New York Homes for Sale with a Guest House

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  /39

  $14,000,000

  • 9 Beds
  • 9.5 Baths
  • 7,000 Sq Ft

  401 Lake Delaware Dr, Andes, NY 13731

  Built on the edge of a glorious 68 acre lake set in a high mountain valley in the scenic Catskill Mountains, the historic Lake Delaware Farm offers a rare opportunity to acquire a piece of a true American legacy that has been in continuous use by the same notable family since the 18th century. The Lake House, among the oldest buildings standing in Delaware County, offers a glimpse into the

  Norah Burden Brown Harris Stevens

  401 Lake Delaware Dr, Andes, NY 13731
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  /72

  $1,495,000

  • 3 Beds
  • 3 Baths
  • 2,566 Sq Ft

  1 Wittenberg Rd, Bearsville, NY 12409

  Welcome to Bearsville Record House, a landmark property with a legacy deeply rooted in American music. Originally built in 1873 and once home to famed Bearsville Records, this storied compound includes two dwellings; the main farmhouse and a guest cottage, plus a studio building waiting to be finished to your specs. A gunite saltwater pool, outdoor kitchen, and fenced-in plum orchard complete the

  Jessica Brasseur Houlihan Lawrence Millbrook Of

  1 Wittenberg Rd, Bearsville, NY 12409
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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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  /36

  $579,000

  • 3 Beds
  • 1.5 Baths
  • 1,498 Sq Ft

  861 Snydertown Rd, Craryville, NY 12521

  Country cottage sitting on a 6 acre property with 3 ponds and a large yard surrounded by lilacs. This 3 bedroom, 2 bathroom home offers a country retreat on a quiet road. There are pine floors throughout the home with the washer and dryer hookup in the pantry, light filled sun room and built in pine bookcase. The kitchen is equipped with stainless steel refrigerator, dishwasher, gas range stove

  Joyce Vale Coldwell Banker Advisor Realty

  861 Snydertown Rd, Craryville, NY 12521
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  /33

  $1,495,000

  • 6 Beds
  • 7 Baths
  • 4,592 Sq Ft

  2080 Upper Meeker Hollow Rd, Roxbury, NY 12474

  Founded in 1803 in Roxbury, NY, this remarkable property carries a rich heritage of hospitality — the stone house once served as an Inn for travelers crossing the mountain from Bovina in the 1800s. Today, the estate spans over 200 acres and blends history with breathtaking natural beauty, offering a rare opportunity to own a piece of the Catskills' past.Beautiful views of the mountains,

  Anne Rajs Corcoran Country Living

  2080 Upper Meeker Hollow Rd, Roxbury, NY 12474
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  /33

  $4,995,000

  • 6 Beds
  • 8.5 Baths
  • 4,900 Sq Ft

  161 South Rd, Westhampton, NY 11977

  Stunning New Construction in Westhampton with Rare 2 Story 4 Seasons Guest house on 1.5 Waterfront Acres with Bay Access. A newly constructed masterpiece by esteemed CMT Builders, this nearly 1.5-acre waterfront estate,positioned on the Westhampton Beach Village fringe, sets a new benchmark for modern Hamptons living. Positioned along the peaceful waters of Tanners Neck Creek with distant views

  Robert Canberg Nest Seekers International LLC

  161 South Rd, Westhampton, NY 11977
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  /46

  $1,795,000

  • 7 Beds
  • 4.5 Baths
  • 4,802 Sq Ft

  1739 New York 214, Lanesville, NY 12450

  Escape to the heart of the Catskills with this extraordinary modern Victorian estate, where timeless architectural charm meets contemporary comfort. Nestled on just under 20 acres of meadows and forest, this spacious 7-bedroom, 5.5-bath residence offers the ultimate mountain lifestyle; ideal as a full-time residence, weekend getaway, multi-generational compound, or income-producing vacation

  Michelle Bergkamp William Pitt Sotheby's Interna

  1739 New York 214, Lanesville, NY 12450
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  /46

  $949,000

  • 3 Beds
  • 2 Baths
  • 1,875 Sq Ft

  1680 Gulf Rd, Callicoon Center, NY 12724

  Overbrook House is a design-forward Catskills retreat on nearly an acre that lives much larger thanks to multiple eye-popping indoor/outdoor spaces including a dreamy separate Guest Studio (not included in square footage). The meticulously styled main house features a den paneled with reclaimed barnwood, while the more formal living room's gas fireplace is great for ease of use and tidiness. A

