Homes in ZIP Code 12496

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  /63

  $1,149,000

  • 5 Beds
  • 5.5 Baths
  • 3,460 Sq Ft

  292 South St Unit 2, Windham, NY 12496

  Incredible Investment Opportunity - Proven Short-Term Rental Income!Welcome to 292 South St, Windham - a luxury townhouse with exceptional income potential, already generating 85,000-110,000 annually while being rented for just a small portion of the year. This high-performing vacation rental has significant upside for buyers active on platforms like Airbnb, Vrbo, and AirDNA. With full-time

  Regina Tortorella Coldwell Banker Village GreenW

  292 South St Unit 2, 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
• 

  

  

  /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

  Last Sold Summary

  • 263 Days On Market

  Last Sold Price $149,000

  Last Listing Agent Anne Jakubowski Bunce Realty
• 

  

  

  /74

  $449,000

  • 4 Beds
  • 4 Baths
  • 2,950 Sq Ft

  25 Vets Rd, Windham, NY 12496

  Welcome to your peaceful sanctuary in the heart of Windham, a rare blend of convenience, natural beauty, and endless potential. Just a short stroll from Main Street and less than half a mile from the slopes, this rambling ranch sits in the perfect spot to enjoy everything Windham has to offer while feeling miles away from it all. Surrounded by lush Macintosh apple and pear trees, grape arbors,

  Regina Tortorella Coldwell Banker Village GreenW

  25 Vets Rd, Windham, NY 12496
• 

  

  

  /59

  $875,000 Sold Jun 20, 2025

  216 New York 296, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 2,342 Sq Ft
  • Built 1940

  Last Sold Summary

  • 27% Below List Price
  • $374/SF
  • 196 Days On Market

  Last Listing Agent Elizabeth 'Beth' Alfeld Keller Williams Realty HV Nort

  216 New York 296, Windham, NY 12496
• 

  

  /4

  Not Listed For Sale

  79 Old Rd, Windham, NY 12496

  79 Old Rd, Windham, NY 12496

  Last Sold Summary

  • 5 Days On Market

  Last Sold Price $125,000

  Last Listing Agent Anjali Arora Corcoran Country Living - Hud
• 

  

  /59

  $759,000

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft

  769 Mitchell Hollow Rd, Windham, NY 12496

  Bright Sparrow Farmhouse - Modern Catskills Farmhouse with Solar Power Backup, Private Pond, Mountain Views & Proven Airbnb Income | Windham, NY Welcome to Bright Sparrow Farmhouse--where modern farmhouse style meets smart, energy-efficient living on over 8.22 private acres with a pond, unobstructed Catskill Mountain views, and a turnkey short-term rental / Airbnb investment property with proven

  Regina Tortorella Coldwell Banker Village GreenW

  769 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /95

  $1,500,000 Sold Mar 19, 2026

  351 N Settlement Rd, Ashland, NY 12407

  • 4 Beds
  • 3.5 Baths
  • 3,610 Sq Ft
  • Built 1890

  Last Sold Summary

  • 6% Below List Price
  • $416/SF
  • 45 Days On Market

  Current Estimated Value $1,589,064

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  351 N Settlement Rd, Ashland, NY 12407
• 

  

  /5

  Est $1,263,491 Not Listed For Sale

  127 Brainard Ridge Rd, Windham, NY 12496

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 2020

  127 Brainard Ridge Rd, Windham, NY 12496

  Last Sold Summary

  • 46% Above List Price
  • $393/SF
  • 97 Days On Market

  Last Sold Price $865,000

  Last Listing Agent Debra Bunce Past Member
• 

  

  /68

  $1,899,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,723 Sq Ft

  4 Goff Rd, Windham, NY 12496

  Are you sitting down? Because this one will take your breath away! This brand new modern mountain masterpiece with an indoor pool, glass walls & slope views is offered fully furnished & turn-key! It's a show stopping contemporary retreat where every inch has been crafted for ultimate luxury, relaxation, and awe-inspiring views. Enveloped in two-story walls of glass, this brand new residence

