Windham, NY Homes

• 

  

  

  /100

  $2,625,000

  Sold Apr 13, 2026

  81 Sundance Dr, Windham, NY 12496

  • 6 Beds
  • 4.5 Baths
  • 5,872 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $447/SF
  • 138 Days On Market

  Current Estimated Value $2,537,337

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  81 Sundance Dr, Windham, NY 12496
• 

  

  

  /56

  Est $1,370,450

  Not Listed For Sale

  86 Timber Trail, Windham, NY 12496

  • 5 Beds
  • 4 Baths
  • 3,887 Sq Ft
  • Built 2019

  86 Timber Trail, Windham, NY 12496

  Last Sold Summary

  • 98 Days On Market

  Last Listing Agent Regina Tortorella Past Member
• 

  

  

  /43

  $389,000

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

  21 French Park Ct Unit 7B, Windham, NY 12496

  If you know Windham Ridge, you know there are only a handful of units with a front row seat to Windham Mountain. Welcome to Unit 7B! With Windham Mountain Club in the background and woods in the foreground your view is nothing but Mother Nature as far as you can see. No rooftops, parked cars, or front doors to see here. Sit on the lovely stone patio and enjoy your morning coffee as you watch the

  Sharon Knudsen Coldwell Banker Village GreenW

  21 French Park Ct Unit 7B, Windham, NY 12496
• 

  

  

  /35

  $755,000

  Sold May 01, 2026

  91 Beaver Hill Rd, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 1,839 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $411/SF
  • 42 Days On Market

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  91 Beaver Hill Rd, Windham, NY 12496
• 

  

  

  /45

  Not Listed For Sale

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

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1983

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

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Sharon Knudsen Coldwell Banker Village GreenW
• 

  

  /89

  $1,749,000

  • 5 Beds
  • 3.5 Baths
  • 3,893 Sq Ft

  33 Elm Ridge Rd, Windham, NY 12496

  Hidden from view at the end of a long private driveway, this extraordinary contemporary retreat is set on 12.69 meticulously maintained acres and offers what is arguably one of the most breathtaking settings in all of Windham. Panoramic mountain views, vibrant sunsets painted in shades of pink and orange, a sparkling private pond, and complete privacy create a setting that feels worlds away from

  Regina Tortorella Coldwell Banker Village GreenW

  33 Elm Ridge Rd, Windham, NY 12496
• 

  

  /16

  $225,000

  Sold Oct 27, 2025

  40 Quads Way, Windham, NY 12496

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

  Last Sold Summary

  • 10% Below List Price
  • $223/SF
  • 115 Days On Market

  Current Estimated Value $247,582

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  40 Quads Way, Windham, NY 12496
• 

  

  /39

  Not Listed For Sale

  4 French Park Dr Unit 4B, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1983

  4 French Park Dr Unit 4B, Windham, NY 12496

  Last Sold Summary

  • 278 Days On Market

  Last Listing Agent Sharri Cunningham Bunce Realty
• 

  

  /101

  $949,000

  • 3 Beds
  • 3 Baths
  • 2,236 Sq Ft

  89 Sky Hill Rd, Windham, NY 12496

  Nestled at the end of a long private driveway in the heart of Windham, NY, this quintessential log cabin offers the perfect blend of mountain charm, privacy, and breathtaking views. Set against a backdrop of mountain and ski slope vistas, this exceptional retreat captures everything buyers dream of when searching for a Catskills getaway, full-time residence, or second home just a short drive from

  Regina Tortorella Coldwell Banker Village GreenW

  89 Sky Hill Rd, Windham, NY 12496
• 

  

  /34

  $1,695,000

  Sold Apr 01, 2026

  11 Whisper Creek Dr Unit 503, Windham, NY 12496

  • 4 Beds
  • 4 Baths
  • 2,030 Sq Ft
  • Built 2016

  Last Sold Summary

  • 6% Below List Price
  • $835/SF
  • 13 Days On Market

  Current Estimated Value $1,508,859

  Last Listing Agent Irene Pinto Brainard Ridge Management

  11 Whisper Creek Dr Unit 503, Windham, NY 12496
• 

  

