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$1,295,000
4 Beds ⋅ 4 Baths ⋅ 1033036 MLS
Thoughtfully custom built and beautifully maintained, this exceptional 4-bedroom, 3.5-bath contemporary, is privately nestled on 1.2 professionally landscaped acres just minutes from the heart of Rhinebeck Village. Offering the perfect balance of elegant design, comfortable living, and resort-style outdoor spaces, this is a home where everyday life feels like a retreat. The welcoming main level is designed for effortless living and entertaining. A stunning kitchen features top-of-the-line appliances, granite countertops, a bar sink, and opens seamlessly to a warm gathering room, creating the perfect place for family and friends to come together. The living room, anchored by a fireplace, flows into the dining room where a dramatic wall of windows fills the home with natural light while framing beautiful views of the property. A powder room, mudroom, and a spacious first-floor primary suite with a private bath complete the main level. Upstairs offers two generously sized bedrooms and a full bath, along with a cozy reading nook tucked into a quiet corner—an inviting space perfect for relaxing with a book. The finished lower level expands the home’s versatility with a fourth bedroom, full bath, recreation area, office, gym, laundry room, and bonus room—ideal for guests, working from home, hobbies, or multigenerational living. Outside is where this property truly shines. The beautifully landscaped grounds provide exceptional privacy, surrounded by mature trees and neighboring homes set comfortably apart. The bluestone patio, sparkling salt water pool, pool house, and outdoor shower create the ultimate backyard oasis. Whether hosting summer gatherings, enjoying quiet mornings by the pool, or watching children and pets play on the expansive lawn, this outdoor setting was designed to be enjoyed throughout the seasons. Equally appealing is the location. Just about a mile from charming Rhinebeck Village, you’ll enjoy easy access to boutique shopping, renowned restaurants, cafés, and year-round community events. Starr Park, the elementary school, and the Amtrak station are all conveniently nearby, making daily life and commuting remarkably easy. Lovingly cared for and thoughtfully enhanced over the years, this home has been the backdrop for countless family celebrations, neighborhood gatherings, and treasured memories. It offers not only beautiful living spaces but also the warmth of an established neighborhood where, neighbors become friends, and the sense of community is truly special. This is a rare opportunity to own an exceptional home in one of the Hudson Valley’s most sought-after locations.

6 Stanford Court, Rhinebeck
$1,150,000
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
$735,000
3 Beds ⋅ 2 Baths ⋅ 1032450 MLS
Resting on 8.6 private acres just minutes from the heart of Rhinebeck Village, this exceptional three-bedroom, two-bath residence has been thoughtfully rebuilt from the ground up, offering the rare combination of timeless Hudson Valley charm and the confidence of virtually new construction. The comprehensive renovation touched nearly every aspect of the home. A new asphalt shingle roof, new siding, energy-efficient windows, spray foam insulation, new rafters, new doors, upgraded 200-amp electrical service, all-new plumbing, a new well pump, new 1,000-gallon septic system with leach field, new hot water heater, Mitsubishi two-zone heating and cooling system, and dehumidifier ensure years of low-maintenance ownership. Inside, engineered white oak floors flow throughout the home. The beautifully designed kitchen features quartzite and granite countertops, all-new appliances, and custom finishes, while both bathrooms have been completely reimagined with radiant heated floors. The exterior has been equally transformed with new siding, rebuilt stonewalls, bluestone walkway & patio, professionally engineered retaining walls with drainage systems, and thoughtfully designed outdoor living spaces overlooking the surrounding woodlands, creating a seamless connection between the home and its natural setting. Minutes to Rhinebeck Village, Rhinecliff Amtrak, acclaimed restaurants, farmers markets, and boutique shopping, this is a rare turnkey opportunity where every major improvement has already been completed—simply move in and enjoy the very best of Hudson Valley!

