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$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
$3,250,000
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
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
$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
$4,250,000
7 Beds ⋅ 5 Baths ⋅ 1026060 MLS
The Canopy House Named for the towering canopy of mature trees that defines its landscape, The Canopy House is a home shaped as much by light as by architecture. Here, the forest is not simply the backdrop, it becomes part of daily life. Walls of glass frame the changing seasons while sunlight filters through the leaves, casting shifting patterns across stone, wood, and slate throughout the day. Set on 10.11 wooded acres just minutes from the heart of Rhinebeck Village, the property offers a rare balance of privacy and connection. Masterfully reidesigned in 2019 by the acclaimed design-build firm The Art of Building, the main residence is a remarkable expression of craftsmanship and thoughtful design. Mid-century modern architecture is complemented by an understated palette of warm woods, natural stone, dark architectural accents, and expansive glass, creating interiors that feel sophisticated, welcoming, and deeply connected to their surroundings. Throughout the home, there is a quiet appreciation for proportion, natural light, and finely crafted detail, reflecting a philosophy of design where beauty is found in simplicity and every space feels intentional. Designed for effortless single-level living, the home's flowing floor plan balances expansive gathering spaces with private sleeping quarters. The soaring great room is anchored by a dramatic double-sided floor-to-ceiling stone fireplace, while three interconnected living spaces, wrapped in walls of glass, create a seamless connection to the surrounding landscape. The chef's kitchen opens naturally to the adjacent living and dining areas, creating an ideal setting for both intimate evenings and effortless entertaining. The primary suite is a true sanctuary, complete with a soaking tub, walk in shower, and views of the surrounding landscape. Three additional bedrooms are thoughtfully positioned in the main house to provide privacy and exceptional livability. Privately positioned beyond the main residence, the 1,132-square-foot guest house functions as a home unto itself, offering two bedrooms, a full kitchen, generous living spaces, a wood-burning stove, an attached bonus room ideal as a studio, gym, or office, and its own outdoor living area. Outside, a 20-by-50 heated gunite pool is nestled among mature trees and layered plantings, creating a private setting and remote setting. Historic stone walls weave throughout the landscape while generous lawns unfold beneath the canopy, reinforcing a setting that feels both timeless and distinctly Hudson Valley. Located just seven minutes from Rhinebeck Village, twelve minutes from Amtrak, and approximately ten minutes from the future Soho Farmhouse Hudson Valley.

3461 Route 9G, 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
$935,000
5 Beds ⋅ 4 Baths ⋅ 1025128 MLS
Experience refined Hudson Valley living in this stunning 5-bedroom, 3-bath Saltbox Colonial, extensively renovated since 2023. Soaring ceilings, a dramatic catwalk, and sleek contemporary finishes create a light-filled, sophisticated retreat. Designed with an open floor plan for effortless entertaining, the home features gleaming hardwood floors, a striking wood-burning fireplace, and beautifully updated living spaces throughout. At the heart of the home is a designer kitchen featuring waterfall granite countertops, state-of-the-art appliances, and seamless flow into the living and dining areas. The spacious primary suite offers a peaceful retreat, while a second bedroom features its own en-suite bath with a glass-enclosed shower, making it ideal for guests or multigenerational living. Three additional bedrooms are generously sized and filled with natural light, creating comfortable and inviting spaces for family, guests, or a home office. Every detail has been thoughtfully considered since the home's 2023 renovation. Recent improvements include a fully renovated kitchen, four beautifully renovated bathrooms, refinished hardwood floors, a new porch sliding door, new washer and dryer, an updated fireplace mantel, professionally cleaned and sanitized ductwork, extensive pool upgrades, and comprehensive well and water system improvements completed by AquaCare. Step outside to your private backyard oasis featuring a refreshing 18 x 36 in-ground pool with new liner, filter and bluestone coping, professionally maintained & perfect for summer entertaining or relaxing afternoons at home. Enjoy dining al fresco on the rear deck, unwind with your favorite book, or take advantage of the expansive yard with plenty of room for gardening, recreation, and enjoying the natural surroundings. The unfinished basement offers excellent potential for future finished living space or abundant storage, while the oversized two-car garage provides ample room for vehicles, tools, and outdoor equipment. Located in the sought-after Vanderburgh Cove community, you're just 2 minutes from the Hudson River, 4 minutes to the Village of Rhinebeck, only 8 minutes to the Rhinecliff Amtrak station, and just minutes from the future SoHo House Hudson Valley. Enjoy easy access to acclaimed restaurants, boutiques, art galleries, farmers' markets, scenic hiking trails, the Culinary Institute of America, the historic Hyde Park estates, and Bard College. Blending modern elegance with timeless Hudson Valley charm, this exceptional home offers sophisticated finishes, thoughtfully designed living spaces, and effortless indoor-outdoor living in one of the Hudson Valley's most desirable communities.

