4,482

Windham, NY Homes

Section Image
  • /16

    $750,000

    • Land
    • 0.58 Acre
    • $1,293,103 per Acre

    247 Club Rd, Windham, NY 12496

    The Last True Ski-On/Ski-Off Lot at Windham Mountain—Step Out & Ski!This is the one and only true ski-on/ski-off lot available at Windham Mountain Club! Imagine waking up to breathtaking mountain views, stepping outside, putting on your skis, and gliding directly onto the slopes—no walking, no hassle, just pure ski-in/ski-out convenience. Located at the end of a no-outlet road, this prime

    Regina Tortorella Coldwell Banker Village GreenW

    247 Club Rd, Windham, NY 12496
    • /15

      Not Listed For Sale

      2942 County Route 10, Windham, NY 12496

      • 4 Beds
      • 1 Bath
      • 2,320 Sq Ft
      • Built 1790
      2942 County Route 10, Windham, NY 12496

      Last Sold Summary

      • $93/SF
      • 394 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  • /41

    $1,400,000

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    17 Stonewall Ln, Windham, NY 12496

    Set within the natural beauty of the Windham Mountain Club, Stonewall Glen is a private mountain enclave defined by thoughtful design, understated luxury, and a deep connection to its surroundings. Conceived as a retreat for those who value privacy, craftsmanship, and a slower rhythm of living, the community offers a refined setting for gathering, entertaining, or quiet escape amid the Catskills’

    John Oliveira Douglas Elliman Real Estate

    17 Stonewall Ln, Windham, NY 12496
    • /22

      Est $387,990 Not Listed For Sale

      278 Big Hollow Rd, Maplecrest, NY 12454

      • 3 Beds
      • 2 Baths
      • 1,908 Sq Ft
      • Built 1979
      278 Big Hollow Rd, Maplecrest, NY 12454

      Last Sold Summary

      • 118% Above List Price
      • $93/SF
      • 19 Days On Market

      Last Sold Price $178,000

      Last Listing Agent Mary King Past Member

  • /41

    $155,000

    • Land
    • 5.99 Acres
    • $25,876 per Acre

    Tbd, Windham, NY 12496

    Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

    Kyla Thomas Howard Hanna Rand Realty

    Tbd, Windham, NY 12496
    • /10

      Est $537,181 Not Listed For Sale

      53 Windham Mt Village, Windham, NY 12496

      • 2 Beds
      • 2 Baths
      • 1,222 Sq Ft
      • Built 1986
      53 Windham Mt Village, Windham, NY 12496

      Last Sold Summary

      • 87% Above List Price
      • $235/SF
      • 143 Days On Market

      Last Sold Price $287,000

      Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  • /18

    $3,400,000

    • 6 Beds
    • 5 Baths
    • 5,000 Sq Ft

    209 Club Rd, Windham, NY 12496

    This is the mountain house everyone else wishes they'd found first. Set on one of Windham's most coveted lots, this 6-bedroom, 5-bath home combines true slope-side access with panoramic views that stretch across the Catskills. It's a genuine ski-in, ski-out property with easy access to Wonderama and Lower Wipeout. In the mornings, clip in and go. At day's end, you can choose your own finale, take

    Patricia Charbonneau Brainard Ridge Management

    209 Club Rd, Windham, NY 12496
    • /10

      Est $626,093 Not Listed For Sale

      225 South St, Windham, NY 12496

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1951
      225 South St, Windham, NY 12496

      Last Sold Summary

      • 205% Above List Price
      • $159/SF
      • 120 Days On Market

      Last Sold Price $205,000

      Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  • /77

    $2,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,600 Sq Ft

    90 Club Rd, Windham, NY 12496

    Spectacular mountain views and steps away from the trails, this chalet is a Windham Mountain classic! One of the original homes on the mountain, it combines rustic charm with modern amenities. The heart of this home is its expansive great room perfect for relaxing after a day on the slopes or entertaining friends and family. Soaring cathedral ceilings with exposed wood beams add a sense of

    Sharri Cunningham Bunce Realty

    90 Club Rd, Windham, NY 12496
    • /2

      Est $588,839 Not Listed For Sale

      79 Windham Mt Village, Windham, NY 12496

      • 2 Beds
      • 2 Baths
      • 1,222 Sq Ft
      • Built 1986
      79 Windham Mt Village, Windham, NY 12496

