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$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
$790,000
3 Beds ⋅ 2 Baths ⋅ 1002822 MLS
This Rhinecliff gem sits on one of the best lots in the Hamlet and is ready for someone with vision. Offered as is, the home features great bones, beautiful hardwood floors, a half bath on the main level, and a full bath upstairs. A kitchen needs to be added, giving you the rare chance to design the heart of the home exactly as you want it. Close to the Rhinecliff train station and only two miles from Rhinebeck Village, the location is unbeatable. Enjoy being moments from the library, the local restaurant, and another new dining spot on the way, and a local market —everything that makes Rhinecliff so special. The property also includes a fantastic outbuilding with electric, gorgeous wood floors, and newly installed pine floors upstairs. It’s an ideal space for an office, studio, workshop, or anything you can imagine. A few virtual photos included for ideas of how it could look. A remarkable opportunity to put your stamp on a true Rhinecliff classic.

67 Kelly Street, Rhinecliff
$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
$1,600,000
997646 MLS
Set high above the surrounding landscape, this remarkable 40-acre property offers sweeping views of the sought-after Catskill Mountain Range and unforgettable sunset skies in every season. A rare opportunity to own a substantial piece of Hudson Valley land, the setting combines natural beauty, open space, and a true sense of tranquility. A beautiful mix of mature hardwoods, evergreens, historic stone walls, and open meadows creates a peaceful environment with exceptional privacy and scenic character. Once productive farmland, the rich soil and gently varied terrain provide endless possibilities for farming, gardening, equestrian use, recreation, or the creation of your ideal country retreat. Whether you envision a full-time residence, weekend escape, or future estate compound, the property offers an inspiring backdrop for a wide range of possibilities. The elevated setting captures expansive western views and dramatic evening light, while the surrounding landscape reflects the timeless beauty of the Hudson Valley countryside. Located just minutes from the Village of Rhinebeck, the property offers convenient access to celebrated restaurants, farmers markets, shopping, arts and culture, and outdoor recreation. Enjoy the best of both worlds — a secluded natural setting with easy access to all the amenities that have made Rhinebeck one of the Hudson Valley’s most beloved destinations. Pending final subdivision approval.

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

15 Charles, Rhinecliff
$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
$825,000
993151 MLS
Panoramic sunset views in Clinton   A wooded 20.8-acre parcel on a scenic country road with Board of Health approval in place.  This unique property is surrounded by rolling farmlands and will provide panoramic views of the Catskill range with minimal clearing.  The site offers exceptional privacy while also being convenient to Rhinebeck (12-minute drive) and also Omega and the Golden Russet general store.  The driveway entrance has been cut and is situated between 220 and 192 Schultz Hill Road in Clinton.

Schultz Hill Road, Staatsburg
$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
$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
$159,000
965893 MLS
Located in the gorgeous lake community of Sepasco Village in Rhinebeck, this building lot is a rare commodity in today's real estate market. It was recently approved by the Dutchess County Board of Health for a 3-bedroom dwelling. The lot has been partially cleared and staked out. The site plan is available upon request. If this location appeals to you, come take a look. It could be where the dream starts for your dream home!

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

"Arc House" Bulls Head Road, Clinton Corners
$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
$39,900
959947 MLS
Situated in the highly desirable Rhinebeck area, this BOHA-approved corner lot presents an excellent opportunity to build a custom one-bedroom, one-bath home. Whether you envision a peaceful weekend retreat, a streamlined downsizing option, or a first home, the property offers a versatile canvas to bring your plans to life. Enjoy a prime location with convenient access to Kingston, local amenities, shops, dining, and outdoor recreation. Just minutes from the Rhinebeck–Kingston Bridge, this lot combines convenience with the charm and vibrancy the area is known for. A rare opportunity to create a thoughtfully designed home in one of the Hudson Valley’s most sought-after locations.

