New York Homes for Sale with a Guest House

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  /41

  $779,000

  • 7 Beds
  • 5 Baths
  • 3,968 Sq Ft

  8643 New York 28, Big Indian, NY 12410

  Catskills Creekside Chalet – Big Indian, Minutes from Belleayre Ski weekends, summer hikes, and fireside nights all begin here at this nearly 4,000 sq ft retreat on 3.1 acres (two parcels included) with creek access. Just minutes from Belleayre Mountain, it’s a true Catskills playground — whether for private use, rental income, or multi-family gatherings. Host up to 20 guests with ease! Designed

  Leslie Hill Hudson Modern Co

  8643 New York 28, Big Indian, NY 12410
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  /36

  $2,999,500

  • 4 Beds
  • 4 Baths

  22 W Gate Rd, Wainscott, NY 11975

  Step into this fully renovated 4-bedroom, 4-bathroom home offering over 3,300± sq. ft. of living space on 0.52± acres in the heart of Wainscott. Designed for versatility, the layout includes two primary bedroom suites with walk-in closets-one on the main level and one upstairs-plus additional rooms ideal for a home office, studio, or guest accommodations. An accessory apartment with private

  Jake Kelly SERHANT.

  22 W Gate Rd, Wainscott, NY 11975
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  /87

  $820,000

  • 6 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  934 S Shore Rd, Northville, NY 12134

  Cozy waterfront estate with 70' of private Great Sacandaga Lake frontage directly across the street! Enjoy a flat, sandy beach with fire pit and 80' dock - perfect for swimming, boating, and relaxing. This 6-bed, 2.5-bath property features two separate living spaces, ideal for extended family or guest privacy. The main home offers 4 bedrooms, open living areas, and stunning lake views from the

  David Ioele Gateway Realty Solutions

  934 S Shore Rd, Northville, NY 12134
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  /42

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,427 Sq Ft

  191 Bullet Hole Rd, Mahopac, NY 10541

  Story book Cape-style home with a legal accessory cottage harmoniously sited on just under four verdant acres. This beloved and meticulously maintained home with its beamed and beadboard ceilings, wide-plank tongue and groove walls, and arts and crafts light fixtures evoking warmth and timelessness, is a true sanctuary. Observe the seasons change from the bright, airy sunroom, listen to music in

  Zebee Amy Voss Julia B Fee Sothebys Int. Rlty

  191 Bullet Hole Rd, Mahopac, NY 10541
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  /95

  $599,900

  • 7 Beds
  • 4 Baths
  • 4,400 Sq Ft

  763 Turnpike Rd, Eagle Bridge, NY 12057

  Welcome to this charming circa 1791 home just minutes to the quaint Village of Cambridge! Picturesque setting includes 41+ acres with frontage on the Owl Kill! Property includes the main house (approx. 3,300+ sq ft) and an accessory building (approximately 1,000+ sq ft). The main home has been well-maintained and includes 4 bedrooms/2 full baths. On the first level, you will find 2 living rooms

  Abbey McCormick KW Platform

  763 Turnpike Rd, Eagle Bridge, NY 12057
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  /40

  $1,400,000

  • 18 Beds
  • 20 Baths
  • 344,124 Sq Ft

  7951 New York 22, Copake Falls, NY 12517

  This might be one of the most exciting opportunities available in Columbia County right now! Zoned both Commercial and Residential, most recently run as Newman Residence Adult Camp &previously known as 'The Rockledge Motel' on just under 16 acres. Mature landscaping and unique stone walls with 1,130 feet of road frontage on Route 22. Original building Cira 1900, added on (20x20 sq. ft additional

  Margaret Bower Avenia Columbia County RE Specialist

  7951 New York 22, Copake Falls, NY 12517
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  /50

  $1,750,000

  • 9 Beds
  • 5 Baths
  • 6,408 Sq Ft

  22 Proctor Rd, Eldred, NY 12732

  Welcome Home to Belle Knowle ("Beautiful Hill") situated on 11+ acres in Eldred NY! This absolutely stunning home offers over 6,000 SF of historic beauty. The property boasts the main house & a converted barn guest house, detached garage w/ loft room above & guest apartment for a grand total of 9 bedrooms & 5 baths. Perfect for a family estate or potential income producing property. Main home

