Windham, NY Homes

• 

  

  

  /22

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  69 Windham Ridge Rd Unit 16F, Windham, NY 12496

  Windham Ridge Townhouse with Ski Slope Views in the ever growing and popular town of Windham.This charming townhouse offers expansive ski slope views and a spacious, open living area that seamlessly flows into the kitchen, complete with a cozy fireplace. It features three bedrooms, including one ideally suited for small children or as a nursery, conveniently located adjacent to the primary

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 897-3745

  69 Windham Ridge Rd Unit 16F, Windham, NY 12496
• 

  

  

  /40

  $42,000 per month

  • 5 Beds
  • 4.5 Baths
  • 2,765 Sq Ft
  • House for Rent

  24 Windham View Rd, Windham, NY 12496

  Fantastic Winter Rental! A warm abundance of natural light greets you as you enter this beautiful 5-bedroom 4.5 bath Contemporary Home. Situated on a quiet road with outstanding views of Windham Mountain. This home offers you a perfect getaway to enjoy a memorable winter season, less than 5 minutes to the slopes! Perfect share for 2 families, plenty of sleeping, plenty of privacy!The

  Patricia Charbonneau Brainard Ridge Management

  24 Windham View Rd, Windham, NY 12496
• 

  

  

  /34

  $420,000 Sold Jul 14, 2025

  • 1,486 Sq Ft
  • $283/SF
  • 33 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1847

  296 Mitchell Hollow Rd, Windham, NY 12496

  Fully Furnished! | Hemlock Cabin | 296 Mitchell Hollow Road | Windham, NY - Tucked away on a coveted country road just three minutes from the Windham Mountain Club, the Hemlock Cabin blends rustic character with modern comfort in one of the Catskills' most sought-after year-round destinations. Sided with durable hemlock with copper detailing, this charming cape sits on 1.1 acres with a large yard

  Allison Morelle Coldwell Banker Village GreenK

  296 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  

  /16

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 889 Sq Ft

  605 Old Rd, Windham, NY 12496

  605 Old Rd, Windham, NY 12496
• 

  

  

  /28

  $314,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  5359 Main St Unit 2C, Windham, NY 12496

  Move-in ready and selling with a fully furnished option! Perfectly positioned on Main Street and only a one-minute drive to Windham Mountain, this beautifully designed 2-bedroom, 2- full bath condo offers a unique blend of character, convenience, and charm. Located above the Tap House Grille with a front facing view of main street and a view of the ski mountain off the back porch! This

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 600-2711

  5359 Main St Unit 2C, Windham, NY 12496
• 

  

  /10

  $1,300 per month

  • 1 Bed
  • 1 Bath
  • 940 Sq Ft
  • Apartment for Rent

  105 Cross Rd, Windham, NY 12496

  Beautiful Apartment in Windham - Convenient Location!This charming apartment is perfectly situated in Windham, just minutes from scenic hiking trails and right off Route 23, offering easy access to Catskill, Cairo, and Hudson. Whether you're here for work or play, you'll love the peaceful surroundings and unbeatable convenience. Ideal for commuters, nature lovers, or anyone looking to enjoy

  Carlos Rodriguez Dugo Realty

  105 Cross Rd, Windham, NY 12496
• 

  

  /9

  $75,000 Sold Jul 11, 2025

  • Land
  • 1.70 Acres
  • $44,118 per Acre

  • 61 Days On Market

  611 Old Rd, Windham, NY 12496

  This lovely 1.7 acre lot is located on a quiet well maintained road. Close to the Town of Windham, Windham Mt. Club, Hunter Mt., golf, hiking and all that Windham & Hunter areas have to offer. What a spot to build your dream home. This property is mostly flat, making it easy to put a driveway in. There is 250 ft. of road frontage, 100 ft.from a private lake, with a few branches removed there

  Mary Donovan Gallagher & Company

  611 Old Rd, Windham, NY 12496
• 

  

  /25

  Not Listed For Sale

  • 3 Beds

  0 Route 10, Windham, NY 12496

  0 Route 10, Windham, NY 12496
• 

  

