Windham, NY Homes

• 

  

  

  /33

  $799,000

  • 6 Beds
  • 3 Baths
  • 2,468 Sq Ft

  5429 New York 23, Windham, NY 12496

  In the Heart of Windham Village Perfectly positioned in the center of it all, this beautifully restored Village home offers effortless access to Windham's vibrant lifestyle--restaurants, pubs, brewery, weekend Farmers Market, and seasonal events all just moments away. The NYC bus route is nearby, making this an ideal getaway with no car required, and popular wedding venues are close at hand.

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  5429 New York 23, Windham, NY 12496
• 

  

  

  /30

  $2,000 Per Month

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

  121 Brainard Ridge Rd, Windham, NY 12496

  Seasonal summer or winter rental. Now is the perfect time to secure your seasonal rental in Windham. This bright and cozy 3-bedroom, 2-bath townhouse is ideally located right on the side of Windham Mountain Club, offering a peaceful setting with convenient access to everything the area has to offer. Inside, you'll find a warm and inviting space filled with natural light, a wood-burning fireplace

  

  Alexis Amico

  Dugo Realty

  121 Brainard Ridge Rd, Windham, NY 12496
• 

  

  

  /60

  $575,000

  Sold Nov 07, 2025

  36 Mount Greenery Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $418/SF
  • 72 Days On Market

  Current Estimated Value $586,705

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  36 Mount Greenery Rd, Windham, NY 12496
• 

  

  

  /25

  Not Listed For Sale

  0 Route 10, Windham, NY 12496

  • 3 Beds
  • Built 2016

  0 Route 10, Windham, NY 12496

  Last Sold Summary

  • 189 Days On Market
• 

  

  

  /22

  $289,000

  • 2 Beds
  • 2 Baths
  • 838 Sq Ft

  5359 Main St Unit 2h., Windham, NY 12496

  Prime Windham Village Location - Step out your door and wander to restaurants, the farmers market, local brewery, miniature golf, movies, and year-round town events. Convenient NYC bus access just moments away makes this the perfect easy escape. Only minutes to Windham Mountain skiing and nearby golf courses, this desirable 2-bedroom, 2-bath condo with slope views offers both lifestyle and

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  5359 Main St Unit 2h., Windham, NY 12496
• 

  

  /14

  $2,150 Per Month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • House for Rent

  18 Brockett Rd, Windham, NY 12496

  Charming 2 bed, 2 bath house, very close to town. Beautifully renovated, clean, light and bright, with hardwood and cork flooring, washer and dryer, dishwasher, gas fireplace, full basement and detached garage. Front porch, back patio and yard for outdoor enjoyment. Available fully, partially or unfurnished. Rent includes internet and use of electric generated by solar panels. No pets.

  Jessica Surbeck Windstar Realty Group, LLC

  18 Brockett Rd, Windham, NY 12496
• 

  $269,000

  Sold Sep 19, 2025

  79 Windham Ridge Rd Unit 17A, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,211 Sq Ft
  • Built 1983

  Last Sold Summary

  • $222/SF
  • 14 Days On Market

  Current Estimated Value $275,529

  Last Listing Agent FRANK GOMEZ Real Broker NY LLC

  79 Windham Ridge Rd Unit 17A, Windham, NY 12496
• 

  

  /34

  Est $1,695,558

  Not Listed For Sale

  21 Sundance Dr, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 4,359 Sq Ft
  • Built 2005

  21 Sundance Dr, Windham, NY 12496

  Last Sold Summary

  • 58 Days On Market
• 

  

  /27

  $799,000

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

  71 Windham Mount Village Unit 71, Windham, NY 12496

  Windham Mt. Village . This Beautiful Townhouse is located at the base of Windham slopes . Just steps from skiing and directly across from the clubhouse and indoor pool, this beautifully updated residence offers exceptional four-season appeal and strong rental demand. The flexible layout is easily adaptable to a 2-bedroom plus sleeping loft, with a separate lockout bedroom/studio-ideal for

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  71 Windham Mount Village Unit 71, Windham, NY 12496
• 

  

