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$999,000
1047993 MLS
Rarely does an opportunity to acquire more than 84 acres in such a convenient Pawling location become available. Set along Route 22 with approximately 900 feet of road frontage, this 84.28-acre parcel offers the space to create a private sanctuary, compound, estate or recreational retreat. Approximately three acres are already cleared, with roughly 10 acres of level land near the front of the property before the terrain gradually rises from approximately 475 feet to an impressive 1,025-foot elevation. With thoughtful clearing, spectacular views may be possible from the higher elevations. The property is surrounded by a diverse variety of mature trees and offers potential for forestry, logging or a forestry exemption, while the expansive acreage provides an ideal setting for hiking, horseback riding, hunting, camping and other outdoor pursuits. The land directly backs up to the Pawling Nature Reserve, a remarkable 1,060-acre preserve featuring miles of hiking trails, mountains, fields, woods and ponds, with connections to the Appalachian Trail. The ability to enjoy this extraordinary protected landscape directly from your own property adds a rare dimension to the setting. The parcel also offers meaningful flexibility for future use, with potential for subdivision and a range of permitted uses including farming, forestry services, a stable and wildlife preserve. Special uses include private clubs, camps, farms, veterinary clinics, kennels, nurseries, nursing homes and riding academies, subject to applicable approvals and regulations. There are no wetlands or floodplain areas identified on the property, further enhancing its potential. Whether envisioned as a secluded country estate, multi-generational compound, equestrian property, private retreat or investment for future development, this is an unusually large and versatile tract of land in the Hudson Valley. Yet despite its expansive and private character, the location is remarkably convenient. The quaint Village of Pawling is less than ten minutes away, offering boutique shops, fine dining, casual eateries, local amenities and the Pawling Metro-North train station, with approximately 90-minute train service to New York City. Large, contiguous parcels with this combination of acreage, elevation, natural resources, recreational access and convenience are increasingly difficult to find.

Route 22, Pawling

$125,000
1043549 MLS
Discover the opportunity to create your own Hudson Valley retreat on this 4-acre parcel in the Town of Milan. Located along an established residential stretch of Fitzsimmons Road, this property offers a peaceful country setting with convenient access to Red Hook, Rhinebeck, Route 199 and the Taconic State Parkway. The parcel is located in Milan’s A3A Agricultural District, where residential and agricultural uses are permitted subject to applicable Town and County approvals. With approximately 4 acres, the property exceeds the district’s basic 3-acre minimum lot-size requirement and may offer potential for a future homesite. Enjoy the privacy and natural surroundings of rural Dutchess County while remaining within easy reach of shopping, dining, recreation and the charming Hudson Valley communities of Red Hook and Rhinebeck. Buyer and buyer’s agent to independently verify zoning, road frontage, survey, septic/BOHA requirements, driveway approval, wetlands, utilities and all intended uses with the appropriate municipal agencies.

Fitzsimmons Road, Red Hook

$200,000
1041156 MLS
An exciting opportunity to build your dream home on approximately 3 acres in desirable Hopewell Junction. Set along a peaceful private road, this beautiful wooded parcel offers the space, privacy and natural surroundings buyers are looking for while remaining convenient to everyday amenities. Located in the Arlington Central School District with easy access to the Taconic State Parkway, Route 55, shopping, dining and recreation, including nearby parks and the area's popular rail trail. Create a custom home surrounded by expansive lawns, gardens and outdoor entertaining areas with plenty of room to enjoy the property. For those seeking an equestrian lifestyle, potential private horse use may be possible subject to Town approvals and applicable zoning requirements. Proposed home renderings are for illustration purposes only. Buyer to perform all due diligence regarding building plans, permits, utilities, septic, well, zoning and permitted uses.

