Windham NY Real Estate & Homes for Rent

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
928205
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1835
A broker reciprocity listing Courtesy: Century 21 New West Properties 518-943-2620
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ADDITIONAL INFORMATION

Handyman special in the heart of the Catskills! This 3-bedroom, 2-bath, 1.5-story home is ready for your finishing touch. Great location just minutes to Windham Mountain, hiking trails, golf, and year-round outdoor fun. Perfect for renovation, investment, or a mountain getaway—bring your vision and make it shine! Perfect for second home, Rental or AirBnB!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
20255264
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1835
A broker reciprocity listing Courtesy: Century 21 New West 518-943-2620
View additional info

ADDITIONAL INFORMATION

Handyman special in the heart of the Catskills! This 3-bedroom, 2-bath, 1.5-story home is ready for your finishing touch. Great location just minutes to Windham Mountain, hiking trails, golf, and year-round outdoor fun. Perfect for renovation, investment, or a mountain getaway—bring your vision and make it shine! Perfect for second home, Rental or AirBnB!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,290
Status:
Active
MLS#:
925738
Type:
Single Family
Lot size:
0.01 Acres
Year built:
2020
A broker reciprocity listing Courtesy: Compass Greater NY, LLC 914-238-0676
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ADDITIONAL INFORMATION

Built in 2020 and maintained in like-new condition, this end-unit townhome offers contemporary design, lasting quality, and proven versatility. Whether you're looking for a strong short-term rental investment or your own Catskills escape, this property checks every box. The bright, open-concept living and dining area flows easily to a private deck, ideal for outdoor meals or quiet relaxation. The modern kitchen features maple cabinetry, granite countertops, and stainless appliances, combining style and durability. Two well-proportioned bedrooms are complemented by two full baths on separate levels - one with a soaking tub upstairs, the other with a shower downstairs. Details like solid wood doors, deep closets, and ducted A/C throughout make this home as functional as it is attractive. Situated at the end of the row for added privacy, the condo is just minutes from Windham Mountain, with Hunter close by. Shops, dining, and the Trailways bus stop are within walking distance, making travel and daily living effortless. Already a successful Airbnb, this property is primed to generate income immediately or serve as your low-maintenance home base in the mountains and it's a great property for skiers. Just minutes from Windham Mountain and a short drive to Hunter, you’re perfectly positioned for slope-side weekends, summer hiking, or daily commutes. The Trailways Bus stop is steps away, and a variety of shops and restaurants lie within walking distance. Sold fully furnished and turnkey, this home is ready to generate rental income immediately or serve as your own retreat. Don’t miss this chance to own a truly versatile Catskills property!

Beds:
6
Baths:
4.00
Sq.Ft.:
4,104
Status:
Active
MLS#:
20255113
Type:
Single Family
Lot size:
0.48 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

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 Catskills. Step inside to a dramatic two-story great room where walls of windows frame the mountain landscape and a floor-to-ceiling stone fireplace adds cozy warmth after a day on the slopes. Exposed beams, a vaulted pine ceiling, cherry paneling, and a coffered dining room ceiling create a sense of elegance and calm that's both rustic and refined. The chef's kitchen is designed for gathering featuring granite countertops, a Viking stainless-steel appliance suite, and a large center island perfect for après-ski evenings with friends and family. Multiple dining areas flow seamlessly into the living space, creating a warm, open feel for entertaining or quiet moments by the fire. Each bedroom feels like its own private sanctuary. The first-floor primary suite includes a tiled walk-in shower and classic clawfoot tub, while the upstairs suite offers a private balcony, sitting area, and jetted tub overlooking a peaceful stream the perfect place to unwind with a view. The walk-out lower level adds even more living space, with a family room, game room, guest bedroom, and full bath. Outside, a stone patio with a private hot tub is surrounded by natural beauty, while a heated boot room with custom built-ins keeps ski days simple and organized. This home has been lovingly maintained, with freshly repainted exterior, deck, and railings giving it a like-new glow. Located beside 400 acres recently acquired by Windham Mountain Club for future expansion, it also offers incredible long-term potential for appreciation and lifestyle value. Whether you're dreaming of a luxurious weekend retreat, a high-end rental, or a full-time mountain escape, this property delivers it all luxury, nature, skiing, and serenity all within easy reach of NYC.

