New York Homes for Sale with a Guest House

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  /53

  $1,275,000

  • 7 Beds
  • 7 Baths
  • 3,896 Sq Ft

  91 & 95 Miller Rd, Canaan, NY 12029

  Last Chance to own a Storybook Historic Estate on 10+ Bucolic Acres in Canaan, NY Offered for the first time in over 40 years, this timeless 10.7-acre estate is the ultimate countryside escape—just 2.5 hours from NYC and 2 hours from Boston. Nestled between the Berkshires and Hudson Valley, the property features two fully restored historic homes that blend 18th- and 19th-century charm

  Jessie Bennett William Pitt Sothebys Intn'l

  91 & 95 Miller Rd, Canaan, NY 12029
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  /47

  $599,000

  • 3 Beds
  • 3 Baths
  • 1,450 Sq Ft

  95 Miller Rd, Canaan, NY 12029

  95 Miller Rd, Canaan, NY - Renovated 1890 Farmhouse with Guest Cottage on 7.9 AcresThis fully renovated 1890 farmhouse sits on a quiet dirt road on 7.9 acres in picturesque Canaan, NY, just a short drive from Tanglewood, Lenox, and the cultural offerings of the Berkshires—an ideal location for weekenders from Boston or those seeking a peaceful year-round retreat.Brimming with

  Jessie Bennett William Pitt Sothebys Intn'l

  95 Miller Rd, Canaan, NY 12029
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  /41

  $649,999

  • 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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  /61

  $799,000

  • 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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  /46

  $7,500,000

  • 6 Beds
  • 6 Baths
  • 3,432 Sq Ft

  660 N Broadway, Saratoga Springs, NY 12866

  An exceptional opportunity for astute Buyers on North Broadway in Saratoga Springs; a sprawling 2.28-acre property hosting two homes mere steps away from downtown. Comprised of four parcels - the Main House, a Carriage House on L72 First St (165.36-72), a vacant lot on L61 First St (165.36-2-61), and 59 Catherine St (165.36-2-47) - this offering invites you to shape your private haven or fashion

  Kelly Quinn Zanella Howard Hanna Capital Inc

  660 N Broadway, Saratoga Springs, NY 12866
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  /50

  $5,850,000

  • 9 Beds
  • 7.5 Baths
  • 8,200 Sq Ft

  8 Stonegate Ln, Glen Head, NY 11545

  Set on 3.32 meticulously landscaped acres, this sophisticated and elegant Gold Coast jewel is a true luxury retreat. The home was designed by esteemed early 20th-century architect Mott B. Schmidt, who was highly regarded for his grand homes, and sought after by many high profile clients. A grand entrance welcomes guests, framed by stately arched trees that line the long, circular driveway. As

  Lisa Ann Heaney Daniel Gale Sothebys Intl Rlty

  8 Stonegate Ln, Glen Head, NY 11545
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  /48

  $225,000

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

  3909 New York 67, Eagle Bridge, NY 12057

  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, (conventional loan or cash purchase).

  Richard Tinkham Berkshire Hathaway Home Services Blake

  3909 New York 67, Eagle Bridge, NY 12057
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  /87

  $525,000

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

  571 International Blvd, Rock Tavern, NY 12575

  The "Crossroads" of New York Interstate 84, Interstate 87 NYS Thruway and 747 International Blvd. One of the most valuable major intersection properties available in NYS. Located at a very desirable intersection designed and engineered specifically for fast, convenient, easy access to Stewart International Airport (SWF) from Interstate 84 and Interstate 87. Including: A beautiful, 2

  Steven Pearl PEARL STEVEN L

  571 International Blvd, Rock Tavern, NY 12575
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  /77

  $2,600,000

  • 16 Beds
  • 8 Baths
  • 7,159 Sq Ft

  4028 County Route 26, Greenville, NY 12083

  Catskills Estate + Proven Income + Endless Possibility4 Parcels | 3 Homes | 2 Massive Barns | Dozens of Uses | 1 Private LakeThis is your once-in-a-generation opportunity to own a legacy compound in the Catskills, where every acre has possibility and positioned for future growth. Spanning over 24 acres across four separate tax parcels, this remarkable offering includes three unique residences—two

