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Windham, NY Houses for Sale

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  • /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
  • /35

    $684,000

    $15K PRICE DROP
    • 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

    Agent Photo

    Carol Shaw

    SHAW COUNTRY REALTY INC

    134 Magda Ln, Windham, NY 12496
  • /45

    $1,850,000

    • 5 Beds
    • 3 Baths
    • 3,740 Sq Ft

    37 The Loop, Windham, NY 12496

    VIEWS -LOCATION Spectacular true log home just a short walk to the slopes of Windham Mountain Club offering the perfect four-season retreat in the heart of the Catskills. This meticulously maintained 5-bedroom, 3-bath home blends warm mountain character with comfort and style, all within minutes of Windham Village restaurants, breweries, movies, golf courses, walking trails, and year-round

    Agent Photo

    Carol Shaw

    SHAW COUNTRY REALTY INC

    37 The Loop, Windham, NY 12496
  • /21

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    135 Route 40, Windham, NY 12496

    Whether you're searching for your first home, a weekend getaway, or a smart investment in the Catskills, this recently renovated ranch in Windham delivers exceptional value. Ideally located just minutes from both Windham Mountain Club and Hunter Mountain, as well as CD Lane Park, hiking, dining, and everything the area has to offer, this move-in-ready home puts four-season recreation right at

    Agent Photo

    Jason Dugo

    Dugo Realty

    135 Route 40, Windham, NY 12496
  • /31

    $379,000

    • 4 Beds
    • 2 Baths
    • 1,414 Sq Ft

    117 Maplecrest Rd, Windham, NY 12496

    There's something instantly welcoming about this refreshed 4-bedroom, 2-bath Country Cape located in the village of Hensonville--small-town charm, a backyard of your own and all that Windham and the Mountaintop have to offer just minutes away.A stone patio welcomes you at the front entrance, with plenty of opportunity to add your own personal touches with planters, seating or seasonal color.

    Agent Photo

    Lisa Jaeger

    Coldwell Banker Village GreenW

    117 Maplecrest Rd, 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
  • /35

    $460,000

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    5134 New York 23, Windham, NY 12496

    Introducing a treasure in the heart of Windham, where charm and convenience beautifully coalesce. This three-bedroom oasis offers a newly renovated, low maintenance home that encapsulates comfort and serenity. Set amidst the breathtaking mountain views, this property boasts an enchanting creekside grotto. The firepit area is an idyllic spot for tranquil evenings under the stars, a feature so

    Agent Photo

    Jason Dugo

    Dugo Realty

    5134 New York 23, Windham, NY 12496
  • /25

    $409,000

    $13K PRICE INCREASE
    • 3 Beds
    • 3.5 Baths
    • 3,683 Sq Ft

    2914 Route 10, Windham, NY 12496

    Escape to the Catskills and enjoy the privacy, space, and year-round lifestyle you've been looking for. Set on more than 5 private acres, this move-in-ready home offers over 2,600 square feet of living space with 3 bedrooms and 3.5 bathrooms, creating the perfect retreat for weekend getaways, full-time living, or a vacation home with income potential. Inside, you'll find spacious living areas

    Agent Photo

    Jack Yao

    Realmart Realty, LLC

    2914 Route 10, Windham, NY 12496
  • /31

    $349,000

    $50K 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.

    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.

    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

    689 Old Rd, Hensonville, NY 12439
  • /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

    $1,149,000

    $24K PRICE INCREASE
    • 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 Owner Financing available with as little as 10 pct down- 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

    Regina Tortorella Coldwell Banker Village GreenW

    3 South St, Windham, NY 12496
  • /64

    $1,899,000

    • 5 Beds
    • 3.5 Baths
    • 4,044 Sq Ft

    22 The Loop, Windham, NY 12496

    A short 1-2 minute walk to the trail access (870 ft)!! Nestled on the scenic slopes of Windham Mountain and just over two hours from NYC, this mountain haven beautifully marries opulence with rustic allure. The home's exterior, featuring cedar shakes and stone, harmonizes with its lush, landscaped surroundings, creating impeccable curb appeal. Inside, a grand two-story great room welcomes you

    Regina Tortorella Coldwell Banker Village GreenW

    22 The Loop, 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
  • /44

    $449,000

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft

    97 Carrington Rd, Windham, NY 12496

    Streamfront Serenity Meets Mountain Views -- Bordering Protected NYC DEP Lands Bordered by 160 acres of DEP land and the pristine Batavia Kill Creek, this beautifully updated split-level retreat delivers the kind of setting buyers come to the Catskills for--wide open meadows, mountain views, and the calming sound of water just steps from your back deck. This is where privacy, nature, and