Beds:
6
Baths:
6.00
Sq.Ft.:
5,872
Status:
Active
MLS#:
20255018
Type:
Single Family
Lot size:
20.02 Acres
Year built:
2007
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Secluded Mountain Estate with 20+ Acres, Panoramic Views & Sport Court in Windham, NY. Privately gated at the very end of Sundance Drive, this extraordinary log estate is one of only five luxury homes in this sought-after enclave each on expansive land, but none offering the privacy, scale, or setting of this one. Set on a sweeping tract with panoramic mountain views, this home blends refined craftsmanship with rustic elegance in a way few properties ever do. Inside, you're welcomed by soaring vaulted ceilings clad in pine, wide-plank cherry-stained wood floors, and custom finishes throughout. The open-concept layout centers around a jaw-dropping great room with a two-story wall of glass and a dramatic stone fireplace. From there, the space flows seamlessly into a chef's kitchen outfitted with commercial-grade stainless steel appliances, dual dishwashers, copper farmhouse sinks, stone countertops, and handcrafted copper lighting that echoes throughout the home. Multiple French doors open to a wraparound deck designed for all-season use, complete with an outdoor fireplace and a covered, wired section ideal for enjoying snowfall or rain in comfort. With six spacious bedrooms, several featuring fireplaces and balconies, the home is made for hosting or relaxing in peace. The primary suite includes custom built-ins, a fireplace, and a spa-style bathroom with forest and mountain views. The main level also offers a dedicated office and ski/boot room. Throughout the home, you'll find a rich mix of wide-plank wood, slate, and bluestone flooring, adding to the upscale mountain lodge aesthetic. The finished walkout level expands your living space significantly with additional bedrooms and bathrooms, a beautifully designed wet bar with copper accents and a third dishwasher, and a wine and cigar room. A dual-sided fireplace connects the large family room with a card/game area, and a fitness center is discreetly tucked off to the side. A second laundry area here complements the one on the main floor for added convenience. No detail was overlooked in construction or design. The home includes full surround sound, air conditioning, a whole-house generator, 8-year-old composite slate replica roof with 50-year warranty, composite decking, and both attached and detached garage spaces. The grounds are just as spectacular as the interior. Professionally landscaped with stone walls, walkways, and mature gardens, the property also features a fire pit gathering area, a full-size sport court with basketball and tennis setup, and acres of manicured lawn and private woods perfect for hiking or quiet exploration. This is a once-in-a-lifetime opportunity to own a private mountain estate less than 1.5 miles from town and just 2 miles from Windham Mountain Ski Resort. Designed for comfort, built for generations, and surrounded by nature, this is more than a home, it's a legacy property. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20255019
Type:
Land
Lot size:
2.3 Acres
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Welcome to North Ridge Estates - Build Your Catskills Dream Getaway Here's your chance to own the last remaining building lot in North Ridge Estates, an exclusive, private enclave known for its high-end vacation homes and newly built million-dollar properties. Set on 2.30 acres, this prime parcel has already been surveyed and features a driveway leading into the heart of the property with a gentle slope, offering the perfect building site to capture distant mountain views and embrace the surrounding natural beauty. Views can be further enhanced with select tree clearing, creating the ideal setting for your future home. With a DEP-approved septic design for a 3-bedroom home and underground electric nearby for easy hookup, much of the essential groundwork has been done — so you can start building sooner. As an added benefit, this is the developer's own lot, and they're willing to share existing house plans with potential buyers. There's even a potential pond site that could further elevate the property's appeal and create a truly special mountain retreat. Located just minutes from Windham Mountain Club, Main Street shops, restaurants, and year-round outdoor recreation, this is the ideal spot for a weekend escape, vacation home, or full-time residence. Opportunities like this are rare — don't miss your chance to bring your vision to life in one of the area's most sought-after developments.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,472
Status:
Active
MLS#:
20254983
Type:
Single Family
Lot size:
1 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

PRICE REDUCTION! — calling all investors, DIY buyers, and project-minded designers! Prime Windham location, major updates done — now it's your turn to finish and make it shine. This spacious 5-bedroom, 3-bath home offers tremendous potential with many big-ticket updates already completed, including a new roof, wood flooring, updated kitchen with granite counters and newer appliances, fresh interior paint, closed-circuit security system, whole-house generator, blacktop circular driveway, new front walkway, and more. The home features two fully equipped kitchens and two wood-burning fireplaces, creating excellent potential for a guest suite or separate income-producing apartment. Original bluestone details and pellet stove inserts add charm and an alternative heat source. Set on a flat 1-acre lot with a generous yard, the property includes multiple outbuildings, 2 car garage is ideal for small vehicles, tools, or hobby storage. An enclosed, powered gazebo provides the perfect canvas for a studio, rec room, or home office. The location is ideal — just minutes from Windham Mountain Club, Main Street shops, dining, and year-round recreation — and surrounded by desirable homes, offering strong long-term value. Whether you're looking for a fix-and-flip, rental property, second home, or full-time residence, this home presents many possibilities. New price makes this a must see to appreciate the potential! 3D Walkthrough Tour available in the digital Lookbook or by request.