  Jill Barnes Cabins & Canoes Real Estate

  22 Proctor Rd, Eldred, NY 12732
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  /32

  $11,250,000

  • 5 Beds
  • 7.5 Baths
  • 14,800 Sq Ft

  46 Ledgerock Ln, Hyde Park, NY 12538

  Ledgerock, the riverfront masterpiece by modern architect Lee Ledbetter is back on the market after undergoing significant infrastructure improvements. This one-of-a-kind estate offers the finest Hudson River and Catskill Mountain views on the market today and is set on 5 private acres. Constructed from the finest materials available, this gorgeous fossilized French limestone & glass compound

  Jason Karadus Corcoran Country Living

  46 Ledgerock Ln, Hyde Park, NY 12538
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  /28

  $2,999,000

  • 6 Beds
  • 4.5 Baths
  • 4,690 Sq Ft

  50 Shore Rd, Pelham, NY 10803

  Just listed-more snowless photos coming next week! Welcome to 50 Shore Road in Pelham Manor, a peaceful sanctuary located directly on the waterfront of the Long Island Sound. Come through the iron gates and step inside to welcoming main rooms with grand views of the Long Island Sound. You’ll love cooking in the chefs kitchen open to the family room, and appreciate the cozy den, the powder room,

  Holly Mellstrom Julia B Fee Sothebys Int. Rlty

  50 Shore Rd, Pelham, NY 10803
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  /55

  $225,000

  • 3 Beds
  • 1.5 Baths
  • 1,768 Sq Ft

  3909 New York 67, Eagle Bridge, NY 12057

  Open house Saturday Oct 25th. 11-1. Two for the price of one this property has a one-bedroom turnkey rented home & and a 3 bedroom 1&1/2 bath 1,770 sq ft two story home that is process of being renovated with hardwood floors and original woodwork throughout. Outside you will find a two-car garage and a third acre lot overlooking the Eagle Bridge This property is not an FHA or USDA home,

  Richard Tinkham Berkshire Hathaway Home Services Blake

  3909 New York 67, Eagle Bridge, NY 12057
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  /64

  $579,000

  • 6 Beds
  • 3.5 Baths
  • 3,931 Sq Ft

  306-308 Broadway, Ulster Park, NY 12487

  This spacious and meticulously maintained home blends classic charm with thoughtful modern updates. The kitchen and eating area feature engineered hardwood floors, quartz countertops, a farmhouse sink, extensive stonework, all-new cabinetry, and new appliances. Partial seasonal mountain views can be enjoyed right from the kitchen sink.The first floor layout includes a large living room

  Rodney Batista Howard Hanna Rand Realty

  306-308 Broadway, Ulster Park, NY 12487
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  /36

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  4320 Us Highway 209, Stone Ridge, NY 12484

  Live, Create, Inspire: A Unique Artist’s Property with a Cottage and Commercial Potential. Nestled in a vibrant, commercially zoned area, this captivating property offers a rare blend of residential comfort and creative freedom. With its signature pitched rooflines, inviting front porch, sturdy solid-wood construction, and Stick style architecture, the exterior radiates Southwestern warmth and

  Kichka Pascaru Christie's Int. Real Estate

  4320 Us Highway 209, Stone Ridge, NY 12484
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  /35

  $18,750,000

  • 11 Beds
  • 7.5 Baths
  • 7,500 Sq Ft

  461 Silvernails Rd, Pine Plains, NY 12567

  Ingadi, the Zulu word for garden, is a true legacy compound all set within 127 acres of pristine land with a total of 11 bedrooms across four distinct residential structures. A magical journey of the senses where the Roeliff Jansen Kill and the Shekomeko Creek merge, ensuring sustainability while creating one of the most spiritually powerful and visually stunning experiences in the Hudson Valley.

