New York Homes for Sale with a Guest House

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  /16

  $199,000

  • 1 Bed
  • 1.5 Baths
  • 3,222 Sq Ft

  6378 U S 9, Chestertown, NY 12817

  This is a Multi-family 2-unit rental in the heart of Chestertown! Walking distance to everything in town- shops, restaurants, etc. Main level is a commercial space w/ half bath (currently not rented) 2nd level- 1 bed/1bath apartment. New metal roof-. Freshly painted, vacant, and easy to show!

  Angie Mead Gallo Realty ADK, Inc

  6378 U S 9, Chestertown, NY 12817
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  /58

  $379,000

  • 5 Beds
  • 2 Baths
  • 2,912 Sq Ft

  1053 Wicker St, Ticonderoga, NY 12883

  Rare mixed-use living and multiple investment opportunity: A 5-bedroom, 2.5-bath Colonial in a prime high-visibility location. Offering the opportunity for additional income with the included 6 unit motel strip and the retired Lester's (as known by the locals) Garage. This property is a value-add gem ready for some TLC and a strategic refresh to maximize its potential in Historic Ticonderoga. The

  Brenda Wells Glebus Realty Inc.

  1053 Wicker St, Ticonderoga, NY 12883
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  /45

  $2,495,000

  Open Sun 12PM - 2PM

  • 7 Beds
  • 6 Baths
  • 4,200 Sq Ft

  130 Cedar Dr, Kerhonkson, NY 12446

  Some properties check every box. This one creates an entirely new standard.Set on five private acres in the heart of the Hudson Valley, this beautifully designed estate offers the rare combination of luxury, flexibility, and room to grow. Whether you're searching for a full-time residence, a weekend retreat, or a multi-generational family compound, every detail has already been thoughtfully

  Diana Polack Compass Greater NY, LLC

  130 Cedar Dr, Kerhonkson, NY 12446
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  /56

  $275,000

  $35K PRICE DROP

  • 8 Beds
  • 3.5 Baths
  • 6,628 Sq Ft

  453 New York 334, Johnstown, NY 12095

  This unique and well-known property, historically recognized as Wemple & Edick's, has long been cherished for its exceptional homemade ice cream, baked goods, and seasonal craft fairs featuring live music and local vendors. Ideally located just minutes from the Historic, city of Johnstown, NY and the NYS Thruway, this offering presents a rare opportunity to carry on a beloved, nostalgic business

  Christine Gerber Howard Hanna Capital Inc

  453 New York 334, Johnstown, NY 12095
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  /50

  $850,000

  • 5 Beds
  • 3 Baths
  • 4,997 Sq Ft

  289 Oak Ridge Rd, Hopewell Junction, NY 12533

  Welcome to 289 Oak Ridge Road, a sprawling 5-acre estate property offering exceptional space, flexibility, and long-term potential in Hopewell Junction. With approximately 5,791 square feet of gross living area across two levels, this expansive residence provides a rare combination of indoor scale, outdoor amenities, and possible future upside. The main house features a flexible layout with

  Ryan Sylvestri 360 Property Management

  289 Oak Ridge Rd, Hopewell Junction, NY 12533
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  /44

  $16,000,000

  $3M PRICE DROP

  • 8 Beds
  • 13 Baths
  • 13,481 Sq Ft

  104 Premium Point Rd, New Rochelle, NY 10801

  The Bluffs at Premium Point introduces ultra-luxury living at the absolute pinnacle of the Premium Point market, setting a new standard within Mamaroneck’s most exclusive, guard-gated peninsula. One of only the coveted “Big Four” landmark estates in this 24/7 secured enclave, this brand-new architectural masterpiece occupies a rare 1.3-acre waterfront sanctuary with horizon-level views found

  Wendy Alper Julia B Fee Sothebys Int. Rlty

  104 Premium Point Rd, New Rochelle, NY 10801
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  /52

  $874,900

  • 5 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  18 E Kelm Pond Rd, Chestertown, NY 12817

  Extraordinary Adirondack retreat situated on 10 private acres, ideally located between Forest Lake and Kelm Pond, offering the perfect blend of privacy, comfort, and versatility. Built in 2016, this unique property features a beautifully designed 3-bedroom, 2.5-bath main residence plus a separate 2-bedroom, 1-bath guest suite along with an oversized garage, making it ideal for extended family,