  Regina Tortorella Coldwell Banker Village GreenW

  4 Goff Rd, Windham, NY 12496
• 

  

  /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
• 

  

  /46

  Est $332,281 Not Listed For Sale

  66 Loo Bridge Ln Unit 12G, Windham, NY 12496

  • 2 Beds
  • 2.5 Baths
  • 1,211 Sq Ft
  • Built 1987

  66 Loo Bridge Ln Unit 12G, Windham, NY 12496

  Last Sold Summary

  • 2% Below List Price
  • $281/SF
  • 173 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Sharri Cunningham Bunce Realty
• 

  

  /67

  $1,749,000

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

  33 Elm Ridge Rd, Windham, NY 12496

  The Mountains Are Calling and I Must Go.'' P.S., I plan to be VERY comfortable when I get there!Welcome to 33 Elm Ridge - the best of the Catskills - the ultimate in mountain opulence. This shingled contemporary makes quite the impression on its incredible setting; 3,900sqft of living space spans over 3 floors which include 5 bds, 3.5 bths & a walk-out basement that's ready to party. It's set on

  Regina Tortorella Coldwell Banker Village GreenW

  33 Elm Ridge Rd, Windham, NY 12496
• 

  

  /33

  $795,000 Sold Oct 27, 2025

  233 Begley Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 2,542 Sq Ft
  • Built 2001

  Last Sold Summary

  • $313/SF
  • 22 Days On Market

  Current Estimated Value $829,120

  Last Listing Agent Lubomir Hodan Shaw Country Realty, Inc.

  233 Begley Rd, Windham, NY 12496
• 

  

  /72

  Est $869,912 Not Listed For Sale

  39 Trail View Ln, Windham, NY 12496

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

  39 Trail View Ln, Windham, NY 12496

  Last Sold Summary

  • 7% Above List Price
  • $207/SF
  • 508 Days On Market

  Last Sold Price $810,000

  Last Listing Agent Regina Tortorella Past Member
• 

  

  /68

  $875,000

  • 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
• 

  

  /44

  $1,400,000 Sold Feb 06, 2026

  2 the Enclave Unit W10, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 2,600 Sq Ft
  • Built 1999

  Last Sold Summary

  • 18% Below List Price
  • $538/SF
  • 117 Days On Market

  Last Listing Agent Patricia Charbonneau Brainard Ridge Management

  2 the Enclave Unit W10, Windham, NY 12496
• 

  /2

  Est $1,925,201 Not Listed For Sale

  502 County Route 10, Windham, NY 12496

  • 4 Beds
  • 4.5 Baths
  • 4,300 Sq Ft
  • Built 2023

  502 County Route 10, Windham, NY 12496

  Last Sold Summary

  • 19% Below List Price
  • $552/SF
  • 108 Days On Market

  Last Sold Price $2,375,000

  Last Listing Agent Angela Lanuto Coldwell Banker Village Green
• 

  

  /42

  $1,650,000

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  10 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

  10 Stonewall Ln, Windham, NY 12496
• 

  

  /54

  Sold Apr 07, 2025

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

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

  Last Sold Summary

  • 92 Days On Market

  Last Listing Agent Regina Tortorella Past Member

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

  

  /10

  Not Listed For Sale

  0 Mount Pisgah Rd, Windham, NY 12496

  • 3 Beds
  • Built 2008

  0 Mount Pisgah Rd, Windham, NY 12496

  Last Sold Summary

  • $23/SF
  • 70 Days On Market

  Last Sold Price $58,000

  Last Listing Agent Gregory Kardos Kardos & Co Real Estate, LLC
• 

  

  /27

  $999,000 Pending

  • 7 Beds
  • 3 Baths
  • 4,281 Sq Ft

  5474 New York 23, Windham, NY 12496

  This large historic home is the original site of Windham's first settler in 1785 and the Reynolds have been entertaining family & friends there since 1959!Located on the west side of town, it is an easy walk to Windham's shops & restaurants.It has a formal living room, (which has been used for an office and playroom), a large dining area and a large, comfortable family room. The kitchen is well

