Windham, NY Homes

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  /30

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 1,916 Sq Ft

  5 Jacob Strasse Rd, Windham, NY 12496

  Modern Mountain Retreat just minutes from Windham Village! Looking for that perfect mix of modern style and cozy mountain living? Welcome to your dream home! This beautifully updated 4-bedroom, 3.5-bathroom escape offers over 3,000 square feet of space, set on five peaceful acres and it's just a few minutes from Windham's village shops, restaurants, and world-class ski slopes.Enter through a

  

  Christine Hinz

  Coldwell Banker Village Green

  (518) 576-1632

  5 Jacob Strasse Rd, Windham, NY 12496
• 

  

  

  /47

  $7,563 per month

  • 4 Beds
  • 2 Baths
  • 2,690 Sq Ft
  • Condo for Rent

  43 Cardinal Dr Unit ID1301703P, Windham, NY 12496

  Welcome to this cozy mountain retreat! This beautiful and spacious cabin is perfect for your next getaway, whether you’re planning a family ski trip, leaf-peeping adventure, or a weekend away with friends. Ideally located just minutes away from Windham Mountain, you can hit the slopes in no time and experience the best of what the mountains have to offer.Guests are expected to do dishes and

  43 Cardinal Dr Unit ID1301703P, Windham, NY 12496
• 

  

  

  /30

  $1,400,000 Sold Sep 18, 2025

  • 2,536 Sq Ft
  • $552/SF
  • 121 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1974

  4 The Loop, Windham, NY 12496

  Welcome to The Loop. Stunningly renovated 4 bedroom, 3 bath 2,536 Sq. Ft. contemporary home located on Windham Mountains west side. Gorgeous light filled open floor plan with eye catching brick wall kitchen, impressive wood flooring, new appliances, beautiful butcher block island and large windowed dining area. More gracious windows and commanding stone wood burning fireplace in the breathtaking

  Patricia Charbonneau Brainard Ridge Management

  4 The Loop, Windham, NY 12496
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  /45

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  4 French Park Dr Unit C-8, Windham, NY 12496

  4 French Park Dr Unit C-8, Windham, NY 12496
• 

  

  

  /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
• 

  

  /38

  $2,300 per month

  • 2 Beds
  • 2 Baths
  • 1,163 Sq Ft
  • Condo for Rent

  5359 New York 23 Unit 2E, Windham, NY 12496

  Opportunity awaits as this beautifully designed 2-bedroom 2 bath Windham condo rental a minute drive to Windham Mountain hits the market! You get the best of everything here as this property is located right on Main Street where you can find everything but also so close to the ski resort! Features include large cozy great room with dining/living room combo with 2 large windows, recessed lighting

  Wayne Newcomb Newcomb Realty Group LLC

  5359 New York 23 Unit 2E, Windham, NY 12496
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  /67

  $725,000 Sold Sep 09, 2025

  • 2,315 Sq Ft
  • $313/SF
  • 22 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2000

  8 Evans Rd, Windham, NY 12496

  Stunning 3,862 Sq Ft Windham Retreat with Ski Slope Views, Pool, A/C, Masonry Patios, Lush Landscaping, Dual 2-Car Garages & Paved Driveway. Pride of ownership radiates throughout this meticulously maintained Windham property, offering 3,862 square feet of finished living space—including a beautifully appointed lower level—in a serene, park-like setting just two minutes from the heart of

  Regina Tortorella Coldwell Banker Village GreenW

  8 Evans Rd, Windham, NY 12496
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  /46

  Est $366,236 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,211 Sq Ft

  66 Loo Bridge Ln Unit 12G, Windham, NY 12496

  66 Loo Bridge Ln Unit 12G, Windham, NY 12496
• 

  

  /38

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  4 French Park Dr Unit 2, Windham, NY 12496

  Discover this charming townhouse in Windham, ideally positioned to offer stunning views of the slopes and boasting a desirable southern exposure. This inviting property features 3 bedrooms and 2 baths, perfect for a family or as a rental investment. The loft area provides additional space, suitable for a home office or extra sleeping quarters. The third bedroom is small but perfect for sleeping 2

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 856-8446

  4 French Park Dr Unit 2, Windham, NY 12496
• 

  

  /65

  $12,000 per month

  • 5 Beds
  • 2 Baths
  • Condo for Rent

  8 Ruland Rd Unit ID1301712P, Maplecrest, NY 12454

  Escape to The Quad Six, a spacious and stylish 5-bedroom, 2-bathroom retreat nestled in the heart of Windham, NY. Perfectly located between Hunter and Windham ski mountains, this home offers the best of the Catskills—whether you’re hitting the slopes, hiking scenic trails, or simply unwinding in nature. With two large living rooms, there’s space for your group to gather, play games, or curl up