Beckrick Drive, Rhinebeck
$9,500,000
25 Beds ⋅ 25 Baths ⋅ 957965 MLS
Belvedere Mansion at Pawling Manor An Enduring Hudson Valley Landmark of Rare Pedigree Set on 9.52 secluded acres just minutes from Rhinebeck, Belvedere Mansion at Pawling Manor stands as one of the Hudson Valley’s most storied and versatile estates. Anchored by a grand, turn-of-the-century Georgian mansion, the property embodies over three centuries of American history while offering a refined canvas for contemporary luxury hospitality or private estate living. The six-bedroom main residence has been recently restored and thoughtfully redesigned, achieving a seamless balance between original architectural detail and sophisticated modern comfort. Period millwork, well-proportioned formal rooms, and historic finishes coexist effortlessly with updated systems and amenities, resulting in interiors that feel both elevated and timeless. Designed for hospitality use, the estate currently encompasses 22 guest rooms (plus three staff rooms) across three buildings, offering immediate operational flexibility. A separate bungalow structure—formerly housing six guest rooms—awaits renovation and presents a compelling opportunity to expand capacity by 4–6 (or more) additional keys, allowing a future owner to further enhance the property’s income potential and/or guest experience. Though located just four miles south of the Village of Rhinebeck, the estate sits within the Town of Hyde Park, in the hamlet of Staatsburg—an area recognized for its developer-friendly environment and strong support of hospitality projects. This unique positioning combines cultural proximity with favorable zoning rarely found in the region. Belvedere Mansion is not merely a residence or venue—it is a legacy estate, shaped by generations of visionaries and tastemakers. Its next steward is invited to guide the property into its next incarnation, whether as a world-class boutique hotel, wellness retreat, cultural destination, or extraordinary private compound. Zoning: Greenbelt, Hotel (nonconforming) History: The history of Pawling Manor begins in 1696, when the land formed part of a 6,000-acre royal patent granted to Colonel Henry Pawling. According to records, by 1760, Pawling’s grandson, Major John Pawling, had established a stone and log residence on the site, anchoring what would become one of the Hudson Valley’s enduring estates. After the original structure was lost to fire in 1899, the current Georgian-style mansion was constructed in 1900 by H.R. Hastings, a prominent figure in New York’s Gilded Age society, reportedly as a wedding gift for his wife, Mary Hastings. The home was designed for entertaining and welcomed a distinguished social circle. The Beaux Art architecture firm Hoppin and Koen is recorded as having designed the current structure. Its principals, Frances Hoppin and Terence Koen were each mentored by McKim, Mead, and White. Hoppin and Koen are responsible for luminary Hudson Valley structures that include Blithewood and Springwood (FDR's Hyde Park home). William Schupp, who expanded it into Pawling Manor Farm, and later the Clyde Miller family. In 1959, the property entered a new era as Pawling Health Manor, a pioneering wellness retreat founded by Dr. Robert and Joy Gross. For more than thirty years, it attracted cultural icons including Elizabeth Taylor, James Earl Jones, Cicely Tyson, Miles Davis, Jerry Stiller, and others. The estate holds a unique boxing legacy, having hosted a regulation ring built by Dr. Gross, a former feather-weight boxing champion, where legendary trainer Cus D’Amato worked with his fighters. In the early 2000s, the property was reborn as Belvedere Mansion, a premier wedding and events destination—most notably serving as the site of Lin-Manuel Miranda’s wedding. Virtual Data Room Registration: https://docsend.com/view/s/aa6... AMENITIES: Three Staff Rooms Commercial Kitchen Bar 2 Fireplaces Tennis Court Private Natural Pond

10 Old Route 9, Staatsburg
$209,000
955800 MLS
Very desirable and sought after residential lot with extensive road frontage along White Schoolhouse Road. The 3.8 acre lot has Board of Health approval for a two bedroom home. Build your dream home, just 5 minutes to the Village of Rhinebeck, yet privacy and country charm exude at this location. 2 Hours to NYC and 5 minutes to both the Taconic Parkway and Amtrak. Bring your vision and personal taste to this serene location.

White Schoolhouse Road, Rhinebeck
$435,000
940182 MLS
This is the nicest building lot available today 4+ private acres in lovely Clinton Corners a rural and quiet area yet 12 minutes from downtown Rhinebeck , 2 minutes from the Taconic parkway and in the Rhinebeck Central School district . The lot is extremely private with a winding driveway that goes to the house site where the view vista is. The lot has a wonderful forest with a mix of trees, The driveway is in the board of health approval is current and staked out it is a simple in ground septic requiring very little fill . The well location is staked as well and the driveway entrance is finished. The location is quiet with only local traffic and a nice feature is a small general store just down the road . This is one of the nicest roads in the township .The owner had a elevated platform built to see the view . I have the survey and health department approval in an electronic format so I can easily send it to you .

Electronics Road, Clinton Corners
$199,999
927805 MLS
Beautiful BOHA Building Lot on Round Lake Road Gorgeous 4.11-acre Board of Health Approved (BOHA) building lot situated on the top of a hill located on picturesque Round Lake Road. Peacefully tucked away among scenic surroundings, yet conveniently situated less than 12 minutes from both Rhinebeck and Red Hook, and only 15 minutes to the Rhinecliff Train Station. A truly beautiful setting — must see to fully appreciate!

Round Lake Road, Rhinebeck
$199,999
927801 MLS
Beautiful BOHA Building Lot on Round Lake Road Gorgeous 3.046-acre Board of Health Approved (BOHA) building lot located on picturesque Round Lake Road. Peacefully tucked away among scenic surroundings, yet conveniently situated less than 12 minutes from both Rhinebeck and Red Hook, and only 15 minutes to the Rhinecliff Train Station. A truly beautiful setting — must see to fully appreciate!

Round Lake Road, 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
$275,000
842946 MLS
This 22 acre parcel in the Town of Rhinebeck is just minutes south of the Village. Lightly wooded with old stone walls and mature trees, there is plenty of road frontage on both Route 9G and Kerr Road. No BOHA or survey. Located in the RC-5 zoning district. Varied terrain and some wetlands - see images.

Rt-9G, Rhinebeck
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