Windham, NY Homes

• 

  

  

  /28

  $299,999 Pending

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  5359 Main St Unit 2C, Windham, NY 12496

  Turn-Key & Motivated Seller Due to Work RelocationLocation is everything—and this condo has it all. Perfectly situated on Main Street and just one minute from Windham Mountain, this beautifully designed 2-bedroom, 2-bath home offers an open single-level floor plan plus a versatile flex space for a home office, guest room, or whatever you need. Enjoy the best of both worlds with views of Main

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 600-2711

  5359 Main St Unit 2C, Windham, NY 12496
• 

  

  

  /11

  $1,950 per month

  • 3 Beds
  • 1 Bath
  • Condo for Rent

  128 South St Unit 3, Windham, NY 12496

  Property Id: 2241166Located in the heart of Windham, NY - Second floor apartment for rent - 3 bed/1 bath, private washer and dryer in unit. This unit is above a store front (Olivia's Wine & Spirits). Garbage, water, and sewer included. In person walk through available upon request depending on schedule availability.

  128 South St Unit 3, 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

  Last Listing Agent Lisa Jaeger Coldwell Banker Village GreenW

  36 Mount Greenery Rd, Windham, NY 12496
• 

  

  

  /27

  Est $352,824 Not Listed For Sale

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

  24 Vets Rd, Windham, NY 12496

  24 Vets Rd, Windham, NY 12496
• 

  

  

  /21

  $319,000

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

  63 Windham Ridge Rd, Windham, NY 12496

  Welcome to the sought after Town of Windham to this beautiful Townhouse complex of Windham Ridge,a 4 Seasons Community that offers a fantastic opportunity for outdoor enthusiasts and those looking for a cozy retreat. Located near the Village, it is close to a variety of amenities, including restaurants, shops and movie theaters while still providing the serenity and access to outdoor activities

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 855-3425

  63 Windham Ridge Rd, 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
• 

  

  /17

  Sold Apr 22, 2025

  70 Begley Rd, Windham, NY 12496

  • Land
  • 7.2 Acres

  Last Sold Summary

  • 189 Days On Market

  Last Listing Agent Regina Tortorella Past Member

  70 Begley Rd, Windham, NY 12496
• 

  

  /64

  Est $636,905 Not Listed For Sale

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

  29 Martin Ln, Hensonville, NY 12439

  29 Martin Ln, Hensonville, NY 12439
• 

  

  /59

  $685,000

  • 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.

  (518) 777-2454

  523 Mitchell Hollow Rd, Windham, NY 12496
• 

  

  /38

  $2,300 per month

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

  5359 New York 23 Unit 2E, Windham, NY 12496

  Opportunity awaits as this beautifully designed 2-bedroom 2 bath Windham condo rental a minute drive to Windham Mountain hits the market! You get the best of everything here as this property is located right on Main Street where you can find everything but also so close to the ski resort! Features include large cozy great room with dining/living room combo with 2 large windows, recessed lighting

  Wayne Newcomb Newcomb Realty Group LLC

  5359 New York 23 Unit 2E, Windham, NY 12496
• 

  

  /34

  $450,000 Sold May 23, 2025

  116 Galway Rd, Windham, NY 12496

  • 3 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $241/SF
  • 66 Days On Market

  Current Estimated Value $482,830

  Last Listing Agent Patrick Dunn Core Real Estate Team

  116 Galway Rd, Windham, NY 12496
• 

  

  /30

  Est $712,337 Not Listed For Sale

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

  121 Thunderbird Terrace, Windham, NY 12496

  121 Thunderbird Terrace, Windham, NY 12496
• 

  

  /29

  $639,000 Pending

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

  19 Brook Hollow Ln, Windham, NY 12496

  Windham - Where Everyone Wants to Be! Just one mile from the heart of Windham Village, this chalet-style raised ranch offers the perfect balance of comfort, style, and mountain living. Beautifully maintained inside and out, the home features 4 bedrooms and 2 full baths, with a bright open floor plan, vaulted ceilings, and a cozy fireplace creating that quintessential ski-town charm. The main

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 749-4476

  19 Brook Hollow Ln, Windham, NY 12496
• 

  

  /30

  $490,000 Sold Jun 20, 2025

  3 Begley Rd, Windham, NY 12496

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

  Last Sold Summary

  • 2% Below List Price
  • $256/SF
  • 96 Days On Market

  Current Estimated Value $351,000

  Last Listing Agent Jessica Surbeck WINDSTAR REALTY GROUP LLC

  3 Begley Rd, Windham, NY 12496
• 

  

  /15

  Not Listed For Sale

  76 Begley Rd, Windham, NY 12496

  76 Begley Rd, Windham, NY 12496
• 

  

  /54

  $850,000

  • 8 Beds
  • 8 Baths
  • 3,712 Sq Ft

  5320 New York 23, Windham, NY 12496

  In the heart of Windham, ''the place to be,'' this rare multi-use property offers endless possibilities for residential, commercial, or mixed-use ventures. Formerly a thriving B&B, it features two buildings with a total of 8 bedrooms and 8 bathrooms, a large open kitchen plus accessory kitchen, and expansive spaces perfect for a restaurant, café, art studio, gallery, retail shop, or rental income

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 261-9298

  5320 New York 23, Windham, NY 12496
• 

  

  /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 $243,799

  Last Listing Agent Mary Donovan Gallagher & Company

  35 Quads Way, Windham, NY 12496
• 

  