  /51

  Not Listed For Sale

  31 French Park Ct, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1986

  31 French Park Ct, Windham, NY 12496

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Kevin Novotny Past Member
• 

  

  /23

  $199,000

  • 1 Bed
  • 1 Bath
  • 435 Sq Ft

  5220 State Route 23 Unit 229, Windham, NY 12496

  Rare Turnkey Income Producer! 2nd-Floor Winwood End Unit with Ski Slope Views Welcome to The Winwood, where affordability meets premium four-season Catskills living. This unique and well-appointed second-floor end unit condominium offers one of the most accessible and value-packed opportunities to own in the highly desirable Windham market. Whether you are searching for a carefree weekend

  Regina Tortorella Coldwell Banker Village GreenW

  5220 State Route 23 Unit 229, Windham, NY 12496
• 

  

  /77

  $930,000

  Sold Nov 14, 2025

  68 Hilltop Dr, Maplecrest, NY 12454

  • 4 Beds
  • 4.5 Baths
  • 3,500 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $266/SF
  • 112 Days On Market

  Current Estimated Value $990,609

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  68 Hilltop Dr, Maplecrest, NY 12454
• 

  

  /21

  Est $203,401

  Not Listed For Sale

  394 State Route 296 Unit 1, Windham, NY 12496

  • 2 Beds
  • 1.5 Baths
  • 750 Sq Ft
  • Built 1920

  394 State Route 296 Unit 1, Windham, NY 12496

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Mariana DeLuca Howard Hanna Capital Inc
• 

  

  /103

  $2,300,000

  • 5 Beds
  • 4.5 Baths
  • 4,069 Sq Ft

  16 White Way, Windham, NY 12496

  There are ski homes, and then there are homes that truly define what ski-in/ski-out living is meant to be. Positioned directly on Windham Mountain Club's coveted White Way trail, this extraordinary timber-frame residence offers what is arguably the most desirable slope-side location on the mountain. No shuttles. No parking lots. No loading gear into the car. Simply step into your heated ski room,

  Regina Tortorella Coldwell Banker Village GreenW

  16 White Way, Windham, NY 12496
• 

  

  /58

  $690,000

  Sold Oct 24, 2025

  73 Cross Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 2,792 Sq Ft
  • Built 2005

  Last Sold Summary

  • $247/SF
  • 124 Days On Market

  Current Estimated Value $729,260

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  73 Cross Rd, Windham, NY 12496
• 

  

  /27

  Not Listed For Sale

  5650 New York 23, Windham, NY 12496

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

  5650 New York 23, Windham, NY 12496

  Last Sold Summary

  • 104 Days On Market

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.
• 

  

  /27

  $5,999,000

  $3M PRICE INCREASE

  • Land
  • 307 Acres
  • $19,541 per Acre

  174 High Peak Rd, Windham, NY 12496

  Look at this stunning 307 acre parcel in the Town of Windham sometimes referred to as 'Southampton North'. This property has extensive road frontage, mountain views with minimal clearing from anywhere on the parcel. The minimum lot size is 5 acres. This is the perfect land for development. The seller participates in the conservation (thinning of the forest every 20 years) program which provides

  Siobhan Scanlan Win Morrison Realty-K

  174 High Peak Rd, Windham, NY 12496
• 

  

  /44

  $440,000

  Sold Jul 20, 2026

  7 Karlstadt Rd, Windham, NY 12496

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Above List Price
  • $437/SF
  • 13 Days On Market

  Current Estimated Value $362,005

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  7 Karlstadt Rd, Windham, NY 12496
• 

  

  /45

  Est $1,252,143

  Not Listed For Sale

  70 Sky Hill Rd, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 3,595 Sq Ft
  • Built 2016

  70 Sky Hill Rd, Windham, NY 12496

  Last Sold Summary

  • 126 Days On Market

  Last Listing Agent Laurie Hanenberg Hunter Windham Real Estate
• 

  

