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$719,000
5 Beds 4 Baths 993548 MLS
WALK TO THE VILLAGE OF RHINEBECK! FABULOUS RHINEBECK INVESTMENT OPPORTUNITY! Rare three family rental property in the Village of Rhinebeck! Fully occupied by long term tenants. Washer and Dryer in every unit! Separate electric meters. This three-family home in the charming Village of Rhinebeck presents a fantastic investment opportunity. Located in a quiet, neighborhood with a park directly across the street, it’s an ideal location for tenants. The property is fully occupied, ensuring immediate rental income from day one. Rhinebeck is an area with a mix of small-town charm and proximity to larger metropolitan hubs, making it an attractive option for renters. With its well-maintained structure and peaceful surroundings, this property offers the potential for steady returns and long-term growth. Access to Landsman Kill for great fishing. Unit 1 is a 1 bedroom ground floor apartment with a bonus room. Unit 2 is a 2 bedroom second floor unit with updated kitchen. Unit 3 is a two floor, 2 bedroom unit with an updated kitchen.

12 S Parsonage Street, 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

$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

$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

$225,000
963229 MLS
Peaceful Double Lot in Sepasco Village with Shared Lake Access. Welcome to a rare opportunity in the tranquil eastern corner of Rhinebeck. This flat and usable .8-acre double lot in Sepasco Village offers a serene setting just moments from the sparkling waters of Lake Sepasco—a glacial, spring-fed lake known for its peaceful beauty, 30-foot depths, and motor-free quiet. Surrounded by trees and nestled within a lightly developed lakeside neighborhood, the lot offers the kind of stillness that invites you to slow down—perfect for reading under the trees, stargazing at night, or simply enjoying the sounds of nature. While the property doesn’t offer direct lake frontage, it comes with deeded access to a shared beach just a short stroll away, ideal for swimming, paddling, and fishing. The lot’s level terrain makes it easy to envision the possibilities—whether you dream of a cozy cabin, a seasonal retreat, or a future primary home (subject to town approvals). With a mix of seasonal and year-round residences nearby, there’s flexibility to shape the property to suit your vision. Located just minutes from Rhinebeck Village and Amtrak, this hidden gem offers the best of both worlds: a quiet, nature-rich escape with convenient access to dining, shops, and culture. Whether you're looking for a weekend sanctuary or a long-term investment, this peaceful double lot is full of potential.

Sepasco Center, Rhinebeck

$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

$1,390,000
3 Beds 3 Baths 922693 MLS
Set just east of the Rhinebeck Village, Wonderland Farm encompasses 65 acres of gently rolling countryside, a landscape defined by open fields, mature woodlands, and the meandering Landsman Kill stream. Recognized by the New York State Agricultural Society as a Century Farm, the property reflects more than a hundred years of continuous agricultural heritage and thoughtful stewardship. At its center stands a classic 1898 farmhouse, offering the enduring appeal of late 19th-century architecture. The home features original hardwood floors, period woodwork, and timeless details that speak to its history while providing a comfortable and welcoming living environment. The property also includes two barns, each with its own architectural and functional significance. The larger barn is a remarkable 1700s hand-hewn post-and-beam structure, an enduring example of early American craftsmanship. Both barns are equipped with electric service, and one includes a half bath, enhancing their usability for a variety of purposes. Their size, authenticity, and utility make them ideal for preservation, restoration, or adaptive reuse as studios, workshops, or event spaces. The Landsman Kill winds through the property, adding natural beauty and ecological diversity. The land presents a balanced mix of meadows, woodlands, and cultivated acreage, currently operating as a working Christmas tree farm. The setting is both pastoral and practical—well-suited to continued agricultural use, conservation, or a thoughtfully planned residential or mixed-use estate. Located within Rhinebeck’s Rural Countryside (RC) zoning district with 5-acre zoning, Wonderland Farm offers exceptional flexibility for future owners. Potential uses include continued agricultural production, residential development, adaptive reuse of existing structures, agritourism, conservation initiatives, and educational or recreational programming, all subject to local approvals. Wonderland Farm represents a rare opportunity to own a property of historic and agricultural significance in one of the Hudson Valley’s most sought-after locations. Its combination of history, natural beauty, and versatility ensures it will continue to be a meaningful and productive landscape for generations to come.

