Homes for Sale near Windham-Ashland-Jewett Central School

/110
$1,490,000
- 6 Beds
- 6 Baths
- 4,284 Sq Ft
93 & 99 Nauvoo Rd, Windham, NY 12496

Come relax in the cool Mediterranean vibes of this lovingly maintained home with gorgeous GUEST HOUSE. The huge wrap around deck is perfect for your alfresco dining while you enjoy the stunning view of Windham Mtn and your enchanting back yard with cozy pond. Sheltered on two sides by state land, this property is a private oasis yet conveniently located close to town. You will

Sharon Knudsen Coldwell Banker Village GreenW

93 & 99 Nauvoo Rd, Windham, NY 12496
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/36
$329,999
- 2 Beds
- 2.5 Baths
- 1,058 Sq Ft
73 Windham Ridge Rd Unit 16-H, Windham, NY 12496

Competitively Priced Catskills End Unit Townhouse - Fully Renovated, Furnished & Move-In Ready!This beautifully updated end-unit townhouse combines modern elegance with mountain charm, offering comfort, style, and unbeatable value.As you enter, you'll be welcomed by a stunning, fully remodeled kitchen outfitted with rich granite surfaces and a convenient breakfast bar, The kitchen

Regina Tortorella Coldwell Banker Village GreenW

73 Windham Ridge Rd Unit 16-H, Windham, NY 12496
/54
$745,000
- 4 Beds
- 4 Baths
- 1,688 Sq Ft
5147 Route 23c, Jewett, NY 12444

Welcome to this modern, functional and stylish contemporary home. Experience world-class skiing, golfing, and dining within minutes of your doorstep, plus easy access to both Windham and Hunter Mountain. Also, Conifer Lake is just a short distance away, and your ownership includes exclusive lake access rights for unlimited summer recreation.The entire house is climate controlled with central

Doina Dewell Coldwell Banker Village GreenW

5147 Route 23c, Jewett, NY 12444
/40
$545,000
- 2 Beds
- 2 Baths
- 1,390 Sq Ft
53 Windham Mount Village, Windham, NY 12496

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

Regina Tortorella Coldwell Banker Village GreenW

53 Windham Mount Village, Windham, NY 12496
/36
$399,000
- 3 Beds
- 1.5 Baths
- 1,152 Sq Ft
315 Begley Rd, Windham, NY 12496

Located just minutes from the heart of Windham, NY, this inviting 3-bedroom, 1.5-bath ranch is the perfect base for four-season living in the Catskills. Set on a spacious, tree-lined lot with a detached two-car garage and generous backyard, the home offers the ideal balance of privacy, convenience, and potential.Step inside to find a warm and welcoming layout featuring a large living area

Regina Tortorella Coldwell Banker Village GreenW

315 Begley Rd, Windham, NY 12496
/59
$779,000 Open Sun 12PM - 2PM
- 4 Beds
- 3.5 Baths
- 2,100 Sq Ft
769 Mitchell Hollow Rd, Windham, NY 12496

Bright Sparrow Farmhouse - Modern Farmhouse on 8+ Acres with Private Pond, Mountain Views & Proven Rental Income | Windham, NY Welcome to Bright Sparrow Farmhouse—your dream Catskills retreat where modern farmhouse style meets timeless charm on over 8.22 private acres with a spring-fed pond, unobstructed mountain views, and a turnkey short-term rental setup with proven income. Located just 10

Regina Tortorella Coldwell Banker Village GreenW

769 Mitchell Hollow Rd, Windham, NY 12496
/96
$1,699,000
- 5 Beds
- 3.5 Baths
- 4,312 Sq Ft
102 Thunderbird Terrace, Windham, NY 12496

Custom Log Cabin with Modern Finishes, The Feel of a New Build, and Stunning Mountain Views- Nestled on nearly 2 acres, this breathtaking custom log cabin combines luxury, charm, and nature. Built with meticulous attention to detail, the home shows as if it is new construction, exuding a fresh and pristine feel throughout, making it indistinguishable from a brand-new build. With 5 bedrooms, 3.5

Regina Tortorella Coldwell Banker Village GreenW

102 Thunderbird Terrace, Windham, NY 12496
/74
$499,000
- 4 Beds
- 4 Baths
- 2,950 Sq Ft
25 Vets Rd, Windham, NY 12496

Peaceful Sanctuary in the Heart of WindhamStep into a unique opportunity to own a stunning property perfectly balancing convenience, tranquility, and potential. Located less than half a mile from Windham Ski Resort and tucked just behind Main Street, this rambling ranch offers the best of both worlds easy access to dining, shopping, bars, skiing, festivals, and concerts, while feeling like a

Regina Tortorella Coldwell Banker Village GreenW

25 Vets Rd, Windham, NY 12496
/72
$2,250,000
- 9 Beds
- 7 Baths
- 4,572 Sq Ft
150 Trailside Rd, Windham, NY 12496

Investor Opportunity: Luxury Slopeside Home at Windham Mountain Club - Airbnb-Ready Income PropertyWelcome to 150 Trailside Road, the most competitively priced slopeside home at Windham Mountain Club—a rare and lucrative opportunity for savvy property investors targeting the booming short-term rental market in the Catskills. With direct access to the slopes, a sprawling 6,859 sq. ft.