Beds:
1
Baths:
1.00
Sq.Ft.:
423
Status:
Active
MLS#:
20254944
Type:
Condo
Year built:
1960
A broker reciprocity listing Courtesy: Weichert Realtors Fontaine 518-945-2125
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ADDITIONAL INFORMATION

Dreaming of a vacation home? This one pays for itself! A turnkey investment opportunity awaits with this one-bedroom, low maintenance condo. Enjoy modern comforts and the benefit of being close to dining, shopping, and the ski slopes. The amenities include a seasonal pool, restaurant& bar, game room, fitness center, movie theater and an on-site coin operated laundry facility. A shuttle bus is also available to take you to the ski slopes.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,368
Status:
Active
MLS#:
20254931
Type:
Single Family
Lot size:
0.75 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Charming & Freshly Renovated Cottage in the Heart of Windham — Just 1 mile from skiing at Windham Mountain Escape to the mountains and fall in love with this newly renovated Catskill Mountain cottage, ideally situated just minutes from world-class skiing and golfing at Windham Resort. Nestled in a prestigious yet charming community only about two hours from NYC, this property blends cozy mountain living with stylish, modern comfort — the perfect retreat for second-home buyers, skiers, golfers, and anyone craving a peaceful escape. Step inside and be welcomed by gleaming hardwood floors, vaulted ceilings, and dark exposed beams that strikingly contrast against crisp white walls, creating a sophisticated yet warm aesthetic. The open-concept living area features a light-filled great room, a modern fireplace, and plenty of space to relax after a day on the slopes or the greens. The sun-drenched kitchen is thoughtfully designed and offers a suite of stainless steel appliances, ample cabinetry, and a spacious breakfast bar — perfect for casual meals or après-ski gatherings. From here, step outside to the freshly stained front porch or the private rear deck, ideal for morning coffee or starlit evenings. This cottage offers four bedrooms, including a private en-suite bedroom, as well as a dedicated ski/boot room for effortless winter gear storage. Split units provide efficient heating and air conditioning year-round, ensuring comfort in every season. Large windows throughout the home capture gorgeous mountain views, bringing the outdoors in. A charming and adorable finished attic, accessed via a ladder, offers a private, cozy hideaway with two additional beds — perfect for guests, or anyone seeking a tucked-away retreat within the home. Located within walking distance to the area's most popular restaurants, enjoy stream-side dining, cozy fire pits, and live music just a short stroll away. Specifically, the home is only 0.18 miles from the beloved Chicken Run Restaurant, 1.33 miles from the Windham Mountain Club and Adventure Park, and just 1.5 miles from scenic golfing — making it ideally positioned for both relaxation and recreation. An attached one-car garage provides additional convenience and storage. The complete renovation of the home was just finished this week, allowing you to move right in and enjoy a worry-free Catskills lifestyle. Best of all, this home offers remarkable affordability in one of the region's most desirable communities — making it a rare opportunity for those seeking a second home or a serene full-time residence. Two of the four bedrooms do not have heat elements in them. The split unit in the living room services the living room and two of the three bedrooms on the first floor. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
20254919
Type:
Single Family
Lot size:
0.02 Acres
Year built:
1986
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Just in time for ski season! Make this your base for winter fun at Windham Mountain Club. Beautifully renovated with comfort and quiet luxury in mind, this gorgeous corner townhouse in the desirable Brainard Ridge development offers a rare expanded floor plan featuring 4-5 bedrooms and 3.5 baths — perfect for hosting all of your loved ones and guests. The chef's kitchen has been tastefully upgraded with an enlarged breakfast bar, custom cabinetry, stainless steel appliances, granite counters, and a built-in bar with wine refrigerator. The main living area exudes a cozy mountain vibe with an authentic bluestone fireplace and vaulted wood ceilings, while the mid-level den with a second fireplace provides a private retreat for reading, work, or overnight guests. The lower ensuite bedroom offers privacy and comfort, while the top-floor primary suite impresses with vaulted ceilings, skylights, and a luxurious bath with jacuzzi tub and steam shower. A partially enclosed loft play area and charming sleeping nook with built-ins and skylight add versatility and charm. This home is being sold fully furnished, complete with quality bedding, kitchenware, and décor — making for a seamless transition to your new vacation lifestyle. A heated mudroom keeps outdoor gear organized, and with easy access to the base lodge and trails, you'll enjoy all four seasons of mountain living. Exceptional as a personal retreat or investment, this slope-side property also offers strong rental potential. Don't miss this rare opportunity in one of Windham's most sought-after communities. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Beds:
6
Baths:
5.00
Sq.Ft.:
4,855
Status:
Active
MLS#:
20254897
Type:
Single Family
Lot size:
12 Acres
Year built:
2012
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