  /36

  $8,495 Per Month

  • 5 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  170 Maplecrest Rd, Hensonville, NY 12439

  WELCOME TO THE MID-CENTURY WINDHAM ART HOUSE WITH LUXURIOUS YEAR-ROUND HOT TUB, OUTDOOR SEASONAL SWIMMING POOL, WALL-TO-WALL FIREPLACE, CUSTOM BAR, 2.7 ACRES LAND WITH PRIVATE CREEK AND MORE! This gorgeous 5 bedroom 2.5 bath home of nearly 3,000 sq ft offers so much: NATURE and PRIVACY, beautiful lawns, a creek, huge trees; RELAX and ENTERTAINMENT, swimming pool, hot tub, fireplace, bar, grill,

  Martina Dechevska Find Real Estate LLC

  170 Maplecrest Rd, Hensonville, NY 12439
• 

  

  /24

  $227,500

  Sold Jun 30, 2025

  35 Quads Way, Windham, NY 12496

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

  Last Sold Summary

  • 5% Below List Price
  • $226/SF
  • 80 Days On Market

  Current Estimated Value $248,938

  Last Listing Agent Mary Donovan Gallagher & Company

  35 Quads Way, Windham, NY 12496
• 

  

  /29

  Not Listed For Sale

  12 - 2C Stonewall Ln, Windham, NY 12496

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

  12 - 2C Stonewall Ln, Windham, NY 12496

  Last Sold Summary

  • 0 Days On Market
• 

  

  /59

  $665,000

  $20K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,184 Sq Ft

  523 Mitchell Hollow Rd, Windham, NY 12496

  Catskills living with standout appeal in Windham—the ultimate four-season destination for skiing, golf, hiking, breweries, and live music venues. This sprawling, rambling layout was designed for memorable gatherings, offering 5 generous bedrooms and 3 full baths, ideal for hosting family, friends, or guests in style. Warm up by the fireplace after a day on the mountain, then step outside to your

  

  Carol Shaw

  Shaw Country Realty, Inc.

  523 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /26

  $13,000 Per Month

  • 2 Beds
  • 2 Baths
  • 295 Sq Ft
  • Townhouse for Rent

  274 County Road 65 Unit 40, Windham, NY 12496

  Seasonal Rental, development has shuttle bus to and from Windham Mt. Club, great location. Lovely 2 bedroom, 2 baths with laundry. Open living area, stone wood burning fireplace, sliding doors to deck. Upper level has 2 bedrooms, living room has pull out couch, Unit sleeps 7 persons. Don't miss out on this lovely rental. ** AVAILABLE for entire 26/27 ski season 13000 or 3,900 per month.

  Mary Donovan Gallagher & Company

  274 County Road 65 Unit 40, Windham, NY 12496
• 

  

  /33

  $639,000

  Sold Jan 30, 2026

  19 Brook Hollow Ln, Windham, NY 12496

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • Built 1983

  Last Sold Summary

  • $285/SF
  • 51 Days On Market

  Current Estimated Value $649,185

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  19 Brook Hollow Ln, Windham, NY 12496
• 

  

  /6

  Not Listed For Sale

  0 Larsen Dr Unit 152095, Windham, NY 12496

  0 Larsen Dr Unit 152095, Windham, NY 12496

  Last Sold Summary

  • 81 Days On Market
• 

  

  /45

  $1,850,000

  • 5 Beds
  • 3 Baths
  • 3,740 Sq Ft

  37 The Loop, Windham, NY 12496

  VIEWS -LOCATION Spectacular true log home just a short walk to the slopes of Windham Mountain Club offering the perfect four-season retreat in the heart of the Catskills. This meticulously maintained 5-bedroom, 3-bath home blends warm mountain character with comfort and style, all within minutes of Windham Village restaurants, breweries, movies, golf courses, walking trails, and year-round

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  37 The Loop, Windham, NY 12496
• 

  

  /3

  $2,100 Per Month

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

  5359 State Route 231, Windham, NY 12496

  Experience easy mountain living in Windham! This charming 2-bedroom, 2-bath condo features a welcoming living room, dedicated dining space, and the convenience of in-unit laundry. Includes assigned parking and is just moments from Windham Mountain—perfect for those seeking relaxation and recreation.