7 Cottage Road, Hopewell Junction

$490,000
1041814 MLS
An Extraordinary Opportunity to Shape the Future of Rhinebeck Village LOT 2 -on South Street 80 ft x 100 ft There are very few moments when history and possibility intersect. After an extensive five-year planning and approval process, 6 Mulberry Street—one of Rhinebeck Village's most storied properties—is entering its next chapter. For the first time, four exceptional residential homesites are being offered for sale, representing what may be the last significant opportunity to build a custom luxury residence within the Village's coveted Historic District. Approved by both the Village of Rhinebeck and the Dutchess County Board of Health, each parcel is ready for construction of a bespoke home of up to approximately 3,000 square feet, thoughtfully designed for modern living with approvals for three bedrooms, a dedicated home office, and a den. These are not simply vacant lots—they are fully entitled opportunities to create homes that will define the next generation of Rhinebeck architecture. Imagine a timeless farmhouse, a refined modern interpretation of a village classic, or an architect-designed estate that seamlessly blends historic character with contemporary luxury. Here, every home becomes part of the fabric of one of America's most beloved small towns. Located just moments from Rhinebeck's celebrated Main Street, residents will enjoy effortless access to award-winning restaurants, independent boutiques, art galleries, cafes, the renowned farmers market, and cultural destinations, while remaining surrounded by the natural beauty of the Hudson Valley. Weekend escapes become unnecessary when every day begins in one of New York's most desirable destinations. With luxury homes in Rhinebeck Village commanding prices well into the multi-million-dollar range and opportunities to build virtually nonexistent, these approved homesites offer a remarkable chance to create a residence tailored precisely to your vision—without the uncertainty, time, and complexity of the entitlement process. Whether you're building your forever home, a weekend retreat from Manhattan, or a lasting legacy, this is an offering of exceptional rarity. A once-in-a-generation opportunity to build something truly extraordinary in the heart of Rhinebeck Village. Each lot is approved for a 3 bedroom + den home up to approximately 3000 sq. ft. This was one tax lot that has been divided into 5 separate tax lots and the updated property tax amounts per lot are not accurately updated in this listing.

6 Mulberry Street, Lot #2, Rhinebeck

$2,200,000
1042427 MLS
Spectacular 10+ acres of breathtaking Hudson River views and frontage with more than 500 feet of direct riverfront and panoramic sunset views. This exceptional building lot features a beautiful stone wall along the historic Wheeler Hill Road, mature trees for privacy, and beautifully landscaped grounds. Potential for subdivision of perhaps 3 or 4 lots with 10.2 acres, 500' of road frontage on Wheeler Hill Road, and R80 (2 acre zoning). Enjoy the short 2 minuter drive to the Metro-North train station for an easy commute to NYC. The property is surrounded by the best of the Hudson Valley — local farm stands and farmers markets, Obercreek Farm & Brewery, apple orchards, and outstanding restaurants. Beacon’s vibrant Main Street is just 10 minutes away. Ideally located just 90 minutes from New York City with convenient access to Metro-North, I-84, and I-87. Existing improvements include a 2,200 square foot home built in 1951 and a detached garage. Driveway is in, power to the existing home and garage, municipal water connection, and other infrastructure already in place. Bring your plans, architect, builder, and vision — opportunities like this are exceedingly rare.

Wheeler Hill Road, Hughsonville

$399,000
1041886 MLS
Private Wooded Retreat with Catskill Mountain Views Discover the beauty and tranquility of this exceptional 9.2-acre wooded parcel in Milan, New York, offering the rare combination of privacy, natural beauty, and convenient access to the Hudson Valley’s most desirable destinations. Tucked away in a peaceful, secluded setting, this property is surrounded by mature trees and abundant natural beauty, creating a private retreat where you can enjoy the quiet of the countryside and spectacular views of the Catskill Mountains. Whether your vision is a secluded country home, weekend escape, or private Hudson Valley sanctuary, this property offers a wonderful opportunity to create something truly special. Located just minutes from the charming villages of Rhinebeck and Red Hook, you'll have easy access to acclaimed restaurants, boutique shopping, farmers markets, historic sites, and the many recreational and cultural attractions of the Hudson Valley, while still enjoying the peace and privacy of your own wooded acreage. The property offers the feeling of being far away from it all without sacrificing convenience. Pending Board of Health approval. A beautiful opportunity to own a private piece of the Hudson Valley in a sought-after location — secluded, scenic, and close to everything that makes Rhinebeck and Red Hook so special.