  /35

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  16 Hickory Hill Rd, Windham, NY 12496

  This gem has direct views of Windham slopes, proximity to golf courses, Windham Village, restaurants, and walking paths, makes it a captivating endeavor. Renovated in 2022 with new roof, skylights and custom kitchen, This property boasts a prime location in a vibrant 4-season community. Offering 3 bedrooms and 2 baths, it includes a sunroom, a fully equipped kitchen featuring a 6-burner

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 667-9038

  16 Hickory Hill Rd, Windham, NY 12496
• 

  

  /49

  $2,250 per month

  • 2 Beds
  • 1.5 Baths
  • 779 Sq Ft
  • Apartment for Rent

  52 County Road 65a Unit . 2, Hensonville, NY 12439

  Newly updated, Fully Furnished - Custom 1-bedroom apartment located in Hensonville, just minutes from Windham. This spacious unit is filled with natural light and features a unique loft bedroom with two beds—perfect for guests. Ideal for a long-term tenant or those seeking a weekend getaway from the city. Enjoy the peace and privacy of a quiet setting with a grassy backyard and a relaxing creek

  Caitlin Cucchiella Core Real Estate Team

  52 County Road 65a Unit . 2, Hensonville, NY 12439
• 

  

  /82

  $522,500 Sold Jul 03, 2025

  • 4,014 Sq Ft
  • $130/SF
  • 141 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 2004

  231 County Route 65, Windham, NY 12496

  A Spectacular Home with 6 Bedrooms, 3 1/2 Baths, & 3 Floors with over 4,000 Sq Ft in Windham with Beautiful Mountain Views! The home could be an extraordinary Airbnb, an impressive family destination near Windham Ski Mountain, or a grand primary home. The main floor features a family room with a pellet stove, a living room with a fireplace, a 1/2 bath, & a kitchen with a dining area. The 2nd

  Theodore Banta III RVW Select Properties

  231 County Route 65, Windham, NY 12496
• 

  

  /28

  Est $411,519 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  904 N Settlement Rd, Windham, NY 12496

  904 N Settlement Rd, Windham, NY 12496
• 

  

  /29

  $1,200,000

  • 4 Beds
  • 3.5 Baths
  • 1,614 Sq Ft

  490 Mill St, Windham, NY 12496

  Windham - ''The Place to Be!''Perched to capture panoramic views of the surrounding mountains and Windham's ski slopes, this beautifully crafted cedar home offers the perfect year-round escape in the heart of the Catskills. Just minutes to Windham Village, you'll enjoy easy access to golf courses, breweries, restaurants, walking paths, live venues, and all the four-season attractions this

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 759-7415

  490 Mill St, Windham, NY 12496
• 

  

  /28

  $2,250 per month

  • 2 Beds
  • 1.5 Baths
  • 776 Sq Ft
  • Apartment for Rent

  52 Route 65a Unit . 1, Hensonville, NY 12439

  Newly updated, Fully Furnished - Custom 1-bedroom apartment w/ 2 beds located in Hensonville, just minutes from Windham. This spacious unit is filled with natural light and features a unique loft bedroom with two beds—perfect for guests. Ideal for a long-term tenant or those seeking a weekend getaway from the city. Enjoy the peace and privacy of a quiet setting with a grassy backyard and a

  Caitlin Cucchiella Core Real Estate Team

  52 Route 65a Unit . 1, Hensonville, NY 12439
• 

  

  /51

  $999,999 Sold Jul 03, 2025

  • 3,260 Sq Ft
  • $307/SF
  • 540 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1996

  39 White Way, Windham, NY 12496

  Location! Location! Location! Looking for a ski-on/ski-off home at Windham Mountain Club? Look no further! Situated on the East mountain, this home has spectacular panoramic views capturing the picturesque mountains, valley and town below. This impressive and sundrenched 6-bedroom, 4-bathroom contemporary home is just 50 ft from trail access. The main level boasts an expansive living area with an