      Last Sold Summary

      • 120% Above List Price
      • $219/SF
      • 234 Days On Market

      Last Sold Price $267,500

      Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  • /11

    $100,000

    • Land
    • 5 Acres
    • $20,000 per Acre

    174 High Peak Rd, Windham, NY 12496

    Owner is offering five acres to be taken out of a larger 352-acre parcel. Additional acreage is available, price to be determined depending on how many acres purchased. Survey map shows potential lot layout, but actual lot lines, taxes, assessment and lot numbers need to be determined. Don't miss this rare opportunity to own your dream of 5, 10, 20, or 30 acres+ on beautiful High Peak Road in

    Fred Mazza Bunce Realty

    174 High Peak Rd, Windham, NY 12496
    • /28

      Est $2,323,838 Not Listed For Sale

      200 Club Rd, Windham, NY 12496

      • 4 Beds
      • 5 Baths
      • 4,112 Sq Ft
      • Built 2011
      200 Club Rd, Windham, NY 12496

      Last Sold Summary

      • 63% Above List Price
      • $347/SF
      • 304 Days On Market

      Last Sold Price $1,425,000

      Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  • /4

    $799,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,118 Sq Ft

    69 County Road 32c, Windham, NY 12496

    • Escape NYC• Catskills Mountain Retreat• New Construction in Windham Area The proposed 2,118-square-foot home is designed for modern Catskill living, featuring soaring vaulted ceilings with exposed beams and dramatic trapezoid windows that capture natural light and panoramic views of the surrounding mountains.The open-concept layout connects the great room, kitchen, and dining area,

    John Pumilia Shaw Country Realty, Inc.

    69 County Road 32c, Windham, NY 12496
    • /10

      Est $310,007 Not Listed For Sale

      81 Windham Ridge Rd Unit 17B, Windham, NY 12496

      • 3 Beds
      • 2.5 Baths
      • 1,211 Sq Ft
      • Built 1986
      81 Windham Ridge Rd Unit 17B, Windham, NY 12496

      Last Sold Summary

      • 42% Above List Price
      • $181/SF
      • 601 Days On Market

      Last Sold Price $219,000

      Last Listing Agent Regina Tortorella Past Member

  • /41

    $2,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    22 Club Rd, Windham, NY 12496

    New Attractive Price! On Windham Mountain. This Stunning and Immaculate, Contemporary, Log and Stone, shows Pride of Ownership in this 4 bedroom, 3.5 bath Spacious living area with wonderful views and lovely stone fireplace. Spacious working kitchen with granite counters, Stainless-Viking appliances, raised bar counter with 3 stools for that quick cup of coffee in and morning. Large wood dining

    Irene Pinto Brainard Ridge Management

    22 Club Rd, Windham, NY 12496
    • /9

      Not Listed For Sale

      497 County Road 56, Maplecrest, NY 12454

      • 2 Beds
      • 1 Bath
      • 1,015 Sq Ft
      • Built 1942
      497 County Road 56, Maplecrest, NY 12454

      Last Sold Summary

      • $82/SF
      • 38 Days On Market

      Last Sold Price $83,100

      Last Listing Agent Ronnie Rebis Grist Mill Real Estate

  • /30

    $489,000

    • 4 Beds
    • 3.5 Baths
    • 2,058 Sq Ft

    274 Brooksburgh Rd Unit 48, Windham, NY 12496

    Ine of just a few larger units in Crystal Pond. First floor has mud-room, half bath with laundry, Kitchen as well ad a dining room, large living room with sliding doors to large deck, lovely stone wood burning fireplace. Lots of light in this unit. Second floor has two main bedrooms each with a full bath.as well as a separate area for home office or TV. Third level has two well sized bedrooms,

    Mary Donovan Gallagher & Company

    274 Brooksburgh Rd Unit 48, Windham, NY 12496
    • /35

      Est $763,590 Not Listed For Sale

      5088 State Route 23, Windham, NY 12496

      • 7 Beds
      • 7 Baths
      • 5,000 Sq Ft
      • Built 1960
      5088 State Route 23, Windham, NY 12496

      Last Sold Summary

      • 70% Above List Price
      • $90/SF
      • 551 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Lisa Jaeger Past Member

  • /41

    $1,345,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,856 Sq Ft

    2 Watch Hill Ln, Windham, NY 12496

    Classic Timber frame Construction, on Windham Mt., Walk to trails. Enjoy the convenience of location in this 4 bedroom 3.5 bath with attached garage to enter a large ski room with all the storage needed. Large formal entrance gives way to Spacious and Comfy Great room with large stone fireplace, vaulted ceilings and plenty of windows to let in the light and the lovely views, leads to a sizable

    Irene Pinto Brainard Ridge Management

    2 Watch Hill Ln, Windham, NY 12496
    • /33

      Not Listed For Sale

      2101 Siam Rd, Windham, NY 12496

      • 2 Beds
      • 2.5 Baths
      • 1,100 Sq Ft
      • Built 1988
      2101 Siam Rd, Windham, NY 12496