  Simran Bajaj Realty Connect USA LLC

  5359 State Route 231, Windham, NY 12496
• 

  

  /14

  $76,000

  Sold Dec 30, 2025

  0 County Route 40, Windham, NY 12454

  • Land
  • 4.9 Acres
  • $15,510 per Acre

  Last Sold Summary

  • 45% Below List Price
  • 204 Days On Market

  Last Listing Agent Anne Jakubowski Bunce Realty

  0 County Route 40, Windham, NY 12454
• 

  

  /29

  Not Listed For Sale

  21 - 4A Stonewall Ln, Windham, NY 12496

  • 5 Beds
  • 4.5 Baths
  • 3,148 Sq Ft
  • Built 2024

  21 - 4A Stonewall Ln, Windham, NY 12496

  Last Sold Summary

  • 0 Days On Market
• 

  

  /41

  $684,000

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

  134 Magda Ln, Windham, NY 12496

  Charming Country Retreat Just Minutes to WindhamNestled on a private dead-end road just minutes from Windham's slopes, golf courses, and vibrant village, this beautiful recently 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

  

  Carol Shaw

  Shaw Country Realty, Inc.

  134 Magda Ln, Windham, NY 12496
• 

  $520,000

  Sold Oct 07, 2025

  21 Nauvoo Rd, Windham, NY 12496

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1956

  Last Sold Summary

  • 10% Below List Price
  • $485/SF
  • 173 Days On Market

  Current Estimated Value $519,744

  Last Listing Agent Joel Craig Coldwell Banker Village Green

  21 Nauvoo Rd, Windham, NY 12496
• 

  

  /11

  Not Listed For Sale

  0 Begley Rd Unit 154599, Windham, NY 12496

  0 Begley Rd Unit 154599, Windham, NY 12496

  Last Sold Summary

  • 25 Days On Market
• 

  

  /37

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,125 Sq Ft

  16 Hickory Hill Rd, Windham, NY 12496

  Windham: ''The place to Be'' for year round outdoor enthusiasts This gem has direct views of Windham slopes, proximity to golf courses, Windham Village, restaurants, walking paths and various venues, 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,

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  16 Hickory Hill Rd, Windham, NY 12496
• 

  

  /67

  $725,000

  Sold Sep 09, 2025

  8 Evans Rd, Windham, NY 12496

  • 5 Beds
  • 3.5 Baths
  • 3,862 Sq Ft
  • Built 2000

  Last Sold Summary

  • 90,638% Above List Price
  • $188/SF
  • 22 Days On Market

  Current Estimated Value $736,592

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  8 Evans Rd, Windham, NY 12496
• 

  

  /29

  Not Listed For Sale

  25 - 4C Stonewall Ln, Windham, NY 12496

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

  25 - 4C Stonewall Ln, Windham, NY 12496

  Last Sold Summary

  • 1 Day On Market
• 

  

  /34

  $239,500

  $10K PRICE DROP

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

  55 Quads Way, Windham, NY 12496

  Price Reduced -- Major Value in Windham! This charming turnkey condo delivers affordable four-season living close to skiing, golf, hiking, dining, and everything buyers love about Windham. Just minutes from Windham Mountain Club, this fully furnished 2-bedroom, 2-bath retreat offers an easy mountain lifestyle in one of the Catskills' most desirable destinations. Enjoy winter days on the slopes,

  

  Lisa Jaeger

  Coldwell Banker Village GreenW

  55 Quads Way, Windham, NY 12496
• 

  $158,000

  Sold Jan 29, 2026

  2 Quads Way, Windham, NY 12496

  • 1 Bed
  • 1 Bath
  • 560 Sq Ft
  • Built 1987

  Last Sold Summary

  • $282/SF
  • 50 Days On Market

  Current Estimated Value $159,366

  Last Listing Agent Gal Ozana Ozana Realty Group

  2 Quads Way, Windham, NY 12496
• 

  