Willow Glen Road, Red Hook

$495,000
1040152 MLS
An Extraordinary Opportunity to Shape the Future of Rhinebeck Village LOT 5 -on South Street 98 ft x 95 ft There are very few moments when history and possibility intersect. After an extensive five-year planning and approval process, 6 Mulberry Street—one of Rhinebeck Village's most storied properties—is entering its next chapter. For the first time, four exceptional residential homesites are being offered for sale, representing what may be the last significant opportunity to build a custom luxury residence within the Village's coveted Historic District. Approved by both the Village of Rhinebeck and the Dutchess County Board of Health, each parcel is ready for construction of a bespoke home of up to approximately 3,000 square feet, thoughtfully designed for modern living with approvals for three bedrooms, a dedicated home office, and a den. These are not simply vacant lots—they are fully entitled opportunities to create homes that will define the next generation of Rhinebeck architecture. Imagine a timeless farmhouse, a refined modern interpretation of a village classic, or an architect-designed estate that seamlessly blends historic character with contemporary luxury. Here, every home becomes part of the fabric of one of America's most beloved small towns. Located just moments from Rhinebeck's celebrated Main Street, residents will enjoy effortless access to award-winning restaurants, independent boutiques, art galleries, cafe & #233;s, the renowned farmers market, and cultural destinations, while remaining surrounded by the natural beauty of the Hudson Valley. Weekend escapes become unnecessary when every day begins in one of New York's most desirable destinations. With luxury homes in Rhinebeck Village commanding prices well into the multi-million-dollar range and opportunities to build virtually nonexistent, these approved homesites offer a remarkable chance to create a residence tailored precisely to your vision—without the uncertainty, time, and complexity of the entitlement process. Whether you're building your forever home, a weekend retreat from Manhattan, or a lasting legacy, this is an offering of exceptional rarity. A once-in-a-generation opportunity to build something truly extraordinary in the heart of Rhinebeck Village. This was one tax lot that has been divided into 5 separate tax lots and the updated property tax amounts per lot are not accurately updated in this listing.

6 Mulberry Street, Lot #5, Rhinebeck

$8,900,000
1038787 MLS
Bull Farm is an extraordinary 422.42-acre assemblage of farmland, woodlands, wetlands, and working agricultural property offering a rare opportunity to create a private estate, equestrian property, working farm, recreational retreat, or multi-generational compound in the heart of Amenia’s scenic Harlem Valley. Comprised of two adjoining parcels, the property includes 389.21 acres with access and road frontage along Sharon Station Road, one of Amenia’s most picturesque country byways, together with a 33.22-acre working horse farm with access and frontage on Route 22. Combined, the parcels offer approximately 3,789 feet of Route 22 frontage. The expansive 389.21-acre parcel includes approximately 100 acres of cleared, productive farmland. The fields are currently cultivated with corn, alternating with soybeans each year. Ponds, streams, wetlands, and wooded areas create a diverse landscape that is particularly attractive for waterfowl hunting and other recreational pursuits. Gentle rolling hills rise throughout the property, revealing astounding panoramic views across the pastoral Harlem Valley. Multiple potential building sites offer privacy, solitude, and breathtaking vistas from sunrise to sunset, while the combination of open fields and mature woodlands creates endless possibilities for farming, livestock, equestrian use, recreation, hunting, or the creation of a remarkable private estate. The 33.22-acre parcel is an established working horse farm featuring a barn, approximately 14 cleared acres, pastures, several run-ins, outbuildings, two small ponds, and streams. The barn includes four horse stalls, two additional stalls currently used for mechanicals, feed and tack, plus four exterior stalls, with two on each side of the barn. A caretaker apartment above the barn provides additional living space. Trails weave through the woods between the two parcels, creating a natural connection throughout this remarkable expanse. Both properties currently benefit from an agricultural exemption, while the 389.21-acre parcel also has a forestry exemption. Current combined taxes with the exemptions are approximately $16,360, compared with approximately $32,628 without the exemptions. Located amid the charming hamlets and villages of the Harlem Valley, Bull Farm offers an exceptional balance of seclusion and convenience. Enjoy easy access to Wassaic, Millbrook, and Millerton, with the Connecticut border and the towns of Sharon and Kent just minutes away. The surrounding area is rich with farmers’ markets, fine dining, charming eateries, vineyards, cultural attractions, and outdoor recreation. The Harlem Valley Rail Trail abuts the property, while nearby destinations include Dover Stone Church, Innisfree Garden, Trevor Zoo, and local shooting preserves. Route 22 provides an easy connection throughout the region, and the Wassaic Metro-North station is approximately 10 minutes away, offering access to New York City in approximately two hours. A truly exceptional opportunity to own a substantial and versatile piece of the Hudson Valley, where productive farmland, natural beauty, sweeping views, and remarkable recreational potential come together in one extraordinary property. Be sure to click on the virtual tour icon to experience the stunning views from multiple locations throughout this incredible property.