  Angela Cugini-Girard eXp Realty

  18 E Kelm Pond Rd, Chestertown, NY 12817
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  /49

  $795,000

  • 4 Beds
  • 3 Baths
  • 2,472 Sq Ft

  134 Irish Cape Rd, Napanoch, NY 12458

  Welcome to Irish Cape Retreat. Perched high above the rolling hills of Napanoch with sweeping mountain and pond views across nearly 20 peaceful acres, this Catskill multi-home compound pairs a newly built contemporary metal-sided main residence with a fully renovated guest cabin tucked into the surrounding woods. Four bedrooms, three bathrooms, and two fully distinct living spaces make it equally

  Jessica Brasseur Houlihan Lawrence Inc.

  134 Irish Cape Rd, Napanoch, NY 12458
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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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  /12

  $699,000

  $41K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,200 Sq Ft

  225 S 11th Ave, Mount Vernon, NY 10550

  Newly renovated and fully vacant semi-detached single-family home offering a versatile mother/daughter layout in the heart of Mount Vernon. This spacious 3-level residence features 4 bedrooms, 3 full bathrooms, and approximately 1860 square feet of living space. Designed for flexibility and comfort, the home includes two kitchens, two living areas, and separate entrances-ideal for extended

  Desaree Ethridge

  225 S 11th Ave, Mount Vernon, NY 10550
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  /48

  $9,995,000

  • 11 Beds
  • 16 Baths
  • 20,000 Sq Ft

  1 Osprey Ct, Port Jefferson, NY 11777

  A Waterfront Legacy Estate on Long Island's North Shore: Set atop more than eight acres of elevated waterfront grounds within the prestigious village of Belle Terre, this extraordinary estate represents one of the most significant offerings on Long Island's North Shore. Properties of this caliber: combining substantial acreage, private shoreline, and exceptional privacy are exceedingly rare. A

  Maida Srdanovic Compass Greater NY LLC

  1 Osprey Ct, Port Jefferson, NY 11777
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  /41

  $4,125,000

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

  328 Mclain St, Bedford Hills, NY 10507

  Refined and timeless, this gracious residence has been meticulously preserved and maintained for over a century. Approached by a gated, tree-lined gravel drive, the house is a distinguished example of early 20th-century Georgian architecture, offering exceptional privacy and a profound sense of tranquility. Set on over five acres in the heart of Bedford Hills, surrounded by majestic specimen

  Christine Foster Corcoran Legends Realty

  328 Mclain St, Bedford Hills, NY 10507
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  /64

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 3,190 Sq Ft

  76 Bowman Rd, Chatham, NY 12037

  A truly magical property tucked away at the end of a quiet country road, yet just minutes from the Village of Chatham. Set amid 10 lush and exceptionally private acres, the centerpiece of this enchanting retreat is a light-filled barn conversion featuring a soaring stone fireplace, wide-plank floors, a lofted primary suite, and a separate guest level with living room, two bedrooms, a full bath,

  Lisa Bouchard Hoe The Kinderhook Group, Inc.

  76 Bowman Rd, Chatham, NY 12037
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  /70

  $739,000

  $56K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,045 Sq Ft

  1525 U S 9, Schroon Lake, NY 12870

  Welcome to 1525 Route 9, Schroon Lake--a spacious 5-bedroom home designed for today's lifestyles. With an expansive floor plan and multiple living areas, this home offers the flexibility families are looking for, whether you're working from home, hosting guests, caring for extended family, or simply enjoying the luxury of having room to spread out. The layout easily accommodates a private in-law

  Brooke Clark Four Seasons Sotheby's International Realty

  1525 U S 9, Schroon Lake, NY 12870
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  /47

  $1,285,000

  $40K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 4,322 Sq Ft

  209 Fish Creek Rd, Saugerties, NY 12477

  If you've ever dreamed of living in a one-of-a-kind space that blends history, creativity, and modern comfort, this is your chance. This remarkable c.1883 church compound has been thoughtfully converted into a one-of-a-kind home on the Saugerties and Woodstock border. The former sanctuary now serves as a dramatic living and entertaining space with soaring ceilings and original stained glass. The