  Jennifer Grimes Country House Realty Inc

  1680 Gulf Rd, Callicoon Center, NY 12724
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  /60

  $539,900

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

  161 Meade Rd, Charlotteville, NY 12036

  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 relaxation, entertaining, and reconnecting with nature. Inside, the

  Matthew Loder Country Boy Realty

  161 Meade Rd, Charlotteville, NY 12036
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  /56

  $498,600

  • 4 Beds
  • 2 Baths
  • 1,638 Sq Ft

  241 Dean Rd, Hudson Falls, NY 12839

  Discover the perfect blend of comfort, privacy, and natural beauty with this inviting 4-bedroom, 2-bath cape home set on approximately 3 acres of serene countryside. The open-concept design creates a welcoming flow between the kitchen, dining, and living areas, ideal for family living and entertaining. Step outside and enjoy your own private spring-fed pond, the perfect spot to relax and take in

  Greg Buckley Barkley Real Estate, LLC

  241 Dean Rd, Hudson Falls, NY 12839
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  /28

  $999,000

  • 5 Beds
  • 4 Baths
  • 3,001 Sq Ft

  138-140 Church St, Saratoga Springs, Inside, NY 12866

  Just a few blocks from the heart of Broadway, 138-140 Church Street offers a combination of location, space, and flexibility in downtown Saratoga Springs. Behind its unassuming façade is a remarkably spacious property with multiple living areas, private quarters, and extensive parking—ideal for multigenerational living or for an owner-occupant seeking income potential.The main residence (138)

  Maria Barr Four Seasons Sotheby's International Realty

  138-140 Church St, Saratoga Springs, Inside, NY 12866
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  /37

  $7,488,000 Open Sun 12:30PM - 2PM

  • 9 Beds
  • 12 Baths
  • 17,587 Sq Ft

  60 Piping Rock Rd, Glen Head, NY 11545

  Welcome to GRAY HORSE FARM - Just Updated & Renovated for 2025 luxury living! Recently transformed with a gut-renovated Top of the line chef's kitchen with new cabinets, countertops, backsplash, floor, and high-end appliances. There are six new designer bathrooms, all-new recessed lighting throughout, upgraded 800-AMP electric and utility systems. This grand estate seamlessly blends timeless

  Aileen Murstein Compass Greater NY LLC

  60 Piping Rock Rd, Glen Head, NY 11545
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  /39

  $314,900

  • 6 Beds
  • 2 Baths
  • 2,448 Sq Ft

  1027 2nd Ave, Schenectady, NY 12303

  2 BUILDINGS FOR THE PRICE OF 1! Huge Potential. Excellent Opportunity to own a Big, Completely Renovated, 2 Family House in the thriving City of Schenectady. Great for Owner Occupied or Investment. Entirely vacant so you can move right in. 3 Bedrooms over 3 Bedrooms. Gorgeous New Kitchens with Granite Countertops and Stainless Steel Appliances. Beautiful New Bathrooms with Ceramic Tile. New Vinyl

  Scott Scorzafava Scorzafava Real Estate Group LLC

  1027 2nd Ave, Schenectady, NY 12303
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  /46

  $39,000,000

  • 9 Beds
  • 15 Baths
  • 55,000 Sq Ft

  104 N Garden Dr, Pawling, NY 12564

  Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

  Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

  104 N Garden Dr, Pawling, NY 12564
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  /31

  $2,500,000

  • 5 Beds
  • 4.5 Baths
  • 2,978 Sq Ft

  177 Tinker St, Woodstock, NY 12498

  Fall in love with this artfully reimagined and expanded 1930 farmhouse, privately set on a gentle hill just moments from the heart of Woodstock. Rich in history and character, this special home was once owned by Michael Lang, the legendary founder of the 1969 Woodstock Festival—adding a rare and meaningful connection to the town's iconic past.Thoughtfully renovated, the home offers a

  Joan Capria Four Seasons Sotheby's Int'l R

  177 Tinker St, Woodstock, NY 12498
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  /46

  $9,600,000

  • 6 Beds
  • 5.5 Baths
  • 9,290 Sq Ft

  512 E Shore Rd, Great Neck, NY 11024

  Welcome to an extraordinary opportunity to own a magnificent waterfront estate located in the heart of Kings Point, one of Long Island’s most coveted communities. Set on 1.5 lush, private acres with sweeping views of the Manhasset Bay/Long Island Sound, this contemporary residence offers the ultimate in luxury, comfort, and resort-style living. This expansive home features 6 bedrooms and 5.5