Regina Tortorella Coldwell Banker Village GreenW

150 Trailside Rd, Windham, NY 12496
/63
$1,149,000
- 5 Beds
- 5.5 Baths
- 3,460 Sq Ft
292 South St Unit 2, Windham, NY 12496

Incredible Investment Opportunity - Proven Short-Term Rental Income!Welcome to 292 South St, Windham - a luxury townhouse with exceptional income potential, already generating 85,000-110,000 annually while being rented for just a small portion of the year. This high-performing vacation rental has significant upside for buyers active on platforms like Airbnb, Vrbo, and AirDNA. With full-time

Regina Tortorella Coldwell Banker Village GreenW

292 South St Unit 2, Windham, NY 12496
/78
$1,199,000
- 4 Beds
- 3.5 Baths
- 3,250 Sq Ft
87 Wilderness Dr, East Jewett, NY 12424

Welcome to your mountain-retreat dream in The Catskills...A rare blend of rustic elegance and modern comfort in this beautifully crafted log home nestled on 5 acres of private woodlands in the heart of the scenic Catskill Mountains. Built in 2005, the residence offers over 3,000sq' of luxurious living space over 3 levels, featuring 4 bedrooms and 3.5 bathrooms - ideal for family living,

Jason Dugo Dugo Realty

87 Wilderness Dr, East Jewett, NY 12424
/15
$1,395,000
- 6 Beds
- 4 Baths
- 3,800 Sq Ft
5628 New York 23, Windham, NY 12496

"Best of Windham" - Exceptional Development Opportunity in the Heart of Windham, NY Discover a rare 5-acre property on the best location in Windham. Offering a unique blend of proximity to Main Street, Skiing within minutes, legacy vacation rentals and prime development potential all while having privacy located high off the main road with beautiful mountain views. This property is more

Agnieszka Wdziekowska Taufield CORE REAL ESTATE TEAM

5628 New York 23, Windham, NY 12496
/32
$799,000
- 3 Beds
- 3.5 Baths
- 2,434 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
/40
$699,999
- 3 Beds
- 2 Baths
- 1,597 Sq Ft
12325 State Highway 23, Ashland, NY 12407

Set on 7 serene acres in the scenic Catskill Mountains, this turnkey 1,597 square foot ranch in Ashland, NY offers the perfect blend of modern comfort and natural beauty. The home features a sun-drenched open-concept kitchen and living area with gleaming hardwood floors and panoramic windows that invite the outside in. The spacious primary suite includes an en suite bath and generous closet

Kevin Fortuna K. Fortuna Realty, Inc.

12325 State Highway 23, Ashland, NY 12407
/49
$799,000
- 6 Beds
- 2 Baths
- 4,294 Sq Ft
293 Carl Rd, Jewett, NY 12444

This Quintessential Country Estate Dream Home Does Really Exist. Welcome Home to This Cozy & Charming 1885 Colonial home with Tall, Coffered Ceilings, 6 Large Bedrooms, 2 Full Bathrooms, Living Room, Kitchen along with Office Space and Studio Space, Large Attic (Storage Galore). Dining room, Living room with Library, Family Living Room plus Several More Living Areas for Entertaining. Plenty of

Chris Boylan EXIT Realty Premier

293 Carl Rd, Jewett, NY 12444
/27
$650,000
- 4 Beds
- 2 Baths
- 1,440 Sq Ft
85 Cambridge Heights Rd, Windham, NY 12496

Enjoy the summer months taking in the beautiful views from the large Trex decking. Warm up in front of the woodburning fireplace in the winter months. Close to Windham Mountain. A great property to enjoy all four seasons. A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.

Sheila Word Coldwell Banker Village GreenW

85 Cambridge Heights Rd, Windham, NY 12496
/37
$1,175,000 Open Sun 12:30PM - 2:30PM
- 3 Beds
- 3.5 Baths
- 3,284 Sq Ft
20 Brookhollow Ln, Windham, NY 12496

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 features three spacious bedrooms and three and a

Pamela King-Belfor Four Seasons Sotheby's Int.