  Byron Anderson Compass Greater NY, LLC

  461 Silvernails Rd, Pine Plains, NY 12567
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  /50

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,521 Sq Ft

  45 Chaffee Creek Rd, Newfield, NY 14867

  Do you love to host? Live, work, and entertain in style with this one-of-a-kind B&B property. Welcome to your next chapter...A peaceful 10-acre estate perfect for unforgettable getaways, special events, and endless recreation. This well-established B&B boasts a spacious main home with 4 bedrooms, 2 bathrooms, and a 2-car garage, complemented by six charming guest cabins nestled around a serene

  Michele Smith Re/Max Plus

  45 Chaffee Creek Rd, Newfield, NY 14867
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  /50

  $1,500,000

  • 3 Beds
  • 1.5 Baths
  • 2,392 Sq Ft

  325 Waterburg Rd, Trumansburg, NY 14886

  In the idyllic countryside of upstate New York, just 15 minutes from Cornell University and its world class equine and veterinary centers and 7 miles from Finger Lakes National Forest and 17,000 acres of riding trails, lies a property of rare distinction and opportunity. This 39.3-acre estate combines professional-grade equestrian infrastructure with refined rural living—crafted for those who

  Brendan Coughlin Howard Hanna S Tier Inc

  325 Waterburg Rd, Trumansburg, NY 14886
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  /18

  $2,650,000 New Construction

  • 4 Beds
  • 5 Baths
  • 2,625 Sq Ft

  131 Oakley Rd, Accord, NY 12404

  Tucked along a quiet bend in one of Accord's most picturesque country roads, this newly built residence feels like stepping into another era - one defined by timeless beauty, quietude, and a deep connection to the land. Sited on four private acres that blend open meadow and mature forest, the home is introduced by a long driveway that winds through the grassland, past a serene pond that borders

  Leslie Foti Coldwell Banker Village Green

  131 Oakley Rd, Accord, NY 12404
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  /31

  $2,850,000

  • 6 Beds
  • 8 Baths
  • 6,100 Sq Ft

  644 Tower Hill Rd, Millbrook, NY 12545

  A true country retreat on 109 picturesque acres on one of Millbrook’s most coveted roads, Tower Hill. This extraordinary country estate offers a rare blend of elegance, comfort, and timeless charm. The main residence, originally built in 1909 and remodeled in 2002, features five or six bedrooms, four full bathrooms, and three half bathrooms, designed for both everyday living and grand

  Byron Anderson Compass Greater NY, LLC

  644 Tower Hill Rd, Millbrook, NY 12545
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  /50

  $1,350,000

  • 4 Beds
  • 2.5 Baths
  • 1,588 Sq Ft

  20 Old Mount Kisco Rd, Armonk, NY 10504

  Lovely home on over 5 acres on 3 tax lots in the Armonk School District. Great for family or rebuilding into your dream home. Additional 1 bedroom cottage, garage building, and storage building. 3D tour can be viewed at:

  Dee Rabady Woodfront Realty, Inc.

  20 Old Mount Kisco Rd, Armonk, NY 10504
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  /26

  $759,000

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  509 Julius Rd, College Point, NY 11356

  LUXURY THREE BEDROOM DUPLEX CONDOMINIUM FOR SALE**Private Gated Silverpointe Estates!This lovely unit sits on a cul de sac/Private block of Julius Road inside Silverpointe Estates .This unit is called the "D" Line which is the largest unit in this Development! ( Some of the pictures are virtually staged in this listing)Community: Upon entry of this private complex, you are greeted

  Alina Yukhtman Golden One Realty Group LLC

  509 Julius Rd, College Point, NY 11356
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  /47

  $5,299,000

  • 6 Beds
  • 8 Baths
  • 8,500 Sq Ft

  717 Short Beach Rd, Saint James, NY 11780

  Experience timeless architecture and peaceful luxury in this Feng Shui inspired estate nestled within the prestigious Short Beach enclave of Nissequogue. Privately sited on 2.49 manicured acres, this unique compound offers unmatched tranquility and thoughtful design, surrounded by a protected wildlife sanctuary. Built in 2011 and oriented to face south, the approx. 8,500 square foot residence