  Regina Tortorella Coldwell Banker Village GreenW

  39 White Way, Windham, NY 12496
• 

  

  /48

  Est $524,188 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 2,404 Sq Ft

  50 County Rd Unit 65, Windham, NY 12496

  50 County Rd Unit 65, Windham, NY 12496
• 

  

  /35

  $699,000

  • 5 Beds
  • 3 Baths
  • 2,640 Sq Ft

  134 Magda Ln, Windham, NY 12496

  Charming Country Retreat Just Minutes to Windham Nestled on a private dead-end road just minutes from Windham's slopes, golf courses, and vibrant village, this beautifully renovated 5-bedroom, 3-bath home sits on 5.5 acres of peaceful country setting. Blending timeless country charm with modern style, the home features warm wood floors, an inviting open kitchen and dining area, and multiple

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 413-0731

  134 Magda Ln, Windham, NY 12496
• 

  

  /30

  $12,000 per month

  • 3 Beds
  • 2 Baths
  • 786 Sq Ft
  • Townhouse for Rent

  121 Brainard Ridge Rd, Windham, NY 12496

  It's never too early to secure your ski season rental. This bright and cozy 3-bedroom, 2-bath townhouse sits right on the side of Windham Mountain Club, offering easy access to the slopes. Walk to the mountain or take a quick drive into town for dining and shopping.Inside, you'll find an inviting space with plenty of natural light, a wood-burning fireplace, and a deck with beautiful mountain

  Alexis Amico Dugo Realty

  121 Brainard Ridge Rd, Windham, NY 12496
• 

  

  /45

  $521,000 Sold Jul 02, 2025

  • 1,840 Sq Ft
  • $283/SF
  • 39 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1986

  13 Boulder Brook Rd, Windham, NY 12496

  Location is everything, this home is situated on 3.60 peaceful acres. Wonderful view of Windham Mountain, a lovely swimming, spring fed pond. There are currently 4 homes in this development, plenty of privacy. Beautiful views from every window in this light and bright home There are 2 entrances, each with mudrooms. Two full upgraded baths. Kitchen has lovely breakfast bar, plenty of storage, it

  Mary Donovan Gallagher & Company

  13 Boulder Brook Rd, Windham, NY 12496
• 

  

  /38

  Est $386,904 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,168 Sq Ft

  251 County Route 65, Hensonville, NY 12439

  

  251 County Route 65, Hensonville, NY 12439
• 

  

  /16

  $249,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  40 Quads Way, Windham, NY 12496

  Mountain Retreat Just Minutes from Windham Slopes!Welcome to your perfect four-season getaway! This spacious 2-bedroom, 2-bath condo offers the ideal mix of comfort, convenience, and recreation in one of the Catskills' most sought-after communities.Enjoy après-ski evenings by the cozy fireplace, summer mornings on your private deck, or a relaxing soak in the hot tub after a day of hiking. The

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 601-3455

  40 Quads Way, Windham, NY 12496
• 

  

  /24

  $2,250 per month

  • 2 Beds
  • 1.5 Baths
  • 779 Sq Ft
  • Apartment for Rent

  52 Route 65a Unit . 2, Hensonville, NY 12439

  Interested renters, submit your application through RentSpree:

  Caitlin Cucchiella Core Real Estate Team

  52 Route 65a Unit . 2, Hensonville, NY 12439
• 

  

  /30

  $490,000 Sold Jun 20, 2025

  • 1,916 Sq Ft
  • $256/SF
  • 96 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1922

  3 Begley Rd, Windham, NY 12496

  Price Improvement!! Who doesn't want to live in the house on the hill, minutes to the Windham Mountain Club? Perched high above the road with views of Windham Mountain, this classic country house has been a beloved family vacation home for over 20 years and a well-reviewed short term rental. Will you be the one to write its next chapter? Spacious and yet cozy (think Hygge!) the flexible floor

  Jessica Surbeck WINDSTAR REALTY GROUP LLC

  3 Begley Rd, Windham, NY 12496
• 

  