  Soheila Sharf S Sharf Realty Inc

  512 E Shore Rd, Great Neck, NY 11024
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  /32

  $1,995,000

  • 3 Beds
  • 3.5 Baths
  • 3,353 Sq Ft

  522 Warren St, Hudson, NY 12534

  522 Warren Street, Hudson NY — A masterfully restored live/work property in the heart of Hudson’s vibrant downtown. Behind its historic 1890s facade lies a complete ground-up renovation that blends refined design, modern systems, and timeless character. The ground floor features a spacious bi-level commercial storefront with high ceilings, a new bath, sun-filled offices, and flexible open space

  Alexis Li Corcoran Country Living

  522 Warren St, Hudson, NY 12534
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  /50

  $2,300,000

  • Land
  • 72.06 Acres
  • $31,918 per Acre

  1458 Trumansburg Rd, Ithaca, NY 14850

  Hidden from view, yet just minutes from Cornell University, this gated equestrian estate offers a setting and opportunity unlike any other. Nestled on 72 terraced acres, a tree-lined lane bordered by classic white fencing leads to a premier horse facility that combines lifestyle, business, and beauty in one extraordinary package. Currently home to a thriving boarding operation, this elite center

  Karen Eldredge Howard Hanna S Tier Inc

  1458 Trumansburg Rd, Ithaca, NY 14850
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  /30

  $6,999,000

  • 8 Beds
  • 10 Baths
  • 5,500 Sq Ft

  69 Halsey St, Southampton, NY 11968

  New construction please verify taxes

  Paul Luciano Utopia Real Estate

  69 Halsey St, Southampton, NY 11968
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  /40

  $975,000

  • 3 Beds
  • 2.5 Baths
  • 2,965 Sq Ft

  819 Van Wagner Rd, Poughkeepsie, NY 12601

  Fox Ridge Farm. A lovely country home on 9+ bucolic acres, privately situated in beautiful Dutchess County, NY. This listing includes two separate parcels; the house on 7.11 acres on one side of the road and a 2.61 acre parcel with a picturesque pond on the other side. The main house dates back to 1830 and this property has been beautifully maintained and carefully preserved over the years. The

  Susan Whalen George T Whalen Real Estate

  819 Van Wagner Rd, Poughkeepsie, NY 12601
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  /80

  $10,900,000

  • 7 Beds
  • 9 Baths
  • 6,218 Sq Ft

  40 Geyser Rd, Saratoga Springs, NY 12866

  Owned by the iconic Queen of Saratoga, the late Marylou Whitney, & her husband the late John Hendrickson, this 120+ acre property embodies the beauty & history of Saratoga Springs. The mansion has 6218 SF, built in 1851, 7 bedrooms, 7 full baths, 2 1/2 baths, 3 covered porches, pool house w/ heated pool & gym, chapel, tennis courts, rose gardens, 2 bay heated detached garage, 9 bay heated

  Andrea Collins Four Seasons Sotheby's International Realty

  40 Geyser Rd, Saratoga Springs, NY 12866
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  /49

  $1,849,000

  • 7 Beds
  • 3.5 Baths
  • 5,700 Sq Ft

  230 W Islip Rd, West Islip, NY 11795

  Welcome to a piece of Paradise! this beautiful 1928 5,700 sq. ft. Georgian Colonial, features 7 large bedrooms, 3.5 baths, 16 rooms total, located on beautiful Sampums deep water creek, a few hundred yards from the Great South Bay. this lavish estate offers, poly/glass siding with a 50yr warranty, new central air, decks and terrace built with azek decking. All new exterior lighting, completely

  Alice Yurkerwich Howard Hanna Coach

  230 W Islip Rd, West Islip, NY 11795
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  /47

  $1,250,000

  • 6 Beds
  • 5.5 Baths
  • 5,653 Sq Ft

  84 Highview Ave, Nanuet, NY 10954

  One-of-a-kind 1930’s farmhouse-style Colonial with separate Carriage House on beautiful Highview Avenue! Main house features renovated kitchen with gorgeous granite counters and peninsula, high-end cabinetry, hooded range, two ovens, built-in microwave, farmhouse sink and luxury vinyl tile flooring. Separate laundry/mud room off kitchen. Dutch door from kitchen leads to formal dining room with