  Pauline Negron Spiller The Agency Northshore NY

  717 Short Beach Rd, Saint James, NY 11780
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  /50

  $5,500,000

  • 4 Beds
  • 5.5 Baths
  • 6,244 Sq Ft

  3585 Route 82, Millbrook, NY 12545

  Welcome to Sunset Ridge Farm. A discreet tree-lined drive with expansive views of two aerated ponds and rolling hills leads to this breathtaking modern farmhouse estate. Set on 10 exquisitely manicured acres with mountain vistas, a heated in-ground pool, spa, and gardens reminiscent of the English countryside, 3585 Route 82 is a truly rare offering — a perfect full-time residence or refined

  Jordan Vaccaro Serhant LLC

  3585 Route 82, Millbrook, NY 12545
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  /50

  $8,475,000

  • 6 Beds
  • 7.5 Baths
  • 12,418 Sq Ft

  367 Prospect Hill Rd, Ancramdale, NY 12503

  First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation,

  George Langa Houlihan Lawrence Inc.

  367 Prospect Hill Rd, Ancramdale, NY 12503
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  /32

  $649,900

  • 4 Beds
  • 3 Baths
  • 2,455 Sq Ft

  446 Shandelee Rd, Livingston Manor, NY 12758

  Wake up to the sound of Shandelee Brook flowing through the property and the rare freedom of fully owned solar living in the Catskills. Set on over 13 private acres in Livingston Manor, this 4-bedroom, 3-bath farmhouse offers a lifestyle rooted in nature, sustainability, and space — space to explore, create, and live with intention. Inside, the home blends rustic character with modern efficiency,

  April DeMaio Keller Williams Hudson Valley

  446 Shandelee Rd, Livingston Manor, NY 12758
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  /25

  $925,000

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  1125 Pequash Ave, Cutchogue, NY 11935

  Fantastic income opportunity awaits South of Main less than a mile from the beach! North Fork charmer includes both a 3 bedroom main house and a separate 1 bedroom accessory apartment over the garage. The main house on Pequash is a 3 bedroom farmhouse style colonial which welcomes you inside with its covered front porch. Interior features include hardwood floors, quartz counters in the open

  Deana Herrick McCreery Herrick Real Estate LLC

  1125 Pequash Ave, Cutchogue, NY 11935
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  /38

  $3,500,000

  • 7 Beds
  • 7 Baths
  • 5,502 Sq Ft

  83 Somerstown Rd, Ossining, NY 10562

  Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country

  Dalia Valdes Julia B Fee Sothebys Int. Rlty

  83 Somerstown Rd, Ossining, NY 10562
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  /31

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 2,384 Sq Ft

  53 Day Rd, Campbell Hall, NY 10916

  A beautifully updated estate on a tranquil dead end road. The 1930s main farmhouse features 3 to 4 bedrooms, 2.5 baths, a stone fireplace, a wood stove and a walk out lower level with a unique entertaining area. A legal one bedroom, tenant house is perfect for extended family or rental income. The property has a mini apple /peach tree orchard- includes several outbuildings: the original dairy

  David White Owner Entry.com

  53 Day Rd, Campbell Hall, NY 10916
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  /50

  $424,900

  • 4 Beds
  • 2 Baths
  • 1,650 Sq Ft

  250 Doc Stark Ln, Stamford, NY 12167

  Welcome to the Perfect Picture Home in the heart of the Catskills, This Catskill Chalet+Studio appartment will provide you with ample space and relaxation with a total of 4 bedrooms and 2 full baths, on a private cul-de-sac road.The property has a successful established airbnb business, or you can live in one and rent the studio.Beautiful stunning views of sunrise and rolling hills +10