    Regina Tortorella Coldwell Banker Village GreenW

    97 Carrington Rd, Windham, NY 12496
  • /52

    $547,000

    $28K PRICE DROP
    • 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

    $999,000

    $150K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 3,460 Sq Ft

    292 South St Unit 2, Windham, NY 12496

    Luxury STR Investment Opportunity Across from Windham Mountain Club -- turnkey option, income-producing, and Owner Financing available with as little as 10 pct down- perfectly positioned in one of the Catskills' most desirable four-season destinations. Proven Short-Term Rental Investment directly across from Windham Mountain Club. Perfectly positioned within walking distance to town and ''The

    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
  • /84

    $1,899,000

    New Construction $201K PRICE DROP
    • 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
  • /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
  • /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
  • /12

    $499,000

    • 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

    John Pumilia Shaw Country Realty, Inc.

    183 N South St N, Windham, NY 12496
  • /48

    $6,500,000

    • 16 Beds
    • 19 Baths
    • 10,000 Sq Ft

    226 State Route 296, Windham, NY 12496

    Windham, NY Investment Offering:Haus Windham is where the mountain meets the moment.17+ Acres; Luxury All-Season Resort; Direct-to-Slope Access; Institutional-Grade Asset.There's a new blueprint for what a mountain escape can be — regenerative, revenue-generating, and designed for a generation that demands both intention and edge. Haus Windham is that blueprint, made real:

    Wendy Maitland Atelier WM LLC

    226 State Route 296, Windham, NY 12496
  • /37

    $299,000

    $126K 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
  • /35

    $385,000

    • 3 Beds
    • 1 Bath
    • 1,893 Sq Ft

    82 County Road 56, Windham, NY 12496

    This property located in the quiet and picturesque town of Maplecrest sits on over four acres of land. It includes three dwellings that are currently being rented along with a 2 garages and a sap house. The front house which sits on the main road has 3 bedrooms/1 bathroom. As you enter the driveway on the left there is a home, garage, sap house, trailer and ranch house at the end. The ranch home

    Kathy Marino Bunce Realty

    82 County Road 56, Windham, NY 12496
  • /29

    $399,000

    • 4 Beds
    • 2.5 Baths
    • 1,227 Sq Ft

    5044 State Route 23, Windham, NY 12496

    Walk to the Windham Path from this newly renovated two story home. Offered fully furnished, stocked with everything you need to greet your next guest, this active Airbnb is ready for the next owner. Two first floor bedrooms each with their own beautifully new tiled bath. New kitchen with butcher block counter tops, new appliances with induction stove. Upstairs 2 more bedroom with its own half

    Cynthia Welch Welch Realty Inc.

    5044 State Route 23, Windham, NY 12496
  • /48

    $349,000

    $91K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    110/2 Highridge Rd, Hensonville, NY 12439

    Charming 3-Bedroom Retreat in Serene Wooded Setting Nestled on a private road in a tranquil wooded haven, this newly renovated 3-bedroom, 2-bath retreat seamlessly blends modern comforts with cozy charm. Perfect as a primary residence, vacation home, or income-generating AirB&B, this property offers exceptional versatility and appeal. Key Features: Upper Level: Spacious bedroom, full bath, and an

    Fred Mazza Bunce Realty

    110/2 Highridge Rd, Hensonville, NY 12439
  • /8

    $119,600

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    366 State Route 296, Windham, NY 12496

    Opportunity awaits in the heart of the Catskills. This bungalow-style home offers approximately 1,456 square feet of living space with 3 bedrooms and 2 full bathrooms situated on an approximately 21,780-square-foot lot. The property also includes a detached garage, full basement, private well, and septic system.Located along Route 296 in Windham, the property enjoys convenient access to

    Christopher Rose Listing by REALHome Services & Solutions

    366 State Route 296, Windham, NY 12496
  • /46

    $1,750,000

    New Construction $25K PRICE DROP
    • 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
  • /28

    $559,000

    • 5 Beds
    • 2 Baths
    • 1,900 Sq Ft

    96 Route 56, Maplecrest, NY 12454

    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 INC

    96 Route 56, Maplecrest, NY 12454
  • /38

    $2,495,000

    $2M PRICE INCREASE
    • 8 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    3 Leon MacGlashan Rd, Windham, NY 12454

    Experience Rustic Elegance and Timeless Wonder at 3 Leon Macglashan RoadNestled on over 210 acres of pristine Catskill landscapes, this extraordinary estate offers an unparalleled opportunity to embrace the serenity, privacy, and natural beauty of Windham, NY. From the moment you arrive, the property captivates with its historic charm, panoramic mountain views, and endless possibilities.