  /25

  Not Listed For Sale

  • 3 Beds

  0 Route 10, Windham, NY 12496

  0 Route 10, Windham, NY 12496
• 

  

  /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. Proud of ownership is seen throughout. The flexible layout is easily adaptable to a 2-bedroom plus sleeping loft, with a separate

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 806-2865

  71 Windham Mount Village Unit 71, Windham, NY 12496
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  /11

  $138,000 Sold Apr 04, 2025

  79 Begley Rd, Windham, NY 12496

  • Land
  • 4.72 Acres
  • $29,237 per Acre

  Last Sold Summary

  • 23% Below List Price
  • 158 Days On Market

  Last Listing Agent Regina Tortorella Past Member

  79 Begley Rd, Windham, NY 12496
• 

  

  /34

  Est $1,665,979 Not Listed For Sale

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

  21 Sundance Dr, Windham, NY 12496

  21 Sundance Dr, Windham, NY 12496
• 

  

  /35

  $699,000

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

  134 Magda Ln, Windham, NY 12496

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

  

  Carol Shaw

  SHAW COUNTRY REALTY INC

  (518) 413-0731

  134 Magda Ln, 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
• 

  

  /6

  Not Listed For Sale

  0 Larsen Dr Unit 152095, Windham, NY 12496

  0 Larsen Dr Unit 152095, Windham, NY 12496
• 

  

  /24

  $334,900

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  504 Rt 40, Windham, NY 12454

  Nestled in the quaint hamlet of Maplecrest, this inviting 2-bedroom home offers the perfect blend of tranquility and convenience. Ideally located between Windham and Hunter Mountains, it's just minutes from world-class skiing, hiking, golf, and other outdoor adventures. Enjoy easy access to nearby CD Lane Park, Colgate Lake, and the iconic Kaaterskill Falls.This home boasts a semi-finished

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 741-2720

  504 Rt 40, Windham, NY 12454
• 

  $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 $519,117

  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
• 

  

  /31

  $399,000

  • 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.

  (518) 667-5960

  436 Big Hollow Rd, Maplecrest, NY 12454
• 

  

  /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 $728,072

  Last Listing Agent Regina Tortorella Coldwell Banker Village GreenW

  8 Evans Rd, Windham, NY 12496
• 

  

  /28

  Est $447,593 Not Listed For Sale

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

  904 N Settlement Rd, Windham, NY 12496

  904 N Settlement Rd, Windham, NY 12496
• 

  

  /5

  $99,000

  • Land
  • 0.5 Acre
  • $198,000 per Acre

  448-2 South St, Windham, NY 12496

  Prime vacant land in the sought-after Town of Windham, offering municipal sewer and electric on site at an unbeatable location. This opportunity includes two level half-acre parcels, selling together or Separate at 99k per parcel. Situated just up the road from Windham Mountain, the Windham Country Club golf course, and the beloved Chicken Run Restaurant—placing you in the heart of one of the

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 740-2939

  448-2 South St, Windham, NY 12496
• 

  

  /13

  $157,500 Pending

  • 1 Bed
  • 1 Bath
  • 560 Sq Ft

  2 Quads Way, Windham, NY 12496

  Located in the heart of Windham, “Land in the Sky,” this condo is your perfect home away from home. Whether you’re an outdoor adventurer or seeking a relaxing getaway, this one-bedroom retreat is designed for comfort and convenience. Families of all sizes will enjoy year-round excitement with on-site amenities including a pool, tennis court, fire pit, and picnic areas.Just 3 minutes from

  

  Gal Ozana

  Ozana Realty Group

  (518) 201-1127

  2 Quads Way, Windham, NY 12496
• 

  

  /48

  Est $567,349 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 2,404 Sq Ft

  50 County Rd Unit 65, Windham, NY 12496

  50 County Rd Unit 65, Windham, NY 12496
• 

  

  /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. This makes this lot desirable with no soil testing and design which could usually take Months and Money.cleared closer to road which

  

  Carol Shaw

  Shaw Country Realty, Inc.

  (518) 809-8670

  539 Route 40, Maplecrest, NY 12454
• 

  

  /51

  $1,117,500 Sold Apr 29, 2025

  292 South St, Windham, NY 12496

  • 5 Beds
  • 5.5 Baths
  • 3,643 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $307/SF
  • 59 Days On Market

  Last Listing Agent Regina Tortorella Past Member

  292 South St, Windham, NY 12496
• 

  

  /31

  Est $261,017 Not Listed For Sale

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

  60 Quads Way, Windham, NY 12496

  60 Quads Way, Windham, NY 12496
• 

  

  /23

  $349,000

  • 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.

  (518) 735-6784

  315 Begley Rd, 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
• 

  

  /38

  Est $406,187 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,168 Sq Ft

  251 County Route 65, Hensonville, NY 12439

  

  251 County Route 65, Hensonville, NY 12439
• 

  

  /47

  $1,750,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 2.5 Baths
  • 4,056 Sq Ft

  5433 New York 23, Windham, NY 12496

  Set right in the heart of the town of Windham, this exceptional brand new construction offers the rare combination of village proximity, mountain views, and income producing potential. Thoughtfully designed as a two-story residence with a private backyard and a separate barn with utilities already in place, the property presents a turnkey opportunity for an accessory dwelling unit, guest house,

  

  Catherine Quintard

  Compass Greater NY, LLC

  (518) 400-5046

  5433 New York 23, Windham, NY 12496

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