4,496

Windham, NY Homes

Section Image
    • /14

      Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,088 Sq Ft

      9 Old State Route 23, Windham, NY 12496

      9 Old State Route 23, Windham, NY 12496
  • /41

    $399,000 Pending

    • 5 Beds
    • 3 Baths
    • 2,472 Sq Ft

    317 Mitchell Hollow Rd, Windham, NY 12496

    PRICE REDUCTION! — calling all investors, DIY buyers, and project-minded designers! Prime Windham location, major updates done — now it's your turn to finish and make it shine. This spacious 5-bedroom, 3-bath home offers tremendous potential with many big-ticket updates already completed, including a new roof, wood flooring, updated kitchen with granite counters and newer appliances, fresh

    Lisa Jaeger Coldwell Banker Village GreenW

    317 Mitchell Hollow Rd, Windham, NY 12496
  • /29

    $285,000 Sold Feb 19, 2025

    18 East Rd Unit 1, Hensonville, NY 12439

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • Built 1981

    Last Sold Summary

    • $239/SF
    • 91 Days On Market

    Last Listing Agent Russell Pelham Real Broker, LLC

    18 East Rd Unit 1, Hensonville, NY 12439
    • /56

      Est $1,366,883 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,887 Sq Ft

      86 Timber Trail, Windham, NY 12496

      86 Timber Trail, Windham, NY 12496
  • /100

    $2,799,000

    • 6 Beds
    • 5.5 Baths
    • 5,872 Sq Ft

    81 Sundance Dr, Windham, NY 12496

    Secluded Mountain Estate with 20+ Acres, Panoramic Views & Sport Court in Windham, NY. Privately gated at the very end of Sundance Drive, this extraordinary log estate is one of only five luxury homes in this sought-after enclave each on expansive land, but none offering the privacy, scale, or setting of this one. Set on a sweeping tract with panoramic mountain views, this home blends refined

    Regina Tortorella Coldwell Banker Village GreenW

    81 Sundance Dr, Windham, NY 12496
  • /29

    $1,650,000 Sold May 09, 2025

    12 - 2C Stonewall Ln, Windham, NY 12496

    • 4 Beds
    • 3.5 Baths
    • 2,700 Sq Ft

    Last Sold Summary

    • $611/SF
    • 0 Days On Market

    Last Listing Agent Pamela King-Belfor Four Seasons Sotheby's Int.

    12 - 2C Stonewall Ln, Windham, NY 12496
    • /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
  • /48

    $749,000

    • 4 Beds
    • 3.5 Baths
    • 2,088 Sq Ft

    93 Maplewood Ave, Windham, NY 12496

    Nestled at the end of a tranquil cul -de-sac, this spacious 3+1 bedroom perched on a hill just a short distance to downtown Windham has breathtaking views of the slopes at Windham Mountain.On the main level, floor-to-ceiling glass sliding doors showcase expansive mountain views. An open-concept layout with vaulted ceilings unites the living room, dining room, and kitchen—all oriented toward

    Doina Dewell Coldwell Banker Village GreenW

    93 Maplewood Ave, Windham, NY 12496
  • /60

    $550,000 Sold Feb 28, 2025

    162 Ruland Rd, Windham, NY 12496

    • 1,849 Sq Ft
    • Built 2020

    Last Sold Summary

    • 4% Below List Price
    • $297/SF
    • 64 Days On Market

    Current Estimated Value $614,704

    Last Listing Agent Regina Tortorella Past Member

    162 Ruland Rd, Windham, NY 12496
    • /51

      Est $372,000 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft

      31 French Park Ct, Windham, NY 12496

      31 French Park Ct, Windham, NY 12496
  • /61

    $1,125,000

    • 5 Beds
    • 5.5 Baths
    • 3,643 Sq Ft

    3 South St, Windham, NY 12496

    Turn-Key Windham Ski Retreat | Modern End Unit with 4 En-Suites, Full Furnishing Option & High Income Potential Personal Use or Income Ready and hitting the market just in time for peak rental demand, this modern end-unit townhome at 292 South Street offers an unbeatable opportunity for both investors and second-home seekers. Featuring four en-suite bedrooms, panoramic slope views, and a sleek

