New York Homes for Sale with a Guest House

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  /47

  $4,349,000

  • 6 Beds
  • 6.5 Baths
  • 5,303 Sq Ft

  1054 Plandome Rd, Manhasset, NY 11030

  Historic Charm Meets Modern Comfort in a Gated Plandome Retreat - Step through the gates of this exceptional property and discover two beautifully restored stone homes—originally the carriage and guest houses of the Shore Gables estate on West Drive, now reimagined for modern living with timeless character. The main house welcomes you with a gracious first floor featuring a formal dining room and

  Kevin Concannon Daniel Gale Sothebys Intl Rlty

  1054 Plandome Rd, Manhasset, NY 11030
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  /35

  $99,000

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  112 Nestle Rd, Fort Plain, NY 13339

  Fantastic location at the corner of Rt 163 and Nestle Rd. Just 2 miles from the Village of Fort Plain. Offering 2 acres and artesian well with plenty of water. Property includes well maintain single wide trailer on full foundation with large covered deck and paved driveway. Property owned by the same family for over 70 years. Another old home with some original woodwork with former dance hall in

  Rebecca Zarski Howard Hanna Capital, Inc.

  112 Nestle Rd, Fort Plain, NY 13339
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  /65

  $549,000

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  40 Paddock Rd, East Durham, NY 12423

  Welcome to The Paddock—a serene East Durham estate where nature, heritage, and creativity converge. This turnkey property, currently a successful Airbnb, offers a peaceful retreat and income opportunity. Set beyond a private gate, it features two renovated homes, a versatile two-story barn, and scenic trails. The main house includes two bedrooms, two baths, a spa-like suite, open kitchen, cozy

  John Iconomou Coldwell Banker Village Green

  40 Paddock Rd, East Durham, NY 12423
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  /60

  $539,900

  • 3 Beds
  • 4 Baths
  • 1,872 Sq Ft

  161 Meade Rd, Charlotteville, NY 12036

  OPEN HOUSE, SUNDAY, 10/26/25; 9:00am to 11:00am Escape to the mountains and experience the perfect balance of rustic charm and modern comfort at this stunning log home retreat on 15.28 serene acres in Summit, NY. Set against a backdrop of rolling hills and vibrant forest, this 3-bedroom, 4-bath residence offers 2,448 square feet of beautifully crafted living space designed for

  Matthew Loder Country Boy Realty

  161 Meade Rd, Charlotteville, NY 12036
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  /49

  $2,750,000

  • 4 Beds
  • 3.5 Baths
  • 4,445 Sq Ft

  132 Finch Rd, North Salem, NY 10560

  Windward Mark Farm.An exceptional 9.4-acre equestrian estate on one of North Salem’s premier dirt roads, surrounded by renowned bridle trails and conservation land. This remarkable property includes a gracious four-bedroom main residence, an exquisite one-bedroom-plus carriage house, and a handsome Amish-built horse barn and shed row—totaling six stalls with a heated tack room, feed room,

  Carol Goldberg Berkshire Hathaway HS NE Prop

  132 Finch Rd, North Salem, NY 10560
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  /45

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2150 State Route 143, Alcove, NY 12007

  Unique opportunity to own a single-family home and separate rental guest house, set on 6.15 acres of beautifully landscaped land! Whether you're envisioning an income-producing property, a private retreat, or space for guests, this home offers endless possibilities.The main residence offers 3 bedrooms and 2 baths with a comfortable, easy-flow layout. The primary suite has been recently

  Christina Fisher Howard Hanna Capital Inc

  2150 State Route 143, Alcove, NY 12007
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  /49

  $3,500,000

  • 4 Beds
  • 4 Baths
  • 4,201 Sq Ft

  289 Upper Byrdcliffe Rd, Woodstock, NY 12498

  Set on nearly 9 serene acres in the heart of Woodstock's historic Byrdcliffe Arts Colony is a rare synthesis of architectural precision and natural harmony—an embodiment of award-winning architect John Storyk's deep understanding of space, sound, and site. Designed in 1969 at the very beginning of Storyk's now-legendary career—just after his groundbreaking work on Jimi Hendrix's Electric Lady

  Sharon Breslau BHHS HUDSON VALLEY PROP-WDST

  289 Upper Byrdcliffe Rd, Woodstock, NY 12498
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  /26

  $779,000

  • 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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  /43