The Ultimate Catskills Retreat — Just Minutes from Windham Resort Nestled on 12 private wooded acres less than seven minutes from Windham Resort, this 5,400 sq. ft. luxury log cabin embodies the best of mountain living — where timeless craftsmanship meets modern comfort. Designed across three levels, the home features six bedrooms, four and a half bathrooms, and radiant heat throughout. Natural wood and stone floors create a seamless flow that blurs the line between the warm interior and its tranquil natural surroundings. At the heart of the home, the dramatic great room stuns with its soaring vaulted ceilings, exposed beams, and a grand wood-burning fireplace. French doors open to an expansive deck, perfect for morning coffee or evening gatherings under the stars. The custom kitchen is beautifully equipped with granite countertops, stainless steel appliances, double ovens, and self-closing hickory cabinetry — ideal for hosting large gatherings or après-ski dinners. A heated ski and boot room keeps winter gear organized, while an enclosed porch off the dining room offers a serene spot to enjoy forest views and the sounds of nature. Upstairs, a spacious loft overlooks the great room and provides flexible space for lounging or extra guests. The second-floor en-suite bedroom features a custom walk-in shower and rich hardwood floors. The lower level is designed for entertaining, complete with a handcrafted wet bar built from timbers sourced on the property, two additional bedrooms, and a full bathroom. Step outside to your brand-new hot tub, tucked among the trees and softly lit at night — the perfect retreat after a day on the slopes. The property itself is a four-season playground: private trails for hiking or ATV riding, a storybook tree house, and a fire pit and tire swing for classic Catskills evenings. Recent upgrades include new roofing and railings on the tree house, a new bar fridge, updated plumbing fixtures and compressors, refinished decks, enhanced stonework, and updated lighting and roofing around the hot tub (2024). Additional highlights include central air, a whole-house generator, a two-car garage plumbed for radiant heat, and smart home upgrades such as remote-entry locks and new smoke detectors. Just 2.5 hours from New York City, this property offers the perfect balance of privacy, luxury, and convenience, moments from Windham's shops, golf, and world-class skiing. With a proven short-term rental history and the option to purchase mostly furnished, this turn-key property is ideal as a getaway, income-producing investment, or year-round residence. Properties of this caliber are rarely available — and impossible to replicate at this price. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Beds:
5
Baths:
6.00
Sq.Ft.:
3,643
Status:
Active
MLS#:
20254832
Type:
Single Family
Lot size:
0.06 Acres
Year built:
2021
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Turn-Key Windham Ski Retreat Modern End Unit with 4 En-Suites, Full Furnishing Option & High Income Potential Personal Use or Income Ready and hitting the market just in time for peak rental demand, this modern end-unit townhome at 292 South Street offers an unbeatable opportunity for both investors and second-home seekers. Featuring four en-suite bedrooms, panoramic slope views, and a sleek open layout built in 2021, it's the perfect blend of luxury and earning potential. Want to start generating income the moment you close? The seller is offering the **option to purchase the unit fully furnished** including kitchenware, linens, and drapes — so you can immediately begin short-term renting or using the home for personal enjoyment this fall and winter season. Whether you're looking to lock in a ski escape before the snow hits or secure a turn-key investment, this property is ready to deliver. Currently grossing between ninety and ninety-five thousand dollars annually with only part-time bookings, the home has proven income performance and **plenty of room to grow**. With increased availability, more active marketing, and consistent short-term rental management, there's clear upside for anyone looking to scale the business side. Windham continues to draw strong year-round interest, with ski season, hiking, festivals, and mountain events fueling rental demand throughout the calendar. Designed for group stays and effortless hosting, the layout features five large bedrooms — four with private bathrooms — along with a spa-like primary suite that includes a private terrace and walk-in closets. The main level offers a bright, open concept living space centered around a chef's kitchen, granite counters, stainless steel appliances, and a cozy fireplace. Step outside onto a 720-square-foot deck and take in sweeping mountain views that keep guests coming back season after season. Additional perks include a heated garage and equipment room, two laundry rooms, central air, and nearly door-to-door shuttle access to Windham's North Lot. As an end-unit, the property is bathed in natural light from three sides, further elevating its comfort and appeal. Annual expenses remain low, with insurance around twenty-five hundred dollars, electricity at twenty-one hundred, and heating fuel roughly thirty-one hundred — all primarily tenant usage. With existing income and clear growth potential, this is a strong financial performer. Seller is open to partial owner financing for qualified buyers and contact info for local property managers is available upon request to help ramp up operations immediately. Optional membership to Windham Mountain Club adds access to premium amenities like spa services, a new golf course coming in 2026, tennis, pool, and more — enhancing both the lifestyle and rental value. Whether you're after a high-yield income property, a low-maintenance second home, or both, this turn-key offering stands out in one of the Northeast's most desirable ski and four-season destinations. Private showings are available now. Lock in your mountain investment before the season begins. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254820
Type:
Land
Lot size:
0.46 Acres
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
View additional info