    Regina Tortorella Coldwell Banker Village GreenW

    3 South St, Windham, NY 12496
  • /22

    $210,000 Sold Mar 14, 2025

    544 N Settlement Rd, Windham, NY 12496

    • 3 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • Built 1987

    Last Sold Summary

    • 12% Below List Price
    • $130/SF
    • 42 Days On Market

    Current Estimated Value $289,569

    Last Listing Agent Jason Dugo Dugo Realty

    544 N Settlement Rd, Windham, NY 12496
    • /28

      Est $615,000 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,528 Sq Ft

      35 Windham Mount Village, Windham, NY 12496

      35 Windham Mount Village, Windham, NY 12496
  • /36

    $329,999 Pending

    • 2 Beds
    • 2.5 Baths
    • 1,058 Sq Ft

    73 Windham Ridge Rd Unit 16-H, Windham, NY 12496

    Competitively Priced Catskills End Unit Townhouse - Fully Renovated, Furnished & Move-In Ready! This beautifully updated end-unit townhouse combines modern elegance with mountain charm, offering comfort, style, and unbeatable value. As you enter, you'll be welcomed by a stunning, fully remodeled kitchen outfitted with rich granite surfaces and a convenient breakfast bar, The kitchen flows

    Regina Tortorella Coldwell Banker Village GreenW

    73 Windham Ridge Rd Unit 16-H, Windham, NY 12496
  • /35

    $581,250 Sold Dec 01, 2025

    528 New York 296, Hensonville, NY 12439

    • 4 Beds
    • 2.5 Baths
    • 2,194 Sq Ft
    • Built 1895

    Last Sold Summary

    • $265/SF
    • 32 Days On Market

    Last Listing Agent Catherine Quintard Compass Greater NY, LLC

    528 New York 296, Hensonville, NY 12439
    • /45

      Est $1,322,293 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 3,595 Sq Ft

      70 Sky Hill Rd, Windham, NY 12496

      70 Sky Hill Rd, Windham, NY 12496
  • /59

    $715,000

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    60 County Route 65 A, Windham, NY 12496

    Price Cut! Windham Creek Lodge is a proven, income-producing short-term rental generating approximately 70K-80K in annual GCI. The recent price reduction enhances the profit margin while offering additional room to scale and maximize returns. Fully renovated in 2023-2024, this modern multi-family chalet is ideally located just minutes from Windham Mountain Club and Hunter Mountain—positioning it

    Lisa Jaeger Coldwell Banker Village GreenW

    60 County Route 65 A, Windham, NY 12496
  • /72

    $810,000 Sold Mar 11, 2025

    39 Trail View Ln, Windham, NY 12496

    • 3 Beds
    • 3 Baths
    • 3,914 Sq Ft
    • Built 2022

    Last Sold Summary

    • 10% Below List Price
    • $207/SF
    • 508 Days On Market

    Current Estimated Value $920,633

    Last Listing Agent Regina Tortorella Past Member

    39 Trail View Ln, Windham, NY 12496
    • /30

      Est $330,685 Not Listed For Sale

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

      274 Route 65 Unit 29, Windham, NY 12496

      274 Route 65 Unit 29, Windham, NY 12496
  • /106

    $3,750,000 New Construction

    • 6 Beds
    • 5 Baths
    • 5,005 Sq Ft

    219 Club Rd, Windham, NY 12496

    Welcome to the ultimate ski-in/ski-out escape at Windham Mountain Club, where modern design, four-season mountain living, and front-row slope access come together in a way that feels both luxurious and totally effortless. This brand-new, custom-built home is perched just steps from the chairlift, making it one of the most desirable on-mountain properties available at WMC today. Designed to bring

