Windham, NY Homes for Sale under $300,000

/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

Jason Dugo

Dugo Realty

135 Route 40, Windham, NY 12496
/22
$269,000

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 838 Sq Ft
5359 Main St Unit 2h., Windham, NY 12496

Prime Windham Village Location - Step out your door and wander to restaurants, the farmers market, local brewery, miniature golf, movies, and year-round town events. Convenient NYC bus access just moments away makes this the perfect easy escape. Only minutes to Windham Mountain skiing and nearby golf courses, this desirable 2-bedroom, 2-bath condo with slope views offers both lifestyle and

Carol Shaw

SHAW COUNTRY REALTY INC

5359 Main St Unit 2h., Windham, NY 12496
/10
$199,000

$199K PRICE INCREASE
- Land
- 2.3 Acres
- $86,522 per Acre
0 N Ridge Extension Unit 20255019, Windham, NY 12496

Price Reduced to 199,000! Build your Catskills retreat on the last remaining building lot in North Ridge Estates, one of Windham's premier private communities surrounded by luxury homes and newly built million-dollar properties. This surveyed 2.30-acre parcel features an existing driveway leading to an ideal building site with a gentle slope and the potential for distant mountain views. Select

Lisa Jaeger

Coldwell Banker Village GreenW

0 N Ridge Extension Unit 20255019, Windham, NY 12496
/13
$199,000
- 2 Beds
- 1 Bath
- 893 Sq Ft
394 State Route 296 Unit 3, Hensonville, NY 12439

Charming Condo in the Heart of Hensonville - Town of Windham Perfectly situated in the heart of Hensonville, this nicely maintained two-story condo offers the ideal Catskills getaway or year-round residence. Just minutes from Windham Mountain, Windham Village, scenic walking paths, golf courses, and only a 10-minute drive to Hunter Mountain, you'll enjoy four seasons of recreation right at your

Carol Shaw

SHAW COUNTRY REALTY INC

394 State Route 296 Unit 3, Hensonville, NY 12439
/22
$269,000

$20K PRICE DROP
- 2 Beds
- 2 Baths
- 838 Sq Ft
5359 Main St, Windham, NY 12496

Prime Windham Village Location: Just outside your door, wander to restaurants, movies, breweries, pubs, miniature golf, seasonal farmers market and year round town events.Convenient NYC bus access just outside your door for easy escape for the weekend. Only minutes to the Windham Mt. Club for skiing and nearby golf courses makes this a desirable location for this 2 bedroom, 2 bath condo with

Carol Shaw

SHAW COUNTRY REALTY INC

5359 Main St, Windham, NY 12496
/13
$99,000
- Land
- 8.24 Acres
- $12,015 per Acre
539 Route 40, Maplecrest, NY 12454

Centrally located between Windham and Hunter, minutes to CD Lane Park, State hiking trails, Colgate Lake and everything this area has to offer. This 8 + acre parcel has a septic design in place designed by Kaaterskill Engineering and submitted to DEP and approved but would need to be updated with the town. This makes this lot desirable with no soil testing and design which could usually take

Carol Shaw

Shaw Country Realty, Inc.

539 Route 40, Maplecrest, NY 12454
/9
$199,000
- Land
- 2.15 Acres
- $92,558 per Acre
0 Route 32c Unit 20263845, Windham, NY 12496

Build Your Dream Home with Stunning Mountain Views up and down this country road- No address yet but plug in #700 there is a shared driveway Escape to the beauty of the Catskills with this exceptional 2.15-acre building parcel located along one of the area's most scenic country roads on the outskirts of Windham. Surrounded by nature and directly across from New York State land, you'll enjoy

Carol Shaw

Shaw Country Realty, Inc.

0 Route 32c Unit 20263845, Windham, NY 12496
/4
$115,000
- Land
- 1.6 Acres
- $71,875 per Acre
0 County Road 65 Unit 20261215, Windham, NY 12496

Windham Townhship (Hensonville) these 2 adjoining lots are set back behind House #225 each lot is .8 acre with total of 1.6 acresPotential sewer hook up to be brought up from road . Sewer goes to first house. There is one .8 acre lot between house and lots for sale. Property starts apprx 351' in from road. Great place for small houses, RV wooded and fairly level

Carol Shaw

Shaw Country Realty, Inc.