  /8

  $325,000

  $100K PRICE INCREASE

  • Land
  • 1.2 Acres
  • $270,833 per Acre

  L37 Panarama Ln, Windham, NY 12496

  Destination Windham! This 1.2 acre parcel is the perfect location to build your primary residence, ski home,weekend getaway, or log cabin. Stunning views of both the town and the mountain!Enjoy the traffic-free,peaceful setting off the mountain. Minutes to the slopes. Walking distance to the golf course and country club.Minutes to Main Street to enjoy the shops and restaurants. The lot has been

  Susan Miller WINDSTAR REALTY GROUP LLC

  L37 Panarama Ln, Windham, NY 12496
• 

  $1,900,000

  Sold Jul 10, 2026

  8 Stonewall Ln, Windham, NY 12496

  • 5 Beds
  • 4.5 Baths
  • 3,150 Sq Ft
  • Built 2025

  Last Sold Summary

  • $603/SF
  • 106 Days On Market

  Last Listing Agent John Oliveira Douglas Elliman Real Estate

  8 Stonewall Ln, Windham, NY 12496
• 

  

  /22

  Est $456,746

  Not Listed For Sale

  544 N Settlement Rd, Windham, NY 12496

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

  544 N Settlement Rd, Windham, NY 12496

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Jason Dugo Dugo Realty
• 

  

  /62

  $425,000

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

  23 French Park Dr Unit 7c, Windham, NY 12496

  Sought after sunny corner unit with beautiful mountain views! Enter through the spacious mud room with two generous sized closets and window. One the first floor is a bedroom next to a bright full bath with shower and large window. A laundry closet is located across the hallway. There's a large sun-kissed living room/dining room with 2 large sky lights and wall of windows. A charming functional

  Anne Jakubowski Bunce Realty

  23 French Park Dr Unit 7c, Windham, NY 12496
• 

  

  /57

  $169,900

  Sold Jun 22, 2026

  Tbd Boulder Brook Lot 8 Rd, Windham, NY 12496

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

  Last Sold Summary

  • 341 Days On Market

  Last Listing Agent Kyla Thomas Howard Hanna Rand Realty

  Tbd Boulder Brook Lot 8 Rd, Windham, NY 12496
• 

  

  /30

  Est $379,498

  Not Listed For Sale

  274 Route 65 Unit 29, Windham, NY 12496

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 1992

  274 Route 65 Unit 29, Windham, NY 12496

  Last Sold Summary

  • 132 Days On Market

  Last Listing Agent Kelly Sharifipour Darby Real Estate of New York Inc
• 

  

  /33

  $335,000

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

  274 County Route 65 Unit 68, Windham, NY 12496

  Step into this LIGHT FILLED CORNER UNIT, well maintained, upgraded unit and fall in love. Beautiful light enters this End Unit. Sliding doors to a patio looking out onto nature. There is an outside ski storage closet. Enter into the welcoming mud room. There is a half bath/laundry room, a lovely galley kitchen with granite counters, propane cook stove a lovely large window, all appliances are

  Mary Donovan Gallagher & Company

  274 County Route 65 Unit 68, Windham, NY 12496
• 

  

  /29

  $475,000

  Sold May 21, 2026

  38 Cambridge Heights Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $417/SF
  • 122 Days On Market

  Current Estimated Value $457,243

  Last Listing Agent Paul Heintz Anatole House LLC

  38 Cambridge Heights Rd, Windham, NY 12496
• 

  

  /9

  Est $1,052,274

  Not Listed For Sale

  248 Club Rd, Windham, NY 12496

  • 1 Bed
  • Built 2025

  248 Club Rd, Windham, NY 12496

  Last Sold Summary

  • 92 Days On Market

  Last Listing Agent Regina Tortorella Past Member
• 

  

  /5

  $154,000

  • Land
  • 17.15 Acres
  • $8,980 per Acre

  0 High Peak Road Lot 61 & 20, Windham, NY 12496

  Nestled in the heart of the Catskills, this 17-acre parcel of unimproved land on High Peak Road offers a rare opportunity to own a significant piece of Greene County's most sought-after landscape. Surrounded by the natural splendor that has made Windham a beloved four-season destination, this blank canvas invites you to bring your vision -- whether a private retreat, a custom dream home, or a

  Sheila Word Coldwell Banker Village GreenW

  0 High Peak Road Lot 61 & 20, Windham, NY 12496
• 

  

