Windham, NY Homes

• 

  

  

  /38

  Est $485,079

  Not Listed For Sale

  153 Slater Rd, Maplecrest, NY 12454

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft
  • Built 1983

  153 Slater Rd, Maplecrest, NY 12454

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living
• 

  

  

  /35

  $460,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  5134 New York 23, Windham, NY 12496

  Introducing a treasure in the heart of Windham, where charm and convenience beautifully coalesce. This three-bedroom oasis offers a newly renovated, low maintenance home that encapsulates comfort and serenity. Set amidst the breathtaking mountain views, this property boasts an enchanting creekside grotto. The firepit area is an idyllic spot for tranquil evenings under the stars, a feature so

  

  Jason Dugo

  Dugo Realty

  5134 New York 23, Windham, NY 12496
• 

  

  

  /55

  $540,000

  Sold Jun 29, 2026

  5376 State Route 23, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,448 Sq Ft
  • Built 1900

  Last Sold Summary

  • 10% Below List Price
  • $221/SF
  • 47 Days On Market

  Current Estimated Value $583,755

  Last Listing Agent Sharri Cunningham Bunce Realty

  5376 State Route 23, Windham, NY 12496
• 

  

  

  /15

  Not Listed For Sale

  0 Ruland Rd Unit 155000, Windham, NY 12454

  0 Ruland Rd Unit 155000, Windham, NY 12454

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Regina Tortorella Coldwell Banker Village Green
• 

  

  

  /7

  $689,000

  • 5 Beds
  • 5 Baths
  • 2,500 Sq Ft

  5355 New York 23, Windham, NY 12496

  CALLING INVESTORS - PRIME WINDHAM VILLAGE OPPORTUNITY Rare opportunity in the heart of Windham Village with exceptional commercial and residential development potential. Positioned in one of the Catskills' most desirable four-season destinations, this property offers investors the chance to capitalize on the continued growth and popularity of Windham.Windham is truly ''the place to be,''

  

  Carol Shaw

  Shaw Country Realty, Inc.

  5355 New York 23, Windham, NY 12496
• 

  

  /50

  $885,000

  Sold Dec 15, 2025

  30 The Loop, Windham, NY 12496

  • 5 Beds
  • 4 Baths
  • 3,100 Sq Ft
  • Built 1970

  Last Sold Summary

  • 11% Below List Price
  • $285/SF
  • 291 Days On Market

  Current Estimated Value $957,063

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  30 The Loop, Windham, NY 12496
• 

  

  /6

  Not Listed For Sale

  80 Begley Rd, Windham, NY 12496

  80 Begley Rd, Windham, NY 12496

  Last Sold Summary

  • 120 Days On Market

  Last Listing Agent Regina Tortorella Past Member
• 

  

  /25

  $415,000

  $19K PRICE INCREASE

  • 3 Beds
  • 3.5 Baths
  • 3,683 Sq Ft

  2914 Route 10, Windham, NY 12496

  Escape to the Catskills and enjoy the privacy, space, and year-round lifestyle you've been looking for. Set on more than 5 private acres, this move-in-ready home offers over 2,600 square feet of living space with 3 bedrooms and 3.5 bathrooms, creating the perfect retreat for weekend getaways, full-time living, or a vacation home with income potential. Inside, you'll find spacious living areas

  

  Jack Yao

  Realmart Realty, LLC

  2914 Route 10, Windham, NY 12496
• 

  

  /7

  $1,998,500

  Sold Jun 26, 2026

  4 Estate View Dr, Windham, NY 12496

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

  Last Sold Summary

  • $400/SF
  • 301 Days On Market

  Last Listing Agent Patrick Dunn KW Platform

  4 Estate View Dr, Windham, NY 12496
• 

  

  /28

  Est $466,315

  Not Listed For Sale

  904 N Settlement Rd, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft
  • Built 2003

  904 N Settlement Rd, Windham, NY 12496

  Last Sold Summary

  • 139 Days On Market

  Last Listing Agent Richard Vizzini Corcoran Country Living
• 

  