  Jane Reynolds Jane H. Reynolds

  5474 New York 23, Windham, NY 12496
• 

  

  /85

  $1,709,999 Sold Feb 09, 2026

  12 Lauren Ln, Windham, NY 12496

  • 6 Beds
  • 4.5 Baths
  • 4,855 Sq Ft
  • Built 2012

  Last Sold Summary

  • 2% Below List Price
  • $352/SF
  • 97 Days On Market

  Current Estimated Value $1,697,294

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  12 Lauren Ln, Windham, NY 12496
• 

  

  /65

  Not Listed For Sale

  128 Mount Pisgah Rd, Windham, NY 12496

  • 5 Beds
  • 5 Baths
  • 4,233 Sq Ft
  • Built 2007

  128 Mount Pisgah Rd, Windham, NY 12496

  Last Sold Summary

  • 4% Below List Price
  • $376/SF
  • 89 Days On Market

  Last Sold Price $1,590,000

  Last Listing Agent Kathy Marino Bunce Realty
• 

  

  /18

  $463,000

  • 3 Beds
  • 2 Baths
  • 1,249 Sq Ft

  111 Brainard Ridge Rd Unit 11B, Windham, NY 12496

  Brainard Ridge Charmer!Ready for 4 season active life style. Charming 3 bedroom, 2 bath plus extra sleeping alcove, Brainard Ridge Townhome. Open and airy floor plan, lots of natural light! Cozy living room with large wood burning fireplace, nice dining area, cheery kitchen, Primary bedroom with ensuite bath, plus extra sleeping alcove. Lower level with bunkroom, and guest bedroom, second

  Patricia Charbonneau Brainard Ridge Management

  111 Brainard Ridge Rd Unit 11B, Windham, NY 12496
• 

  

  /40

  $2,250,000 Sold May 15, 2025

  18 White Way, Windham, NY 12496

  • 6 Beds
  • 6 Baths
  • 4,228 Sq Ft
  • Built 2015

  Last Sold Summary

  • 10% Below List Price
  • $532/SF
  • 82 Days On Market

  Current Estimated Value $2,326,496

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  18 White Way, Windham, NY 12496
• 

  

  /26

  Est $475,770 Not Listed For Sale

  111 Carrington Rd, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 1,526 Sq Ft
  • Built 2008

  111 Carrington Rd, Windham, NY 12496

  Last Sold Summary

  • 29% Above List Price
  • $242/SF
  • 119 Days On Market

  Last Sold Price $370,000

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

  

  /44

  $1,775,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,218 Sq Ft

  31 Windham Farms Rd, Windham, NY 12496

  Modern Mountain Luxury | Windham, New YorkExperience contemporary mountain living at its finest in this exceptional new-construction residence, perfectly positioned just one mile from the Village of Windham. Thoughtfully designed and impeccably built, this light-filled retreat captures the essence of refined modern living in the heart of the Catskills. The home's sophisticated open layout

  Pamela King-Belfor Four Seasons Sotheby's Int.

  31 Windham Farms Rd, Windham, NY 12496
• 

  

  /42

  $437,825 Sold Apr 22, 2025

  27 Steep Hill Rd, Ashland, NY 12407

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1969

  Last Sold Summary

  • 12% Below List Price
  • $228/SF
  • 294 Days On Market

  Current Estimated Value $446,733

  Last Listing Agent Regina Tortorella Past Member

  27 Steep Hill Rd, Ashland, NY 12407
• 

  

  /28

  Not Listed For Sale

  11025 New York 23, Windham, NY 12496

  • 3 Beds
  • 1.5 Baths
  • 1,647 Sq Ft
  • Built 1800

  11025 New York 23, Windham, NY 12496

  Last Sold Summary

  • $97/SF
  • 137 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Susan Miller Past Member
• 

  

