Rhinebeck Real Estate

Rhinebeck Real Estate

Rhinebeck: A Charming Town in Dutchess County, New York

Nestled in the heart of Dutchess County, New York, the picturesque town of Rhinebeck offers a perfect blend of small-town charm and modern amenities. With its rich history, stunning landscapes, and vibrant community, Rhinebeck is a sought-after destination for those seeking a tranquil and idyllic lifestyle.

One of the town's most notable features is its historic architecture. Rhinebeck boasts a collection of beautifully preserved buildings, including elegant Victorian homes, quaint cottages, and stately mansions. Walking through the tree-lined streets, you'll feel like you've stepped back in time, immersing yourself in the town's rich heritage.

Nature enthusiasts will be delighted by the abundance of outdoor activities available in Rhinebeck. The town is surrounded by breathtaking natural beauty, with the Hudson River to the west and the rolling hills of the Hudson Valley to the east. From hiking and biking trails to scenic parks and gardens, there's no shortage of opportunities to explore the great outdoors.

Rhinebeck also offers a thriving arts and culture scene. The town is home to several art galleries, theaters, and music venues, showcasing the talents of local artists and performers. Throughout the year, Rhinebeck hosts various festivals and events, including the renowned Dutchess County Fair, which attracts visitors from near and far.

In addition to its cultural offerings, Rhinebeck provides excellent dining and shopping experiences. The town features an array of charming boutiques, antique shops, and specialty stores, where you can find unique treasures and one-of-a-kind gifts. From cozy cafes to upscale restaurants, Rhinebeck's culinary scene caters to all tastes, offering a diverse range of cuisines.

With its convenient location just two hours north of New York City, Rhinebeck is an ideal place to call home for those seeking a peaceful retreat while still having access to urban amenities. Whether you're looking to settle down or invest in real estate, Rhinebeck offers a warm and welcoming community with a rich tapestry of history, nature, and culture.

Newest Listings in 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
$245,000
1030926 MLS
A wonderful quiet lot on a local traffic road 10 minutes to Rhinebeck and 10 minutes to red hook also 10 minutes to taconic parkway at 199, Property will be delivered with a new BOHA . A lovely property in a great location I have a survey map .SIGN WILL BE ON BY END OF DAY

Pond 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
$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
$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
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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.