  Michael Friedmann eRealty Advisors, Inc

  250 Doc Stark Ln, Stamford, NY 12167
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  /21

  $1,799,990

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  59 Dyke Rd, Setauket, NY 11733

  Existing Home and Land with Grandfathered Boat House and Boat Ramp. 3 Bedroom, 1 Bath home (renovated 1999) on 1.78 private acres with waterfront acces to Little Bay and Setauket Harbour. 1,400 SF of living space plus partial basement, cottage, and additional structures on the property. Quiet, private location with water views and direct access to Port Jefferson and Stony Brook. Don't miss theis

  Bryan Coco Kelly Real Estate Inc

  59 Dyke Rd, Setauket, NY 11733
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  /23

  $2,400,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,420 Sq Ft

  420 Wittenberg Rd, Bearsville, NY 12409

  Woodstock Custom Compound - Create your own private family compound on 2.44 serene acres in the Woodstock Hamlet of Wittenberg—an exceptional to-be-built offering that brings together architectural vision, artisan materials, and the craftsmanship of noted builder James Nelson. This unique project includes a three-bedroom, three-and-a-half-bath main residence, a one-bedroom guest house, and a

  Peter Cantine Halter Associates Realty

  420 Wittenberg Rd, Bearsville, NY 12409
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  /53

  $999,000

  • 6 Beds
  • 4 Baths
  • 3,930 Sq Ft

  455 Post Hill Rd, Craryville, NY 12521

  An Historic, Solar-Powered home on 11 Private Acres in the Hudson Valley.Set on a quiet hilltop at the end of a long drive, this private property offers timeless craftsmanship, modern comfort, and a rare sense of seclusion — all within two hours of New York City.Originally an 1880s Pennsylvania barn, the main house was meticulously dismantled and reassembled beam by beam, blending

  John Barbato Compass, Hillsdale

  455 Post Hill Rd, Craryville, NY 12521
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  /39

  $1,799,000

  • 6 Beds
  • 3.5 Baths
  • 3,023 Sq Ft

  2320 Glasco Turnpike, Woodstock, NY 12498

  For the first time in its history, this 12-acre family estate—designed, built, and cherished by a prominent Woodstock family—comes to market. It's a rare opportunity for the next generation to build their own private compound for extended family or multiple guests. The property boasts a babbling brook, waterfall, two vintage Woodstock cottages, and acres of woods to explore. Located less than a

  George Denise Keller Williams Realty HV Nort

  2320 Glasco Turnpike, Woodstock, NY 12498
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  /50

  $1,885,000

  • 7 Beds
  • 4.5 Baths
  • 2,346 Sq Ft

  1 Canal Rd, Hampton Bays, NY 11946

  This property is a perfect opportunity as a Family Compound or Investment property. Situated on a beautiful lot with water views from every angle is a two story home with a large living room with fireplace, dining area, half bath and kitchen. Two bedrooms on the second floor share a full bath, plus a primary bedroom with full bath and walk-in closet. Off the living room is a large deck perfect

  Denise Rosko Hamptons Realty Associates LLC

  1 Canal Rd, Hampton Bays, NY 11946
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  /40

  $2,750,000

  • 5 Beds
  • 4 Baths
  • 4,100 Sq Ft

  3120 Grathwohl Rd, New Suffolk, NY 11956

  Presenting a very special compound in the tiny village of New Suffolk. This slice of paradise is situated on the easterly side of West Creek along Grathwohl Road. This move in ready home is an oasis, consisting of the main house, beautifully appointed inground pool, pool house, outdoor kitchen and offered with this amazing property is a private guest cottage that can be used as overflow for

  Frederick Markham Daniel Gale Sothebys Intl Rlty

  3120 Grathwohl Rd, New Suffolk, NY 11956
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  /61

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  258 Watson Hollow Rd, West Shokan, NY 12494

  Spacious 3 bedroom home with breathtaking mountain views. Perched on a hill, this home offers panoramic mountain views and sits on 19.20 acres bordered by a serene stream. There is a front entrance to the home that brings you into the lower level foyer room with blue stone flooring.. On this level is a finished game room/ office space/TV room with plenty of finished space. You also have access to