  $12,800,000

  • 10 Beds
  • 15 Baths
  • 20,000 Sq Ft

  53 Simonson Rd, Glen Head, NY 11545

  Situated behind two private gates, in one of Long Island’s most prestigious enclaves, this newly constructed 10 bedroom, 15 bathroom modern estate is a masterclass in elevated design and luxurious living. Set on an expansive, meticulously landscaped property, the residence pairs timeless architectural grandeur with sleek, contemporary finishes to create a rare and refined sanctuary.A

  Jason Friedman Daniel Gale Sothebys Intl Rlty

  53 Simonson Rd, Glen Head, NY 11545
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  /51

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  76 Smith Rd, Preston-Potter Hollow, NY 12469

  Mountain-View Farmhouse Compound on 60 Magical Acres Welcome to 76 Smith Road, a countryside retreat where historic charm meets some of the most beautiful mountain views in the region. Set on 60 private acres, it's a full world of its own with a classic farmhouse, a barn, studio space with guest suite, and a charming one-bedroom cottage tucked nearby. A long, tree-lined driveway creates a

  Leigh Bokser Compass Greater NY, LLC

  76 Smith Rd, Preston-Potter Hollow, NY 12469
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  /44

  $4,495,000

  • 5 Beds
  • 4.5 Baths
  • 6,230 Sq Ft

  328 (Lot 1) Mclain St, Bedford Hills, NY 10507

  Set back from the road in one of Bedford’s loveliest estate areas, down a tree-lined drive, sits 328 McLain Street. Designed and built in 1906 by the distinguished firm of Delano & Aldrich as the country retreat of Judge Learned Hand, this gracious Colonial residence is nestled on 5.5 acres, with specimen trees, sweeping lawns, and perennial gardens that create a setting of rare serenity. The

  Christine Foster Corcoran Legends Realty

  328 (Lot 1) Mclain St, Bedford Hills, NY 10507
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  /65

  $2,589,000

  • 5 Beds
  • 6 Baths
  • 3,600 Sq Ft

  282 Ridge Rd, Schodack Landing, NY 12156

  Welcome to your 112 acre dream home/farm. The main house, built 2024, has 3 bedrooms, 2.5 baths and a wonderful front porch. Open concept living room - kitchen with large center island. 30' x 60' Morton barn/garage. The secondary home (Cape Cod) has 2 bedrooms, 2.5 baths built in 2023. Great for guest house, in-law or rental. The fully insulated 42' x 124' equine Morton barn has 16 stalls,

  Karen Westman Berkshire Hathaway HomeService

  282 Ridge Rd, Schodack Landing, NY 12156
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  /36

  $389,900

  • 3 Beds
  • 4 Baths
  • 3,298 Sq Ft

  453 County Route 47, Argyle, NY 12809

  RARE OPPORTUNITY-Lovely newer three bedroom, two full bathroom ranch home with potential for multiple streams of income that include a former brewery zoned F.1 ,hop farm, Christmas tree farm, AirBNB cabins w/ full bathhouse and a glamping area. All of this on a beautiful 8 acre setting. The Ranch house estimated 1378 sq ft, former brewery building estimated 1920 sq ft. While the brewery is no

  Jay Walsh Red Door Realty NY Inc

  453 County Route 47, Argyle, NY 12809
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  /43

  $1,150,000

  • 4 Beds
  • 3 Baths
  • 2,021 Sq Ft

  1799 Wading River Manor Rd, Wading River, NY 11792

  Endless Possibilities & Opportunities for Buyers Looking for an Updated Home with a Separate Guest Cottage for the Extended Family. There is also a Barn that could possiblybe used for Horses and 1 1/2 Acres of Property that could be used as a Gentleman's Farm. The Barn can also be a Delight for Car Enthusiasts as it has a Working Car Lift and 2 Garage Doors, one is 12' high. The Main House

  Mildred Thomas Signature Premier Properties

  1799 Wading River Manor Rd, Wading River, NY 11792
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  /48

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  5881 U S 44, Kerhonkson, NY 12446

  Extraordinary Investment & Lifestyle Opportunity at the Foot of the Shawangunks. So much potential!!With sweeping views of the iconic Shawangunk Ridge and direct access to some of the region's most celebrated hiking, climbing, and outdoor recreation, this unique property presents a rare blend of natural beauty, income potential, and versatility.Set on two adjoining parcels offered