  /10

  $199,000

  $199K PRICE INCREASE

  • Land
  • 2.3 Acres
  • $86,522 per Acre

  0 N Ridge Extension Unit 20255019, Windham, NY 12496

  Price Reduced to 199,000! Build your Catskills retreat on the last remaining building lot in North Ridge Estates, one of Windham's premier private communities surrounded by luxury homes and newly built million-dollar properties. This surveyed 2.30-acre parcel features an existing driveway leading to an ideal building site with a gentle slope and the potential for distant mountain views. Select

  

  Lisa Jaeger

  Coldwell Banker Village GreenW

  0 N Ridge Extension Unit 20255019, Windham, NY 12496
• 

  

  /35

  $815,000

  Sold Dec 24, 2025

  2 Biff Andrus Rd, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 3,500 Sq Ft
  • Built 2002

  Last Sold Summary

  • 18% Below List Price
  • $233/SF
  • 346 Days On Market

  Current Estimated Value $895,011

  Last Listing Agent Richard Vizzini Corcoran Country Living

  2 Biff Andrus Rd, Windham, NY 12496
• 

  

  /26

  Est $786,946

  Not Listed For Sale

  22 Brook Hollow Ln, Windham, NY 12496

  • 4 Beds
  • 2 Baths
  • 2,842 Sq Ft
  • Built 2007

  22 Brook Hollow Ln, Windham, NY 12496

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Wyatt Dusenbury Compass Greater NY, LLC
• 

  

  /22

  $325,000

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

  315 Begley Rd, Windham, NY 12496

  Just minutes from the village of Windham, skiing, and golf, this meticulously maintained ranch is set on a beautiful country road in a true four-season community. The easy, flowing floor plan features a bright eat-in kitchen that opens directly to a spacious rear deck-perfect for outdoor dining and entertaining. Inside, you'll find three comfortable bedrooms, 1.5 baths, and a welcoming living

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  315 Begley Rd, Windham, NY 12496
• 

  $505,000

  Sold Jul 28, 2026

  34 Old Rd, Windham, NY 12496

  • 3 Beds
  • 1.5 Baths
  • 2,084 Sq Ft
  • Built 1971

  Last Sold Summary

  • 14% Below List Price
  • $242/SF
  • 143 Days On Market

  Current Estimated Value $527,053

  Last Listing Agent Michael Mariani Patricia Forgione's Realty

  34 Old Rd, Windham, NY 12496
• 

  

  /31

  Est $246,578

  Not Listed For Sale

  60 Quads Way, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  60 Quads Way, Windham, NY 12496

  Last Sold Summary

  • 350 Days On Market

  Last Listing Agent Brian Cohen RHR Realty Group
• 

  

  /22

  $269,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 838 Sq Ft

  5359 Main St, Windham, NY 12496

  Prime Windham Village Location: Just outside your door, wander to restaurants, movies, breweries, pubs, miniature golf, seasonal farmers market and year round town events.Convenient NYC bus access just outside your door for easy escape for the weekend. Only minutes to the Windham Mt. Club for skiing and nearby golf courses makes this a desirable location for this 2 bedroom, 2 bath condo with

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  5359 Main St, Windham, NY 12496
• 

  

  /15

  $81,500

  Sold Aug 13, 2025

  1 - 886 Mill St, Windham, NY 12496

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

  Last Sold Summary

  • 14% Below List Price
  • 268 Days On Market

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  1 - 886 Mill St, Windham, NY 12496
• 

  

  /64

  Est $587,508

  Not Listed For Sale

  29 Martin Ln, Hensonville, NY 12439

  • 4 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • Built 1994

  29 Martin Ln, Hensonville, NY 12439

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Regina Tortorella Past Member
• 

  

  /31

  $349,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  436 Big Hollow Rd, Maplecrest, NY 12454

  Up the road from thousands of acres of state hiking trails and from CD Lane Park with swimming, kayaking, and family fun, this location is a true four-season retreat. Minutes to Windham and Hunter ski resorts, golf courses, and local venues, the setting offers year-round recreation at your doorstep.Set back from a quiet country road on nearly 4 acres, this property is all about the outdoors.