  Catherine Quintard Compass Greater NY, LLC

  209 Fish Creek Rd, Saugerties, NY 12477
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  /56

  $249,900

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

  218 County Highway 38, East Worcester, NY 12064

  WELCOME to a well-cared for 3 bedroom, 2 full bath 1900 colonial property, beautifully sitting on TWO ACRES+- of mixed open meadow and woodland. Just 30 minutes from Cooperstown and Suny Onteonta and just under an hour from Albany International Airport. There is a brand-new boiler system and 10X20- 2 story back deck. The living room and dining room area have stunning ceiling woodwork along with

  Joshua Shuhart Coldwell Banker Prime Properties

  218 County Highway 38, East Worcester, NY 12064
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  /50

  $2,500,000

  • 4 Beds
  • 5.5 Baths
  • 4,960 Sq Ft

  163 Hapeman Hill Rd, Red Hook, NY 12571

  Nestled in the heart of the Hudson Valley, this exceptional custom-built compound offers a rare blend of elegance, privacy, and ease. Set on 3.15 acres of beautifully landscaped grounds, the property unfolds as a true retreat—featuring a main residence with a heated three-car attached garage, a legal guest house, a commercial-sized detached garage, a heated in-ground pool, pool pavilion, and

  Sean Eidle BHHS Hudson Valley Properties

  163 Hapeman Hill Rd, Red Hook, NY 12571
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  /31

  $995,000

  $184K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,661 Sq Ft

  5-15 Old Depot Way, Stanfordville, NY 12581

  If you crave a truly unique property, love history or dream of hosting short term rentals, this property might be your ticket to ride. Built in 1889, the historic Train Station in the hamlet of Stanfordville is the only existing station remaining along the original former P&C line that ran alongside Wappinger Creek (known as one of the top 10 trout streams in NYS). Originally, the buildings

  George Langa Houlihan Lawrence Inc.

  5-15 Old Depot Way, Stanfordville, NY 12581
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  /50

  $2,409,990

  • 4 Beds
  • 5.5 Baths
  • 4,031 Sq Ft

  35 Old Snake Hill Rd, Pound Ridge, NY 10576

  Antique lovers... A near impossible to find rare gem set on a small quiet back road of only a handful of homes - step into the timeless charm of the landmarked Sarles-Bode house, a quintessential c.1750 home in Pound Ridge, NY. This is a rare offering where timeless character and everyday livability come together in the main house, guest house, gunite pool and extensive outdoor entertainment

  Giulio Possenti The Higgins Group Inc

  35 Old Snake Hill Rd, Pound Ridge, NY 10576
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  /73

  $1,199,000

  $150K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,768 Sq Ft

  25 Rockledge Rd, East Chatham, NY 12060

  Open House 5/30 12:00-2:30!!! Welcome to this one-of-a-kind mountain oasis with breathtaking views of the Taconic Range. Set on 10 private acres, this extraordinary upstate retreat features a stunning 3,768 SF custom lodge-style home, a 3-car garage with a private guest suite, an in-ground pool with pool house, and an additional 2-car garage. The main residence blends rustic elegance with modern

  Paige Amsler Crystal Coleman Realty LLC

  25 Rockledge Rd, East Chatham, NY 12060
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  /23

  $489,999

  $175K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,400 Sq Ft

  155 Church Ave, Ballston Spa, NY 12020

  ATTENTION INVESTORS, FLIPPERS, SMART BUYERS! LIVE IN MAIN HOUSE, LET TENANTS HELP PAY YOUR MORTGAGE! $1800 MONTHLY RENTS (UNDER MARKET). IDEAL DSCR LOAN PROPERTY. EASY TO SEE, PRESENT ALL OFFERS!

  Rory O'connor Saratoga Real Property, Inc.