  Janeen Smith Coldwell Banker Realty

  84 Highview Ave, Nanuet, NY 10954
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  /79

  $3,995,000

  • 6 Beds
  • 4.5 Baths
  • 3,868 Sq Ft

  2988 Lake Shore Dr, Lake George, NY 12845

  Excellent value at this lakefront 5,668 SF, 6 BR, 4.5 bath residence built in 2004 and lightly lived in. The main level features a vaulted great room, lake-facing kitchen/dining wing, and private primary suite with walk-in closets and luxury bath. Upstairs offers 5 BR's (2 w/lakeviews) and 2 baths. Walk-out lower level has open layout w/kitchen and bath - ideal for entertaining. Quality finishes

  Nic Ketter Realize Brokers

  2988 Lake Shore Dr, Lake George, NY 12845
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  /48

  $1,695,000 Open Sun 12PM - 1:30PM

  • 4 Beds
  • 3.5 Baths
  • 1,702 Sq Ft

  26 S Menantic Rd, Shelter Island, NY 11964

  Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  26 S Menantic Rd, Shelter Island, NY 11964
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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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  /92

  $24,900,000

  • 6 Beds
  • 13 Baths
  • 19,341 Sq Ft

  637 N Broadway, Saratoga Springs, NY 12866

  A one-of-a-kind opportunity to own this luxurious Saratoga Springs Estate on prestigious North Broadway! This magnificent property comes furnished (exclusions apply) & has been meticulously updated w/new state-of-the-art mechanical systems including electrical, heating, plumbing, lighting, Savant home control system & new home security system. This 19,000SF estate features an exquisite primary

  Julie Bonacio Julie & Co Realty LLC

  637 N Broadway, Saratoga Springs, NY 12866
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  /40

  $1,395,000

  • 5 Beds
  • 4 Baths
  • 4,512 Sq Ft

  226 County Route 17, Valatie, NY 12184

  Welcome to historic Surdeval Farm, a spacious 4,500 square-foot, five-bedroom, four-bath homestead on 24.5 acres located between the charming villages of Chatham, Kinderhook, and Valatie. Over the decades the original early 1800’s core home was expanded and rearranged and it is now ready for its next chapter. The formal entrance to the home is from the grand tree-lined circular driveway to the

  Peggy Lampman Peggy Lampman

  226 County Route 17, Valatie, NY 12184
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  /45

  $3,500,000

  • 8 Beds
  • 4.5 Baths
  • 3,010 Sq Ft

  2039 Salt Point Turnpike, Salt Point, NY 12578

  Welcome to This Hudson Farm – a distinctive 157+ acre estate spanning 2039–2105 Salt Point Turnpike, where the beauty of the Hudson Valley meets the ultimate opportunity to enjoy as much—or as little—of the farming lifestyle as you desire. Positioned between Rhinebeck and Millbrook, and just minutes from the Taconic State Parkway, this remarkable offering blends historic charm with modern

  Lindsay Rothman Compass Greater NY LLC

  2039 Salt Point Turnpike, Salt Point, NY 12578
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  /22

  $2,100,000

  • Land
  • 70.5 Acres
  • $29,787 per Acre

  243 Vineyard Ave Unit 251, Highland, NY 12528

  Spectacular 70 acre parcel located right outside the village of Highland. May be used as a farm or subdivided. Parcel has 3 rentals located on it in addition to 1 vacant house. Also on this property is a very large steel building with high ceilings and oversized garage doors as well as a barn! Close commuter location - Metro North, NYS Thruway, Mohonk Mountains and Hudson Valley Rail Trail.

  John Quinn Quinn Realty Group Inc.

  243 Vineyard Ave Unit 251, Highland, NY 12528
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  /47

  $1,290,000 New Construction

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

  134 Irish Cape Rd, Napanoch, NY 12458

  Your private mountain top awaits on 19 pristine acres with a stunning metal sided modern new construction home and an over the top tiny home for your guests. Come explore this gorgeous oasis of natural beauty and modern convenience with wistful mountain views from both homes and your own private pond. The new construction home truly brings nature inside with a full wall of windows and sliders

  Mercedes Ross Coldwell Banker Village Green

  134 Irish Cape Rd, Napanoch, NY 12458
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  /25

  $680,000

  • 3 Beds
  • 2 Baths
  • 1,619 Sq Ft

  517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516

  Discover 515-517 East Mountain Road North—a turnkey ranch perched atop the mountain, where timeless charm meets contemporary living on over 2 acres. This exceptional home artfully blends old-world details with modern additions, creating a perfect harmony of character and comfort.The main house has been beautifully renovated and expanded, featuring a brand-new 264 sq. ft. addition that