  /17

  Est $540,015 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,017 Sq Ft

  120 Mount Greenery Rd, Windham, NY 12496

  120 Mount Greenery Rd, Windham, NY 12496
• 

  

  /28

  $549,500

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft

  215 Siam Rd, Windham, NY 12496

  Nestled in the scenic beauty of Windham, NY, this unique octagon house offers a truly one-of-a-kind retreat close to skiing, golf, and hiking adventures. Set on over 5 acres of parklike surroundings, this property provides plenty of space for relaxation and exploration. The main home features 3 bedrooms and 2.5 baths, offering comfort and charm with stunning mountain views with surround windows

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 757-0479

  215 Siam Rd, Windham, NY 12496
• 

  

  /55

  $65,000 per month

  • 5 Beds
  • 5.5 Baths
  • 3,643 Sq Ft
  • Townhouse for Rent

  292 South St, Windham, NY 12496

  Your 2024-2025 Windham Vacation Rental awaits! Nestled at the edge of Windham Mountain Club's North Lot, this stunning property offers unparalleled convenience and luxury for large groups and ski enthusiasts alike. Here's why this property is perfect vacation rental for the upcoming 2024-2025 ski season:Key Features & Amenities*Sleeps 12 comfortably with 1 king bed, 3 queen beds, and 2 sets of

  Regina Tortorella Coldwell Banker Village GreenW

  292 South St, Windham, NY 12496
• 

  

  /59

  $875,000 Sold Jun 20, 2025

  • 2,342 Sq Ft
  • $374/SF
  • 196 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1940

  216 New York 296, Windham, NY 12496

  Discover the perfect blend of modern comfort and serene seclusion in this 2,342 sq ft, 3 bed/3 bath contemporary Cape. Located in the heart of Windham yet offering complete privacy, this home is a tranquil retreat. Renovated in 2005, it features a chef's kitchen, a comfortable living room with a wood-burning fireplace, and French doors that lead to a stone patio ideal for entertaining. The main

  Beth Alfeld Keller Williams Realty HV Nort

  216 New York 296, Windham, NY 12496
• 

  

  /57

  Est $1,134,997 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,316 Sq Ft

  38 Galway Rd, Windham, NY 12496

  

  38 Galway Rd, Windham, NY 12496
• 

  

  /24

  $319,000

  • 2 Beds
  • 2.5 Baths
  • 1,178 Sq Ft

  63 Windham Ridge Rd Unit 16C, Windham, NY 12496

  Welcome to the sought after Town of Windham to this beautiful Townhouse complex of Windham Ridge. 4 Seasons Community that offers a fantastic opportunity for outdoor enthusiasts and those looking for a cozy retreat. Located near the Village, it is close to a variety of amenities, including restaurants, shops and movie theaters while still providing the serenity and access to outdoor activities

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 559-2706

  63 Windham Ridge Rd Unit 16C, Windham, NY 12496
• 

  

  /44

  $840,000 Sold Jun 20, 2025

  • 2,294 Sq Ft
  • $366/SF
  • 31 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2003

  429 Mill St, Windham, NY 12496

  Discover serenity in this exquisite cedar contemporary home with seasonal slope views nestled in a private wooded setting, just 5 minutes from the charming resort town of Windham and a mere 2.5 hours outside of New York City. This stunning property offers a harmonious blend of rustic charm and modern amenities. Step inside to find a home that radiates warmth and sophistication. Hardwood floors

  Regina Tortorella Coldwell Banker Village GreenW

  429 Mill St, Windham, NY 12496
• 

  

  /7

  Est $182,368 Not Listed For Sale

  • 2 Beds

  32 Hickory Hill Rd, Windham, NY 12496

  32 Hickory Hill Rd, Windham, NY 12496
• 

  