621 Milan Hollow Road, Rhinebeck
$899,900
2 Beds ⋅ 2 Baths ⋅ 1032111 MLS
Cricket's Corner is tucked away on almost four beautifully landscaped acres. This sun-filled inviting two-bedroom home offers privacy, tranquility, and a wonderful connection to nature. Set back from the road, the property features a peaceful pond that attracts local wildlife, a pool and mature trees and gardens lovingly cultivated over the years, and a serene setting ideal for relaxing or entertaining. Inside, the home is filled with fantastic natural light and hard wood floors throughout. The welcoming front entry opens into a bright living room where windows on every wall fill the space with natural light, while a handsome wood burning fireplace with a stone surround creates warmth and provides a beautiful gathering spot during every season. The dining room complete with its own fireplace flows effortlessly into the beautifully updated kitchen. Elegant stone counter tops are complemented by a striking tile backsplash, stainless steel appliances and a large center island topped with locally sourced black walnut wood, a beautiful focal point for gathering and entertaining guests alike. A door off the kitchen leads to deck creating a seamless connection between indoor and outdoor living in this peaceful setting. A den with a fireplace provides an ideal space for a home office, library or quiet retreat. There are two gracious bedrooms and two updated bathrooms. A spacious basement offers abundant storage and room for a workshop, gym or workspace. Outdoors, the property is equally enchanting. Enjoy the beautiful in-ground pool, and beautifully maintained grounds that reflect years of thoughtful care. A beautiful pond makes this a fantastic home for gardeners, bird lovers and anyone who appreciates the outdoors. Whether you're searching for a peaceful weekend escape or a full-time place to call home, this special property offers privacy and an exceptional connection to nature. Located in an area known for its scenic beauty and conveniently located just minutes from Rhinebeck, you’ll enjoy easy access to acclaimed restaurants, shopping, farmers’ markets, and all the Hudson Valley has to offer.

50 Field Road, Clinton Corners
$995,000
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
$705,000
5 Beds ⋅ 3 Baths ⋅ 1030245 MLS
A rare legal two-family just steps from the Rhinecliff Amtrak station and minutes to Rhinebeck village. Currently configured with a 2-bedroom apartment on the first floor and a 3-bedroom apartment above, this home offers immediate income potential or flexible multi-generational living. Or, envision converting the upstairs kitchen into a large ensuite primary bathroom with access to a private rear deck overlooking the backyard. Set on nearly an acre across two parcels, recent upgrades include a brand new roof (2026), new HVAC system (2026), hot water heater (2022), and sump pump (2022). A detached garage on the adjacent parcel has a new roof and offers conversion potential for studio, guest house, or workspace, subject to town approval. Space, flexibility, and village-level convenience in one of the Hudson Valley's most sought-after locations.

420 Rhinecliff Road, Rhinebeck
$705,000
5 Beds ⋅ 3 Baths ⋅ 1030248 MLS
A rare legal two-family just steps from the Rhinecliff Amtrak station and minutes to Rhinebeck village. Currently configured with a 2-bedroom apartment on the first floor and a 3-bedroom apartment above, this home offers immediate income potential, flexible multi-generational living, or the option to convert to a single-family residence. Envision transforming the upstairs kitchen into a large ensuite primary bathroom with access to a private rear deck overlooking the backyard. Set on nearly an acre across two parcels, recent upgrades include a brand new roof (2026), new HVAC system (2026), hot water heater (2022), and sump pump (2022). A detached garage on the adjacent parcel has a new roof and offers conversion potential for studio, guest house, or workspace, subject to town approval. Space, flexibility, and village-level convenience in one of the Hudson Valley's most sought-after locations.

420 Rhinecliff Road, Rhinebeck
$849,000
3 Beds ⋅ 2 Baths ⋅ 1030333 MLS
A Rare 1900 Stone Gem in the Heart of Rhinebeck Village Step back in time while enjoying the best of village living in this extraordinary 1,660-square-foot stone home, built in 1900 with a level of integrity and artistry rarely seen today. Steeped in Hudson Valley history, this one-of-a-kind residence offers a flawless blend of historic soul and enduring quality. Unmatched Historic Character & Details • Historic Stone Architecture: Built with thick, hand-laid stone masonry that offers timeless beauty, natural insulation, and lasting durability. Naturally cool in the summer and warm in the winter. • Pristine Interior Finish: Featuring pristine, original plaster walls framed by smooth, timeless arched doorways. Golden oak wood plank flooring throughout the home. Original hand-worked wood trim runs through each room. • Fully Restored Wavy Glass Windows: Original wavy glass windows—complete with fully operational rope-and-pulley balance systems—flood every room with warm, textured light. The towering, vaulted staircase features an original double-hung window that illuminates the walls. • Authentic Craftsmanship: From the structural joinery to the fine architectural accents, every detail reflects turn-of-the-century building traditions. • Classic Comfort and Modern Convenience: This classic, comfortable retreat is move-in ready, with a 2-car garage, newly installed plumbing throughout the home, and an upgraded 200 amp electric service panel, this home is as trouble-free as it is beautiful. The Rhinebeck Lifestyle Tucked away in the desirable village of Rhinebeck, this home offers classic Hudson Valley charm just moments from local dining, boutique shopping, and historic landmarks. Whether you are seeking a turnkey historic retreat or an enduring village classic, this home is truly a rare find.