    Jake Garay Serhant LLC

    3 Leon MacGlashan Rd, Windham, NY 12454
  • /42

    $1,330,000

    New Construction
    • 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
  • /50

    $1,599,000

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

    5433 New York 23, Windham, NY 12496

    Contemporary design blends with historic character in this thoughtfully renovated single-family classic colonial home located on charming Main Street in Windham. Originally built in 1930 and fully redesigned in 2024, this turnkey home creates the perfect environment for hosting lavish get-togethers and unforgettable family memories. Gaze into the skies to celebrate summer fireworks from your

    Doug Blum Windstar Realty Group, LLC

    5433 New York 23, Windham, NY 12496
  • /26

    $599,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,250 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 LLC

    406 Campbell Rd, Windham, NY 12496
  • /56

    $899,000

    • 6 Beds
    • 5 Baths
    • 3,104 Sq Ft

    5628 State Route 23, Windham, NY 12496

    Welcome to your private Catskills sanctuary. Perfectly positioned on Main Street in Windham, this unique property offers the ultimate flexible layout that lends itself to multiple situations: a multi-generational family compound, a premium vacation escape where friends and family can gather-while still enjoying their own private spaces, a pass through income property with excellent ROI and very

    Susan Miller WINDSTAR REALTY GROUP LLC

    5628 State Route 23, Windham, NY 12496
  • /76

    $895,000

    New Construction $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    2074-2080 County Route 10, Windham, NY 12496

    Two separate homes! A rare Catskills treat! Own your own Catskills compound. These homes create the perfect setting for extended households, weekend guests or a private retreat with income potential. 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

    Lisa Gambella WINDSTAR REALTY GROUP LLC

    2074-2080 County Route 10, Windham, NY 12496
  • /69

    $1,599,000

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

    5433 State Route 23, Windham, NY 12496

    Contemporary design blends with historic character in this thoughtfully renovated single-family classic colonial home located on charming Main Street in Windham. Originally built in 1930 and fully redesigned in 2024, this turnkey home creates the perfect environment for hosting lavish get-togethers and unforgettable family memories. Gaze into the skies to celebrate summer fireworks from your

    Doug Blum WINDSTAR REALTY GROUP LLC

    5433 State Route 23, Windham, NY 12496
  • /58

    $3,649,000

    Pre-Foreclosure
    • 5 Beds
    • 7 Baths
    • 5,532 Sq Ft

    6 White Way, Windham, NY 12496

    Welcome to White Way Mountain House, an Aspen-inspired log and post-and-beam mountain retreat set ski-in, ski-off on the White Way Trail at Windham Mountain. Spanning 5,532 square feet across three levels, this five-bedroom, seven-bath chalet was designed for the full mountain living experience: two wood-burning stone fireplaces, radiant heat throughout, a dedicated ski and boot room with heated

    Anthony D'Argenzio Houlihan Lawrence Inc.

    6 White Way, Windham, NY 12496

Showing Results 1 - 40, Page 1 of 2

Why Live in Windham

Windham, NY, located in the Catskills, has been a popular destination since the 1820s, with tourism booming after the opening of a ski resort in 1960. The Windham Mountain Club remains a major attraction, offering skiing, an 18-hole golf course, and horseback riding. Beyond the slopes, the area is known for hiking, mountain biking, and fishing, with The Windham Path providing a nearly 2-mile trail suitable for leisurely hikes and cycling. The town's Main Street features local restaurants, shops, and historic churches, with The Chicken Run offering live music and hearty meals. For groceries, residents often visit the Main Street Market or travel 15 miles to the nearest Hannaford supermarket. Homes in Windham range from condos and townhouses with resort amenities to private single-family chalets, often designed with timbering, stone foundations, and A-frame roofs. The Windham-Ashland-Jewett Central School District serves all grade levels on one campus, maintaining small class sizes and offering college-level courses. Community events, such as free summer concerts and the Autumn Affair Fall Fest, are organized by the Windham Chamber of Commerce. Windham is accessible via state Route 23, with Interstate 87 providing routes to Albany, 30 miles away, and New York City, 120 miles away. For medical care, residents travel 40 miles to Margaretville Hospital.

Single Family Home Price Trends

Median Home Price
$684,500
Median 3-Bedroom Home Price
$575,000
Median 4-Bedroom Home Price
$749,000
Median 5-Bedroom Home Price
$1,750,000
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