20 Brookhollow Ln, Windham, NY 12496
/7
$45,000
- Land
- 0.84 Acre
- $53,571 per Acre
0 Goshen St Unit 20255305, Jewett, NY 12444

Elevated lot with distant ski slope views seeking a tiny house to be nestled in the Catskill Mountains. Southern exposure with mature trees and stone walls makes this a perfect lot for glamping. Centrally located between Windham Mountain Club and Hunter Mountain Ski Resort makes this your own private retreat. Come escape and own a little piece of the Catskill Mountains.

Laurie Hanenberg Hunter Windham Real Estate

0 Goshen St Unit 20255305, Jewett, NY 12444
/26
$215,000
- 3 Beds
- 1.5 Baths
- 1,200 Sq Ft
384 New York 296, Hensonville, NY 12439

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!

Brian Kozloski Century 21 New West

384 New York 296, Hensonville, NY 12439
/28
$234,500
- Land
- 2.3 Acres
- $101,957 per Acre
0 N Ridge Extension Unit 20255019, Windham, NY 12496

Welcome to North Ridge Estates - Build Your Catskills Dream GetawayHere'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

Lisa Jaeger Coldwell Banker Village GreenW

0 N Ridge Extension Unit 20255019, Windham, NY 12496
/42
$425,000
- 5 Beds
- 3 Baths
- 2,472 Sq Ft
317 Mitchell Hollow Rd, Windham, NY 12496

Breathe New Life Into This Mid-Century Split Ranch Full of Potential! Opportunity is knocking with this spacious 5-bedroom, 3-bath home — ready for someone to bring their vision and creativity. Many of the big-ticket updates are already complete, including a new roof, wood flooring, kitchen and appliances, fresh paint, closed circuit security system, whole-house generator, black top circular

Lisa Jaeger Coldwell Banker Village GreenW

317 Mitchell Hollow Rd, Windham, NY 12496
/19
$550,000
- 7 Beds
- 2.5 Baths
- 3,114 Sq Ft
804 Mitchell Hollow Rd, Windham, NY 12496

Huge price reduction. For the first time on the market in almost 50 years we are offering this unique home and property for sale.The Greek style home has seven bedrooms, two and half baths. a large living room, a large dining room with wainscotingwalls, cabinets and ceiling, old style kitchen, large workshop or spare room and a large front porch to enjoy the views.All this on 18 acres with

Chris Tripsas Reliant Property Services

804 Mitchell Hollow Rd, Windham, NY 12496
/27
$170,000
- 1 Bed
- 1 Bath
- 423 Sq Ft
5220 New York 23 Unit 126, Windham, NY 12496

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

Savannah Delaney Weichert Realtors Fontaine

5220 New York 23 Unit 126, Windham, NY 12496
/85
$1,749,999
- 6 Beds
- 4.5 Baths
- 4,855 Sq Ft
12 Lauren Ln, Windham, NY 12496

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

Regina Tortorella Coldwell Banker Village GreenW

12 Lauren Ln, Windham, NY 12496
/19
$399,000
- Land
- 0.46 Acre
- $867,391 per Acre
2 Twin Maples Ln, Windham, NY 12496

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:

Regina Tortorella Coldwell Banker Village GreenW

2 Twin Maples Ln, Windham, NY 12496
/8
$149,000
- Land
- 2.52 Acres
- $59,127 per Acre
557 Campbell Rd, Ashland, NY 12496

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

Laurie Hanenberg Hunter Windham Real Estate

557 Campbell Rd, Ashland, NY 12496
/38
$2,495,000
- 8 Beds
- 3.5 Baths
- 5,500 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.

Cameron Ashkarkhizani Serhant LLC

3 Leon MacGlashan Rd, Windham, NY 12454
/59
$1,599,000
- 4 Beds
- 4.5 Baths
- 2,083 Sq Ft
3 the Enclave, Windham, NY 12496

Luxury Ski Townhouse in the Heart of Windham Mountain Club's Premier Enclave CommunityDiscover 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

Regina Tortorella Coldwell Banker Village GreenW

3 the Enclave, Windham, NY 12496
/25
$415,000
- 3 Beds
- 3.5 Baths
- 3,683 Sq Ft
2914 Route 10, Windham, NY 12496

This large 3 bed, 3.5 bath home sits on 5 peaceful acres and has plenty of space inside and out. Built in 1993, it offers 2,610 sq ft of living space. The home has new tile floors, central A/C, and a 10-year-old roof. We are located just a short drive from popular ski slopes, restaurants and other entertainment. Interior in good livable condition. We are in the process of obtaining interior

Qizhan Yao Realmart Realty, LLC

2914 Route 10, Windham, NY 12496
/51
$399,000
- 3 Beds
- 2 Baths
- 1,876 Sq Ft
370 Begley Rd, Windham, NY 12496

Rare Opportunity Surrounded by 700 Acres of State LandThat's right—700 acres of forever-protected State Land at your doorstep! Step into your own personal oasis where you can hike, hunt, explore, or simply enjoy the peace and quiet with birdsong, wildlife, and the whispering wind through the trees.This spotless 1,800 sq ft modular ranch offers a bright and open floor plan with