  Natalia Rathbauer Julia B Fee Sothebys Int. Rlty

  517 E Mountain Rd N Unit 515-517, Cold Spring, NY 10516
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  /88

  $650,000

  • 4 Beds
  • 1.5 Baths
  • 2,340 Sq Ft

  176 High Rock Rd, West Coxsackie, NY 12192

  Tucked deep in the woods yet only minutes from major routes, this timeless colonial retreat offers both privacy and possibility. Designed in the style of early American homesteads but built with enduring modern materials, the residence blends history and function with grace. Inside, you'll find craftsmanship rooted in the land itself. The creek stone fireplace was built from stone gathered on the

  Marisa Multari Miranda Real Estate Group Inc

  176 High Rock Rd, West Coxsackie, NY 12192
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  /37

  $12,000,000

  • 5 Beds
  • 5.5 Baths
  • 7,538 Sq Ft

  48 Raafenberg Rd, Tarrytown, NY 10591

  Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central

  David Turner Compass Greater NY, LLC

  48 Raafenberg Rd, Tarrytown, NY 10591
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  /12

  $425,000

  • 5 Beds
  • 2.5 Baths
  • 3,507 Sq Ft

  398 Angola Rd, Cornwall, NY 12518

  Stately 1800s Colonial on nearly 5 acres. Over 3,500 sq. ft. with front parlor, open kitchen with granite and pantry, large dining room, fireplace, large family room, and wraparound porch. Second floor features primary suite and bath, two additional bedrooms, study nook, laundry, and full bath. Third floor includes two bedrooms, half bath, and recreation room. Will need repairs. Separate 2/3

  Desiree Beecham River Realty Services, Inc.

  398 Angola Rd, Cornwall, NY 12518
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  /49

  $9,995,000

  • 11 Beds
  • 16 Baths
  • 18,665 Sq Ft

  1 Osprey Ct, Port Jefferson, NY 11777

  A Waterfront Legacy Estate on the North Shore of Long Island: Set on over eight acres of elevated waterfront land in the coveted enclave of Belle Terre, this extraordinary estate represents one of the rarest offerings on the North Shore of Long Island, where properties of this scale, privacy, and acreage are exceptionally limited. With approximately 300 feet of private shoreline and sweeping

  Maida Srdanovic Compass Greater NY LLC

  1 Osprey Ct, Port Jefferson, NY 11777
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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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  /41

  $550,000

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

  53 W Corbett Rd, Montgomery, NY 12549

  Nestled on a serene hillside, this lovely four story contemporary home offers a perfect balance of modern luxury and natural beauty. Move in worry free as there has just been a full renovation. New roof, new mechanicals, new windows & doors, new fixtures. This unique home is bathed in natural light from large windows that frame views of the nearby mountains & wilderness. Both the walls and the

  Heather Macauley eXp Realty

  53 W Corbett Rd, Montgomery, NY 12549
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  /50

  $1,795,000

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

  53 Old Neck Rd S, Center Moriches, NY 11934

  Experience the ultimate in coastal living with this extraordinary waterfront compound, privately nestled in the sought-after Holiday Beach community. This rare offering features a spacious main residence & a fully renovated guest cottage, perfectly designed for luxurious living and effortless entertaining.The main house welcomes you with a flowing layout that includes a dramatic great room,

  Rachel Hujber Signature Homes of New York

  53 Old Neck Rd S, Center Moriches, NY 11934
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  /41

  $2,049,000

  • 3 Beds
  • 3 Baths
  • 1,923 Sq Ft

  12910 Main Rd, East Marion, NY 11939

  WONDERFUL RETREAT TO THE TRANQUILITY OF THE NORTH FORK! COME AND VISIT AND SEE FOR YOURSELF! Paradise Found on Gardiner’s Bay! This is a rare 2 for 1 opportunity, consisting of a beautiful 2 Bedroom, 2 Bath Bayfront Main House, PLUS a 1 Bedroom, 1 Bath Guest Cottage! The property is fully bulk-headed with approximately 70 feet of serene and captivating beachfront along Gardiner’s Bay, and has

  Richard Connelly Douglas Elliman Real Estate

  12910 Main Rd, East Marion, NY 11939

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