0 County Road 65 Unit 20261215, Windham, NY 12496
/23
$199,000
- 1 Bed
- 1 Bath
- 435 Sq Ft
5220 State Route 23 Unit 229, Windham, NY 12496

Rare Turnkey Income Producer! 2nd-Floor Winwood End Unit with Ski Slope ViewsWelcome to The Winwood, where affordability meets premium four-season Catskills living. This unique and well-appointed second-floor end unit condominium offers one of the most accessible and value-packed opportunities to own in the highly desirable Windham market.Whether you are searching for a carefree

Regina Tortorella Coldwell Banker Village GreenW

5220 State Route 23 Unit 229, Windham, NY 12496
/5
$154,000
- Land
- 17.15 Acres
- $8,980 per Acre
0 High Peak Road Lot 61 & 20, Windham, NY 12496

Nestled in the heart of the Catskills, this 17-acre parcel of unimproved land on High Peak Road offers a rare opportunity to own a significant piece of Greene County's most sought-after landscape. Surrounded by the natural splendor that has made Windham a beloved four-season destination, this blank canvas invites you to bring your vision -- whether a private retreat, a custom dream home, or a

Sheila Word Coldwell Banker Village GreenW

0 High Peak Road Lot 61 & 20, Windham, NY 12496
/11
$135,000
- Land
- 1.2 Acres
- $112,500 per Acre
L19.12 South St, Windham, NY 12496

Build your Catskills getaway on this 1.2-acre unimproved lot located on South Street in Windham, NY. Offering a peaceful setting with convenient access to Windham Mountain Club, village amenities, dining, and year-round recreation. Adjoining 1 acre lot for sale separately. A great opportunity for a custom home, weekend retreat, or long-term investment. Bring your vision and create a home that

Susan Miller WINDSTAR REALTY GROUP LLC

L19.12 South St, Windham, NY 12496
/23
$240,000
- 2 Beds
- 1.5 Baths
- 1,008 Sq Ft
45 Quads Way, Windham, NY 12496

Lovely, well maintained condo situated in Windham. This condo is ready for its new owners. Situated close to the Windham Mountain Club, State hiking and biking trails as well as golf, dining, movies and all that the Windham area has to offer. A 15 minute drive to Hunter Mt. as we.. The first level has ann eat in kitchen, half bath, living room with fireplace, sliding doors to a lovely deck with

Mary Donovan Gallagher & Company

45 Quads Way, Windham, NY 12496
/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
/9
$75,000
- Land
- 2 Acres
- $37,500 per Acre
0 Trailview Ln, Windham, NY 12496

Transform Your Vision at Trail View-Dreaming of the perfect place to make your vision a reality? Trail View is where it all begins-a breathtaking 2-acre lot nestled in the heart of Windham, offering stunning slope views and endless possibilities. Whether you're planning your dream home, a cozy vacation cabin, or a chic rental property, this lot is ready to bring your ideas to life! Imagine

Regina Tortorella Coldwell Banker Village GreenW

0 Trailview Ln, Windham, NY 12496
/14
$75,000
- Land
- 1 Acre
- $75,000 per Acre
0 Mountain View Rd, Windham, NY 12496

Your 1 Acre in Windham Awaits! For everyone who's ever called us and said, "I just want a small piece of land to hold onto, "maybe build on it someday." This one is for you! This 1-acre wooded lot on a private country road offers the ideal setting for your next project. Whether you're planning to build a cozy cabin, dream home, or vacation rental, this mostly level property is ready for you to

Regina Tortorella Coldwell Banker Village GreenW

0 Mountain View Rd, Windham, NY 12496
/14
$120,000
- Land
- 1 Acre
- $120,000 per Acre
L19.11 South St, Windham, NY 12496

Build your Catskills getaway on this 1acre unimproved lot located on South Street in Windham, NY. Offering a peaceful setting with convenient access to Windham Mountain Club, village amenities, dining, and year-round recreation. Adjoining 1.2 acre lot for sale separately. A great opportunity for a custom home, weekend retreat, or long-term investment. Bring your vision and create a home that

Susan Miller WINDSTAR REALTY GROUP LLC

L19.11 South St, Windham, NY 12496
/6
$257,000
- Land
- 25,700 Sq Ft
- $435,593 per Acre
57 South St, Windham, NY 12496

Unique opportunity - one of the LAST lots on South Street! Flat parcel overlooking the golf course. Close access to everything Windham has to offer: ski, golf, biking, movie theater, shops and downtown restaurants. Utilities access on site: water (town), sewer (town), electric (NYSEG).

Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

57 South St, Windham, NY 12496
/48
$179,900
- Land
- 5.61 Acres
- $32,068 per Acre
Tbd Boulder Brook Rd Lot 11, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. On this specific lot, an area has been cleared and

Philip Kelly Howard Hanna Rand Realty

Tbd Boulder Brook Rd Lot 11, Windham, NY 12496
/21
$99,000
- Land
- 7.06 Acres
- $14,023 per Acre
0 Mitchell Hollow Rd, Windham, NY 12496

7.06 Acres in Windham -- Surveyed, Perc Tested & Ready for the Next StepAn excellent opportunity to build in Windham with much of the preliminary site work already completed. This 7.06-acre surveyed parcel offers approximately 431 feet of road frontage on a town-maintained road, a mostly level and cleared building area, a newly installed driveway, mountain views, and electric

Regina Tortorella Coldwell Banker Village GreenW

0 Mitchell Hollow Rd, Windham, NY 12496
/17
$300,000
- Land
- 7.52 Acres
- $39,894 per Acre
1 Estate View Dr, Windham, NY 12496

Only a select number of lots remain! Welcome to Windham Luxury Estates, where an exceptional opportunity awaits with this fully approved, shovel ready 7.5 acre residential building lot. This premier parcel includes complete engineering, topographical and survey maps, along with a fully approved DEP septic design for an estate sized home, making the building process as seamless as possible.

Patrick Dunn KW Platform

1 Estate View Dr, Windham, NY 12496
/16
$269,000

$11K PRICE DROP
- 2 Beds
- 2.5 Baths
- 1,058 Sq Ft
45 Windham Ridge Rd Unit C, Windham, NY 12496

Nestled in the heart of the Catskills, this beautifully updated 2-bedroom, 2.5-bath townhome offers stunning views of Windham Mountain Club and the perfect blend of comfort, style, and four-season recreation. Featuring approximately 1,300 square feet of living space, this turnkey retreat showcases a newly remodeled kitchen with quartz countertops, new appliances, and modern finishes throughout.

Mary Jo Warner Listing by Howard Hanna

45 Windham Ridge Rd Unit C, Windham, NY 12496
/37
$285,000

$10K PRICE DROP
- 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/ski home, 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
/29
$227,900

$7K PRICE DROP
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
41 Quads Way, Windham, NY 12496

Perfect Condo Getaway Beautiful 2bd, 2bth with a woodburning fireplace condo located minutes to Windham Mountain skiing and 15 minutes to hunter Mountain. This well priced home is a blink away from the town of Windham with all the restaurant's, night life and local brewery's to enjoy and be home in minutes. There is porch that backs up to a wooded area. Enjoy resort-style amenities including a

Brian Cohen RHR Realty Group

41 Quads Way, Windham, NY 12496
/49
$155,000
- Land
- 5.99 Acres
- $25,876 per Acre
Tbd Boulder Brook Lot B14, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Kyla Thomas Howard Hanna Rand Realty

Tbd Boulder Brook Lot B14, Windham, NY 12496
/51
$155,000
- Land
- 5.99 Acres
- $25,876 per Acre
Tbd Boulder Brook Lot B14, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Philip Kelly Howard Hanna Rand Realty

Tbd Boulder Brook Lot B14, Windham, NY 12496
/23
$297,000

$13K PRICE DROP
- 2 Beds
- 2 Baths
- 1,890 Sq Ft
504 County Route 40, Maplecrest, NY 12454

Totally renovated 2-bedroom, 2-full bath ranch-style home featuring an open floor plan and a full finished walk-out basement that offers versatile living space with the potential for additional bedrooms. The interior showcases a new kitchen with quartz countertops, an undermount sink, a tiled backsplash, maple cabinetry, and high-quality appliances. Additional updates include ceramic tiled

Douglas Schenk RE/MAX Capital

504 County Route 40, Maplecrest, NY 12454
/4
$89,000
- Land
- 2.3 Acres
- $38,696 per Acre
0 Windham Woods Rd Unit 20264075, Windham, NY 12454

Own Your Piece of Paradise in Windham, NYIf you've always dreamed of owning a piece of paradise, this is your opportunity. Located just 21⁄2 hours from New York City, Windham is known as the ''Jewel of the Catskill Mountains.''Enjoy the perfect blend of mountain living and convenience. You'll be close to golf, restaurants, lodging, and the town walking path. Take a short walk to Elm Ridge

John Pumilia Shaw Country Realty, Inc.