      Last Sold Summary

      • $157/SF
      • 30 Days On Market

      Last Sold Price $172,500

      Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  • /49

    $149,000

    • Land
    • 5.25 Acres
    • $28,381 per Acre

    TBD Boulder Brook Lot 13b Rd, Windham, NY 12496

    Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

    Kyla Thomas Howard Hanna Rand Realty

    TBD Boulder Brook Lot 13b Rd, Windham, NY 12496
    • /17

      Not Listed For Sale

      0 Slater Rd Unit 20161584, Maplecrest, NY 12454

      0 Slater Rd Unit 20161584, Maplecrest, NY 12454

      Last Sold Summary

      • 67 Days On Market

      Last Sold Price $8,500

      Last Listing Agent Sharon Knudsen Past Member

  • /40

    $155,000

    • Land
    • 5.99 Acres
    • $25,876 per Acre

    TBD Boulder Brook Rd Unit Lot 14, Windham, NY 12496

    Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

    Kyla Thomas Howard Hanna Rand Realty

    TBD Boulder Brook Rd Unit Lot 14, Windham, NY 12496
    • /8

      Not Listed For Sale

      0 Trailside Rd Unit 20162071, Windham, NY 12496

      0 Trailside Rd Unit 20162071, Windham, NY 12496

      Last Sold Summary

      • 178 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  • /49

    $569,900

    • Land
    • 40.02 Acres
    • $14,240 per Acre

    TBD Boulder Brook Rd Unit Lots 33-38, Windham, NY 12496

    A Rare Opportunity in the Heart of Windham, NY. Welcome to Boulder Brook, an extraordinary and rare offering in the majestic Catskills. Just minutes from the slopes of Windham Ski Resort, this private subdivision presents a unique chance to own an entire mountain retreat or select from four individually surveyed lots, all nestled along a quiet, established country road. Boulder Brook is a blend

    Kyla Thomas Howard Hanna Rand Realty

    TBD Boulder Brook Rd Unit Lots 33-38, Windham, NY 12496
    • /32

      Est $1,310,165 Not Listed For Sale

      2831 County Road 10, Windham, NY 12496

      • 4 Beds
      • 4.5 Baths
      • 4,574 Sq Ft
      • Built 2007
      2831 County Road 10, Windham, NY 12496

      Last Sold Summary

      • 66% Above List Price
      • $172/SF
      • 326 Days On Market

      Last Sold Price $788,700

      Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  • /32

    $325,000

    • 2 Beds
    • 2.5 Baths
    • 1,295 Sq Ft

    274 County Route 65 Unit 55, Windham, NY 12496

    Step into this immaculate, well furnished home! Unit being sold ''as is'', fully furnished. This Is a well maintained unit, move right in and be comfortable. There is an outside storage closet, Mud room, half bath and laundry on first level along with a lovely kitchen, granite counters, SS appliances. Lovely living room with propane fireplace, sliding doors to a patio and a bay window, Plenty of

    Mary Donovan Gallagher & Company

    274 County Route 65 Unit 55, Windham, NY 12496
    • /25

      Not Listed For Sale

      10 French Park Ct, Windham, NY 12496

      • 3 Beds
      • 2.5 Baths
      • 1,545 Sq Ft
      • Built 1987
      10 French Park Ct, Windham, NY 12496

      Last Sold Summary

      • $159/SF
      • 197 Days On Market

      Last Sold Price $245,000

      Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  • /27

    $650,000

    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft

    85 Cambridge Heights Rd, Windham, NY 12496

    Enjoy the summer months taking in the beautiful views from the large Trex decking. Warm up in front of the woodburning fireplace in the winter months. Close to Windham Mountain. A great property to enjoy all four seasons. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

    Sheila Word Coldwell Banker Village GreenW

    85 Cambridge Heights Rd, Windham, NY 12496
    • /10

      Not Listed For Sale

      5220 State Route 23, Windham, NY 12496

      • 1 Bed
      • 1 Bath
      • 458 Sq Ft
      • Built 1960
      5220 State Route 23, Windham, NY 12496

      Last Sold Summary

      • $140/SF
      • 65 Days On Market

      Last Sold Price $64,000

      Last Listing Agent Jeffery Dolfinger 24/7 Realty

  • /8

    $99,900

    • Land
    • 1.1 Acres
    • $90,818 per Acre

    L46.111 Panarama Ln, Windham, NY 12496

    Build your dream mountain getaway on this 1.1 acre unimproved lot just minutes from the Windham Mountain Club expansion. Surrounded by natural beauty, this property offers privacy, fresh air, and easy access to skiing, hiking, biking, golf, and charming village amenities. A perfect canvas for a custom Catskills home.A great opportunity in a rapidly evolving Catskills destination.