ADDITIONAL INFORMATION

Premier Building Lot at Windham Mountain Club - Ready for Your Dream Home. Bring your vision to life on this shovel-ready homesite located in Village East, an exclusive enclave within the prestigious Windham Mountain Club. Whether you're a builder, investor, or avid skier dreaming of a luxury mountain retreat, this property offers the perfect foundation for your next project. Turnkey Build-Ready: Includes architectural plans approved by the WMO Board of Directors, so you can break ground without delay. Fully Serviced: Community water, community sewer, underground electric, high-speed internet, and cable are all available right on the road. Expansive Views: With selective clearing, enjoy sweeping mountain panoramas that frame the landscape beautifully in every season. Spacious Lot: Featuring 130 feet of frontage and approximately 170 feet of depth, the property provides ample room for a luxury residence and outdoor living spaces. Flexible Development Options. Land Only: Purchase the lot and build your custom design. Land + Plans: Acquire the property with approved plans for an 8,000 sq. ft., 6-bedroom, 6.5-bath luxury home, perfectly suited to the site. Land + Turnkey Build: Partner with the current owner, a professional home builder, to bring the approved plans to life seamlessly. Prime Location with Strong Upside. The Windham Mountain Club's recent acquisition of 400 acres adjacent to the property opens the door to exciting future expansion—creating strong potential for appreciation and investment growth. Ideal for builders seeking a premium, ready-to-go project, luxury buyers envisioning a bespoke vacation home in a top-tier resort community, skiers and snowboarders looking for unparalleled access to slopes and year-round recreation, & investors aiming to capitalize on the Windham area's growth and exclusivity. Don't miss this rare opportunity to secure one of the finest buildable lots at Windham Mountain. Call today to start building your dream home in Village East at Windham Mountain Club.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254808
Type:
Land
Lot size:
2.5 Acres
A broker reciprocity listing Courtesy: Hunter Windham Real Estate 518-965-8439
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ADDITIONAL INFORMATION

The perfect elevated woodland for your mountain escape either an : A Frame, Chalet or Mtn. Modern you will find this forest inviting. Shovel ready, DEP approved septic plans and lot survey and driveway. Access to electric along the road, town approved curb cut installed. Lets start building, call today.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254807
Type:
Land
Lot size:
2.5 Acres
A broker reciprocity listing Courtesy: Hunter Windham Real Estate 518-965-8439
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ADDITIONAL INFORMATION

Private wooded lot offering DEP septic approval and lot survey; shovel ready to build you mountain dream house or investment property. Adjacent lot available to create a family/ friend neighboring property. Just minutes to Windham Mountain Club and Christmans Golf .

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254780
Type:
Land
Lot size:
2.52 Acres
A broker reciprocity listing Courtesy: Hunter Windham Real Estate 518-965-8439
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ADDITIONAL INFORMATION

Amongst the pines find an enviable 2.5 acre parcel with full survey, and DEP approved septic plans. This perfect canvas is shovel ready for building your very own A Frame, Log Home or Mountain Modern Chalet. Now is your chance to select one of three all approved lots with complete property line survey, site plan for house, well and septic locations and fully engineered septic plans for a three-bedroom house. Pre-installed driveways addressing full access from town-maintained Campbell Road and access to electric utilities. Walk through the untouched forest, as sunlight reflects off the pine boughs and envision your very own weekend getaway. The lots are thoughtfully designed to maximize privacy while still allowing homeowners to be creative. Whether you choose to build your dream home or invest in a vacation retreat, this idyllic spot promises an unparalleled escape from everyday stresses. With nearby access to all-season recreational activities such as skiing, hiking trails, and golf courses, there is never a shortage of things to do or explore. Lets walk and talk about your plans, be introduced to iconic local builders and make the dream a reality. No hassle, all approved and ready to go !