  /13

  $99,000

  • Land
  • 8 Acres
  • $12,015 per Acre

  539 Route 40, Maplecrest, NY 12454

  Centrally located between Windham and Hunter, minutes to CD Lane Park, State hiking trails, Colgate Lake and everything this area has to offer. This 8 + acre parcel has a septic design in place designed by Kaaterskill Engineering and submitted to DEP and approved. This makes this lot desirable with no soil testing and design which could usually take Months and Money.cleared closer to road which

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 809-8670

  539 Route 40, Maplecrest, NY 12454
• 

  

  /15

  $212,500 Sold Jun 13, 2025

  • Land
  • 10 Acres
  • $21,250 per Acre

  • 57 Days On Market

  0 Ruland Rd Unit 155000, Windham, NY 12454

  Secluded 10-acre building lot with stream, cascading waterfall, mountain views, underground utilities and fiber optic cable run to property, all bordered by thousands of acres of protected forest owned by the state and city of NY. Underground utilities and fiber optic cable are conveniently located at the site. Additionally, there's an option to purchase the adjoining property, which includes an

  Regina Tortorella Coldwell Banker Village Green

  0 Ruland Rd Unit 155000, Windham, NY 12454
• 

  

  /10

  Est $1,143,683 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,596 Sq Ft

  99 Buckskin Loop, Windham, NY 12496

  99 Buckskin Loop, Windham, NY 12496
• 

  

  /54

  $1,495,000 Pending

  • 6 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  12 Jacob Strasse Rd, Windham, NY 12496

  Welcome to High Peak, an exquisite modern retreat perched high above Windham with uninterrupted views of Windham's High Peak mountain, and the surrounding mountains. Custom-built and thoughtfully designed across three expansive levels, this one-of-a-kind home is a rare blend of architectural precision, natural light, and breathtaking landscape. Sited on over 3 acres, the setting is as exceptional

  

  Catherine Quintard

  Compass Greater NY, LLC

  (518) 667-5945

  12 Jacob Strasse Rd, Windham, NY 12496
• 

  

  /28

  $340,000 Sold Jun 13, 2025

  • 1,440 Sq Ft
  • $236/SF
  • 188 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1969

  34 Old Rd, Windham, NY 12496

  Escape to this warm and inviting3+-bedroom, 1.5-bath home, just minutes from Windham Village and the ski slopes. Boasting a country-style kitchen with granite countertops, a cozy Harmon pellet stove insert, and beautiful hardwood floors, this home blends comfort with charm. An office space provides extra flexibility, and the laundry area can easily function as a 4th bedroom. Step outside to enjoy

  Carol Shaw Shaw Country Realty, Inc.

  34 Old Rd, Windham, NY 12496
• 

  

  /35

  Est $621,308 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  861 County Route 10, Windham, NY 12496

  861 County Route 10, Windham, NY 12496
• 

  

  /54

  $850,000

  • 8 Beds
  • 8 Baths
  • 3,712 Sq Ft

  5320 New York 23, Windham, NY 12496

  In the heart of Windham, ''the place to be,'' this rare multi-use property offers endless possibilities for residential, commercial, or mixed-use ventures. Formerly a thriving B&B, it features two buildings with a total of 8 bedrooms and 8 bathrooms, a large open kitchen plus accessory kitchen, and expansive spaces perfect for a restaurant, cafe, art studio, gallery, retail shop, or rental income

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 261-9298

  5320 New York 23, Windham, NY 12496
• 

  

  /24

  $210,000 Sold Jun 11, 2025

  • Land
  • 5.00 Acres
  • $42,000 per Acre

  • 271 Days On Market

  359 Begley Rd, Windham, NY 12496

  Beautiful 5 acre parcel in a very desirable area just waiting for you to come build your dream home. Located only 5 minutes from the heart of Windham, yet all the privacy, peace and quiet you could ask for. All the foot work has been done so you just need to find your builder. The driveway, well, underground electric and septic have all been approved and installed. The septic was designed and

  Sharon Knudsen Coldwell Banker Village Green

  359 Begley Rd, Windham, NY 12496
• 

  Est $572,059 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft

  543 N Settlement Rd, Windham, NY 12496

  543 N Settlement Rd, Windham, NY 12496

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