    Susan Miller WINDSTAR REALTY GROUP LLC

    L46.111 Panarama Ln, Windham, NY 12496
    • /10

      Not Listed For Sale

      3208 Rt 10, Ashland, NY 12496

      • 3 Beds
      • 2 Baths
      • 1,920 Sq Ft
      • Built 2007
      3208 Rt 10, Ashland, NY 12496

      Last Sold Summary

      • $186/SF
      • 144 Days On Market

      Last Sold Price $357,000

      Last Listing Agent Laurie Hanenberg Hunter Windham Real Estate

  • /78

    $569,900

    • Land
    • 40.07 Acres
    • $14,223 per Acre

    Tbd Boulder Brook Lot 33-38 Rd, Windham, NY 12496

    A Rare Opportunity in the Heart of Windham, NY. Welcome to Boulder Brook, an extraordinary and rare offering in the majestic Catskills. Just minutes from the slopes of Windham Ski Resort, this private subdivision presents a unique chance to own an entire mountain retreat or select from four individually surveyed lots, all nestled along a quiet, established country road. Boulder Brook is a blend

    Kyla Thomas Howard Hanna Rand Realty

    Tbd Boulder Brook Lot 33-38 Rd, Windham, NY 12496
    • /12

      Not Listed For Sale

      40/1 Townhouse Ln, Windham, NY 12496

      • 2 Beds
      • 2 Baths
      • 1,218 Sq Ft
      • Built 1982
      40/1 Townhouse Ln, Windham, NY 12496

      Last Sold Summary

      • $115/SF
      • 176 Days On Market

      Last Sold Price $140,000

      Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  • /17

    $599,000

    • Land
    • 69.02 Acres
    • $8,679 per Acre

    0 High Peak Lot 111-112, Windham, NY 12496

    Discover a rare 65.3± acre Catskills property on High Peak Road in Windham, NY, offering an extraordinary blend of open meadows, mature forests, and stream frontage. With generous road frontage and multiple potential building sites, this land provides exceptional opportunity for anyone looking to build a dream home, create a residential compound, or invest in one of the most desirable regions of

    Regina Tortorella Coldwell Banker Village GreenW

    0 High Peak Lot 111-112, Windham, NY 12496
    • /35

      Est $712,985 Not Listed For Sale

      11080 State Route 23, Windham, NY 12496

      • 5 Beds
      • 5 Baths
      • 5,792 Sq Ft
      • Built 1792
      11080 State Route 23, Windham, NY 12496

      Last Sold Summary

      • 134% Above List Price
      • $53/SF
      • 429 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Jacqueline Coyle Past Member

  • /28

    $699,000

    • Land
    • 60 Acres
    • $11,650 per Acre

    760 County Route 10, Windham, NY 12496

    Once-in-a-Lifetime Land Offering in Windham, NY - 60 Acres Bordering Forever Wild Mountain PreserveWelcome to a truly rare opportunity in the heart of the Catskills. 60 pristine acres in Windham, NY, a town where large tracts of land are no longer available, especially not ones of this caliber. This extraordinary parcel is one of the last of its kind, uniquely bordered along the rear and side

    Regina Tortorella Coldwell Banker Village GreenW

    760 County Route 10, Windham, NY 12496
    • /31

      Not Listed For Sale

      10 N Enclave Dr, Windham, NY 12496

      • 3 Beds
      • 3 Baths
      • 1,548 Sq Ft
      • Built 2005
      10 N Enclave Dr, Windham, NY 12496

      Last Sold Summary

      • $423/SF
      • 121 Days On Market

      Last Sold Price $655,000

      Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  • /38

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,163 Sq Ft

    5359 New York 23, Windham, NY 12496

    Opportunity awaits as this beautifully designed 2 bedroom 2 bath Windham Condo 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 and

    Wayne Newcomb Newcomb Realty Group LLC

    5359 New York 23, Windham, NY 12496
    • /23

      Not Listed For Sale

      443 Big Hollow Rd, Maplecrest, NY 12454

      • 1 Bed
      • 1 Bath
      • 625 Sq Ft
      • Built 1965
      443 Big Hollow Rd, Maplecrest, NY 12454

      Last Sold Summary

      • $264/SF
      • 108 Days On Market

      Last Sold Price $165,000

      Last Listing Agent Mary King Past Member

Showing Results 321 - 360, Page 9 of 18

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