5246 Route 22, Amenia

$915,000
1030167 MLS
It is a very rare occurrence when a parcel this desirable, this beautiful, with this solitude, and with the truly inspirational views available here, becomes available. 88 Top of the Hill is the only undeveloped parcel remaining that will be serviced by Top of the Hill Lane; a cooperatively owned, half mile long private drive, serving only 4 parcels, encompassing 103.36 total acres. Top of the Hill Lane is a quintessential, delightfully private, country accessway, framed by fenced hay fields or wooded tree line all the way from Jamison Hill Rd. to the parcel being offered. It's like taking a step back from the constant reminder of civilization. Once you arrive at the parcel, and venture out onto one of the recently mowed areas, the sanctity immediately embraces you, and the majestic views to the west, overlooking the rolling hills and fields between you and the Hudson River; and capped by the crowns of the Catskill Mtns in the far distance, solidifies that sensation of perfection, And, there is more. In addition to that potentially breathtaking house site, there are multiple-choices on the property where you could construct a secondary dwelling; for either guest accommodations, or to be used as a help's quarters, or perhaps a rental. The Town of Stanford provides this benefit where parcels exceed the statutory zoning requirement, by a given amount, which this parcel easily exceeds. In fact, one extraordinary site for a world class guest house could be captured overlooking the scenic pond cratered in the small hollow designated as a wetland. Additionally, this site simultaneously provides a separate, extremely beautiful opportunity to enjoy those amazing western views to the Catskills. It would be a to-die-for opportunity to construct a modern architectural masterpiece, with a solid glass exterior facing west, on that rock ledge overlooking the pond; where it also would catch those marvelous sunsets and Catskill views. Guests getting the opportunity to spend a weekend in that environment would simply not want to leave... If all this sounds very enticing, and perhaps a little too good to be true, please be assured you will not be disappointed in what is described here; nor in the remaining desirable features of this acreage. Schedule a visit and discover all the facets that makes this such a wonderful opportunity; truly a jewel. Re; the aforementioned Third-party Approval special listing condition must be noted. The next-door neighbor has a VERBAL Right of First Refusal. Further information is available,

88 Top of the Hill Lane, Stanfordville

$3,000,000
1037367 MLS
Immerse yourself in the allure of 207.73 acres of picturesque land, thoughtfully combined from two lots to form an exceptional estate expanse. This captivating property, nestled within an esteemed estate area, offers a harmonious blend of lush woodlands, inviting meadows, tranquil ponds, babbling streams, and captivating vistas. The location is truly unparalleled, presenting an outstanding opportunity to build your dreams. Positioned at the pinnacle of desirability, this prime location boasts convenience and connectivity. A mere 10-minute drive brings you to the Metro-North train station, ensuring effortless access to the city. Additionally, the trendy village of Millerton is a mere 5-minute drive away, providing a delightful array of amenities and cultural attractions. Embrace the pinnacle of estate living with this remarkable offering.