46 N Parsonage Street, Rhinebeck
$595,000
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
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 1028649 MLS
Just five minutes from the heart of Rhinebeck Village and approximately 90 miles from NYC, this private 26+ acre equestrian estate embodies the ideal balance of rustic warmth and elevated modern living. Rebuilt from the studs up between 2017 and 2019 and thoughtfully expanded in 2025, this 3-bedroom, 2.5-bath, 3,723-square-foot Colonial is completely turnkey. You can walk right in and immediately begin enjoying peaceful, relaxed country living without changing a thing. The residence captures a welcoming, timeless aesthetic tailored for both cozy gatherings and effortless entertaining. At its center is a breathtaking 900-square-foot Great Room featuring dramatic 20-foot vaulted ceilings, exposed timber beams, twin Hunter ceiling fans, and a grand propane fireplace that anchors the space with warmth. A stylish half bathroom is conveniently located on the same floor as the Great Room. From the Great Room, the open layout flows naturally into the dining area, where French doors open directly onto an expansive rear deck for indoor-outdoor living, and into the chef's kitchen outfitted with warm custom cabinetry, rich cherry countertops, and updated appliances. Completing the main level are two generously sized bedrooms and a full bathroom featuring a double vanity and tub. Sun-drenched interiors throughout feature 96 Andersen divided light, double-pane windows framing idyllic natural views. Walk upstairs to the second floor for ultimate quiet and seclusion, the primary suite is a true private retreat featuring its own ensuite bathroom with a custom walk-in shower and double vanity. Connected to the primary bedroom is a designated office space, which flows directly into a private 220-square-foot artist studio with its own mini-split for heating and cooling - offering a serene, creative sanctuary away from the main living areas. The home's exterior radiates classic Hudson Valley charm, enhanced by bluestone walkways (2025), a grand covered front porch ideal for morning coffee, and lush professional landscaping adorned with blooming hydrangeas and seasonal flowers. Mechanicals are fully modernized for effortless living, including central air conditioning, three-zone hydronic propane heating, an updated concrete septic system (2019), and well (2015). Beyond the home, the tranquil 26-acre setting features one of Rhinebeck's original equestrian setups. The grounds include a historic 50x120 steel-framed indoor riding arena that was refurbished with limestone footing, observation room, lighting, and ventilation, alongside a fully equipped six-stall barn with a tack room, feed room, hayloft, power, and water, plus multiple paddocks and run-in sheds. This rare offering delivers warm country charm, high-end comfort, and complete privacy - all just moments from Rhinebeck's premier dining, shopping, and attractions. This is the epitome of Hudson Valley living.