  8 Ruland Rd Unit ID1301712P, Maplecrest, NY 12454
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  /75

  $1,450,000 Sold Sep 05, 2025

  • 4,140 Sq Ft
  • $350/SF
  • 55 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2017

  16 High Rd W, Windham, NY 12496

  Ski Slope Views, Stream, Designer Finishes - Fully Furnished & Move-In Ready! Why Build When You Can Have It All Right Now? Escape the city in style—this is the ultimate Upstate retreat for luxury buyers looking to skip the hassle of building and move straight into a turn-key, fully furnished, designer-finished chalet. Just 2.5 hours from NYC and 10 minutes from Windham Mountain, this

  Regina Tortorella Coldwell Banker Village GreenW

  16 High Rd W, 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

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,900 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. The perfect country

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 351-7588

  215 Siam Rd, 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
• 

  

  /46

  $585,000 Sold Aug 29, 2025

  • 1,510 Sq Ft
  • $387/SF
  • 181 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  14 - 57 Windham Mountain Village, Windham, NY 12496

  Don't miss out on this extraordinary opportunity to own a stunning townhouse at the base of Windham Mountain Club...an ideal haven for skiing enthusiasts! This beautifully maintained 3-bedroom, 3-bathroom home is just steps from the slopes, offering unparalleled convenience for your mountain adventures. As a homeowner in Windham Mountain Village, you'll enjoy exclusive access to a range of

  Russell Pelham Real Broker, LLC

  14 - 57 Windham Mountain Village, Windham, NY 12496
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  /25

  Not Listed For Sale

  • 3 Beds

  0 Route 10, Windham, NY 12496

  0 Route 10, Windham, NY 12496
• 

  

  /16

  $239,000 Pending

  • 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 apres-ski evenings by the cozy fireplace, summer mornings on your private deck, or a relaxing soak in the hot tub after a day of

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 601-3455

  40 Quads Way, Windham, NY 12496
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  /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
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  /33

  $283,500 Sold Aug 26, 2025

  • 1,290 Sq Ft
  • $220/SF
  • 47 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2020

  71 County Road 65 Unit 4, Hensonville, NY 12439

  Built in 2020 and maintained to like-new condition, this contemporary townhome offers sleek design, quality construction, and versatile appeal - perfect whether you're seeking a turnkey rental or a full-time residence.The bright, open-plan living area flows onto a private deck ideal for outdoor dining, relaxing, or entertaining. The sleek kitchen showcases maple cabinetry and modern finishes,

  Susanna Scott-Mitchell Compass Greater NY, LLC

  71 County Road 65 Unit 4, Hensonville, NY 12439
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  /34

  Est $1,480,868 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,359 Sq Ft

  21 Sundance Dr, Windham, NY 12496

  21 Sundance Dr, Windham, NY 12496
• 

  

  /21

  $319,000

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

  63 Windham Ridge Rd, Windham, NY 12496

  Welcome to the sought after Town of Windham to this beautiful Townhouse complex of Windham Ridge,a 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) 855-3425

  63 Windham Ridge Rd, Windham, NY 12496
• 

  

  /43

  $518,000 Sold Aug 21, 2025

  • 1,450 Sq Ft
  • $357/SF
  • 59 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2020

  996 County Route 10, Windham, NY 12496

  Crafted in 2020 by the renowned Vermont Frame Company, this beautifully designed timber frame home combines timeless craftsmanship with modern convenience. Featuring traditional mortise and tenon joinery and exposed post-and-beam construction, the home exudes warmth, character, and durability.The main level offers 1,450 sq ft of thoughtfully designed living space with soaring vaulted

  Lisa Jaeger Coldwell Banker Village GreenW

  996 County Route 10, Windham, NY 12496
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  /28

  Est $460,498 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
• 

  

  /28

  $305,000

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

  5359 Main St Unit 2C, Windham, NY 12496

  Thinking about ski season? You're not alone. Location is key. Move-In Ready with Option to Buy Fully Furnished!Located right on Main Street and just a one-minute drive to Windham Mountain, this beautifully designed 2-bedroom, 2-bath condo is single-level and also includes a flex space that can be used as a home office, guest room, etc — whatever works best for your lifestyle.Situated

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 600-2711

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

  

  /43

  $927,000 Sold Aug 15, 2025

  • 1,944 Sq Ft
  • $477/SF
  • 30 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  92 Northridge Exd, Windham, NY 12496

