New York Homes for Sale with a Guest House

• 

  

  

  /87

  $625,000

  • 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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  /16

  $5,750,000

  • 9 Beds
  • 7.5 Baths
  • 5,809 Sq Ft

  40 Sunset Rd, Great Neck, NY 11024

  A Rare opportunity to own a waterfront compound on Long Island’s Gold Coast within the prestigious Village of Kings Point ,New York. This gated and fenced 1.02-acre estate sits within a private cul-de-sac and offers a 185-foot deep-water private pier and sea wall promenade with stunning views of the Manhattan skyline. The main Colonial-style residence features three full floors and basement

  Lisa Testagrose Coldwell Banker American Homes

  40 Sunset Rd, Great Neck, NY 11024
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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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  /116

  $595,000

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

  7 Western Ave, Amsterdam, NY 12010

  Charlton - Galway SD - TWO for the price of one! This exceptional property is a botanist's/horticulturist's dream! 1.68 carefully cultivated acres w/orchard, mature perennials, rare trees & specimens, vege garden, Japanese tea room w/koi pond & plant/seedling stands. This property is locally known for its beauty w/many having taken bonsai classes here. The main home is a 3BR/1BA/2car ranch

  Kathleen Gordon Inglenook Realty Inc

  7 Western Ave, Amsterdam, NY 12010
• 

  

  

  /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 Open Sat 11AM - 12:30PM

  • 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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  /18

  $1,250,000

  • 5 Beds
  • 4.5 Baths
  • 1,950 Sq Ft

  884 Brooklyn Ave, Brooklyn, NY 11203

  This beautiful home at 884 Brooklyn Ave. in Prime East Flatbush is located on a peaceful, tree-lined street and offers everything homebuyers look for. First floor: Spacious, airy, sun-drenched living room & dining room (flex 1 bedroom or office), powder room, Breathtaking oversized chef's kitchen leading to a welcoming patio / private deck, backyard & parking garage. Second floor: 3

  Dov Chein BROOKLYN VERTICAL INC

  884 Brooklyn Ave, Brooklyn, NY 11203
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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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  /50

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  90 Main St, Chester, NY 10918

  "The House on the Hill" Proudly offered for the first time in over 70 years. This expansive and character-rich home overlooks the heart of the village while offering nearly 10 acres of space, privacy, and endless potential. Set across three separate parcels totaling 9.68 acres, the property features a main house with approximately 4,000 sq ft, a charming 2-bedroom guest cottage, a large dairy

  STEVEN WROBEL JR. Serhant LLC

  90 Main St, Chester, NY 10918
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  /30

  $175,000

  • 7 Beds
  • 3 Baths
  • 2,450 Sq Ft

  72 S Judson St, Gloversville, NY 12078

  Attention investors and owner occupants alike! This 3 unit Gloversville home features a main house and rear house. Main house is comprised of two 3 bedroom units. Back house is a 1 bedroom unit. All 3 apartments are spacious. Property features off street parking and separate utilities

  Robert Taylor KW Platform

  72 S Judson St, Gloversville, NY 12078
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  /60

  $895,000

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

  60 Cooper St, Lake George, NY 12845

  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 large main bathroom. Attached is a complete 2 bedroom 1 bath

  Allen Van Hoff Howard Hanna

  60 Cooper St, Lake George, NY 12845
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  /44

  $1,299,000

  • 5 Beds
  • 3 Baths
  • 3,696 Sq Ft

  3207-3209 New York 212, Bearsville, NY 12409

  Enchanting Woodstock Compound with Craftsman Home, Historic Barn & Cottage. Welcome to a truly rare offering in the heart of the Catskills—just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring three distinct

  Michelle Bergkamp Corcoran Country Living

  3207-3209 New York 212, Bearsville, NY 12409
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  /64

  $3,800,000

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

  153 County Road 6, Germantown, NY 12526

  Down a long, picturesque driveway, just around the corner from the exquisite Clermont Historic Estate, lies Barnswood, a strapping country compound on eight sprawling acres.The grounds at Barnswood were once part of the extensive Livingston estate established in the 1600s, and were reunited with the Livingston family at the turn of the 20th century when Alice and John Henry Livingston

  Raj Kumar Four Seasons Sotheby's Int.