    Regina Tortorella Coldwell Banker Village GreenW

    219 Club Rd, Windham, NY 12496
  • /55

    $355,000 Sold Jan 09, 2026

    23 Townhouse Ln Unit 1, Windham, NY 12496

    • 3 Beds
    • 2.5 Baths
    • 1,846 Sq Ft
    • Built 1980

    Last Sold Summary

    • 9% Below List Price
    • $192/SF
    • 101 Days On Market

    Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

    23 Townhouse Ln Unit 1, Windham, NY 12496
    • /9

      Est $724,466 Not Listed For Sale

      248 Club Rd, Windham, NY 12496

      248 Club Rd, Windham, NY 12496
  • /64

    $1,899,000

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    22 The Loop, Windham, NY 12496

    Walk to the Slopes! Nestled on the scenic slopes of Windham Mountain and just over two hours from NYC, this mountain haven beautifully marries opulence with rustic allure. The home's exterior, featuring cedar shakes and stone, harmonizes with its lush, landscaped surroundings, creating impeccable curb appeal. Inside, a grand two-story great room welcomes you with a magnificent wall of glass

    Regina Tortorella Coldwell Banker Village GreenW

    22 The Loop, Windham, NY 12496
  • /46

    $585,000 Sold Aug 29, 2025

    14 - 57 Windham Mountain Village, Windham, NY 12496

    • 3 Beds
    • 2.5 Baths
    • 1,510 Sq Ft
    • Built 1986

    Last Sold Summary

    • 11% Below List Price
    • $387/SF
    • 181 Days On Market

    Last Listing Agent Russell Pelham Real Broker, LLC

    14 - 57 Windham Mountain Village, Windham, NY 12496
    • /18

      Est $257,841 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft

      14 Martin Ln, Hensonville, NY 12439

      14 Martin Ln, Hensonville, NY 12439
  • /22

    $1,950,000

    • 5 Beds
    • 3.5 Baths
    • 4,834 Sq Ft

    77 Beaver Hill Rd, Windham, NY 12496

    Designed by a renowned Manhattan architect known for 20M dollar Aspen ski homes, this 4,834-square-foot Catskills estate offers world-class design and unparalleled craftsmanship. Built as the architect's personal residence, it's a sanctuary for relaxation, entertaining, and year-round mountain living. Set on over four private acres bordering the protected Bataviakill Watershed, the home

    Regina Tortorella Coldwell Banker Village GreenW

    77 Beaver Hill Rd, Windham, NY 12496
  • /24

    $210,000 Sold Jun 11, 2025

    359 Begley Rd, Windham, NY 12496

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

    Last Sold Summary

    • 33% Below List Price
    • 271 Days On Market

    Current Estimated Value $242,853

    Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW

    359 Begley Rd, Windham, NY 12496
    • /2

      Est $568,671 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,622 Sq Ft

      770 Mitchell Hollow Rd, Windham, NY 12496

      770 Mitchell Hollow Rd, Windham, NY 12496
  • /65

    $515,000

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

    215 Siam Rd, Windham, NY 12496

    Welcome to the Windham Round House, one of the area's most distinctive and architecturally unique round homes. Lovingly designed and built by the original owners, this octagon-style residence sits on 5 private acres with open lawns, a charming stone wall, evergreen woods beyond, multiple outbuildings including a two-car garage—offers a remarkable setting that must be seen to be fully appreciated.