4 Cove Road, Rhinebeck
$1,450,000
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
$849,000
3 Beds ⋅ 3 Baths ⋅ 1019924 MLS
Set perfectly on a peaceful country road just minutes from the heart of Rhinebeck, this recently renovated home offers the perfect balance of modern comfort and year-round retreat. Inside, thoughtful updates create a warm and welcoming atmosphere centered around the wood-burning fireplace - the heart of the home and the perfect place to gather on crisp Hudson Valley evenings. The interiors blend contemporary finishes with timeless character, creating spaces that feel both stylish and effortlessly livable. Designed for entertaining and relaxation, the home truly shines outdoors. A generous screened-in porch extends the living space into the surrounding landscape, offering the ideal setting for morning coffee, summer dinners, or quiet afternoons with a book. Two separate fire pit areas invite evenings under the stars, while the hot tub provides the perfect place to unwind after a day exploring everything the Hudson Valley has to offer. The fully finished lower level adds valuable living space, ideal for a media room, rec room, guest accommodations, or creative studio. The climate-controlled garage offers even more versatility, making an excellent office, workshop, fitness space, or additional recreation area. Just 90 minutes from the George Washington Bridge, this home offers an effortless escape to the heart of the Hudson Valley. Located just minutes from the Village of Rhinebeck, you'll enjoy easy access to beloved local favorites including Pretty to Think So, The Amsterdam, Le Petit Bistro, and The Shelter Wine Bar, along with charming boutiques, farmers markets, and year-round cultural attractions. The nearby Rhinecliff Amtrak station also offers a convenient direct connection to Manhattan, making weekend getaways and full-time living equally appealing.

438 White Schoolhouse Road, Rhinebeck
$1,375,000
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
$1,500,000
4 Beds ⋅ 2 Baths ⋅ 1015551 MLS
A significant property, the Southern gateway to the town of Red Hook along the Route 9 corridor and owned by one family for over four decades. This offering consists of 60 acres on three parcels sold together: in Town of Red Hook, 37 acres of prime open farmland, a 10-acre homestead parcel with a circa-1860 Victorian farmhouse, multiple barns, and a garage, and in the town of Rhinebeck, an additional 12.6 acres of agricultural land to the rear. The main barn dates to the 1700’s. The farm has a long working history — vegetables, hay, livestock, flowers — and the landscape shows it. Wide open fields, a treeline border, and the kind of unobstructed sky that’s getting harder to find this close to the village. The timber-frame barn is substantial, with original trusses and stall configurations intact. A former milking parlor, outbuildings, and a farm stand structure round out the complex. The farmhouse retains its period character — a proper Victorian Italianate with corbeled eaves, multiple porches, original wide-plank floors, a turned staircase, and a Federal-style mantel with sunburst detail. It needs significant work and is priced accordingly. The land is the draw. No conservation easement encumbers the property. The 50 acres of land have 100+ ft of road access, but requires roadway. Subdivision potential exists. The land includes a quaint sugar shack and a small pond. Additional acreage on Route 9 is available. Approximately 1.5 miles from the center of Red Hook Village, 3.5 miles from the center of Rhinebeck Village and less than 2 hours from NYC.

7115 Albany Post Road, Rhinebeck
$399,000
3 Beds ⋅ 2 Baths ⋅ 1012369 MLS
Three-bedroom, 1.5-bath ranch situated on nearly one acre in Rhinebeck. The property offers a spacious side yard and a convenient location close to village amenities, shopping, dining, and commuter routes. The home is ready for updating and presents an opportunity for buyers looking to make improvements and add their own style. The walkout lower level includes an attached garage and a separate room with a bathroom and fireplace that could serve as a home office, hobby room, or additional living space. Whether you’re looking for a primary residence, investment opportunity, or a project in a desirable Rhinebeck location, this property offers plenty of potential on a generously sized lot.