  155 Church Ave, Ballston Spa, NY 12020
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  /38

  $714,000

  • 2 Beds
  • 2 Baths
  • 982 Sq Ft

  24 Mohican Rd, Bolton Landing, NY 12814

  Completely reimagined, this exceptional cottage offers the perfect blend of Adirondack charm and modern luxury in one of Bolton Landing's most desirable locations. Situated just down the road from the kayak launch on Lake George at Bixby Beach and just a short, level walk or golf cart ride to the village center where you'll enjoy easy access to restaurants, shops, marinas, parks, and year-round

  Glenn T. Harris eXp Realty

  24 Mohican Rd, Bolton Landing, NY 12814
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  /37

  $3,995,000

  $1M PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 4,718 Sq Ft

  39 Old Snake Hill Rd, Pound Ridge, NY 10576

  Behind private gates, nearly six acres of bucolic countryside unfold around a spring-fed lake — a setting that feels worlds away, yet sits just one hour from Manhattan.Gut-renovated to the studs and reimagined from the ground up, this Pound Ridge estate blends Mid-Century Modern design with original stone construction and hand-hewn beams — a rare marriage of architectural integrity and

  Angela Kessel Houlihan Lawrence Inc.

  39 Old Snake Hill Rd, Pound Ridge, NY 10576
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  /6

  $1,488,000

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

  6538 51st Rd, Woodside, NY 11377

  Investor/Developer Opportunity in Woodside, Queens. Rare 50x100 corner lot with R4-1 zoning featuring three existing structures: a two-family dwelling with (2) residential units, each offering 2 bedrooms, 1 bathroom, living room, and dining room; a separate one-family dwelling with a similar 2-bedroom layout; and a detached 3-car garage. Property also includes a large rear garden/open yard area.

  Eddie McGowan DynamicEdge Realty LLC

  6538 51st Rd, Woodside, NY 11377
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  /48

  $3,999,000

  New Construction $251K PRICE DROP

  • 4 Beds
  • 7 Baths
  • 5,500 Sq Ft

  141A N Ferry Rd, Sag Harbor, NY 11963

  Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to

  Annmarie Seddio Atlas Sales Realty

  141A N Ferry Rd, Sag Harbor, NY 11963
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  /50

  $398,000

  • 5 Beds
  • 3 Baths
  • 2,956 Sq Ft

  340 State Route 38, Dryden, NY 13053

  Victorian sass with room to roam—this is a rare opportunity, first time on the market in 27 years, where historic charm meets serious flexibility and income potential. Spanning 3 full levels of living space plus a beautifully renovated accessory apartment, this home offers scale, character, and room to grow in every direction. The recently refreshed exterior and renewed front porch set the

  Christine DelVecchio Warren Real Estate of Ithaca Inc.

  340 State Route 38, Dryden, NY 13053
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  /61

  $694,000

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

  2439 County Route 5, New Lebanon, NY 12125

  Escape to your own private retreat! Nestled on 22.2 scenic acres and backing directly to Hand Hollow State Forest, this unique property offers the perfect blend of country living, recreation, and convenience.The charming 2,000-square-foot Cape features 3 bedrooms, 2 full baths, a dedicated home office, and a sun-filled sunroom where you can relax and enjoy peaceful Mountain views and surrounding

  Sandy Speranza Howard Hanna Capital Inc

  2439 County Route 5, New Lebanon, NY 12125
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  /47

  $3,749,500

  $251K PRICE DROP

  • 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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  /36

  $890,000

  $59K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,900 Sq Ft

  3880 County Route 30, Salem, NY 12865

  The Ultimate Getaway. The perfect country retreat! Long drive to total privacy. A historical home from the 1700’s, once originally part of a hay farm. Over 50 glorious acres with beautiful open meadows, spring-fed pond, fruit trees and flowering gardens. Unique Post “& Beam Converted Barn, dating to 1763. Remarkable interior spaces with vaulted ceilings, hardwood floors, exposed beams and open

  Cristina Civetta Ginnel Real Estate

  3880 County Route 30, Salem, NY 12865
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  /64

  $1,599,000

  $80K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,434 Sq Ft

  7 Whitehall St, Staten Island, NY 10306

  Step into a home where craftsmanship, space, and versatility come together seamlessly in the heart of Oakwood. This custom-built brick single-family home, completed in 2015, showcases premium finishes throughout and offers the kind of thoughtful design that stands out from the moment you arrive. Featuring 4 spacious bedrooms and 4 bathrooms, the layout is ideal for both everyday living and

  Gabriella DiDomenico Prodigy Real Estate Inc.