  

  Carol Shaw

  Shaw Country Realty, Inc.

  436 Big Hollow Rd, Maplecrest, NY 12454
• 

  

  /73

  $1,810,000

  Sold Mar 05, 2026

  150 Trailside Rd, Windham, NY 12496

  • 9 Beds
  • 7 Baths
  • 6,859 Sq Ft
  • Built 2001

  Last Sold Summary

  • 20% Below List Price
  • $264/SF
  • 304 Days On Market

  Current Estimated Value $1,838,462

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  150 Trailside Rd, Windham, NY 12496
• 

  

  /30

  Est $740,199

  Not Listed For Sale

  67 Clarence D Lane Rd Unit 1, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1973

  67 Clarence D Lane Rd Unit 1, Windham, NY 12496

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Elizabeth Alfeld Keller Williams Realty HV Nort
• 

  

  /13

  $99,000

  • Land
  • 8.24 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 but would need to be updated with the town. This makes this lot desirable with no soil testing and design which could usually take

  

  Carol Shaw

  Shaw Country Realty, Inc.

  539 Route 40, Maplecrest, NY 12454
• 

  $147,000

  Sold Jul 06, 2026

  7 Quads Way, Windham, NY 12496

  • 1 Bath
  • 560 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $262/SF
  • 87 Days On Market

  Current Estimated Value $159,286

  Last Listing Agent Emelisa Mendoza RE/MAX Town & Country

  7 Quads Way, Windham, NY 12496
• 

  

  /17

  Est $643,250

  Not Listed For Sale

  120 Mount Greenery Rd, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 2,017 Sq Ft
  • Built 1988

  120 Mount Greenery Rd, Windham, NY 12496

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Robert Conway Berkshire Hathaway Home Services Blake
• 

  

  /42

  $315,000

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  689 Old Rd, Hensonville, NY 12439

  Step into the charm of this 1930s 2-bedroom, 2-bath ranch, just minutes from the Village of Windham and Windham Mountain. Nestled on a full acre and bordered by 25.5 acres of protected NYC watershed land, the property offers rare privacy and a seamless connection to nature. Wake up to the gentle sounds of a seasonal creek and lush surrounding greenery, a true mountain escape.Outside, a

  

  Mark McAlpine

  Compass Greater New York, LLC

  689 Old Rd, Hensonville, NY 12439
• 

  

  /73

  $715,000

  Sold Nov 24, 2025

  122 Old Rd, Windham, NY 12496

  • 4 Beds
  • 2.5 Baths
  • 1,823 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $392/SF
  • 42 Days On Market

  Current Estimated Value $750,804

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  122 Old Rd, Windham, NY 12496
• 

  

  /54

  Est $1,426,618

  Not Listed For Sale

  12 Jacob Strasse Rd, Windham, NY 12496

  • 6 Beds
  • 5.5 Baths
  • 5,500 Sq Ft
  • Built 1988

  12 Jacob Strasse Rd, Windham, NY 12496

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Catherine Quintard Compass Greater NY, LLC
• 

  

  /48

  $749,000

  $100K PRICE DROP

  • 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
• 

  

  /41

  $640,000

  Sold Nov 21, 2025

  212 South St, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $286/SF
  • 69 Days On Market

  Last Listing Agent Mary Donovan Gallagher & Company

  212 South St, Windham, NY 12496
• 

  

  /18

  Est $199,683

  Not Listed For Sale

  26 Mill St, Windham, NY 12496

  • 3 Beds
  • 1 Bath
  • 824 Sq Ft
  • Built 1940

  26 Mill St, Windham, NY 12496

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Claudia Zucker Living Structures
• 

