31

Windham, NY Homes for Sale under $800,000

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  • /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

    Agent Photo

    Carol Shaw

    Shaw Country Realty, Inc.

    134 Magda Ln, Windham, NY 12496
  • /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,

    Agent Photo

    Carol Shaw

    SHAW COUNTRY REALTY INC

    16 Hickory Hill Rd, Windham, NY 12496
  • /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.

    Agent Photo

    Carol Shaw

    SHAW COUNTRY REALTY INC

    5429 New York 23, 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. The flexible layout is easily adaptable to a 2-bedroom plus sleeping loft, with a separate lockout bedroom/studio-ideal for

    Agent Photo

    Carol Shaw

    SHAW COUNTRY REALTY INC

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

    Agent Photo

    Carol Shaw

    Shaw Country Realty, Inc.

    523 Mitchell Hollow Rd, Windham, NY 12496
  • /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,''

    Agent Photo

    Carol Shaw

    Shaw Country Realty, Inc.

    5355 New York 23, Windham, NY 12496
  • /33

    $789,000

    $11K PRICE DROP
    • 6 Beds
    • 3.5 Baths
    • 4,368 Sq Ft

    559 Case Rd, Windham, NY 12496

    AT 559, ITS TIME! TO MAKE YOUR CASE FOR WINDHAM. Welcome to 559 Case Road in Ashland-Windham, a spacious Colonial set on almost 8 private acres, surrounded by the natural beauty of the Catskills in the Upper Hudson Valley. Offering 6 bedrooms and 3.5 bathrooms, this property is a great full-time residence, weekend retreat, or investment property. A sun-filled entryway with soaring ceilings and

    Agent Photo

    Al Iaquinta

    Iaquinta Premier Properties

    559 Case Rd, Windham, NY 12496
  • /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
  • /49

    $569,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,182 Sq Ft

    150 Vining Rd, Windham, NY 12496

    150 Vining Road, Windham, NY Beautifully renovated contemporary mountain retreat set on 1 acre of lush lawn just minutes from the Windham Mountain Club. Blending rustic charm with modern finishes, this inviting home offers 1,394 square feet of above-grade living space plus an additional 788 square feet in the finished lower level--totaling 2,182 square feet of living space designed for

    Regina Tortorella Coldwell Banker Village GreenW

    150 Vining Rd, Windham, NY 12496
  • /30

    $525,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,335 Sq Ft

    20 Sutton Hollow Rd, Windham, NY 12496

    Modern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! This turn-key, completely renovated modern farmhouse is ready to welcome you! Just 12 minutes from the Windham Mountain Club and only a short drive to Hunter and Belleayre, this stylish 3-bedroom plus open sleeping loft retreat delivers four-season Catskill charm with designer finishes and a prime location for

    Regina Tortorella Coldwell Banker Village GreenW

    20 Sutton Hollow Rd, Windham, NY 12496
  • /52

    $575,000

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

    591 & 587 Co Rd 56, Windham, NY 12496

    Looking for a charming home set perfectly on a country road with privacy, mountain views, adjacent to thousands of acres of state land, AND close to Catskill Park trailheads, CD Lane Park and Windham Mtn Club? Come visit 591 County Route 56 - you won't be disappointed! Enter the warm and welcoming living room where the cathedral ceiling and sky lights allow the sun to stream in to brighten your

    Sharon Knudsen Coldwell Banker Village GreenW

    591 & 587 Co Rd 56, Windham, NY 12496
  • /40

    $545,000

    • 2 Beds
    • 2 Baths
    • 1,390 Sq Ft

    53 Windham Mount Village, Windham, NY 12496

    Renovated Windham Mountain Village Townhouse - Steps to Slopes & Lodge, Walk to Lift, Season Tenant in Place, Income from Day One, Pool & Tennis Access-Located at the Windham Mountain Club, this beautifully updated 2-bedroom, (plus a flex room that is used as a third bedroom), 2-bathroom townhouse in Windham Mountain Village offers the perfect blend of a peaceful Catskills retreat and a smart

    Regina Tortorella Coldwell Banker Village GreenW

    53 Windham Mount Village, Windham, NY 12496
  • /59

    $699,000

    $100K PRICE DROP
    • 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
  • /12

    $550,000

    • 2 Beds
    • 1 Bath
    • 1,122 Sq Ft

    183 N South St N, Windham, NY 12496

    Exceptional Opportunity in a Prime Windham Location! property is sub- dividable. Owner is motivated bring offers!!!Transform this property into a true showpiece — take this Chevy and turn it into a Rolls Royce! Situated directly across from the Windham Country Club, enjoy unobstructed views of the golf course. This property also offers potential for subdivision, adding long-term investment

    John Pumilia Shaw Country Realty, Inc.

