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Windham, NY Homes for Sale with Garage

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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.

    (518) 608-3522

    134 Magda Ln, Windham, NY 12496
  • /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

    Agent Photo

    Carol Shaw

    Shaw Country Realty, Inc.

    (518) 777-2454

    523 Mitchell Hollow Rd, Windham, NY 12496
  • /33

    $800,000

    • 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

    (518) 800-3084

    559 Case Rd, Windham, NY 12496
  • /31

    $379,000

    $20K PRICE DROP
    • 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.

    Agent Photo

    Carol Shaw

    Shaw Country Realty, Inc.

    (518) 667-5960

    436 Big Hollow Rd, Maplecrest, NY 12454
  • /24

    $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

    Agent Photo

    Carol Shaw

    Shaw Country Realty, Inc.

    (518) 735-6784

    315 Begley Rd, Windham, NY 12496
  • /42

    $315,000

    • 2 Beds
    • 2 Baths
    • 1,542 Sq Ft

    689 Old Rd, Hensonville, NY 12439

    Step into the charm of this 1930s 2-bedroom, 2-bath ranch, just minutes from the Village of Windham and Windham Mountain. Nestled on a full acre and bordered by 25.5 acres of protected NYC watershed land, the property offers rare privacy and a seamless connection to nature. Wake up to the gentle sounds of a seasonal creek and lush surrounding greenery, a true mountain escape.Outside, a

    Agent Photo

    Mark McAlpine

    Compass Greater New York, LLC

    (518) 872-6656

    689 Old Rd, Hensonville, NY 12439
  • /86

    $1,699,000

    • 5 Beds
    • 5.5 Baths
    • 4,848 Sq Ft

    27 Anchor Camp Rd, Windham, NY 12496

    Luxury Windham Log Cabin Retreat Near Windham Mountain Club | Air Conditioned, Ski Slope Views, Stream, Hot Tub & STR Potential! The Catskills dream that buyers have spent years searching for finally exists--and it's less than 5 minutes from Windham Mountain Club. Privately tucked away on nearly 6 acres in one of Windham's most desirable newer luxury home enclaves, this spectacular

    Regina Tortorella Coldwell Banker Village GreenW

    27 Anchor Camp Rd, Windham, NY 12496
  • /109

    $2,175,000

    • 6 Beds
    • 4.5 Baths
    • 4,104 Sq Ft

    19 Twin Maples, Windham, NY 12496

    Experience mountain luxury at its finest in this stunning post-and-beam home at Windham Mountain Club's exclusive Village East community just a little over two hours from New York City. Designed for those who love the outdoors but don't want to sacrifice comfort, this 6-bedroom, 3.5-bath retreat spans more than 4,100 sq ft and combines timeless craftsmanship with breathtaking views of the

    Regina Tortorella Coldwell Banker Village GreenW

    19 Twin Maples, 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
  • /63

    $1,149,000

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

    292 South St Unit 2, Windham, NY 12496

    Turn-Key Furnished Investment Opportunity Across from Windham Mountain Club with Existing Bookings Ready to Transfer to the New Owner for Immediate Income Proven Short-Term Rental Investment directly across from Windham Mountain Club. Perfectly positioned within walking distance to town and ''The Valley,'' Windham Mountain Club's exciting new amenities expansion, this luxury townhouse offers

    Regina Tortorella Coldwell Banker Village GreenW

    292 South St Unit 2, Windham, NY 12496
  • /74

    $425,000

    $274K PRICE DROP
    • 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
  • /67

    $1,749,000

    $351K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,893 Sq Ft

    33 Elm Ridge Rd, Windham, NY 12496

    200,000 PRICE REDUCTION. Exceptional value for this private Catskills estate--offering a setting that would be difficult to replicate at this price point. Welcome to 33 Elm Ridge, a beautifully sited contemporary home on 12+ acres of manicured, park-like grounds. A long, private driveway leads to a peaceful setting with mountain views, a private pond, and an outbuilding, all just minutes from

    Regina Tortorella Coldwell Banker Village GreenW

    33 Elm Ridge 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
  • /97

    $1,349,000

    • 4 Beds
    • 3.5 Baths
    • 3,977 Sq Ft

    78 Buckskin Loop, Windham, NY 12496

    Welcome to Windmont--Windham's most exclusive gated community--where luxury living meets the serenity of a private, thousand-acre natural preserve. Opportunities to own here are few and far between, making this a truly rare offering. Enter through secured gates and follow a scenic road to a paved, winding driveway that leads to this beautifully updated contemporary home, privately sited on 5

    Regina Tortorella Coldwell Banker Village GreenW

    78 Buckskin Loop, Windham, NY 12496
  • /61

    $1,125,000

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

    3 South St, Windham, NY 12496

    Luxury STR Investment Opportunity Across from Windham Mountain Club -- turnkey option, income-producing, and perfectly positioned in one of the Catskills' most desirable four-season destinations. Located within walking distance to Windham's restaurants, shops, nightlife, and ''The Valley,'' Windham Mountain Club's exciting new expansion featuring pools, tennis, pickleball, spa amenities, golf,

    Regina Tortorella Coldwell Banker Village GreenW

    3 South St, Windham, NY 12496
  • /78

    $935,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    2074-2080 County Route 10, Windham, NY 12496

    Set on 12 breathtaking acres with sweeping views of Windham Mountain and the surrounding ranges, this exceptional 3-bedroom, 2-bath property offers a rare combination of luxury, versatility, and investment opportunity. Offered only due to relocation, this is a truly one-of-a-kind Catskills retreat. The beautifully appointed, recently completed main residence features spacious living areas,