  Jason Dugo Dugo Realty

  4028 County Route 26, Greenville, NY 12083
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  /118

  $595,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,282 Sq Ft

  7 Western Ave, Amsterdam, NY 12010

  Charlton - Galway SD - A little house, a house of my own, out of the wind and rains way. Isn't that what most of us desire? BE prepared this is a very complex property! The main home is a cozy 3BR/1BA featuring very fine amenities not found in today's construction without exceptional cost. Solid wood floors, doors, cabinetry, brick fireplace & hearth, picture windows, copper sink, custom

  Kathleen Gordon Inglenook Realty Inc

  7 Western Ave, Amsterdam, NY 12010
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  /41

  $359,000

  • 3 Beds
  • 4 Baths
  • 1,084 Sq Ft

  7 Bonnie Brook Rd, Roscoe, NY 12776

  Welcome to your lucky day! What can be said except that there awaits a whimsical and magical mini homestead estate with pool, sauna, hot tub, greenhouse, guest quarters, separate wood fired specialty kitchen, garden spaces, huge garage, greenhouse and charm to spare in this tiny corner of the Catskills simply inviting you and priced to sell! Oh... and apologies it is streamside as well!

  James Karpowicz Coldwell Banker Timberland Pro

  7 Bonnie Brook Rd, Roscoe, NY 12776
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  /45

  $4,500,000

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

  139 A N Ferry Rd, Shelter Island Heights, NY 11965

  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

  139 A N Ferry Rd, Shelter Island Heights, NY 11965
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  /44

  $3,600,000

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

  76 Medbury Rd, Porter Corners, NY 12859

  This pristine 60+ acre equine facility boasts 2 barns, 50 stalls, a 5/8-mile training track with starting gate, multiple arenas, enclosed exercise area, and 10 safe pastures with run-in sheds. Additionally, there are 2 residences, including a luxury 4,700 sq/ft farmhouse with 4 beds/2.5 baths, red oak floors, stainless appliances, and a wood-burning fireplace. Enjoy spa-like comforts in the

  Kelly Quinn Zanella Howard Hanna Capital Inc

  76 Medbury Rd, Porter Corners, NY 12859
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  /41

  $389,000

  • 3 Beds
  • 2.5 Baths
  • 1,603 Sq Ft

  280 Continental Rd, Napanoch, NY 12458

  Property with 2 separate living units, the front house is a 2 bedroom 1.5 bath home completely redone in 2010. Kitchen has ss appliances, granite counters, 2 pantry closets, mudroom/laundry has ceramic tile floors, large coat closet, washer and dryer with room for a large freezer or a small table and chair set. The open floor plan includes dining area and living room with shiny engineered

  Gail Vesely Lucille Hand Real Estate

  280 Continental Rd, Napanoch, NY 12458
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  /60

  $870,000

  • 6 Beds
  • 5 Baths
  • 4,152 Sq Ft

  60 Cooper St, Lake George, NY 12845

  NEW PRICE! $870,000! Open House Sunday 9/28/2025 12pm to 3pm! Welcome to 60 Cooper Street in the Lake George Village! Enjoy year round Adirondack fun in this large, well appointed home with a beautiful great room, gas fireplace, modern kitchen with island and pantry, large family room with half bath, large primary bedroom suite, beautiful primary spa like bathroom, 3 queensize bedrooms and a

  Allen Van Hoff Howard Hanna

  60 Cooper St, Lake George, NY 12845
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  /49

  $2,500,000

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

  163 Hapeman Hill Rd, Red Hook, NY 12571

  Nestled in the heart of the Hudson Valley, this striking custom-built compound offers a rare combination of luxury, privacy, and serenity. Set on 3.15 acres of beautifully landscaped grounds, the estate includes a main residence, a legal accessory apartment/guest house, a commercial-sized detached garage, an in-ground heated pool, a pool pavilion, and multiple outdoor living spaces—all

  Sean Eidle BHHS Hudson Valley Properties

  163 Hapeman Hill Rd, Red Hook, NY 12571
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  /60

  $2,950,000

  • 8 Beds
  • 10 Baths
  • 8,062 Sq Ft

  170-176 Woodlawn Ave, Saratoga Springs, NY 12866

  This unique custom carriage house is a hidden gem. Previously used as part of a corporate estate and a not for profit office, it is ready to transform into a residence. The fully enclosed perimeter creates a unique outdoor space with a trellis, fountains, gardens, outdoor kitchen area, and beautiful stonework at every turn. There is a fully equipped commercial grade kitchen with walk ins, island