  153 County Road 6, Germantown, NY 12526
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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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  /50

  $4,500,000

  • 4 Beds
  • 5 Baths
  • 8,750 Sq Ft

  161 Piping Rock Rd, Locust Valley, NY 11560

  LOCUST VALLEY. Set behind a long, private drive in the heart of Locust Valley, this elegant estate spans over 3 acres of lush, manicured grounds and gardens —offering serenity, sophistication, and the ultimate in estate-style living. Built in 1924 and recently modernized, the stately Colonial main residence is timeless in its design, seamlessly blending classic charm with updated finishes;

  Maria Babaev Douglas Elliman Real Estate

  161 Piping Rock Rd, Locust Valley, NY 11560
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  /60

  $3,490,000

  • 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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  /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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  /15

  $469,000

  • 4 Beds
  • 4 Baths
  • 2,719 Sq Ft

  310 Old Kings Hwy, Saugerties, NY 12477

  Spectacular stone waterfront home . . Stunning Plattekill Creek frontage, unbelievable grounds with mature plantings. The home has amazing period details- huge hearth fireplace, wideboard floors, gracious center hall entryway and hand hewn beams. Guest house/artist retreat- with water views.. This is an incomparable property ! Minutes from Woodstock/Saugerties/Kingston! Glorious!

  Thomas Fedorson Greene County Realty

  310 Old Kings Hwy, Saugerties, NY 12477
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  /32

  $1,199,000

  • 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

  $1,974,999

  • 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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  /33

  $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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  /53

  $799,900

  • 5 Beds
  • 2 Baths
  • 1,768 Sq Ft

  5387-5391 New York 8, Chestertown, NY 12817

  Experience rustic charm and modern comfort in this beautifully renovated farmhouse with 173 feet of direct lakefront and a private beach. Ideal as a year-round home, seasonal retreat, or income-generating rental, it features 5 spacious bedrooms and 2 full baths. The large backyard includes a versatile two-season outbuilding—great for parties or intimate weddings. Enjoy paddle boards, kayaks, a

  Philomena Prinzo Howard Hanna Capital Inc

  5387-5391 New York 8, Chestertown, NY 12817
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  /40

  $2,450,000

  • 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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  /41

  $1,300,000

  • 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 Open Sat 11AM - 1PM

  • 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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  /41

  $6,500,000

  • 4 Beds
  • 4.5 Baths
  • 4,370 Sq Ft

  14 Heather Ln, Huntington, NY 11743

  A Rare Waterview Lloyd Harbor GemPrepare to be captivated by this extraordinary, fully renovated waterview residence offering sweeping, unobstructed views of Lloyd Harbor extending all the way to Connecticut. This home is more than a place to live—it's a lifestyle. With water vistas from every room and just steps to a private association beach, this property seamlessly blends luxury, comfort,

  DiAnne Gale Daniel Gale Sothebys Intl Rlty

  14 Heather Ln, Huntington, NY 11743
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  /49

  $798,000

  • 3 Beds
  • 4 Baths
  • 3,375 Sq Ft

  280 Newton Rd, Stephentown, NY 12169

  The historic Newton House, an 1800's homestead with modern amenities, situated along the Black River. Main House built in 1826 by Ezra Newton, and the family ran a general store in what is now the guest house.Modern improvements include a POOL HOUSE with Endless Wave Pool, Jacuzzi, Suana, and Exercise Area.MAIN HOUSE fully renovated but maintains 1800's character. Newly constructed 2nd

  Jeffrey McKinney Beach & Bartolo Realtors Inc

  280 Newton Rd, Stephentown, NY 12169
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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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  /35

  $1,695,000

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

  15 Old Farm Rd, Rhinebeck, NY 12572

  Tucked on a quiet private road under ten minutes from Rhinebeck Village, this 5-bedroom custom craftsman estate offers beautiful, high quality art-deco style for those seeking a break from the sea of sterile new builds and stark modernism. Built with the utmost quality, oak floors, premium custom windows and doors, and brass hardware throughout. A bevy of high technology make the home energy

  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

  $3,495,000

  • 2 Beds
  • 2 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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  /55

  $350,000

  • 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 currently operates as a 1-bedroom

  Krista Polumbo Coldwell Banker Prime Properties

  197 Stanton Rd, Shushan, NY 12873
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  /6

  $150,000

  • Land
  • 4.50 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
• 

  

  /88

  $549,000

  • 12 Beds
  • 12 Baths

  3314 U S 9, Hudson, NY 12534

  Investment Opportunity! Diverse Income-Generating Property on 2.45 Acres! Welcome to a unique investment opportunity nestled in a serene setting, boasting a diverse portfolio of rental units that promise reliable cash flow and growth potential. This property features a four-unit apartment building, a charming cottage, two mobile homes, as well as additional income from garages and storage units,

  Barbara Robinson Red Apple Realty

  3314 U S 9, Hudson, NY 12534
• 

  

  /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 or 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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