    Lisa Gambella WINDSTAR REALTY GROUP LLC

    2074-2080 County Route 10, Windham, NY 12496
  • /45

    $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
  • /33

    $749,000

    $50K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,279 Sq Ft

    415 Old Rd, Windham, NY 12496

    Don't miss this unique opportunity to establish a year-round retreat in the Catskill Mountains, ideal for hosting family and friends on two separate lots. The grounds offer apple picking, fishing in the pond, and swimming, while children can enjoy outdoor activities and grandparents relax on the upper deck with scenic mountain views--all accessible from your own front yard. In winter, prepare for

    Laurie Hanenberg Hunter Windham Real Estate

    415 Old Rd, Windham, NY 12496
  • /37

    $425,000

    • 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
  • /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
  • /31

    $525,000

    $64K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,084 Sq Ft

    34 Old Rd, Windham, NY 12496

    Discover an exceptional Windham, NY mountain retreat just ~2 miles from Windham Mountain, offering both lifestyle appeal and income potential. This spacious, rustic 3-bedroom, 1.5-bath home features two separate living rooms—one on the first floor and one on the second floor—providing flexible space for entertaining, relaxing, or multi-group living. A cozy fireplace, open living areas, modern

    Michael Mariani Patricia Forgione's Realty

    34 Old Rd, Windham, NY 12496
  • /40

    $1,950,000

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

    15 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

    15 Stonewall Ln, Windham, NY 12496
  • /38

    $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 is ideal as a year-round getaway, investment rental, or full-time residence. Step inside to an inviting open-concept living

    Judy Gregory Gilcrest Properties

    149 Peck Rd, Maplecrest, NY 12454
  • /45

    $349,999

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,739 Sq Ft

    477 Campbell Rd, Windham, NY 12496

    Your wonderful Summer weekend getaway! 7 glorious acres, 8 minutes to Windham Mountain! Charming Updated Home with mature trees, beautiful plantings and landscapes. Welcome to this inviting 3-bedroom, 1-bath home set on 7 beautiful acres offering privacy, space, and stunning natural surroundings. Located only 8 minutes from the local ski area, it's the perfect retreat for outdoor enthusiasts or

    Robyn Tricinelli Century 21 Alliance

    477 Campbell Rd, Windham, NY 12496
  • /77

    $599,900

    • 3 Beds
    • 3 Baths
    • 1,870 Sq Ft

    513 County Road 10, Windham, NY 12496

    Mountain Majesty Meets Everyday Luxury on 2.8 Serene Acres! Escape to the perfect blend of rustic warmth and contemporary functionality. Nestled against the spectacular backdrop of Windham Mountain, this exceptional log home effortlessly serves as an active full-time residence or the ultimate four-season mountain getaway. The main level features a bright, open-concept floor plan designed for both

    Ted Banta RVW Select Properties

    513 County Road 10, Windham, NY 12496
  • /48

    $449,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,287 Sq Ft

    18 Maplewood Ave, Windham, NY 12496

    Charming 4-Bedroom Ranch on 1.6 Acres in Windham, NY Discover your dream retreat in the heart of the Catskills! Nestled in the picturesque village of Windham, just minutes from vibrant downtown and the renowned Windham Mountain Resort with its array of restaurants and shops, this spacious 4-bedroom, 2-bathroom ranch offers the perfect blend of comfort and charm. Situated on a generous 1.6-acre

    Fred Mazza Bunce Realty

    18 Maplewood Ave, 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

    HISTORIC Batavia Kill Property - 7.2 Acres with Redevelopment Potential. The property includes two residences, a small one room spring house, and a barn, all in need of renovation, offering flexibility for restoration, rental income, staff housing, or guest accommodations.A rare multi-use setting along the scenic Batavia Kill, featuring open meadows, sweeping hill views, and a peaceful

    Susan Lennon Coldwell Banker Timberland

    200 & 212 Co Rd 40, Windham, NY 12496
  • /41

    $1,450,000

    New Construction $50K PRICE INCREASE
    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    17 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

    17 Stonewall Ln, Windham, NY 12496
  • /41

    $1,700,000

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

    23 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

    23 Stonewall Ln, Windham, NY 12496
  • /22

    $279,990

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 800 Sq Ft

    107 Route 40 Rd, Windham, NY 12496

    Charming 2 bed home near Windham Mountain. Close to 3 additional ski hills within 35 min. Endless outdoor adverntures await.Welcome to this beautiful 2 bd 1 ba home tucked away in the small hamlet of Hensonville NY. Located minutes from local restaurants and activities. This inviting property offers the ideal blend of comfort and location. Wheather you are looking for a full time residence,

    Brian Cohen RHR Realty Group

    107 Route 40 Rd, Windham, NY 12496
  • /27

    $599,000

    $166K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    9 Pinekill Ln, Windham, NY 12496

    Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-bedroom, 2-bath home, updated in 2022, Located within walking distance to CD Lane Park for swimming, boating, and BBQs, and close to the Catskill Forest Preserve for hiking and biking, this property is perfect for outdoor enthusiasts. Inside, you'll find a spacious open floor plan with a modern kitchen and

    Serena Shi Sany Realty Group LLC

    9 Pinekill Ln, Windham, NY 12496

Home Trends in Windham, NY

Housing Trends

Median Sale Price
$680,000
Median Single Family Sale Price
$685,000
Median Townhouse Sale Price
$377,000
Median 2 Bedroom Sale Price
$274,500
Median 1 Bedroom Sale Price
$154,000
Average Price Per Sq Ft
$339
Number of Homes for Sale
67
Last 12 months Home Sales
87
Months of Supply
9.20
Median List Price
$699,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
39%
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