  Julie Bonacio Julie & Co Realty, LLC

  170-176 Woodlawn Ave, Saratoga Springs, NY 12866
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  /46

  $977,000

  • 4 Beds
  • 3.5 Baths
  • 1,949 Sq Ft

  175 Mcnamara Rd, Spring Valley, NY 10977

  Welcome to 175 McNamara Road, an exceptional opportunity to own a beautiful property nestled in the heart of Spring Valley over looking the mountains. This charming home offers a perfect blend of comfort, space, and convenience. Step inside to discover music and art throughout the home, and an inviting atmosphere full of charm. The living and dining areas flow seamlessly, creating a perfect

  Dovid Tilson Shefa Realty

  175 Mcnamara Rd, Spring Valley, NY 10977
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  /28

  $1,999,999

  • 5 Beds
  • 2 Baths
  • 2,618 Sq Ft

  148 Creek Rd, Staatsburg, NY 12580

  Welcome to 148 N creek, a stunning property boasting 136 acres of preserved farmland. The sale features a charming 5 bedroom 2 bath farmhouse from the 1800s, several restored and updated barns, . This property is also home to an active farm brewery and agrotourism center. The acreage is protected by the Winnakee Land Conservancy, with future upgrades in mind. Upgraded electric, septic, and well

  EUGENE VALOY BHHS Hudson Valley Properties

  148 Creek Rd, Staatsburg, NY 12580
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  /36

  $799,000

  • 5 Beds
  • 4 Baths
  • 2,888 Sq Ft

  37 S Plank Rd, Westtown, NY 10998

  Nestled in a peaceful rural setting, this inviting gentleman’s farm offers over 3 acres of land, complete with a tranquil pond, multiple dwellings, and an array of outbuildings. This exceptional property offers a perfect blend of rustic charm, functionality, and versatility and is perfect for those looking to embrace country living with room to grow a home-based business. The heart of the

  Vikki Garby BHG Real Estate Green Team

  37 S Plank Rd, Westtown, NY 10998
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  /96

  $1,650,000

  • 9 Beds
  • 9.5 Baths
  • 5,195 Sq Ft

  632 Albany Turnpike, Old Chatham, NY 12136

  Step back in time and own a piece of Old Chatham history with the distinguished Samuel Wilbor House. Built circa 1770 and listed on the National Register of Historic Places, this exceptional estate offers a unique opportunity to live amidst authentic historic character. Once home to New York State Senator Samuel Wilbor, this is one of Columbia County's few remaining brick Georgians, and is a

  Anthony D'Argenzio Houlihan Lawrence Inc.

  632 Albany Turnpike, Old Chatham, NY 12136
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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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  /32

  $1,099,000

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

  138 Church St, Saratoga Springs, NY 12866

  Located just blocks from Broadway, this distinctive downtown Saratoga property offers flexible living space with a modern aesthetic and sun-filled interior. The building, which once housed businesses including a law office, bike shop, and art gallery, has been thoughtfully converted to residential use and retains its mixed-use zoning. The owner is nearing completion on a two-family layout in the

  Maria Barr Four Seasons Sotheby's International Realty

  138 Church St, Saratoga Springs, NY 12866
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  /63

  $1,924,999

  • 4 Beds
  • 3 Baths
  • 2,591 Sq Ft

  536 E Shore Dr, Adirondack, NY 12808

  Nestled on Schroon Lake, this exceptional retreat boasts 209 feet of pristine waterfront on over an acre of land. Two distinct homes provide 4,423 sq ft of living space—perfect for multi-generational families or lucrative short-term rentals. Experience breathtaking 180-degree lake views and magical sunsets from the tiered waterfront featuring a sandy beach. Accessibility is ensured with a

  Erin Steinbach Julie & Co Realty, LLC

  536 E Shore Dr, Adirondack, NY 12808
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  /34

  $1,995,000

  • 3 Beds
  • 2 Baths
  • 2,212 Sq Ft

  300 Sheldon Ave, Tarrytown, NY 10591

  A TRULY UNIQUE OFFERING — Multi-structure estate on 17+acres in an idyllic ultra-private setting in the highly desirable Rivertowns in lower Westchester County, and in close proximity to NYC. With three existing structures (Primary Residence, Caretaker Cabin, Art Studio) this one-of-a-kind storybook estate offers expansive gardens, park-like grounds, brook-fed ponds... and is ready for the right