3553 Route 9G, Rhinebeck
$685,000
4 Beds ⋅ 2 Baths ⋅ 1011291 MLS
On a quiet dead-end street close to Rhinebeck Village, this IMMACULATE 4 bedroom, 2 bath home with 2078 SF is move in ready for you. Taxes are low. There are oak floors, wonderful light, an open floor plan, a DR,LR, & a FR with a fireplace, plus there's a great kitchen w/quartz counters & an island. Outside is beautiful & private w/lawns front & back, stone walls, huge trees, & a WONDERFUL INGROUND POOL. Two porches, one glassed, one screened, bring the outside in & are perfect for fun & entertaining. Enjoy Rhinebeck's farmer's market, shopping, dining, & upstate films. Amtrak, BARD, & the TSP are all close by. What a great opportunity to find the perfect country home!

6 Kipsbergen Drive, Rhinebeck
$595,000
4 Beds ⋅ 2 Baths ⋅ 1005161 MLS
-A Rhinebeck Village Classic- Nestled beneath towering shade trees in the heart of Rhinebeck Village, this charming 1933 Craftsman-inspired cottage offers the increasingly rare combination of walkability, character, and opportunity. Original hardwood floors, period details, inviting covered porches, and a detached garage speak to the home's enduring charm, while four bedrooms and two baths provide generous space for modern living. Rich in authenticity and filled with potential, this beloved home invites its next steward to thoughtfully restore, reimagine, and make it their own. Just moments from Rhinebeck's vibrant Main Street—with its celebrated restaurants, boutiques, farmers market, and cultural attractions—this is a rare opportunity to own a piece of village history while creating the next chapter of its story. A true Rhinebeck Village classic, ready for its next chapter!!

79 S Parsonage Street, Rhinebeck
$495,000
2 Beds ⋅ 2 Baths ⋅ 1006368 MLS
Circa 1830, this sweet cottage blends historic character with an idyllic Sawkill Creekside setting just 7 minutes from both Red Hook and Rhinebeck. Original wide-board wood floors, exposed beams, and nearly 200 years of preserved detail bring warmth and authenticity to the 2-bedroom, 1.5-bath home. Set amid mature woodland and open grassy clearings, the property feels private and peaceful, with quiet neighbors and the soothing sound of water throughout. Primary and full bath on the 2nd floor. Additional space in the lower level with access to outdoors Behind the cottage, approximately 450 feet of the Saw Kill Creek—a Class A trout stream—winds through the woods, offering a place to cool off on summer days, cast a fishing line, or simply enjoy the view from the back deck above. A rocking-chair front porch welcomes you home, while practical updates include a newer septic tank, 200-amp electrical service, propane heat, owned water softener, and a roof installed in 2010. washer & dryer do not convey Accepted Offer

1231 Route 308, Rhinebeck
$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
$3,850,000
7 Beds ⋅ 7 Baths ⋅ 1003365 MLS
WhistleWood Farm A rare multi-use estate set on just under 40 acres in the heart of Rhinebeck, NY. Currently operating as a successful bed-and-breakfast, event venue, and horse boarding facility, WhistleWood Farm offers exceptional flexibility for both residential and commercial buyers seeking a true Hudson Valley destination property. Comprised of three parcels totaling nearly 40 acres, the property is equally suited as a private compound, gentleman’s farm, equestrian retreat, boutique hospitality venture, or wellness-focused escape. Existing hospitality and equestrian infrastructure provide a strong foundation for continued or expanded use. The main residence spans approximately 4,500 square feet and features 5 bedrooms, 5 full baths, and 2 kitchens—offering remarkable flexibility for private living, guest accommodations, or hospitality operations. Complementing the main house is an beautifully appointed 1,500-square-foot carriage house with three bedrooms and three baths, rich in character and perfectly suited for guests, extended stays, or expanded event and hospitality use. Walking trails through the woods create a rare sense of privacy and connection to the landscape just moments from the heart of Rhinebeck Village—with its celebrated dining, farm-to-table restaurants, boutiques, and nearby Amtrak access. For the tennis enthusiast, premier tennis facilities conveniently located next door further enhance the property’s lifestyle appeal. Open meadows, mature trees, and a coveted Village-adjacent setting make WhistleWood Farm a truly rare offering—equally compelling as a private estate, hospitality investment, or legacy property in the Hudson Valley. Additional features include solar power, further enhancing the property’s efficiency and long-term sustainability.