Beds:
8
Baths:
4.00
Sq.Ft.:
3,350
Status:
Active
MLS#:
20254706
Type:
Single Family
Lot size:
210 Acres
Year built:
1887
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7668
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ADDITIONAL INFORMATION

Experience Rustic Elegance and Timeless Wonder at 3 Leon Macglashan Road Nestled 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. Every corner of this land tells a story, blending the allure of yesteryear with the comfort and functionality of modern living. The centerpiece is a majestic 10-bedroom farmhouse, meticulously crafted with original hand-hewn beams, expansive living spaces, and timeless architectural details. Each room reflects a careful balance of rustic character and modern convenience, offering the perfect environment for family gatherings, creative retreats, or hosting guests. The home's generous layout includes multiple living areas, formal dining spaces, cozy nooks, and a chef-inspired kitchen ready for culinary adventures. Step outside and discover a landscape of sublime wonder. Two crystal-clear streams meander through open meadows, surrounded by mature forests and wildlife habitats. This property offers a rare combination of seclusion and accessibility, with trails and pathways that invite exploration, reflection, or adventure. With over 210 acres, there is room for equestrian pursuits, hiking, sustainable farming, or a private compound. The land's unrestricted potential makes it a perfect canvas for those seeking a retreat, a creative haven, or even a boutique inn or event venue. Beyond the natural beauty, the property's strategic location allows you to enjoy the cultural and recreational richness of the Catskills. Local attractions, hiking trails, ski resorts, and charming nearby towns provide seasonal and year-round experiences, while the estate's expansive acreage ensures ultimate privacy. Whether watching the sunrise over the mountains, listening to the streams, or entertaining friends in the warm embrace of the farmhouse, every day feels like a retreat into timeless elegance. Additional features include ample outbuildings, stone walls, and scenic viewpoints that further enhance the property's charm. The estate's mix of meadows, forested areas, and waterways provides a rare combination of natural beauty and functional versatility. Whether your dream is a serene family retreat, an artist's sanctuary, a sustainable farm, or a private resort, this property delivers the space, privacy, and inspiration to bring that vision to life. This is a once in a lifetime opportunity to own one of the most distinctive and desirable properties in the Catskills. Its combination of historic elegance, natural splendor, and boundless potential ensures that 3 Leon Macglashan Road is not just a home, but a legacy to cherish for generations. Discover a property where every sunrise feels like a masterpiece, every stream whispers serenity, and every room tells a story. Here, rustic elegance meets timeless wonder, creating an experience unlike any other in the region. For those seeking a rare estate with soul, character, and endless possibilities, this is the address where dreams are realized, adventures begin, and memories last a lifetime.

Beds:
4
Baths:
5.00
Sq.Ft.:
2,893
Status:
Active
MLS#:
20254690
Type:
Townhouse
Lot size:
0.04 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Luxury Ski Townhouse in the Heart of Windham Mountain Club's Premier Enclave Community Discover the ultimate ski lifestyle in this luxurious tri-level townhouse, ideally located in the exclusive Enclave at Windham Mountain Club. Just steps from the slopes, base lodge, pool, fitness center, and restaurants, this home offers unmatched convenience—no car needed. Simply step outside and immerse yourself in the vibrant mountain experience. With 2,800 square feet of thoughtfully designed living space, this home features 4 private en-suite bedrooms, each providing a peaceful retreat after a day on the slopes. The primary suite is a true sanctuary, showcasing vaulted ceilings and a stunning wall of glass that fills the space with natural light and frames breathtaking views. The main level is perfect for entertaining, with an open-concept layout that invites après-ski gatherings. Relax by the wood-burning fireplace in the great room or step onto the deck overlooking the pool to enjoy the crisp mountain air. The updated kitchen blends modern style with rustic charm, featuring white cabinets, a subway tile backsplash, butcher block countertops, and stainless steel appliances. The lower level is your personal après-ski haven, complete with a cozy family room, a sauna to unwind, a dedicated ski/boot room, and a laundry area for added convenience. An attached garage provides easy access during snowy winters. Every detail of this home is designed for comfort and ease, from air conditioning and central vacuum to a floor plan that balances open gathering spaces with private retreats. The en-suite bathrooms have been beautifully updated with plank tile flooring, sleek tiled showers, and contemporary fixtures, adding a touch of luxury throughout. Additional highlights include a private ski locker, exclusive access to The Enclave's premier amenities, and the ease of maintenance-free living. Whether you're hosting friends for a weekend on the slopes or enjoying a quiet evening by the fire, this home offers the perfect blend of luxury, comfort, and adventure. Priced competitively in this sought-after community, this is your chance to own a piece of Windham Mountain's premier ski lifestyle. Your mountain escape awaits—don't miss it! A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254648
Type:
Single Family
Lot size:
5.7 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