SKUNKS MISERY Lot 3 Road, Millerton

$1,550,000
1037363 MLS
An Extraordinary Estate Opportunity Set within an exclusive and highly coveted estate enclave, this remarkable property offers a rare opportunity to create a truly exceptional country estate. Encompassing an exquisite blend of rolling meadows, mature woodlands, tranquil ponds, meandering streams, and breathtaking pastoral vistas, the land possesses the natural beauty, privacy, and scale rarely found in such a convenient location. The property evokes the timeless elegance of a private country estate, offering an unparalleled setting for a magnificent residence, compound, or distinguished weekend retreat. Expansive open land and picturesque natural features provide endless possibilities for gardens, equestrian pursuits, recreational amenities, or simply enjoying the extraordinary beauty and tranquility of the surroundings. Yet this secluded setting is remarkably well connected. The Metro-North train station is approximately 10 minutes away, providing convenient access to New York City, while the sophisticated and charming village of Millerton is just 5 minutes away, offering exceptional dining, boutique shopping, galleries, and a vibrant cultural scene.

SKUNKS MISERY Lot 1 Road, Millerton

$1,450,000
1037317 MLS
A Picturesque Private Retreat in the Heart of the Country Set along a quiet country lane, this picturesque property offers an exceptional sense of privacy and seclusion, surrounded by the natural beauty of the countryside. Expansive meadows and verdant pastures flow into mature woodlands, creating a diverse and beautiful landscape centered around a generously sized pond. Sweeping views further enhance the property’s peaceful and scenic character. A true haven for outdoor enthusiasts, the property offers an extraordinary setting for hunting, fishing, hiking, and enjoying the outdoors. Whether envisioned as a private country retreat, a sportsman’s paradise, or a potential estate, this remarkable parcel provides the space, privacy, and natural beauty to create something truly special. Yet despite its secluded setting, the property is conveniently located just minutes from the fashionable village of Millerton, with its restaurants, shops, galleries, and other amenities. The Metro-North train station is approximately 10 minutes away, providing easy access for commuting or weekend escapes. Private, picturesque, and rich in recreational possibilities, this is a rare opportunity to own a substantial country property in one of the Hudson Valley’s most desirable areas.

SKUNKS MISERY Lot 2 Road, Millerton

$799,999
1035627 MLS
3 PARCELS 93.3 ACRES! Discover a rare opportunity in the heart of Pleasant Valley with this expansive offering of three contiguous parcels totaling approximately 93 acres. Whether you're looking to build a private estate, establish a compound, invest in land, or explore development potential, this property offers exceptional flexibility with subdivision possibilities (subject to municipal approvals). The rolling landscape provides a beautiful blend of open space, natural surroundings, and privacy while remaining conveniently located near major roadways, shopping, dining, and the Taconic State Parkway. With ample acreage and multiple parcels, the possibilities are endless for builders, developers, investors, or those seeking a truly unique landholding in the Hudson Valley.

46 South Avenue, Pleasant Valley

$225,000
1029622 MLS
Discover the opportunity to build your custom home on this exceptional 8.44-acre homesite in Brady Brook Falls, an established community of estate properties nestled in Pawling's scenic countryside. Offering a beautiful mix of open areas and mature woodlands, the property provides a peaceful setting with plenty of space to create the home you've envisioned. Much of the preparation has already been completed, making it easy to begin your project. The lot is ready to build with an approved site plan, Board of Health approval for a septic system, and building plans that have already been approved by the HOA Architectural Review Committee. Buyers may choose to use the approved plans or submit their own custom design for architectural review. Residents of Brady Brook Falls enjoy approximately 100 acres of shared open space with trails for walking, hiking, and other passive outdoor recreation, creating a unique balance of natural beauty and thoughtfully planned community living. This property requires no fill for septic and is fully staked out including septic, well and driveway. Conveniently located just minutes from the Village of Pawling, you'll enjoy easy access to charming shops, restaurants, the seasonal farmers market, golf courses, and the Metro-North train station, offering a convenient connection to New York City. Whether you're ready to build immediately or planning for the future, this is a rare opportunity to own one of the area's premier building lots with valuable approvals already in place.