  

  /97

  $1,349,000

  • 4 Beds
  • 3.5 Baths
  • 3,977 Sq Ft

  78 Buckskin Loop, Windham, NY 12496

  Welcome to Windmont--Windham's most exclusive gated community--where luxury living meets the serenity of a private, thousand-acre natural preserve. Opportunities to own here are few and far between, making this a truly rare offering. Enter through secured gates and follow a scenic road to a paved, winding driveway that leads to this beautifully updated contemporary home, privately sited on 5

  Regina Tortorella Coldwell Banker Village GreenW

  78 Buckskin Loop, Windham, NY 12496
• 

  

  /67

  $840,000

  Sold Jun 26, 2026

  116 Nilson Dr, Windham, NY 12496

  • 4 Beds
  • 3.5 Baths
  • 3,075 Sq Ft
  • Built 1976

  Last Sold Summary

  • 8% Below List Price
  • $273/SF
  • 191 Days On Market

  Current Estimated Value $826,720

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  116 Nilson Dr, Windham, NY 12496
• 

  

  /30

  Est $657,343

  Not Listed For Sale

  121 Thunderbird Terrace, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 1941

  121 Thunderbird Terrace, Windham, NY 12496

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Paul Heintz Anatole House LLC
• 

  

  /69

  $549,000

  Under Contract

  • 4 Beds
  • 1.5 Baths
  • 1,764 Sq Ft

  329 State Route 296, Windham, NY 12496

  Trade traffic for tree-lined roads. Replace sirens with birdsong. Wake up on your wraparound porch with a cup of coffee and embrace the slower pace of Catskills living. Nestled in the charming Hamlet of Hensonville, this beautifully renovated four-bedroom farmhouse captures everything buyers love about Windham, NY. Blending timeless country character with thoughtfully curated modern finishes,

  Regina Tortorella Coldwell Banker Village GreenW

  329 State Route 296, Windham, NY 12496
• 

  

  /41

  $999,000

  Sold Dec 30, 2025

  51 Barnum Rd, Windham, NY 12496

  • 6 Beds
  • 4.5 Baths
  • 2,679 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Above List Price
  • $373/SF
  • 15 Days On Market

  Last Listing Agent Catherine Quintard Compass Greater NY, LLC

  51 Barnum Rd, Windham, NY 12496
• 

  

  /72

  Est $738,197

  Not Listed For Sale

  23 Manor Dr, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 2,485 Sq Ft
  • Built 2024

  23 Manor Dr, Windham, NY 12496

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Corey Marikovics Past Member
• 

  

  /61

  $1,149,000

  $24K PRICE INCREASE

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

  3 South St, Windham, NY 12496

  Luxury STR Investment Opportunity Across from Windham Mountain Club -- turnkey option, income-producing, and Owner Financing available with as little as 10 pct down- perfectly positioned in one of the Catskills' most desirable four-season destinations. Located within walking distance to Windham's restaurants, shops, nightlife, and ''The Valley,'' Windham Mountain Club's exciting new expansion

  Regina Tortorella Coldwell Banker Village GreenW

  3 South St, Windham, NY 12496
• 

  

  /43

  $518,000

  Sold Aug 21, 2025

  996 County Route 10, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 2020

  Last Sold Summary

  • 5% Below List Price
  • $357/SF
  • 59 Days On Market

  Current Estimated Value $524,561

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  996 County Route 10, Windham, NY 12496
• 

  

  /30

  Est $346,000

  Not Listed For Sale

  3 Begley Rd, Windham, NY 12496

  • 4 Beds
  • 2 Baths
  • 1,916 Sq Ft
  • Built 1922

  3 Begley Rd, Windham, NY 12496

  Last Sold Summary

  • 96 Days On Market

  Last Listing Agent Jessica Surbeck WINDSTAR REALTY GROUP LLC

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