5.7 Acres with Utilities in Place - Perfect Setting for Your Dream Home This 5.7-acre property offers the ideal blend of open fields and wooded areas, creating a beautiful mix of natural landscapes and privacy. While there is an existing single-wide mobile home on site, it has been vacant for some time, is not considered habitable, and has not been given value. The true value here lies in the land itself and the ease of building, thanks to improvements already in place. The property is equipped with a well, electricity, a driveway, and a septic system. The size and condition of the septic are unknown, and buyers are encouraged to have a septic inspection completed to determine whether it can be used or requires replacement. Offering an impressive 955 feet of road frontage, the property is easily accessible, with trees along the frontage that enhance privacy. A cleared home site, tucked away from the road, creates a private and ready-to-build setting for a future residence. With both open fields and wooded areas, this land offers flexibility for a variety of uses, whether as a year-round residence, a vacation retreat, or a recreational escape. Its location is hard to beat—less than five minutes to shopping, dining, and town conveniences, six to seven miles to skiing at Windham Mountain Resort, and only fifteen to twenty minutes from Hunter Mountain Resort. This property is all about potential. With existing utilities and a private, cleared site already established, it is truly a blank canvas awaiting the next owner's vision.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254649
Type:
Land
Lot size:
5.7 Acres
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
View additional info

ADDITIONAL INFORMATION

5.7 Acres with Utilities in Place - Perfect Setting for Your Dream Home This 5.7-acre property offers the ideal blend of open fields and wooded areas, creating a beautiful mix of natural landscapes and privacy. While there is an existing single-wide mobile home on site, it has been vacant for some time, is not considered habitable, and has not been given value. The true value here lies in the land itself and the ease of building, thanks to improvements already in place. The property is equipped with a well, electricity, a driveway, and a septic system. The size and condition of the septic are unknown, and buyers are encouraged to have a septic inspection completed to determine whether it can be used or requires replacement. Offering an impressive 955 feet of road frontage, the property is easily accessible, with trees along the frontage that enhance privacy. A cleared home site, tucked away from the road, creates a private and ready-to-build setting for a future residence. With both open fields and wooded areas, this land offers flexibility for a variety of uses, whether as a year-round residence, a vacation retreat, or a recreational escape. Its location is hard to beat—less than five minutes to shopping, dining, and town conveniences, six to seven miles to skiing at Windham Mountain Resort, and only fifteen to twenty minutes from Hunter Mountain Resort. This property is all about potential. With existing utilities and a private, cleared site already established, it is truly a blank canvas awaiting the next owner's vision.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,088
Status:
Active
MLS#:
20254677
Type:
Single Family
Lot size:
2.2 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

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 the serene landscape. The master suite shares these same captivating views. Wake up to breathtaking mountain views while enjoying your coffee on the expansive new deck that spans the full length of the home, where the gentle sounds of the creek below complement your panoramic vistas of the ski slopes. The spacious finished lower level offers versatile entertainment space that can serve as a game room, office, or media room. Large windows flood the area with natural light, while ample storage keeps everything organized. Convenient direct access leads to the oversized single-car garage, plus a walk-out exit for easy outdoor access. An attached one-bedroom suite with a sleeping loft and dedicated washer and dryer provides excellent potential as a rental unit, offering additional income opportunity for the homeowner. A perfect retreat for those seeking tranquility, scenic beauty, convenience and financial advantages. Only minutes to the town of Windham where you have all the entertainment at your fingertips. Not to mention an ideal retreat for the avid skiers. Sold furnished. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254628
Type:
Land
Lot size:
0.59 Acres
A broker reciprocity listing Courtesy: ListWithFreedom.com 855-456-4945
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ADDITIONAL INFORMATION

Unique opportunity - one of the LAST lots on South Street! Flat parcel overlooking the golf course. Walking distance to everything Windham has to offer - ski, golf, biking, movie theater, shops and downtown restaurants. Utilities - This lot is serviced by municipal water, municipal sewer, electric, and cable directly off the road.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,058
Status:
Active
MLS#:
20254605
Type:
Townhouse
Lot size:
0.02 Acres
Year built:
1992
A broker reciprocity listing Courtesy: Shaw Country Realty, Inc. 518-734-3500
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ADDITIONAL INFORMATION

Charming 4-Bedroom Townhome Just Minutes from Windham Slopes!Discover this beautifully designed townhome in a vibrant four-season community, just five minutes from Windham's premier ski slopes, golf courses, scenic walking paths, top-rated restaurants, and stunning hiking trails. This thoughtfully crafted three-level home offers:4 Spacious Bedrooms - Plenty of space for family and guestsCozy up after a day of adventure by the stone fireplace or outside by theExpansive Deck which is Perfect for relaxing and entertainingThis unit has a Creative Multi-Level Layout - A unique design that maximizes space and comfortEnjoy the perfect blend of nature, recreation, and modern living in this growing community. Don't miss this opportunity And for the skiers, take advantage of the shuttle bus that brings you directly to the slopes and a private ski closet outside your front door. There's also a inground community pool.