Lisa Jaeger Coldwell Banker Village GreenW

370 Begley Rd, Windham, NY 12496
/13
$199,000
611 Mitchell Hollow Rd, Windham, NY 12496

5.7 Acres with Utilities in Place - Perfect Setting for Your Dream HomeThis 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

Regina Tortorella Coldwell Banker Village GreenW

611 Mitchell Hollow Rd, Windham, NY 12496
/20
$479,000
- 4 Beds
- 3 Baths
- 2,058 Sq Ft
274 N Brooksburg Rd Unit 35, Windham, NY 12496

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

John Pumilia Shaw Country Realty, Inc.

274 N Brooksburg Rd Unit 35, Windham, NY 12496
/5
$253,000
- Land
- 0.59 Acre
- $428,814 per Acre
57 South St, Windham, NY 12496

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.

Aira Ilao ListWithFreedom.com

57 South St, Windham, NY 12496
/9
$500,000
- Land
- 0.52 Acre
- $961,538 per Acre
220 & 240 Club Rd, Windham, NY 12496

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

Patricia Charbonneau Brainard Ridge Management

220 & 240 Club Rd, Windham, NY 12496
/65
$1,999,999
- 5 Beds
- 4 Baths
- 3,409 Sq Ft
5433 New York 23, Windham, NY 12496

A One-of-a-Kind Masterpiece in the Heart of Windham, NY!Welcome to Main Street Magic—an exceptional, fully reimagined 5-bedroom, 4-bathroom home (2 full, 2 half) located just 2 hours from NYC in the sought-after Catskills town of Windham. This stunning property perfectly blends historic charm with modern luxury and lifestyle-driven design.Step inside to soaring 13' vaulted

Caitlin Cucchiella Hunt Real Estate ERA

5433 New York 23, Windham, NY 12496
/38
$295,000
- 2 Beds
- 2 Baths
- 1,290 Sq Ft
71 County Road 65 Unit 6, Hensonville, NY 12439

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

Susanna Scott-Mitchell Compass Greater NY, LLC

71 County Road 65 Unit 6, Hensonville, NY 12439
/11
$295,000
- 2 Beds
- 2.5 Baths
- 1,211 Sq Ft
76 Loo Bridge Ln, Windham, NY 12496

Cozy Mountain Condo in Windham - Perfect for Family Retreats or Investment Discover this inviting 2-bedroom, 2.5-bath condo with a loft (C of O included), just 10 minutes from Windham Mountain Ski Resort. The open living room with kitchen creates a warm, social space, while large windows bring in natural light and serene views. Surrounded by woods and mountains, this home offers peace and

Agnieszka Wdziekowska Taufield CORE REAL ESTATE TEAM

76 Loo Bridge Ln, Windham, NY 12496
/11
$275,000
- Land
- 0.32 Acre
- $859,375 per Acre
0 Twin Maples Ln Unit 20254325, Windham, NY 12496

Great Opportunity! Priced to sell!Escape to the Catskills, build your home away from home on this desirable building lot located on Windham Mountain's Private and Tranquil Community of Trailside East. This parcel has gentle sloping grade, will have access to far reaching mountain and valley views with clearing. Parcel has access to water, sewer, underground electric, high speed cable-fiber,

Irene Pinto Brainard Ridge Management

0 Twin Maples Ln Unit 20254325, Windham, NY 12496
/61
$429,000
- 4 Beds
- 2 Baths
- 2,091 Sq Ft
2070 Route 23c, East Jewett, NY 12424

Welcome to your private woodland retreat! This charming four-bedroom, two-bathroom home is nestled on 3.6 lush acres, offering the perfect escape from the hustle and bustle. A private stream runs alongside the house and barn, creating a serene and tranquil atmosphere. Connected to the new deck, a quaint footbridge crosses over the creek and provides a beautiful spot to enjoy the

Bridget Leach Hunter Mountain Realty

2070 Route 23c, East Jewett, NY 12424
/29
$500,000 Open Sat 12PM - 2PM
- 3 Beds
- 2 Baths
- 1,180 Sq Ft
38 Cambridge Heights Rd, Windham, NY 12496

Welcome to Alpine Cabin, your dream mountain getaway! Nestled just steps away from the slopes, this charming cabin combines rustic elegance with modern comforts perfect for a cozy winter retreat or an adventurous alpine escape. Situated at the base of the Windham Mountain Club with views of the slopes beyond, and just 130 miles from New York City. The fireplace in the living area is perfect for

Paul Heintz Anatole House LLC

38 Cambridge Heights Rd, Windham, NY 12496

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