    183 N South St N, Windham, NY 12496
  • /9

    $500,000

    • Land
    • 22,651 Sq Ft
    • $961,538 per Acre

    220 & 240 Club Rd, Windham, NY 12496

    Be captivated by the breathtaking, panoramic views that will mesmerize you from dusk till dawn from either of these 2 building lots, with ski access being offered by Windham Mountain Club. Let your imagine soar with the possibilities of designing your dream home to last for generations on one of the few remaining building lots offered by Windham Mountain Club. Envision waking up in your mountain

    Patricia Charbonneau Brainard Ridge Management

    220 & 240 Club Rd, Windham, NY 12496
  • /39

    $639,000

    $21K PRICE DROP
    • 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
  • /37

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 1,545 Sq Ft

    149 Peck Rd, Maplecrest, NY 12454

    Tucked away in a peaceful, semi-private setting just minutes from Windham Mountain Ski Resort, this distinctive 1978 contemporary offers the perfect blend of rustic charm and modern comfort. With 3 bedrooms, 2.5 baths, and the ability to comfortably sleep 10, this property isideal as a year-round getaway, investment rental, or full-time residence.Step inside to an inviting open-concept

    Judy Gregory Gilcrest Properties

    149 Peck Rd, Maplecrest, NY 12454
  • /34

    $685,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    730 Mill St, Windham, NY 12496

    Wonderful Windham Cape Cod on picturesque 6.8 acres, gazebo, and private pond! Welcome to this country gem! Many renovations in 2016: with a one car garage, breezeway, well equipped kitchen with granite counters, island and lovely, sun filled first floor ensuite bedroom with beautiful views out to the deck and gorgeous grounds. The main floor offers a second full bath, dining area and

    Patricia Charbonneau Brainard Ridge Management

    730 Mill St, Windham, NY 12496
  • /35

    $790,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,112 Sq Ft

    97 Clarence D Lane Rd Unit D, Windham, NY 12496

    Welcome to your new mountain home! This spacious 4-bedroom, 2-bath townhouse on Windham Mountain offers the perfect blend of ski-lodge charm and modern comfort, moments to the slopes. With 2,112 square feet of living space, there's plenty of room to gather, relax, and make lasting memories in every season. Inside, you'll find soaring wood-beamed ceilings, a dramatic stone hearth, and two

    Jessica Surbeck Windstar Realty Group, LLC

    97 Clarence D Lane Rd Unit D, Windham, NY 12496
  • /27

    $565,000

    • 5 Beds
    • 2 Baths

    96 56, Windham, NY 12496

    An amazing opportunity to own the perfect mountain retreat! This legal two-family home offers incredible flexibility as a two-unit investment property or an owner-occupied home with income-producing potential. The main house features a living room and formal dining room with beautifully refinished hardwood floors, an updated kitchen with granite countertops and brand-new stainless steel

    Doris Kennedy Kennedy L I Realty

    96 56, Windham, NY 12496
  • /33

    $610,000

    • 4 Beds
    • 2.5 Baths
    • 2,227 Sq Ft

    49 Brainard Ridge Rd Unit 3A, Windham, NY 12496

    Move in ready! Warm and Welcoming describes this beautiful, Brainard Ridge large end unit, 4 bedroom 2.5 bath with a sun drenched extra den/family room. Beautifully renovated kitchen with new Cambria Windermere Quarts countertops, attractive wood cabinets, new electric stove, refrigerator and microwave. Spacious living area with wood burning fireplace to enjoy relaxing moments with family and

    Patricia Charbonneau Brainard Ridge Management

    49 Brainard Ridge Rd Unit 3A, Windham, NY 12496
  • /20

    $599,000

    • 2 Beds
    • 1.5 Baths
    • 1,204 Sq Ft

    406 Campbell Rd, Windham, NY 12496

    Welcome to 406 Campbell Road, a peaceful Catskills retreat tucked among mature trees just minutes from the heart of Windham. This inviting home offers the perfect blend of privacy, comfort, and year-round recreation. Relax on the spacious covered front porch overlooking beautifully crafted bluestone walkways and landscaped grounds. The setting creates a true mountain-lodge atmosphere while

    Agnieszka Wdziekowska Taufield Venture Fox Realty Group

    406 Campbell Rd, Windham, NY 12496
  • /54

    $575,000

    $124K PRICE DROP
    • 7 Beds
    • 3 Baths
    • 3,485 Sq Ft

    200 & 212 Co Rd 40, Windham, NY 12496

    Mixed-Commercial (Inn/Lodge/Residential) with 7.2 Acres and 4 existing structures on the Batavia Kill Creek featuring open meadows, sweeping hill views, and a peaceful natural backdrop. This property offers a unique opportunity to reimagine a hospitality destination, retreat center, multi-structure compound, or private residential estate, to name a few. The original inn building has been removed,