Beds:
n/a
Baths:
2.00
Sq.Ft.:
5,300
Status:
Active
MLS#:
20254555
Type:
Other
Lot size:
0.14 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Coldwell Banker Village GreenW 518-734-4200
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ADDITIONAL INFORMATION

Prime opportunity to own a thriving restaurant and bar in the heart of Windham, one of the Catskills' most desirable towns. Lilly's Steak and Cocktails sits on bustling Main Street with excellent visibility, easy street parking, and handicap accessibility. The welcoming bar and warm wood-toned dining room seat up to 98 guests, with a private dining room perfect for special occasions. Guests can also enjoy the scenic back deck overlooking Mad Creek and the Batavia Kill. The restaurant features a full commercial kitchen with updated appliances, spacious prep areas, large storage, dishwashing facilities, and renovated public restrooms, a/c mini splits and a modern POS system is included. This high-profile location boasts robust income, with profit and loss statements available for review to qualified buyers. Beyond the restaurant's strong receipts, the property also offers two upstairs apartments generating nearly 4k per month in rental income. To ensure a smooth transition, the seller is willing to remain on for training and support, offering the new owner the benefit of experience and continuity. Turnkey and ready for new ownership, this property presents a rare chance to acquire a profitable restaurant with additional income streams in a growing Catskills community. Perfect for a seasoned restaurateur, investor, or chef-owner ready to capitalize on Windham's year-round tourism and vibrant Main Street scene. Financials available with NDA. Serious inquiries only.

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
20254495
Type:
Land
Lot size:
0.52 Acres
A broker reciprocity listing Courtesy: Brainard Ridge Management 518-734-5333
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ADDITIONAL INFORMATION

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 retreat taking in the fresh mountain air as you think about the exciting day ahead. The vibrant community of Windham, nature's recreational paradise awaits! Enjoy skiing, snowboarding, hiking, biking, horseback riding, golf, fine restaurants, farmers markets, indie bookstore, local shops, yoga, and so much more. Lots offer community water and sewer as well as underground electric and DSL cable already in place to make for a stress-free build. There are 2 individual Lots being offered at 500,000 (thousand) per lot. 220 Club Road tax map: 95.13-2-15 (0.52 ac.) 240 Club Road tax map: 95.13-2-14 (0.48 ac.) Please note: Initial 33,000(thousand) road impact fee is an additional fee that is due to the WMO Association under Section of the Second Amendment out of the closing proceeds. A purchaser understands and agrees that in addition to the purchase price, at such time as a building permit is issued on the premises or on the 4th anniversary of the closing date, whichever shall occur sooner, a road impact fee of 33,000(thousand) is required to be paid to the WMO

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025, OneKey MLS, Inc. All Rights Reserved.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Real estate listings held by brokerage firms other than Xome are marked with IDX logo and the detailed information about them includes the name of the listing broker. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025 by the Hudson Valley Catskill Region MLS and Ulster County Board of Realtors, Inc. All Rights Reserved.



Windham Real Estate

Windham is located in New York. Windham, New York has a population of 1,553. Windham is less family-centric than the surrounding county with 23.28% of the households containing married families with children. The county average for households married with children is 26.95%.

The median household income in Windham, New York is $55,781. The median household income for the surrounding county is $62,810 compared to the national median of $69,021. The median age of people living in Windham is 49.6 years.

Windham Weather

The average high temperature in July is 78.4 degrees, with an average low temperature in January of 10.7 degrees. The average rainfall is approximately 48 inches per year, with 45 inches of snow per year.

Windham Map

Windham Real Estate Market Conditions

  • Median sales price

    $690,000
    24.5%
    change since last quarter
  • # Active listings

    206
    30-day change

Windham Schools and Demographics

Education near Windham, NY

City County
High School Graduates 84.53 87.93
College Degree - 2 year 9.37 11.42
College Degree - 4 year 26.25 25.62
Graduate Degree 8.53 9.07
Expenditures per Student 29,481 29,481
Students per Teacher 9.9 9.9

Elementary Schools near Windham, NY

Grades Students P/T Ratio ZIP
Hunter Elementary School PK - 06 190 8.6 12442

Middle Schools near Windham, NY

Grades Students P/T Ratio ZIP
Cairo-Durham Elementary School KG - 02 136 13.8 12422

High Schools near Windham, NY

Grades Students P/T Ratio ZIP
Hunter-Tannersville Middle School High School 07 - 12 155 7.2 12485

Ungraded Schools near Windham, NY

Grades Students P/T Ratio ZIP
Gilboa-Conesville Central School PK - 12 339 10 12076
Windham Ashland Central School KG - 12 316 8.8 12496

Demographics near Windham, NY

City County
Neighborhood Type Small Town
Population 1,553 48,026
Population Density 34 74
Median Age 49.6 46.6
People per Household 2.7 2.6
Median Household Income 55,781 62,810
Average Income per Capita 35,661 33,894

Real estate near Windham