  Jeanne Boice Howard Hanna Rand Realty

  5881 U S 44, Kerhonkson, NY 12446
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  /16

  $185,000

  • 2 Beds
  • 2 Baths
  • 1,453 Sq Ft

  243 Brooky Hollow Rd, Middleburgh, NY 12122

  Charming cottage in the woods giving total treehouse vibes! This cozy retreat is the perfect hideaway for artists, writers, and dreamers seeking inspiration and serenity. Perched high on a hill overlooking the Little Schoharie Creek, the soothing sounds of the water set the tone for peaceful mornings on the deck.The property includes 3.69 acres and an additional rustic one-room log cabin just

  Lisa Tenneson Four Star Realty Group Inc

  243 Brooky Hollow Rd, Middleburgh, NY 12122
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  /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 investorsDiscover this beautifully maintained multi-family property offering a perfect blend of space, updates, and character. The main home features two distinct units. The lower level includes 3 spacious bedrooms, 2

  rosemary mcginn Century 21 Full Service Realty

  159 Grandview Ave, Monsey, NY 10952
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  /11

  $925,000

  • 3 Beds
  • 2.5 Baths
  • 1,462 Sq Ft

  155 Milton Ave, Staten Island, NY 10306

  Welcome to this stunning custom-built newer construction -a one-family, 3-bedroom home offering four levels of thoughtfully designed living space. Located just minutes from beaches, parks, shopping, and transportation, this residence combines convenience with luxury. Enjoy upgraded hardwood floors, a designer kitchen featuring granite countertops and stainless-steel appliances, and ample parking

  Vito Angelo REMAX REAL ESTATE PROFESSIONALS

  155 Milton Ave, Staten Island, NY 10306
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  /47

  $3,749,500

  • 3 Beds
  • 3 Baths
  • 2,800 Sq Ft

  2 Strongs Ln, Water Mill, NY 11976

  Stylish and Secluded Water Mill SanctuaryDiscover this elegant Water Mill summer retreat, perfectly situated in the heart of the Hamptons. Surrounded by meticulously landscaped grounds, the residence offers sunlit interiors, refined yet comfortable living spaces, and a thoughtfully designed layout that seamlessly accommodates both everyday living and entertaining. Outdoors, a private pool is

  Jake Kelly Serhant East End LLC

  2 Strongs Ln, Water Mill, NY 11976
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  /32

  $649,900

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

  446 Shandelee Rd, Livingston Manor, NY 12758

  MAJOR PRICE DROP! Wake up to the sound of Shandelee Brook and the freedom of fully owned solar living in the Catskills.Tucked on 13+ peaceful acres, this 4-bedroom, 3-bath farmhouse blends rustic character with modern sustainability—featuring fully owned solar panels that keep energy costs low while you live close to nature. Inside, the home glows with custom cherry woodwork, a grand

  April DeMaio Keller Williams Hudson Valley

  446 Shandelee Rd, Livingston Manor, NY 12758
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  /37

  $330,000

  • 3 Beds
  • 3 Baths
  • 1,488 Sq Ft

  105 Division St, Sharon Springs, NY 13459

  Village home with artist studio/guest house/rental/commercial space. Lovely 3bedroom cottage offers perfect blend of light, space and serenity. Tucked in a peaceful setting steps away from Main Street shops and restaurants. Inside is bright and airy w thoughtful details throughout. Relax on the front porch or screened side porch to enjoy the sound of Brimstone Creek. Home and renovated

  Michelle Curran Howard Hanna Capital, Inc.

  105 Division St, Sharon Springs, NY 13459
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  /41

  $10,850,000

  • 5 Beds
  • 3.5 Baths
  • 6,340 Sq Ft

  118 Finkle Rd, Ancramdale, NY 12503

  Set among the beautiful rolling hills on 203 acres is this private estate that takes you back in time. The farm was built in 2008 around a c.1754 Dutch barn that was dismantled from upstate NY and transformed into an incredible great room with 34' soaring ceilings, a brick fireplace and two huge French doors to take in the view. Designed by Cynthia Filkoff with 6,340 square feet, the main house

  Paula Redmond Corcoran Country Living - Mill

  118 Finkle Rd, Ancramdale, NY 12503
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  /75

  $775,000

  • 5 Beds
  • 5 Baths
  • 9,300 Sq Ft

  3645 Route 67, Freehold, NY 12431

  Freehold Country Inn - Bar & Restaurant Opportunity in the Catskills Step into a turnkey business in the heart of the Catskills with the Freehold Country Inn, a rustic and inviting bar and restaurant with multiple income streams and endless potential. The property features a 3,500 sq. ft. restaurant with seating for 80 in the dining rooms and 15 at the bar. A full commercial kitchen, active