  Daniel Bucci Coldwell Banker Realty

  300 Sheldon Ave, Tarrytown, NY 10591
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  /40

  $2,250,000

  • 3 Beds
  • 3 Baths
  • 2,755 Sq Ft

  292 White Hill Ln, Hillsdale, NY 12529

  Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side brings in the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

  Jennifer Harvey Compass Greater NY LLC

  292 White Hill Ln, Hillsdale, NY 12529
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  /69

  $1,495,000

  • 6 Beds
  • 4 Baths
  • 3,794 Sq Ft

  500 Pond View Way, Petersburgh, NY 12138

  Introducing 500 Pond View Way, a bold modern retreat set on 700 feet of pristine lakefront on Dyken Pond. Designed by the internationally renowned firm Kallos Turin, this one-of-a-kind home blends dramatic architecture with serene waterfront living. It features soaring ceilings, white oak accents, and custom-built-ins throughout. The Great Room offers a sleek modern kitchen, a spacious dining

  Rebekah O'neil Howard Hanna Capital Inc

  500 Pond View Way, Petersburgh, NY 12138
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  /41

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 2,155 Sq Ft

  329 Route 6n, Mahopac, NY 10541

  Opportunity rarely seen- Welcome to a true 4 season treasure- this circa 1860 property consists of a 3 bedroom tastefully updated farmhouse, stone carriage house-perfect for guests and a 1300 sq ft post and beam barn ideal as an artist/ musicians/ dance studio or just use it as a 3. 5 bay garage....This mini estate less than one hour from NYC is magnificent and was masterfully restored with

  Maureen Connolly Coldwell Banker Realty

  329 Route 6n, Mahopac, NY 10541
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  /30

  $2,100,000

  • 6 Beds
  • 7.5 Baths
  • 5,056 Sq Ft

  88 Minew Rd, Lexington, NY 12452

  Vly Mountain Retreat — Contemporary Luxury Meets Untamed Beauty in the Catskills. Discover Vly Mountain Retreat, a private, architecturally sophisticated estate in Lexington—one of upstate New York's best-kept secrets. Framed by uninterrupted views of the Catskill Mountains and set on 9 meticulously designed acres, this exclusive compound seamlessly fuses modern luxury with the natural

  Felicity Taylor Corcoran Country Living

  88 Minew Rd, Lexington, NY 12452
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  /49

  $1,178,800

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  955 Fire Lane 6, King Ferry, NY 13081

  Life is Short Live on the Lake! In the Fingerlakes Region of New York, located on east side of Cayuga Lake, you will find this Year Round Lake Property with over 100 feet of Prime Lake frontage. The Shout Out features include, Main House, separate Studio Cottage (used occasionally as Airbnb & Guest House), Two docks, Two levels of Decks, Large Lake Side Covered Seating Gazebo, Private Stone

  Melissa Miller Fedrizzi RE/MAX In Motion

  955 Fire Lane 6, King Ferry, NY 13081
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  /29

  $1,600,000

  • 5 Beds
  • 5.5 Baths
  • 5,238 Sq Ft

  15 Old Farm Rd, Rhinebeck, NY 12572

  Perched on a gentle rise along a private road just ten minutes from Rhinebeck Village, this 5-bedroom custom Craftsman estate—designed by a renowned local architect—seamlessly blends dramatic Art Deco-inspired style with modern comforts. Wide oak floors, premium windows and doors, and brass hardware set the tone, while a suite of advanced systems make the home energy-efficient and off-grid ready.

  Zev Eisenberg Hudson Modern

  15 Old Farm Rd, Rhinebeck, NY 12572
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  /52

  $1,299,000

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

  199 Echo Hill Rd, Saugerties, NY 12477

  36 bucolic acres with two houses for the price of one. The property features a seasonal waterfall and a couple of small streams and plenty of trails to enjoy all from your own backyard. The property is within 15 minutes from the heart of Woodstock and Saugerties. The main house features a fully finished basement with three separate rooms including a dry bar and a crafting room with a half bath.