  Charming Log Home Retreat Near Windham Mountain: Ideal for Nature Enthusiasts!Discover the perfect blend of adventure and relaxation with this stunning log home, nestled in a serene location just a stone's throw from the exciting slopes of Windham Mountain. Embrace the beauty of nature with convenient access to skiing, hiking, mountain biking, dining, golf, and more.Property

  Mark McAlpine Compass Greater New York, LLC

  92 Northridge Exd, Windham, NY 12496
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  /48

  Est $540,797 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
• 

  

  /39

  $359,000

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  4 French Park Dr Unit 1 (2a), Windham, NY 12496

  Discover this charming townhouse in Windham, ideally positioned to offer stunning views of the slopes and boasting a desirable southern exposure. This inviting property features 3 bedrooms and 2 baths, perfect for a family or as a rental investment. The loft area provides additional space, suitable for a home office or extra sleeping quarters. The third bedroom is small but perfect for sleeping 2

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 808-3327

  4 French Park Dr Unit 1 (2a), Windham, NY 12496
• 

  

  /17

  $65,000 Sold Aug 14, 2025

  • Land
  • 5.01 Acres
  • $12,974 per Acre

  • 291 Days On Market

  Tbd Hollow View Rd, Windham, NY 12496

  Extremely private and only accessible via a gated road, Hollow View Rd in Windham offers the ultimate privacy and security for your dream home. On 5.01 sloped acres, this private, dead end road retreat is tucked away providing the peace and quiet you've been looking for.This sleepy road is hosts many large, beautiful homes going up the mountain. Close to skiing, and the many shops and

  Arlena Armstrong Anatole House LLC

  Tbd Hollow View Rd, Windham, NY 12496
• 

  

  /38

  Est $405,986 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
• 

  

  /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
• 

  

  /15

  $81,500 Sold Aug 13, 2025

  • Land
  • 1.2 Acres
  • $67,917 per Acre

  • 268 Days On Market

  1 - 886 Mill St, Windham, NY 12496

  Best land deal in Windham! Looking for the right property with mountain views to build your dream home in Windham without breaking the bank- your search is over! This gorgeous parcel is a sunny south facing meadow-like setting with lovely mountain views and seasonal views of Windham Mt Club slopes. The land has been meticulously prepared for your vision, complete with a property survey,

  Lisa Jaeger Coldwell Banker Village GreenW

  1 - 886 Mill St, Windham, NY 12496
• 

  

  /17

  Est $585,080 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
• 

  

  /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
• 

  

  /31

  $550,000 Sold Aug 08, 2025

  • 2,270 Sq Ft
  • $242/SF
  • 119 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1972

  89 Siam Rd, Windham, NY 12496

  New Price! Swiss Chalet-inspired home close proximity to Windham's Main Street and Windham Mt Club Resort. This cozy fully furnished 5-bedroom, 2-bath home spans 2,270 sq ft offers an inviting blend of rustic warmth with a touch of modern sophistication. The moment you step inside, you'll be captivated by 2- authentic bluestone fireplaces and wood beamed ceilings that imbue that alpine vibe. The

  Lisa Jaeger Coldwell Banker Village GreenW

  89 Siam Rd, Windham, NY 12496
• 

  

  /57

  Est $1,186,588 Not Listed For Sale

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

  38 Galway Rd, Windham, NY 12496

  

  38 Galway Rd, Windham, NY 12496
• 

  

  /28

  $525,000

  • 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
• 

  

  /54

  $1,350,000 Sold Aug 08, 2025

  • 5,500 Sq Ft
  • $245/SF
  • 41 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1988

  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

  12 Jacob Strasse Rd, Windham, NY 12496
• 

  

  /7

  Est $185,589 Not Listed For Sale

  • 2 Beds

  32 Hickory Hill Rd, Windham, NY 12496

  32 Hickory Hill Rd, Windham, NY 12496
• 

  

  /19

  $334,900

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft

  504 Route 40, Maplecrest, NY 12454

  Nestled in the quaint hamlet of Maplecrest, this inviting 2-bedroom home offers the perfect blend of tranquility and convenience. Ideally located between Windham and Hunter Mountains, it's just minutes from world-class skiing, hiking, golf, and other outdoor adventures. Enjoy easy access to nearby CD Lane Park, Colgate Lake, and the iconic Kaaterskill Falls.This home boasts a semi-finished

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 759-6904

  504 Route 40, Maplecrest, NY 12454
• 

  

  /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

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