191 White Schoolhouse Rd, Rhinebeck

$9,750,000
8 Beds 6 Baths 915710 MLS
Stonecrest on the Hudson is a stunningly designed home on 16 inspiringly landscaped acres with extensive views of the river and the Catskills. A creation of stone, metal, and glass, the home, though imposing, inhabits its environment with seamless grace and is curated for comfort and meditative living. Many exquisite features make Stonecrest one-of-a-kind, impossible to duplicate. Upon approach, visitors notice the striking geometric roof lines and large portico. Inside, the home is open to light and nature through windows and soaring walls of glass. In the great room, forty-foot ceilings, a floor-to-ceiling stone fireplace surround, and curved transoms atop doors and windows make entry into Stonecrest a breathtaking experience. At the same time, there are many private spots for contemplation and quiet reflection that balance the grandeur of this remarkable home. In the south wing are a chef’s kitchen with butler’s pantry and a formal dining room that opens to a bluestone terrace. Top of the line appliances, honed granite countertops, and double sinks and dishwashers ensure that anything can happen in this room, from an afternoon snack to a formal dinner for 30 people. The butler’s pantry has a second subzero refrigerator, a wine cooler, and sink. Also on this side of the house is an all-season sitting room and a mud room with its own covered portico for deliveries and access to the 3-car garage. On the north end of the home is a hallway art gallery, a private deck, an en suite guest bedroom, and best of all, a hidden library awaiting behind a secret door, with floor to ceiling windows, a fireplace, access to a private bluestone patio, and views of the river. The second floor can be reached by one of two gracious open stairways. A wide walkway that overlooks the great room extends the length of this second level. At one end is the primary suite that includes a private deck, a walk-through closet with separate dressing rooms and vanity space, and a spacious bathroom with jacuzzi and glass-bricked shower. The primary bedroom has windows on both sides with views of the river and sloping lawns. Next door is a second en suite bedroom that could also serve as a sitting room, den, or office. At the south side of the second story are two more en suite bedrooms, a media room, and entrance to an apartment annex with an open concept kitchen and living space, bedroom, and full bath. Perfect for employees or guests, this cozy space can be accessed from the back staircase for added privacy. On the lowest floor, a walk-out basement, an enormous space for creative pursuits, has easy access from inside or outside the home. Ample windows, a surround-sound system, and generous storage make this area versatile and convenient. Also on this level is a theater room and a second laundry/utility room. This property as it exists today cannot be recreated. For example, directly above the Hudson River, there is a resort-style saltwater swimming pool with stone pool house that includes a full kitchen and gathering space. Current zoning laws do not permit this kind of design nowadays. Countless stunning gems throughout the property include a reflecting pool with firepit and river views, an amphitheater facing the Hudson, a quarter-mile spiral labyrinth with stone paths divided by wild thyme, and a Koi-stocked pond with falling water. Seating areas dot the edge of the property above the river where spending hours watching the ships go by becomes a tranquil act of meditation. Though the home is an easy distance from charming Hudson Valley towns like Rhinebeck and a one-minute drive to the Rhinecliff Amtrak station, Stonecrest on the Hudson is as private and lost to time as an enchanted kingdom

40 Morton Road, Rhinebeck

$960,000
912345 MLS
Rare Hudson Riverfront Land Opportunity in Rhinebeck Along the prestigious and highly coveted Mill Road, this extraordinary 4 acre parcel offers a rare chance to own 300 feet of direct Hudson River frontage in one of the most sought-after areas of Rhinebeck. Framed by breathtaking sunsets over the Catskill Mountains, this property invites you to create a private retreat surrounded by nature’s beauty. With scenic trails, winding backroads perfect for biking, and endless hiking nearby, it’s an ideal setting for outdoor enthusiasts. Whether your vision is a modern architectural masterpiece, a timeless country estate, or a serene escape, this land provides the ultimate canvas. Just minutes to the vibrant Village of Rhinebeck, where farm-to-table restaurants, boutique shopping, and Amtrak access await, this property offers both seclusion and convenience. Opportunities to own Hudson Riverfront property in Rhinebeck are exceedingly rare—don’t miss the chance to bring your dream lifestyle to life in the heart of the Hudson Valley. Board of Health Approved. Survey Available.

Mill Road, Rhinebeck

$2,495,000
3 Beds 2 Baths H6315329 MLS
(To Be Built) Sleek and sophisticated, this modernist residence echoes the subtle ripples of nearby Round Pond, to which Lakeside has lake access rights. The architecture is comprised of three wings joined on a single level to create dynamic indoor and outdoor living spaces, perfect for the ease of single level living. Lakeside is located in Rhinebeck on 4.5 acres, primarily wooded with beautiful terrain, rock outcroppings and mossy knolls. Access stunning Round Pond a short walk away via shared dock, perfect for morning swims or weekend kayaking adventures. This desirable non-motor lake is the perfect complement to modern home. Less than 10 minutes to Rhinebeck village, the property feels remote yet easily accessible from NYC by road and rail. The property’s inspired interiors showcase natural materials and textures celebrating the structure of the home — a quintessential country respite. The form, clad in black with lighter accents, allows for separation of spaces including open plan living + entertaining with more private owners’ suite. Living spaces on this single level home share views to the outdoor entertaining patio and grounds — the perfect spot for outdoor entertaining after a day on the lake. A double sided fireplace adds separation and drama to the living spaces. The luxe kitchen features a large eat-at island and a second scullery kitchen for additional prep & storage. An attached two car garage connects to the family entrance with mud room and laundry. Privately located, the spacious primary bedroom suite includes glazed sleeping room, freestanding bathtub, shower, double vanity, radiant floor heat, WC and stunning views to the natural setting. An office/gym completes the owners’ domain. Secondary guest bedrooms and a covered porch complete the residence. The interior design features luxury materials including oak hardwood floors, designer finishes, Danish cabinetry, Bosch appliances and high efficiency HVAC. Includes septic, private water well, underground utilities and driveway. To be built by the Rhinebeck based Upstate Modernist team. Amenities: Dressing Area, Soaking Tub, Storage, Parking Features:2 Car Attached,

40 Lakeside Drive, 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.