  7 Whitehall St, Staten Island, NY 10306
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  /54

  $12,750,000

  $2M PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 5,888 Sq Ft

  199 Eichybush Rd, Kinderhook, NY 12106

  DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling

  Michael Stasi Corcoran Country Living

  199 Eichybush Rd, Kinderhook, NY 12106
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  /36

  $5,900,000

  $500K PRICE INCREASE

  • 3 Beds
  • 4 Baths
  • 5,300 Sq Ft

  2159 New York 296, Hunter, NY 12442

  Mountain Top Estate !Private Air Strip! 555 acres !Truly one of kind property features a custom built Contempo, with awesome Mtn views. For aircraft enthusiasts, this property has its own registered 2600' private airstrip with 2 Hangers. Parcels of this nature remain in families for generations, and it is a rarity for one of this magnitude to come to market. Seems to be a remote and private part

  Nan Potter Potter Realty

  2159 New York 296, Hunter, NY 12442
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  /52

  $5,950,000

  $2M PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 6,438 Sq Ft

  890 Bald Mountain Rd, Austerlitz, NY 12017

  Welcome to Bald Mountain Estate, an extraordinary private compound spanning 85 breathtaking acres overlooking the Hudson Valley and the Berkshire Hills. This four-building, ultra-contemporary estate epitomizes modern country luxury, featuring floor-to-ceiling glass walls and a steel infrastructure that creates a distinctive blend of rusticelegance and architectural sophistication.The

  Lisa Bouchard Hoe The Kinderhook Group, Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017
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  /39

  $4,295,000

  • 9 Beds
  • 6.5 Baths
  • 6,000 Sq Ft

  283-289 Starr Ridge Rd Unit 283-289 and 299, Brewster, NY 10509

  OldWalls is one of the area’s finest historic properties, originally envisioned by the legendary American sculptor Chester Beach and his artist wife Eleanor. Completed in 1918, the estate was constructed of massive hand-laid native stone with walls over two feet thick, crowned by a slate roof — a testament to old-world craftsmanship rarely seen today.The compound includes nine bedrooms across

  Claudia Atkinson Ginnel Real Estate

  283-289 Starr Ridge Rd Unit 283-289 and 299, Brewster, NY 10509
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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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  /7

  $379,999

  • 2 Beds
  • 1 Bath
  • 1,674 Sq Ft

  127 N Washington St, Athens, NY 12015

  Expansive 1.3-Acre Riverfront Site with Potential!Located along the Hudson River waterfront in the Village of Athens, this property offers a unique setting with views of the river and distant hills.Discover a rare opportunity in the Village of Athens at 127-129 North Washington Street. This property features an expansive 1.30-acre lot--a significant land holding for the village--extending

  Manga Mwazi Corcoran Country Living

  127 N Washington St, Athens, NY 12015
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  /50

  $2,200,000

  • 6 Beds
  • 6.5 Baths
  • 6,087 Sq Ft

  281 Phillips Hill Rd, New City, NY 10956

  A sweeping, tree-lined driveway sets an elegant tone as it leads to this distinguished Colonial estate, gracefully set on two acres of lush, meticulously landscaped grounds. Together with a separate guest house, the property offers approximately 8,250 square feet of refined living space. The main residence and guest house collectively provide six bedrooms and seven bathrooms, thoughtfully

  David Jacobi Keller Williams Valley Realty

  281 Phillips Hill Rd, New City, NY 10956
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  /50

  $625,000

  $50K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,116 Sq Ft

  226 Hines Rd, Newfield, NY 14867

  Experience breathtaking views just minutes from the hub of Ithaca NY and Cornell University - just Southwest of Upper Treman State Park. Lovingly restored farmhouse in Ithaca Schools with original Greek Revival architecture showcased with period details as well as tasteful updates. The main house features 3 bedrooms and 3 full baths plus a main level home office with walk-in closet that offers

  Christine DelVecchio Warren Real Estate of Ithaca Inc.

  226 Hines Rd, Newfield, NY 14867

Showing Results 241 - 278, Page 7 of 7