11 Haggerty Hill Road, Rhinebeck
$779,000
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
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
$599,000
2 Beds ⋅ 2 Baths ⋅ 1026621 MLS
This sprawling expanded ranch, set back on a long drive and surrounded by beautifully landscaped grounds, is a rare offering that combines exceptional craftsmanship, thoughtful design, and an unbeatable Hudson Valley location. Quality contractor-owned and meticulously maintained, pride of ownership is evident throughout. The show-stopping living room features dramatic exposed truss-style beams, skylights that fill the space with natural light, and a wood stove set on a cozy brick hearth. A stunning oversized entry foyer showcases 10" wide yellow pine flooring and connects two distinct living areas, creating an ideal floor plan for extended family, multigenerational living, or a private guest, teen, or in-law suite. This 2BR home really lives like a 4BR plus. The oak kitchen is designed for everyday living and entertaining, offering stainless steel appliances, a breakfast bar, breakfast nook, and beautiful, durable terra cotta flooring that opens seamlessly to the great room. Outdoor living is just as impressive with a spectacular three-level multi-tiered deck, delightful bluestone patio with fire pit, and unilock paver accents, perfect for relaxing or entertaining while enjoying the peaceful surroundings. Additional highlights include deeded lake rights, an oversized heated three-car garage with expansive driveway parking, and an immaculate unfinished basement offering abundant storage and incredible potential for future expansion. Ideally located just minutes from the Omega Institute, the Village of Rhinebeck, the Taconic State Parkway, and all the shopping, dining, recreation, and cultural attractions the Hudson Valley has to offer. With sought-after Rhinebeck schools, low taxes, and an incredibly versatile floor plan, this meticulously maintained home offers the perfect blend of comfort, quality, and convenience. Whether you're entertaining a crowd, accommodating extended family, looking for room to grow, or searching for the ideal heated three-car garage for your vehicles, hobbies, or workshop, this exceptional home is designed to meet your needs today and for years to come.

70 Camp Drive, Rhinebeck
$725,000
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
$690,000
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
$1,375,000
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
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
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
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
$1,975,000
5 Beds ⋅ 3 Baths ⋅ 998837 MLS
Welcome to Knickerbocker Farm, an elegant circa 1790 farmhouse overlooking rolling meadows, a tranquil pond, and two antique barns, on over 12 acres, just three miles from the heart of Rhinebeck. Enter through the classic front hall with its graceful staircase and sense of history. The living, dining, and sitting rooms are graciously proportioned, each featuring 10-foot ceilings, decorative crown and base moldings, marble fireplaces, and beautifully preserved wide-board floors that flow throughout the home. Pocket doors connect the living room and sitting rooms, adding both charm and flexibility. Sunlight pours into the corner sunroom from the east and south, while the eat-in kitchen, anchored by a striking stone fireplace, offers a warm gathering space for casual dining. French doors open to a mahogany back deck, perfect for enjoying the sweeping pastoral views. A first-floor bedroom and full bath allow for guest accommodations or one-level living. Upstairs, four sunlit bedrooms include two spacious rooms, a cozy smaller bedroom, and one tucked away in its own wing, as well as two full baths. A full walk-up attic provides generous storage. The stately front porch spans the home’s facade, inviting quiet moments of relaxation and connection to the landscape. Knickerbocker Farm is both enchanting and timeless - elegantly designed yet comfortable to live in, with thoughtful details and sweet nooks throughout. A true Hudson Valley treasure.

565 Route 308, Rhinebeck
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 999816 MLS
Did someone say"I want a New House", Well its arrived... Don't miss the charming surprisingly expansive and yet still cozy cottage, As you open the front door you are greeted by an expansive open floor plan. Looking from the front door through the Great Room the lush greenbelt greets your eyes! In between the view line and the front door the magic happened. Completely renovated from the walls in, complete electrical upgrade, completely new HVAC to maximize Energy Efficiency, Re-sheetrocked walls and New Insulation, as well as Flooring, Cabinetry and Windows, just to identify the major points of upgrades. The floor plan has been reconfigured to enlarge the Great Room and completly open to encompass the kitchen and Dinning and Living areas as one delighful space. The kitchen's large Center Island and High-end Appliances complemented by Quartz Countertops. The Living Room anchors the views between a Stone Fireplace built from local stone and the wall of windows showcasing the spectacular pastural views.. The Primary Bedroom has been completly reconfigured to include a sumpuous Primary Bathroom, Spacious Closets and the designer included a Laundry area. Don't miss the sweet screened in porch off the Great Room, designed to give you restipe from the day! The second floor has 2 extremely large Bedrooms and another Gorgeous Bathroom, both Bedrooms have vaulted ceilings and private views of the pastures out to the remote treeline. We are NOT finished yet, the Lower Level is also remodeled into a Media Room, with a Wet Bar and Game room the Multi-Panel door/window completly folds into itself alowing your get togthers to flow without walls from the inside out! We are not done, the wonderful Home does have everything you need. Besides the 5 private acre lot there is a Barn. Two complete floors do what you want with the Barn, Entertain, Man-cave, store you priceless Car Collection, your possibilities are endless... You have to consider this Beautiful home on your next tour of Rhinebeck, minutes form the Village of Rhinebeck and the Taconic yet bathed in peace and quiet You just cannot go wrong here.....