  /44

  $1,175,000

  • 5 Beds
  • 3 Baths
  • 4,489 Sq Ft

  32 Glennamaddy Rd, Windham, NY 12496

  STUNNING LOCATION! Situated above Windham Ridge this Custom designed & built (by one of Windham's top builders) Contemporary style home has direct ski slope views in a special setting. Conveniently just 2 minutes to Windham Village & 5 minutes to Windham Mountain. Extraordinary mountain home. Efficient & economical design. Upon entering, a bit of a WOW, with 25ft. Beamed, vaulted ceilings &

  Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

  32 Glennamaddy Rd, Windham, NY 12496
• 

  

  /26

  $425,000 Sold Dec 15, 2025

  410 Big Hollow Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1970

  Last Sold Summary

  • $316/SF
  • 28 Days On Market

  Last Listing Agent Diana Polack Compass Greater NY, LLC

  410 Big Hollow Rd, Windham, NY 12496
• 

  

  /5

  Not Listed For Sale

  0 Case Rd, Ashland, NY 12496

  0 Case Rd, Ashland, NY 12496

  Last Sold Summary

  • 135 Days On Market

  Last Sold Price $67,000

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

  

  /39

  $1,360,000 Open Sat 12:30PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,280 Sq Ft

  305 Mitchell Hollow Rd, Windham, NY 12496

  Modern Mountain Luxury | Windham, New York. Experience contemporary mountain living at its finest in this exceptional new-construction residence, perfectly positioned just one mile from the Village of Windham. Thoughtfully designed and impeccably built, this light-filled retreat captures the essence of refined modern living in the heart of the Catskills. The home's sophisticated open layout

  Pamela King-Belfor Four Seasons Sotheby's Int.

  305 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /9

  $440,000 Sold Oct 27, 2025

  65 Sundance Dr, Windham, NY 12496

  • Land
  • 15.36 Acres
  • $28,646 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 219 Days On Market

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  65 Sundance Dr, Windham, NY 12496
• 

  

  /27

  Est $673,840 Not Listed For Sale

  118 Brainard Ridge Rd Unit 14D, Windham, NY 12496

  • 3 Beds
  • 2.5 Baths
  • 1,702 Sq Ft
  • Built 1985

  118 Brainard Ridge Rd Unit 14D, Windham, NY 12496

  Last Sold Summary

  • 83% Above List Price
  • $216/SF
  • 396 Days On Market

  Last Sold Price $367,500

  Last Listing Agent Sharri Cunningham Bunce Realty
• 

  

  /36

  $399,000

  • 4 Beds
  • 3.5 Baths
  • 1,717 Sq Ft

  274 Brooksburgh Rd Unit 67, Windham, NY 12496

  This 4 bedroom, 3.5 bath unit is ''like New''. Halfbath/laudry, kitchen with granite counters, upgraded cabinets, SS appliances, tile flooring. This is open concept. Nice counter in the kitchen with stool, open to the dining and living room area. Living room has a gas fireplace and sliding doors to a patio with a lovely view. Second floor has two main bedrooms with their full baths, third level

  Mary Donovan Gallagher & Company

  274 Brooksburgh Rd Unit 67, Windham, NY 12496
• 

  

  /26

  $695,000 Sold May 16, 2025

  23 Circle Rd, Windham, NY 12496

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $348/SF
  • 106 Days On Market

  Current Estimated Value $715,279

  Last Listing Agent Carol Shaw Shaw Country Realty, Inc.

  23 Circle Rd, Windham, NY 12496
• 

  

  /30

  Est $788,713 Not Listed For Sale

  208 South St, Windham, NY 12496

  • 5 Beds
  • 3.5 Baths
  • 2,280 Sq Ft
  • Built 1920

  208 South St, Windham, NY 12496

  Last Sold Summary

  • 12% Below List Price
  • $395/SF
  • 171 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Jamie Sittner Find Advisors
• 

  

  /8

  $325,000

  • 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

Showing Results 121 - 160, Page 4 of 18