  Jason Dugo Dugo Realty

  3645 Route 67, Freehold, NY 12431
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  /49

  $3,150,000

  • 4 Beds
  • 3.5 Baths
  • 5,000 Sq Ft

  12 Bishop Park Rd, Pound Ridge, NY 10576

  Generational Compound with all the luxuries & amenities one desires. Cascading pool with waterfall spa, guest house, pond, gardens and private property. Set down a quiet lane this resort-style estate is prime living-just one hour from NYC. A tranquil place to call home for the discerning buyer who can spot special custom home. A thoughtful and tasteful full renovation was completed in 2013. The

  Michael Kaplan Michael J. Kaplan

  12 Bishop Park Rd, Pound Ridge, NY 10576
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  /28

  $380,000

  • 3 Beds
  • 3 Baths
  • 2,630 Sq Ft

  25 County Route 413, Westerlo, NY 12193

  This must see home located at 25 County Route 413 in Westerlo, NY nestled in the Heldeberg mountains was built in 2001. This home has 3 Bedrooms 2 full baths laundry, living and family & dining rooms. There is a wood fireplace. A new roof on the house and garage, new front and sliding doors. The guest/in-law house was built in 2006 has 2 bedrooms a full handicap accessible bath, a full kitchen

  Mark Karten Karten Real Estate Services LLC

  25 County Route 413, Westerlo, NY 12193
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  /30

  $289,000

  • 2 Beds
  • 1.5 Baths
  • 1,576 Sq Ft

  38 Diane Ct, Cohoes, NY 12047

  This Well Maintained Townhome located on a cul de sac in a desirable neighborhood, is Offered by the Original Owners, close to shopping and all services. Custom features include built in bookcases, Gas Fireplace and Large private fenced backyard with deck off of kitchen. Job opportunity forces owner relocation.

  Terry Jandreau Davidson Real Estate Group, LLC

  38 Diane Ct, Cohoes, NY 12047
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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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  /50

  $720,000

  • 3 Beds
  • 1.5 Baths
  • 2,020 Sq Ft

  1600 County Route 7a, Copake, NY 12516

  Gorgeous Views and Private Setting at this Historic Hill-Top Home. The house was built in 1850 and originally located down the road, near the Copake Clock. In 1990, the structure was moved to the current location with original details, including WIDE-PLANK HARD WOOD FLOORS, beautiful Wood Accents and BUILT-INS. The Main House has 3 BEDROOMS, 2 BATHS, an Eat-In Kitchen and Dining Room with a

  Jeffrey McKinney Beach & Bartolo Realtors

  1600 County Route 7a, Copake, NY 12516
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  /42

  $179,900

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft

  473 North Rd, Saint Johnsville, NY 13452

  Hunters Welcome or if your looking to build, what a property! Secluded, quiet and nature lovers are welcome! Cabin was used for hunting and relaxing after work. Land has been mowed with paths throughtout! Stoves uncluded to heat! Outside side shower and bathroom, can be heated as well. Electric on site. Two wells and Septic

  Laurie Weingart Krutz Properties, LLC

  473 North Rd, Saint Johnsville, NY 13452
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  /12

  $1,600,000

  • Land
  • 73 Acres
  • $21,918 per Acre

  10252 Short Cut Rd, Cato, NY 13033

  73 acres of partially developed farmland and 3 large buildings for your generational farming or development opportunity. First time on market in over 60 years. 5 minute drive to NYS Thruway Weedsport Exit. Well established 19 acre turnkey blueberry farm with significant farm equipment and 19,000 blueberry plants. One 8,000sf main building and 2 10,000sf pole barns with 3 phase electric. One pole

  Mike Barry Pyramid Brokerage Company - Co

  10252 Short Cut Rd, Cato, NY 13033
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  /62

  $539,000

  • 5 Beds
  • 1.5 Baths
  • 1,865 Sq Ft

  37 Elm St, Delhi, NY 13753

  The ease of village life on a slice of private park -this bright and spacious Victorian must be seen. Tall rooms with full height french windows open to let in sunlight and the fresh Catskills air. Full of interesting angles, cozy nooks and a wood stove, the house's rooms lend themselves to multiple uses and possibilities. Downstairs there is a comfortable kitchen, a half-bath and plus a claw