    Lisa Jaeger Coldwell Banker Village GreenW

    215 Siam Rd, Windham, NY 12496
  • /45

    $521,000 Sold Jul 02, 2025

    13 Boulder Brook Rd, Windham, NY 12496

    • 4 Beds
    • 2 Baths
    • 1,840 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Below List Price
    • $283/SF
    • 39 Days On Market

    Current Estimated Value $564,852

    Last Listing Agent Mary Donovan Gallagher & Company

    13 Boulder Brook Rd, Windham, NY 12496
    • /7

      Not Listed For Sale

      TBD Mill St, Windham, NY 12496

      TBD Mill St, Windham, NY 12496
  • /109

    $2,175,000

    • 6 Beds
    • 3.5 Baths
    • 4,104 Sq Ft

    19 Twin Maples, Windham, NY 12496

    Experience mountain luxury at its finest in this stunning post-and-beam home at Windham Mountain Club's exclusive Village East community just a little over two hours from New York City. Designed for those who love the outdoors but don't want to sacrifice comfort, this 6-bedroom, 3.5-bath retreat spans more than 4,100 sq ft and combines timeless craftsmanship with breathtaking views of the

    Regina Tortorella Coldwell Banker Village GreenW

    19 Twin Maples, Windham, NY 12496
  • /27

    $445,000 Sold Feb 21, 2025

    5650 New York 23, Windham, NY 12496

    • 5 Beds
    • 3 Baths
    • 2,468 Sq Ft
    • Built 1987

    Last Sold Summary

    • 11% Below List Price
    • $180/SF
    • 104 Days On Market

    Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

    5650 New York 23, Windham, NY 12496
    • /31

      Est $431,392 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,486 Sq Ft

      296 Mitchell Hollow Rd, Windham, NY 12496

      296 Mitchell Hollow Rd, Windham, NY 12496
  • /63

    $575,000

    • 4 Beds
    • 4.5 Baths
    • 3,190 Sq Ft

    274 Route 65 Unit 28, Windham, NY 12496

    Not your ordinary townhouse—this Crystal Pond ''builder's special'' is one of only a few that were ever built with this expanded three-level, 3,190 sq ft floor plan. Designed for comfort, space, and easy living, this corner unit is a true standout in the development. From the covered entry, step into a welcoming heated mudroom with built-in cubbies, hooks, and bench seating—ideal for ski gear and

    Lisa Jaeger Coldwell Banker Village GreenW

    274 Route 65 Unit 28, Windham, NY 12496
  • /50

    $702,000 Sold Dec 22, 2025

    73 Beaver Hill Rd, Windham, NY 12496

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $281/SF
    • 75 Days On Market

    Last Listing Agent Patricia Charbonneau Brainard Ridge Management

    73 Beaver Hill Rd, Windham, NY 12496
    • /11

      Not Listed For Sale

      0 N Ridge Extension Lot 25 Unit 145406, Windham, NY 12496

      0 N Ridge Extension Lot 25 Unit 145406, Windham, NY 12496
  • /96

    $1,649,000

    • 5 Beds
    • 3.5 Baths
    • 4,312 Sq Ft

    102 Thunderbird Terrace, Windham, NY 12496

    Custom Log Cabin with Modern Finishes, The Feel of a New Build, and Stunning Mountain Views- Nestled on nearly 2 acres, this breathtaking custom log cabin combines luxury, charm, and nature. Built with meticulous attention to detail, the home shows as if it is new construction, exuding a fresh and pristine feel throughout, making it indistinguishable from a brand-new build. With 5 bedrooms, 3.5

    Regina Tortorella Coldwell Banker Village GreenW

    102 Thunderbird Terrace, Windham, NY 12496
  • /73

    $599,000 Sold Jan 08, 2026

    110 Maplecrest Rd, Windham, NY 12439

    • 8 Beds
    • 4 Baths
    • 3,577 Sq Ft
    • Built 1920

    Last Sold Summary

    • 6% Below List Price
    • $167/SF
    • 125 Days On Market

    Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

    110 Maplecrest Rd, Windham, NY 12439
    • /4

      Not Listed For Sale

      79 Old Rd, Windham, NY 12496

      79 Old Rd, Windham, NY 12496

Showing Results 81 - 120, Page 3 of 18

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