14 Akindale Road, Pawling

$650,000
1034674 MLS
Discover the potential of this well-equipped 11.3-acre horse farm, offering an ideal setup for equestrian enthusiasts, trainers, or those looking to create their own private country retreat. The property features a spacious 10-stall barn complete with running water, a convenient half bath, septic system, 200-amp electric service, and ample space to support a variety of agricultural or equestrian uses. With open acreage and room to expand, this property provides endless opportunities for boarding, training, recreation, or simply enjoying the rural lifestyle. Whether you're starting a new venture or bringing your horses home, this versatile property is ready for your vision. All details to be verified by buyer's agent.

151 Homan Road, Stanfordville

$495,000
1033743 MLS
4 parcels totaling a combined 19.26 private acres, this rare offering presents an exceptional opportunity for investors, builders, or buyers looking to create a one-of-a-kind country retreat. There is an existing stone cottage on the property that is full of character but requires a complete renovation, including replacement of all mechanical systems, the well pump, and the septic system. For those with vision, the reward is the chance to restore a charming home in an idyllic setting with exceptional privacy. The offering includes four contiguous parcels, providing flexibility for future development, resale, or the creation of a private estate. In addition to the parcel with the cottage, the property includes tax parcel numbers 139395 (6.56 acres), 117349 (6.00 acres), and 078409 (5.00 acres). Located just 1.5 miles from the Taconic State Parkway and only 1 mile from the commercial heart of LaGrangeville, the property offers the perfect balance of seclusion and convenience. Whether you're seeking a renovation project with significant upside or acreage with subdivision potential, this unique offering presents endless possibilities.

147 Lauer Road, Poughkeepsie

$175,000
1022374 MLS
Beautiful Private 6.4-Acre Lot in the Town of Pawling – Build Your Dream Home, Discover the perfect setting for your dream home on this beautiful, private 6.4-acre parcel in the desirable Town of Pawling. Offering peace, privacy, and a picturesque natural setting, this property is an exceptional opportunity to create your own country retreat while remaining close to the conveniences of town. Just minutes away is Metro North Train Station in the charming Village of Pawling. The village features a variety of restaurants, pubs, boutique shops, and seasonal attractions, including the popular summer farmers market. Golf enthusiasts will enjoy the Dutcher Golf Course, while Lakeside Park offers swimming, scenic walking trails, and picnic areas for outdoor recreation. For nature lovers, the renowned Appalachian Trail is nearby, providing miles of hiking and breathtaking views. During the winter months, Thunder Ridge Ski Area offers skiing and snowboarding just a short drive away. Experience the best of country living with easy access to year-round recreation, local amenities, and small-town charm.

Woodin Lane, Pawling

$850,000
1025339 MLS
Where panoramic mountain views, protected farmland, open skies, and endless possibility come together. Set across approximately 32 acres on two adjoining parcels, this extraordinary Millerton offering presents a rare opportunity to create something truly special. The primary 22-acre parcel is productive farmland with an agricultural assessment in place, helping to keep property taxes low, and is currently leased to a highly regarded local farmer, providing income potential while preserving the land's agricultural heritage. Thoughtful planning has already been done. Architectural plans for a custom home and guest cottage have been maintained with the Department of Health, with approvals in place for well, septic, and electric. A county-approved driveway has already been roughed in, allowing you to move one step closer to building. Plans for an approximately 1,800-square-foot barn are also available, with the barn package ready for construction if desired. The offering also includes an additional approximately 10-acre parcel of protected wetlands adjacent to the rail trail, ensuring the natural landscape remains preserved while adding privacy and recreation at your doorstep. Surrounded by rolling farmland and panoramic mountain views in every direction, this is a property that invites you to slow down, spread out, and build a home that embraces the beauty of the Hudson Valley. Whether your vision is a modern country retreat, a full-time residence, or a legacy property to be enjoyed for generations, the opportunity here is truly exceptional.

1275 Boston Corners Road, Millerton

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.