  Michael Barros Win Morrison Realty

  199 Echo Hill Rd, Saugerties, NY 12477
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  /50

  $1,375,000

  • 8 Beds
  • 4.5 Baths
  • 6,594 Sq Ft

  23 Maple Rd, Cornwall On Hudson, NY 12520

  Step into the past & dance into your future in this singular marvel of what can become your family compound or an opportunity to create a lifestyle that combines` business with country living. Have you dreamed of owning a a home (or home away from home) that is just over an an hour from the city? A place to gather with family and friends….a place to swim in your own pool, play tennis on your own

  Michael Taraboulos Christie's Int. Real Estate

  23 Maple Rd, Cornwall On Hudson, NY 12520
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  /36

  $3,295,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 3 Baths

  148 Fairview Ave, Montauk, NY 11954

  Magical Oasis: Incredible opportunity to own this one-of-a-kind magical oasis built by Carl Fisher in 1925. This truly unique property has so many special qualities - from the main house (with the first pool ever built in Montauk!), to the incredible lush grounds with their amazing variety of old growth specimen trees, perennials and lawns, to the charming stone wall around the property that

  Veronica DeSousa William Raveis (Montauk)

  148 Fairview Ave, Montauk, NY 11954
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  /50

  $1,799,000

  • Land
  • 335 Acres
  • $5,370 per Acre

  65 Armstrong Rd, Hardenburgh, NY 12406

  Own Paradise: this historic farm estate has passed thru generations since the 1800s and is now on market for the first time. At the end of a town-maintained dead-end road in the Catskills is The Odell Farm, 335 splendid acres of forest, meadows, pond, and stream adjoining thousands of acres of protected state land. This private and delightfully secluded retreat consists of the original 4BR 1.5

  Dara Barr Keller Williams Upstate NY Pro

  65 Armstrong Rd, Hardenburgh, NY 12406
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  /54

  $349,000

  • 4 Beds
  • 1.5 Baths
  • 1,770 Sq Ft

  197 Stanton Rd, Shushan, NY 12873

  Why choose between income and lifestyle when you can have both? Tucked near the Battenkill River, this property includes 2 fully furnished, personality-packed homes—one of which is a profitable Airbnb earning $48,000/year. The cute A-frame is a guest favorite, complete with a romantic clawfoot tub and picture-perfect views. Next door, a converted garage with brand new roof currently operates as a

  Krista Polumbo Coldwell Banker Prime Properties

  197 Stanton Rd, Shushan, NY 12873
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  /6

  $150,000

  • Land
  • 4.5 Acres
  • $33,333 per Acre

  251 Highland Rd, Greenville, NY 12083

  Looking for an investment property with character, potential, and natural beauty? This 4.5-acre parcel in Greenville, NY, offers a rare opportunity to own a thriving short-term rental setup with room to grow.Nestled in a quiet, wooded setting just minutes from town, the property features two turnkey Airbnb rentals:A cozy yurt that has delighted guests for the past four yearsA charmingly converted

  Stephanie Hamilton Country Views Realty Inc

  251 Highland Rd, Greenville, NY 12083
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  /49

  $199,900

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  810 Benton Hollow Rd, Woodbourne, NY 12788

  2-for-1 Opportunity – Cape Cod Home + Guest House on 1 Acre. MOTIVATED SELLERDon’t miss this incredible investment and handyman special—two homes on one peaceful, one-acre lot in the Tri-Valley School District. Whether you’re looking for a renovation project, rental potential, or a multi-generational living setup, this property offers endless possibilities. The main home is a classic

  Beth Johnston-Groth Malek Properties

  810 Benton Hollow Rd, Woodbourne, NY 12788
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  /33

  $12,500,000

  • 5 Beds
  • 6.5 Baths
  • 6,054 Sq Ft

  129 W Meadow Ln, Millbrook, NY 12545

  Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance

  Candy Anderson Compass Greater NY, LLC

  129 W Meadow Ln, Millbrook, NY 12545
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  /46

  $799,900

  • 7 Beds
  • 5 Baths
  • 3,226 Sq Ft

  108 Main St, Livingston Manor, NY 12758

  Located in one of Sullivan County Catskill's hottest downtowns in the heart of Livingston Manor, this incredible offering is a once in a lifetime opportunity. Two homes, on two lots offer great flexibility for multi-generational living, rental income, or creative restoration. One home was originally a multi-family which can be converted back (kitchens are still intact) and the other is

  Carol Malek Malek Properties, Inc.

  108 Main St, Livingston Manor, NY 12758

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