52 Pells Road, Rhinebeck
$349,000
2 Beds ⋅ 1 Baths ⋅ 1002328 MLS
Charming Rhinebeck Cottage with Lake Rights & Modern Updates ?Tucked away on a peaceful, wooded hillside at 6 Woods Road, this updated 2-bedroom plus a BONUS room cottage perfectly balances tranquil country living with everyday convenience. Located just 8 minutes from downtown Rhinebeck world-class dining and shops, and a quick 11-minute drive from the Taconic State Parkway, it is an ideal weekend retreat or full-time residence. Step inside to find a beautifully refreshed interior boasting extensive modern updates. The master bedroom serves as a private sanctuary, complete with its own private deck—the absolute perfect spot to enjoy your morning coffee surrounded by nature. Outside, you'll find plenty of parking for guests and deeded access to Round Pond one of the area's most peaceful, serene pond. Enjoy the best of the Hudson Valley right from your doorstep!

6 Woods Road, 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
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 997184 MLS
A charming farm house freshly painted and wide board floors refinished newer kitchen and a nice sun room . Park like grounds and home has a long set back from road .Mountain view is one of the most scenic roads in Clinton with many great properties and estates. Mostly local traffic and you are minutes from the Taconic Parkway and less than 10 minutes from downtown Rhinebeck . A wonderful property . The additional land can be easily cleared for animals and it is subdividable.

292 Mountain View Road, Rhinebeck
$2,750,000
3 Beds ⋅ 4 Baths ⋅ 987569 MLS
Milan Hall Farm circa 1750 Truly exceptional. Completely private. Set across 87 acres of open field and quiet forest, Milan Hall Farm unfolds as a rare Hudson Valley offering—where land, history, and thoughtful stewardship meet. A winding stream and natural waterfall trace the landscape, alongside a private 1.3-mile walking trail through the woods, all bordered by enduring stone walls that speak to the property's agricultural past. Protected under conservation easement with the Winnakee Land Trust and New York State forestry program, the land offers both privacy and permanence. The farmhouse, dating to the mid-18th century, has been carefully expanded to accommodate modern living while honoring its origins. Three bedrooms, each with en-suite baths, are complemented by a light-filled conservatory, a quiet library, and multiple gathering spaces anchored by wood-burning stoves. A broad porch overlooks the gardens, while bluestone patios extend living outdoors. The grounds are meticulously maintained, with layered gardens, mature plantings, and curated outdoor spaces throughout. A separate guest cottage, complete with a full kitchen, one bedroom, bath, sitting area, and wood-burning stove, provides a welcoming retreat for extended stays or visiting family and friends. Further enhancing the estate is a thoughtfully designated three-acre building envelope within the Conservation Easement, offering the rare opportunity to add complementary structures such as an accessory dwelling, swimming pool, pool house, studio, sheds, or other accessory buildings. Existing improvements also present opportunities for thoughtful expansion and adaptation, whether by enhancing the guest cottage, exploring the potential for additional space above the existing two-car garage (subject to approvals), reimagining the historic barn, or creating additional living, work, or wellness spaces. Together, these possibilities allow the estate to evolve over time while preserving its extraordinary privacy and the integrity of the surrounding landscape. The beautifully preserved 1853 post-and-beam barn, equipped with electric and water, presents endless possibilities as a studio, workshop, or future living space. Additional outbuildings, including a two-car garage, support both function and form. Modern amenities—including solar power, central air, and a whole-house generator—blend seamlessly with the home's historic character, bringing comfort and efficiency to everyday living. Just minutes from Rhinebeck Village, Amtrak, and some of the Hudson Valley's most celebrated restaurants, boutiques, and cultural destinations, Milan Hall Farm feels worlds away while remaining remarkably convenient.

457 Round Lake Road, Rhinebeck
$459,000
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
$499,999
3 Beds ⋅ 2 Baths ⋅ 979526 MLS
Solid, Well-Loved Home with Pool, Pond & Fantastic Yard. This very solid, well-maintained home offers the kind of space and setting that’s getting harder to find. The property features an inground pool with a charming cabana, perfect for summer days, and a great big yard that stretches out to a peaceful pond, creating a private, natural backdrop for everyday living. Inside, the home is comfortable and functional, with a kitchen updated with stainless steel appliances. Some areas could use a bit of TLC, giving the next owner the opportunity to add their own style and value. A full basement provides excellent storage or potential for additional living space. Being sold as-is.

2518 Route 9G, 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

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.