  /22

  $250,000

  Sold Jun 15, 2026

  63 Windham Ridge Rd Unit 16C, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,178 Sq Ft
  • Built 1986

  Last Sold Summary

  • 22% Below List Price
  • $212/SF
  • 59 Days On Market

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  63 Windham Ridge Rd Unit 16C, Windham, NY 12496
• 

  

  /18

  Est $275,570

  Not Listed For Sale

  14 Martin Ln, Hensonville, NY 12439

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1985

  14 Martin Ln, Hensonville, NY 12439

  Last Sold Summary

  • 157 Days On Market

  Last Listing Agent Alexis Amico Dugo Realty
• 

  

  /37

  $349,000

  $76K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  751 Mitchell Hollow Rd, Windham, NY 12496

  Charming 3-bedroom, 2-bath ranch set on over an acre of picturesque property in Windham. Offering the ease of single-level living and sold completely furnished, this move-in-ready home is the perfect mountain retreat, full-time residence, or weekend getaway. The home is in a highly desirable area close to local restaurants, parks, hiking trails and the Windham Mountain Resort. Inside, enjoy

  Kathy Marino Bunce Realty

  751 Mitchell Hollow Rd, Windham, NY 12496
• 

  /2

  $960,000

  Sold Nov 07, 2025

  149 Magda Ln, Windham, NY 12496

  • 4 Beds
  • 5 Baths
  • 2,140 Sq Ft
  • Built 1988

  Last Sold Summary

  • 4% Below List Price
  • $449/SF

  Current Estimated Value $987,412

  Last Listing Agent non-member non member NON MLS OFFICE

  149 Magda Ln, Windham, NY 12496
• 

  

  /7

  Not Listed For Sale

  TBD Mill St, Windham, NY 12496

  TBD Mill St, Windham, NY 12496

  Last Sold Summary

  • 135 Days On Market

  Last Listing Agent Louis Naccarato Corcoran Country Living
• 

  

  /11

  $135,000

  • Land
  • 1.2 Acres
  • $112,500 per Acre

  L19.12 South St, Windham, NY 12496

  Build your Catskills getaway on this 1.2-acre unimproved lot located on South Street in Windham, NY. Offering a peaceful setting with convenient access to Windham Mountain Club, village amenities, dining, and year-round recreation. Adjoining 1 acre lot for sale separately. A great opportunity for a custom home, weekend retreat, or long-term investment. Bring your vision and create a home that

  Susan Miller WINDSTAR REALTY GROUP LLC

  L19.12 South St, Windham, NY 12496
• 

  

  /37

  $999,999

  Sold Mar 10, 2026

  20 Brookhollow Ln, Windham, NY 12496

  • 3 Beds
  • 3.5 Baths
  • 3,284 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $305/SF
  • 68 Days On Market

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

  20 Brookhollow Ln, Windham, NY 12496
• 

  

  /31

  Est $430,041

  Not Listed For Sale

  296 Mitchell Hollow Rd, Windham, NY 12496

  • 3 Beds
  • 1 Bath
  • 1,486 Sq Ft
  • Built 1847

  296 Mitchell Hollow Rd, Windham, NY 12496

  Last Sold Summary

  • 183 Days On Market

  Last Listing Agent Sharon Knudsen Past Member
• 

  

  /39

  $639,000

  $21K PRICE DROP Pending

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

  60 Route 65a, Windham, NY 12439

  Welcome to Windham Creek Lodge. Are you looking for a money maker? a year-round residence? or your private get away? Here it is! Located just minutes from Windham Mountain and short ride to Hunter Mountain. It's currently used as short term rental with a proven rental track record. It was renovated in 2023-2024 including both updated kitchens and baths, appliances, two new electric fireplaces,

  Douglas Schenk RE/MAX Capital

  60 Route 65a, Windham, NY 12439
• 

  

  /39

  $340,000

  Sold Dec 17, 2025

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

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1983

  Last Sold Summary

  • 5% Below List Price
  • $244/SF
  • 88 Days On Market

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

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

Showing Results 121 - 160, Page 4 of 18