334 Lake Drive, Rhinebeck
$695,000
3 Beds ⋅ 2 Baths ⋅ 998103 MLS
Rare opportunity in the historic hamlet of Rhinecliff. This well-kept home, originally built in 1859, offers timeless charm along with everyday comfort, the house was updated over the years and is featuring three bedrooms, two full baths, parking space for two cars, and a large storage/workshop shed. The fully fenced, level backyard provides a wonderful space for relaxing, gardening, entertaining, or having pets. Living in Rhinecliff offers a unique combination of historic character, riverfront beauty, small-community living, and direct access to New York City. The area is known for its preserved Victorian, Colonial, and 19th-century architecture, creating a timeless Hudson Valley atmosphere. Nearby Rhinebeck offers boutique shopping, farm-to-table restaurants, cafes, arts, and cultural events, while residents also enjoy river walks, hiking trails, and boating access. The Rhinecliff–Kingston Amtrak Station is just three houses away with convenient sidewalk access, making travel to New York City an easy approximately 90-minute train ride. The station is so close that your car can stay in your driveway. Rhinecliff and Rhinebeck continue to be highly sought-after markets, especially among buyers seeking weekend retreats, second homes, or full-time relocation from the city. Strong demand and enduring appeal make this a rare opportunity to enjoy the perfect balance of history, tranquility, elegance, and accessibility. Please note that the Range and Refrigerator are brand new!

15 Charles, Rhinecliff
$459,000
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
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
$544,900
1 Beds ⋅ 1 Baths ⋅ 978117 MLS
**TO BE BUILT** Custom Farmhouse Ranch – just minutes from the Village of Rhinebeck! Situated on a .72 acre corner lot, this home features a stunning rocking chair front porch, open concept kitchen and living room with vaulted ceilings and a gas fireplace, spacious one bedroom with a walk-in closet, full bath with custom tiled shower, plus a den. Excellent location just minutes to Rhinebeck Village, Kingston, shopping, dining, and more, with easy access to major commuter routes. Bring your vision and build your dream home in the heart of the Hudson Valley—whether you’re looking for a weekend retreat or full-time living, opportunity awaits!

Beckrick Drive, Rhinebeck
$1,695,000
4 Beds ⋅ 5 Baths ⋅ 969504 MLS
Set in a beautiful rural landscape on 20.677 acres with seasonal views of Silver Lake, this inviting property captures the essence of Hudson Valley living—peaceful, scenic, and just a short drive to the Village of Rhinebeck. Built in 2007, the thoughtfully designed home offers over 4,000 square feet of comfortable living space with 4 bedrooms and 4.5 baths, complemented by a detached 8 car garage with studio space above. A covered porch welcomes you into the home’s entry, opening to a spacious living room that serves as the heart of the house. Here, soaring 18-foot ceilings, a dramatic two-story slate-surround fireplace with woodstove insert, and two French doors leading to a large wraparound deck create an ideal setting for both everyday living and entertaining. The chef’s kitchen provides a large center island, high end appliances, and looks out into the dining/living room. The first-floor primary suite provides a private retreat with two walk-in closets and a spa-like bath featuring a large walk-in shower and Jacuzzi tub. The main level also includes a den, half bath, laundry room, and accesses the attached 2-car garage. Upstairs are two additional bedrooms, a full bath, and a generous 12’ x 23’ bonus room well suited for a home office, studio, or media space. The finished basement further expands the living area with a family room, wine room, sauna, and full bath. A standout feature of the property is the impressive 1,728 square foot detached two-bay garage with capacity for 8 cars plus a carport, constructed in 2021. Ideal for car enthusiasts, collectors, or those seeking flexible workspace, one bay features two lifts and an exceptional 14’8” ceiling height. The entire structure is equipped with heat and AC, has a rear covered porch, expansive loft/attic storage, and its own Generac generator. Additional highlights include a fenced dog run, shed, whole-house Generac generator and rights to Silver Lake—making this a rare offering that blends comfort, privacy, and ideal location.

