minutes to Rhinebeck Village and Rhinecliff Amtrak HORSE FACILITY FEATURES: • Up to 12 stalls • Southern pine stalls with rubber stall mats • Stalls configured as 12x12 or 12x24 • Dutch doors from each stall leading outdoors • Wash racks • Tractor barn with four bays • Grass riding ring • Riding arena with TravelRight footing • Seven pastures and one paddock • Keep Safe fencing throughout • Apartment above the barn for staff, guests, or caretakers

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. HOME FEATURES: • Approx. 4,600-square-foot main residence • Five bedrooms • Multiple gathering and entertaining spaces • Apartment within the main house • Two kitchens • Beamed and cathedral ceilings • Fireplaces • Separate 1,500-square-foot carriage house • Two-bedroom, two-bath carriage house • Additional apartment above the barn • Country views from many rooms • Flexible layout for private residential • Minutes to Rhinebeck Village and Rhinecliff Amtrak LOT FEATURES: • Nearly 40 acres in Rhinebeck, New York • Original stone walls throughout the property • Seven fenced pastures and one paddock • Two ponds • Over two miles of walking and riding trails • Keep Safe fencing throughout • Grass riding ring • Riding arena with TravelRight footing • Mature trees and open meadows • Minutes to Rhinebeck Village and Rhinecliff Amtrak HORSE FACILITY FEATURES: • Up to 12 stalls • Southern pine stalls with rubber stall mats • Stalls configured as 12x12 or 12x24 • Dutch doors from each stall leading outdoors • Wash racks • Tractor barn with four bays • Grass riding ring • Riding arena with TravelRight footing • Seven pastures and one paddock • Keep Safe fencing throughout • Apartment above the barn for staff, guests, or caretakers

52 Pells Road, Rhinebeck

$2,495,000

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