  /60

  Est $587,758

  Not Listed For Sale

  162 Ruland Rd, Windham, NY 12496

  • 1 Bed
  • 1,849 Sq Ft
  • Built 2020

  162 Ruland Rd, Windham, NY 12496

  Last Sold Summary

  • 64 Days On Market
• 

  

  /67

  $875,000

  $40K PRICE DROP Pending

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

  116 Nilson Dr, Windham, NY 12496

  Fall in love with the ease of single-level living wrapped in privacy, beauty, and timeless style. Set on three peaceful acres, this thoughtfully reimagined home feels like a hidden retreat -- close to everything, yet wonderfully your own. From the moment you enter, the home welcomes you with warmth and refinement. Arched openings, crown moldings, and curated details create an elegant flow from

  

  Lisa Jaeger

  Coldwell Banker Village GreenW

  116 Nilson Dr, Windham, NY 12496
• 

  

  /9

  $75,000

  Sold Jul 11, 2025

  611 Old Rd, Windham, NY 12496

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

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Mary Donovan Gallagher & Company

  611 Old Rd, Windham, NY 12496
• 

  

  /39

  Est $331,781

  Not Listed For Sale

  51 Carrington Rd, Windham, NY 12496

  • 1 Bed
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1984

  51 Carrington Rd, Windham, NY 12496

  Last Sold Summary

  • 89 Days On Market
• 

  

  /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
• 

  

  /47

  $169,900

  Sold Jun 22, 2026

  8 Boulder Brook Rd, Windham, NY 12496

  • Land
  • 6.17 Acres
  • $27,536 per Acre

  Last Sold Summary

  • 221 Days On Market

  Last Listing Agent Kyla Thomas Howard Hanna Rand Realty

  8 Boulder Brook Rd, Windham, NY 12496
• 

  

  /54

  Not Listed For Sale

  11 Whisper Creek Dr Unit 601B, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 1,506 Sq Ft
  • Built 2019

  11 Whisper Creek Dr Unit 601B, Windham, NY 12496

  Last Sold Summary

  • 92 Days On Market
• 

  

  /24

  $415,000

  $19K PRICE INCREASE

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

  2914 Route 10, Windham, NY 12496

  Set on 5 peaceful acres in the heart of the Catskills, this spacious 3-bedroom, 3.5-bathroom home offers the perfect blend of comfort, convenience, and mountain living. Built in 1993, the home features 2,610 square feet of living space with a functional layout designed for both everyday living and entertaining. Enjoy the fresh, modern feel of new tile flooring, a clean white interior and

  

  Jack Yao

  Realmart Realty, LLC

  2914 Route 10, Windham, NY 12496
• 

  

  /33

  $283,500

  Sold Aug 26, 2025

  71 County Road 65 Unit 4, Hensonville, NY 12439

  • 2 Beds
  • 2 Baths
  • 1,290 Sq Ft
  • Built 2020

  Last Sold Summary

  • 4% Below List Price
  • $220/SF
  • 47 Days On Market

  Current Estimated Value $380,394

  Last Listing Agent Susanna Scott-Mitchell Compass Greater NY, LLC

  71 County Road 65 Unit 4, Hensonville, NY 12439
• 

  

  /27

  Est $353,087

  Not Listed For Sale

  24 Vets Rd, Windham, NY 12496

  • 3 Beds
  • 1.5 Baths
  • 1,588 Sq Ft
  • Built 1947

  24 Vets Rd, Windham, NY 12496

  Last Sold Summary

  • 36 Days On Market
• 

  

  /20

  $325,000

  $24K PRICE DROP

  • 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
• 

  

  /75

  $1,450,000

  Sold Sep 05, 2025

  16 High Rd W, Windham, NY 12496

  • 5 Beds
  • 4.5 Baths
  • 4,140 Sq Ft
  • Built 2017

  Last Sold Summary

  • 3% Below List Price
  • $350/SF
  • 55 Days On Market

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  16 High Rd W, Windham, NY 12496

Showing Results 1 - 40, Page 1 of 18