    Susan Lennon Coldwell Banker Timberland

    200 & 212 Co Rd 40, Windham, NY 12496
  • /16

    $750,000

    • Land
    • 25,264 Sq Ft
    • $1,293,103 per Acre

    247 Club Rd, Windham, NY 12496

    The Last True Ski-On/Ski-Off Lot at Windham Mountain—Step Out & Ski!This is the one and only true ski-on/ski-off lot available at Windham Mountain Club! Imagine waking up to breathtaking mountain views, stepping outside, putting on your skis, and gliding directly onto the slopes—no walking, no hassle, just pure ski-in/ski-out convenience. Located at the end of a no-outlet road, this prime

    Regina Tortorella Coldwell Banker Village GreenW

    247 Club Rd, Windham, NY 12496
  • /39

    $639,000

    $21K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    60 Route 65-A, Windham, NY 12496

    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 65-A, Windham, NY 12496
  • /4

    $799,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,118 Sq Ft

    69 County Road 32c, Windham, NY 12496

    • Escape NYC• Catskills Mountain Retreat• New Construction in Windham Area The proposed 2,118-square-foot home is designed for modern Catskill living, featuring soaring vaulted ceilings with exposed beams and dramatic trapezoid windows that capture natural light and panoramic views of the surrounding mountains.The open-concept layout connects the great room, kitchen, and dining area,

    John Pumilia Shaw Country Realty, Inc.

    69 County Road 32c, Windham, NY 12496
  • /56

    $598,000

    • 3 Beds
    • 1.5 Baths
    • 1,718 Sq Ft

    320 State Route 296, Windham, NY 12496

    Charming and newly renovated, this home, reminiscent of an Arts and Crafts Bungalow or Cottage, is a must see. With cedar shake siding and a wrap-around porch, this little gem beckons you to pull up a rocking chair, visit with neighbors & friends and watch the world go by. From top to bottom, this home has been updated and refreshed! The custom kitchen flows seamlessly into the dining area -

    Sharri Cunningham Bunce Realty

    320 State Route 296, Windham, NY 12496
  • /79

    $749,000

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

    37 Cambridge Heights Rd, Windham, NY 12496

    Perched on a hill in one of Windham's premier locations, this two-story chalet/contemporary home offers breathtaking panoramic views of the surrounding mountains and views of Windham Resort. Just minutes from the ski slopes, downtown, and local restaurants, this well-manicured property perfectly combines privacy, convenience, and year-round recreation.The home features three bedrooms and

    Kathy Marino Bunce Realty

    37 Cambridge Heights Rd, Windham, NY 12496
  • /53

    $579,000

    • 6 Beds
    • 3 Baths
    • 1,680 Sq Ft

    49 Chase Dr, Hensonville, NY 12439

    A rare income-generating property nestled in the heart of the Catskills -- fully positioned to capitalize on year-round ski and outdoor tourism.This turnkey investment property features two self-contained apartments, each ideally suited for short-term rental on Airbnb. With ski season drawing visitors from across the region, the property's proximity to both Windham Mountain Club and Hunter

    Sheila Word Coldwell Banker Village GreenW

    49 Chase Dr, Hensonville, NY 12439
  • /17

    $599,000

    • Land
    • 69.02 Acres
    • $8,679 per Acre

    0 High Peak Lot 111-112, Windham, NY 12496

    Discover a rare 65.3± acre Catskills property on High Peak Road in Windham, NY, offering an extraordinary blend of open meadows, mature forests, and stream frontage. With generous road frontage and multiple potential building sites, this land provides exceptional opportunity for anyone looking to build a dream home, create a residential compound, or invest in one of the most desirable regions of

    Regina Tortorella Coldwell Banker Village GreenW

    0 High Peak Lot 111-112, Windham, NY 12496
  • /46

    $795,000

    • 4 Beds
    • 3.5 Baths
    • 3,292 Sq Ft

    24 Case Rd, Windham, NY 12496

    Located amongst rolling hills and an adjacent stream, you will find this custom-built gem! Home offers 4 bedrooms, 3.5 baths, sited on 8.64 acres. Minutes away from Windham Mountain, golf, and the Town of Windham, this meticulously maintained home is bright, airy and can comfortably sleep10. Home boasts an open floor plan on the main level with 3 bedrooms, 2.5 baths, den/office, LR with solid oak

    Patricia Charbonneau Brainard Ridge Management

    24 Case Rd, Windham, NY 12496

Home Price Trends

Median Sale Price
$702,000
Median Single Family Sale Price
$694,500
Median Townhouse Sale Price
$412,000
Median 2 Bedroom Sale Price
$319,000
Median 1 Bedroom Sale Price
$158,000
Average Price Per Sq Ft
$358
Number of Homes for Sale
79
Last 12 months Home Sales
87
Months of Supply
10.90
Median List Price
$700,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
52%
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