203 Silver Lake Road, Rhinebeck
$2,385,000
4 Beds ⋅ 4 Baths ⋅ 955667 MLS
Arc House, conceived by Palette Architecture, is a refined exploration of balance - where modern form meets the quiet beauty of nature. Designed as a to-be-built retreat for the post-urban lifestyle, this home blends architectural precision with a warm, elemental materiality, offering a deeply restorative escape just moments from the Taconic Parkway and the cultural heart of the Hudson Valley. Set atop a gentle rise and enveloped by forest, the home’s distinctive upwardly curved roofline introduces a graceful sense of movement, lifting the structure toward the canopy while echoing the contours of the surrounding landscape. A natural cedar wood siding box sits atop a stone base to ground the architecture in the site, allowing the home to age beautifully and harmonize with its environment. From a distance, its profile feels both intentional and unobtrusive—modern, yet timeless. The 4-bedroom, 3.5-bath residence spans approximately 3,100 square feet and is carefully sited to ensure privacy and immersion in nature. Upon arrival, interiors unfold with quiet drama: expansive European windows frame rolling wooded ridgelines, flooding the home with natural light and dissolving boundaries between indoors and out. Social spaces appear to float above the terrain, creating an elevated vantage point from which to experience the seasons in constant motion. A dedicated work-from-home office offers a thoughtful separation between professional focus and domestic calm. Throughout the home, a restrained palette of natural materials, warm woods, marble, and hand-crafted tile cultivates a sense of clarity and ease. Outdoor living areas extend seamlessly from the interior, offering a series of curated environments - sun-drenched decks, shaded retreats, and intimate gathering spaces - each designed to foster connection with the land. An optional in-ground pool package further enhances the retreat experience, transforming the property into a private resort for summer living and entertaining. Additional options such as supplemental solar, a fire pit, and other bespoke enhancements allow owners to tailor the home to their lifestyle. Highlights include high-efficiency panelized construction, natural wood and stone cladding, triple-pane European windows and sliding doors, expansive decks with cable railings, wide-plank oak and stone/tile flooring, custom cabinetry, Miele appliances, a wood-burning fireplace, and integrated recessed lighting. Located near Rhinebeck, Red Hook, and Millbrook, "Arc House" represents a thoughtful convergence of design, nature, and modern comfort - an elevated yet grounding place to call home.

"Arc House" Bulls Head Road, Clinton Corners
$990,000
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
$2,645,000
4 Beds ⋅ 5 Baths ⋅ 811877 MLS
"Lift House," a soon-to-be-built residence, embodies modernism in its purest form, blending natural elements with contemporary design in perfect harmony. Set on 14 acres, the home appears to rise from the earth itself, its elevated floor plan enhancing its connection to the landscape. Warm Accoya wood siding spirals around the structure, supported by two muted burgundy brick volumes and framed by a grid of bronze columns. These natural hues seamlessly integrate with the land, while also standing apart, creating a dynamic dialogue between the home and its environment. A serene koi pond reflects both the site’s colors and the architecture’s striking forms. The entry experience is carefully choreographed: a meandering pathway through a garden courtyard leads to a dramatic hardwood pivot door, welcoming guests into the home. Inside, open spaces, clean lines, and a restrained material palette create an effortless flow. The great room, the heart of the home, features soaring ceilings and expansive glazing that flood the space with natural light. A stone-clad fireplace anchors the room, subtly dividing it from the kitchen and dining areas. The gourmet kitchen is a study in contemporary elegance, with walnut and lacquered cabinetry, top-of-the-line appliances, and a grand marble island. The dining area, framed by sweeping views of the grounds, offers an ideal setting for both intimate meals and large gatherings. The home includes four spacious bedrooms and four and a half bathrooms, including a primary suite with a spa-like bath, custom walk-in closet, and a private terrace bathed in southern light. On the mezzanine level, with southern exposure and sweeping views, the home office provides a quiet, private workspace. The lower lounge area opens to both covered and open patios designed for cooking, dining, and relaxation. An in-ground pool can be added to complete the space, and the lounge can be converted into an attached pool house with a wet bar and full bath. Sustainability is seamlessly integrated into the design, with triple-pane windows, extensive insulation, and energy-efficient systems throughout. The home incorporates passive solar strategies and eco-conscious materials, ensuring that luxury and nature coexist in perfect balance.

"Lift House" Bulls Head Road, Clinton Corners
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