  Siobhan Scanlan Win Morrison Realty-K

  258 Watson Hollow Rd, West Shokan, NY 12494
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  /26

  $719,000

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft

  11005 Main Rd, East Marion, NY 11939

  East Marion, North Fork – Classic Farmhouse with Legal Cottage & Barn, Priced to Sell!Don’t miss this rare opportunity to own a charming piece of North Fork history—just moments from Truman’s Beach and all the beloved attractions of the East End. Set on a shy acre, this character-filled property features an older, maintained farmhouse, a legal guest cottage, and a versatile two-story barn

  Nicholas Planamento William Raveis New York LLC

  11005 Main Rd, East Marion, NY 11939
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  /24

  $2,000,000

  • Land
  • 149 Acres
  • $13,423 per Acre

  8543 United States Route 209, Ellenville, NY 12428

  149 acres of beautiful farmland with the Sandburgh stream running through it, stunning vistas of the Shawangunk Ridge, three sweet 1930 cottages and three iconic barns, lovingly and locally known as the Kelly Farm, are now available for sale. Located along busy Route 209 with generous road frontage, this property is an exciting mix of fertile farmland and residential. Historically the property

  Carolyn Peters-Baker Keller Williams Realty HV Nort

  8543 United States Route 209, Ellenville, NY 12428
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  /29

  $2,500,000

  • 4 Beds
  • 3 Baths
  • 3,058 Sq Ft

  14 Gunn Ln, Queensbury, NY 12804

  An exceptional opportunity to acquire a 50% interest in a spectacular lakefront estate on Lake George. This property is perfectly situated on 155 feet of private lake front on Harris Bay, in desirable Cleverdale. This offering is for a one-half interest, as tenants in common, in the entire property. It includes a main lake house and three separate guest cabins. The entire estate includes 3

  Josie Reo MLS 4 Less Realty

  14 Gunn Ln, Queensbury, NY 12804
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  /100

  $1,318,000

  • Land
  • 94.96 Acres
  • $13,880 per Acre

  528 Dyken Pond Rd, Petersburg, NY 12138

  *SECLUDED/ISOLATED: Atop Rensselaer Plateau this 100 year family owned sprawling 95 acre OASIS is under 1 hour to active city life; Capital District NY, Berkshires MA & Southern VT! *HEALTHY ENVIRONS: Mountain fresh air is healthier, cleaner with less humidity & pollution. LAND: sand gravel banks, streams, fields, treed woods -low footprint. *WATER: 180 acre spring fed crystal clear lake. This is

  Joseph Milanese Milanese Joe

  528 Dyken Pond Rd, Petersburg, NY 12138
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  /94

  $1,695,000

  • 8 Beds
  • 8 Baths
  • 5,118 Sq Ft

  1017 Bruyn Turnpike, Wallkill, NY 12589

  Welcome to Bruyn Estate, an exceptional Hudson Valley compound that brings together historic character and modern comfort across two remarkable homes: a restored 1835 Greek Revival farmhouse on the National Register of Historic Places, and a reimagined Dog-Trot-style log home built from 1850s barn beams. Set on 8.5 acres, the property is steeped in history: in the 1800s, it was a sheep farm that

  Anthony D'Argenzio Houlihan Lawrence

  1017 Bruyn Turnpike, Wallkill, NY 12589
• 

  

  /49

  $1,249,000

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  159 Grandview Ave, Monsey, NY 10952

  Multi-Family Retreat with Pool Great opportunity to Purchase a property to generate rental income to provide financial stability and help cover monthly expenses also great for investors. Easy enough to bring make this a single family giving you 5+ bedrooms and 3 full bathsDiscover this beautifully maintained multi-family property offering a perfect blend of space, updates, and character. The

  rosemary mcginn Century 21 Full Service Realty

  159 Grandview Ave, Monsey, NY 10952

Showing Results 41 - 80, Page 2 of 5