  Susan Barnett UPSTATE COUNTRY REALTY

  37 Elm St, Delhi, NY 13753
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  /34

  $3,495,000

  • 3 Beds
  • 2.5 Baths
  • 3,525 Sq Ft

  21 Saddle Ln, East Hampton, NY 11937

  Discover a truly unique and special retreat at this masterpiece of artistic charm and modern luxury, featuring two artist studios and set against the serene backdrop of a private wooded haven in the Northwest Woods. Formerly owned by renowned artists Connie Fox and William King, this exquisite and fully renovated 3 bedroom, 2.5 bathroom residence spans over 3,500 sq ft on a lush 1 acre lot. Step

  Bryan Midlam Compass

  21 Saddle Ln, East Hampton, NY 11937
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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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  /46

  $485,000

  • 4 Beds
  • 3 Baths
  • 1,304 Sq Ft

  571-575 County Route 2, Accord, NY 12404

  Enchanting and cozy farmhouse with spacious one bedroom cottage! Perfect for overflow guest, a studio, an at home business or just good old income. Set between Stone Ridge and Olive, this sweet property has much to offer. Main house connects to the back of the guest cottage via a 30 ft multileveled deck maintaining privacy for both residences. Access to the cottage is from a separate path. The

  Amy Levine Howard Hanna Rand Realty

  571-575 County Route 2, Accord, NY 12404
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  /87

  $895,000

  • 3 Beds
  • 2 Baths
  • 2,328 Sq Ft

  7341 Fishhouse Rd, Broadalbin, NY 12025

  Discover the charm and endless potential of this well-maintained 1890 farmhouse nestled on over 32 picturesque acres in Saratoga County within the Broadalbin School District. This unique property offers an abundance of space, history, and versatility, making it a rare opportunity for those seeking a country lifestyle with modern conveniences close by.The inviting main farmhouse welcomes you

  Shelley Yerdon Coldwell Banker Prime Properties

  7341 Fishhouse Rd, Broadalbin, NY 12025
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  /45

  $305,000

  • 3 Beds
  • 2.5 Baths
  • 1,482 Sq Ft

  661 Straits Corners Rd, Candor, NY 13743

  Tucked away on 5 peaceful acres in Candor, this home offers all the space and comfort you’ve been dreaming of, with a detached income apartment and easy access to everything the Southern Tier has to offer. Step inside to a welcoming entryway, where the home opens to the right with a family room and to the left with the main living quarters. The living room is highlighted by a cozy electric

  Alanie Woodin RE/MAX In Motion

  661 Straits Corners Rd, Candor, NY 13743
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  /42

  $899,000

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  73 Lake Ellis Rd, Wingdale, NY 12594

  Welcome to your private equestrian retreat, just 4 miles from the Harlem–Valley Wingdale Train Station, 4 miles to charming Kent, CT, a mile away to the Appalachian Trail & easy access to Route 7 & Route 22. Set on a secluded private road off Lake Ellis, this property offers both convenience & privacy. Equestrian amenities include a main barn with 6 (12x10) stalls w/ hay loft, heated wash stall,

  Christine Ricci Keller Williams NY Realty

  73 Lake Ellis Rd, Wingdale, NY 12594
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  /50

  $5,900,000

  • 7 Beds
  • 7.5 Baths
  • 5,165 Sq Ft

  - New York 23, Hudson, NY 12534

  Mountain views, historic charm, hiking trails and 100 private acres, just minutes toeverything Hudson....what's not to love.Say hello to your new Hudson Valley venture. As you pull up the winding tree-lined drive its like entering another world; serene andwelcoming. The grand estate slowly comes into view. A stately Manor house sits on alush hilltop, a three bedroom cottage

  Jennifer Capala William Pitt Sothebys Intn'l

  - New York 23, Hudson, NY 12534
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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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  /67

  $1,350,000

  • 5 Beds
  • 2.5 Baths
  • 1,596 Sq Ft

  226 Sand Point Rd, Caroga Lake, NY 12032

  Come explore ''Punky Cove'' nestled on the shore of pristine Canada Lake. This lakeside compound, situated on 1.53 private acres, offers a unique lake living lifestyle. This is a vintage Adirondack property boasting a main lodge and separate adorable guest cottage (approx 300 square feet) with its own loo and shower) both with private decks offering expansive views across Canada Lake. Enjoy the

  Timothy Doherty Berkshire Hathaway Home Services Blake

  226 Sand Point Rd, Caroga Lake, NY 12032

Showing Results 81 - 120, Page 3 of 7