0 Windham Woods Rd Unit 20264075, Windham, NY 12454
/22
$285,000

$15K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,446 Sq Ft
542 Mitchell Hollow Rd, Windham, NY 12496

Welcome to 542 Mitchell Hollow Road, Windham, NY, a charming home set on a beautifully maintained property in the heart of the Catskills. This inviting residence offers a wonderful combination of comfort, space, and natural surroundings, making it ideal as a full-time home, weekend retreat, or investment opportunity. Expansive decking provides excellent outdoor living space for relaxing,

Shpresa Camaj Real Broker NY LLC

542 Mitchell Hollow Rd, Windham, NY 12496
/11
$174,999

$20K PRICE DROP
- Land
- 5.6 Acres
- $31,250 per Acre
0 Peck Rd, Windham, NY 12454

If you have always dreamed of building the country home you've always wanted, it all starts with the right location. Let Windham, New York -- known as ''The Gem of the Catskills'' -- be that location.Windham is one of the Catskills' most sought-after destinations, offering year-round recreation including skiing, golf, hiking, trout fishing, mountain biking, and much more. With great

John Pumilia Shaw Country Realty, Inc.

0 Peck Rd, Windham, NY 12454
/49
$149,000
- Land
- 5.25 Acres
- $28,381 per Acre
TBD Boulder Brook Lot 13b Rd, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Kyla Thomas Howard Hanna Rand Realty

TBD Boulder Brook Lot 13b Rd, Windham, NY 12496
/60
$149,000
- Land
- 5.33 Acres
- $27,955 per Acre
Tbd Boulder Brook Rd Lot B13, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Philip Kelly Howard Hanna Rand Realty

Tbd Boulder Brook Rd Lot B13, Windham, NY 12496
/55
$159,900
- Land
- 3.23 Acres
- $49,505 per Acre
Tbd Boulder Brook Rd Lot B12, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Philip Kelly Howard Hanna Rand Realty

Tbd Boulder Brook Rd Lot B12, Windham, NY 12496
/16
$290,000
- Land
- 5.42 Acres
- $53,506 per Acre
2 Estate View Dr, Windham, NY 12496

Only a select number of lots remain! Lot 2 is an elevated homesite just before the cul-de-sac, offering incredible mountain views for under 300,000. Welcome to Windham Luxury Estates, where an exceptional opportunity awaits with this fully approved, shovel ready 5.42 acre residential building lot. This premier parcel includes complete engineering, topographical and survey maps, along with a fully

Patrick Dunn KW Platform

2 Estate View Dr, Windham, NY 12496
/11
$99,900
- Land
- 1.1 Acres
- $90,818 per Acre
L46.111 Panarama Ln, Windham, NY 12496

Build your dream mountain getaway on this 1.1 acre unimproved lot just minutes from the Windham Mountain Club expansion. Surrounded by natural beauty, this property offers privacy, fresh air, and easy access to skiing, hiking, biking, golf, and charming village amenities. A perfect canvas for a custom Catskills home.A great opportunity in a rapidly evolving Catskills destination.

Susan Miller WINDSTAR REALTY GROUP LLC

L46.111 Panarama Ln, Windham, NY 12496
/49
$159,900
- Land
- 8.72 Acres
- $18,337 per Acre
TBD Boulder Brook Lot B12 Rd, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Kyla Thomas Howard Hanna Rand Realty

TBD Boulder Brook Lot B12 Rd, Windham, NY 12496
/28
$247,985

$42K PRICE DROP
- 2 Beds
- 1 Bath
- 800 Sq Ft
107 Route 40 Rd, Windham, NY 12496

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

Brian Cohen RHR Realty Group

107 Route 40 Rd, Windham, NY 12496
/50
$179,900
- Land
- 5.99 Acres
- $30,033 per Acre
TBD Boulder Brook Lot 11 Rd, Windham, NY 12496

Build Your Dream in the Catskills. Located within the newly developed 6-lot Boulder Brook subdivision, this lot offers the perfect blend of community and convenience, just minutes from Windham Ski Resort. Set on a quiet cul-de-sac, each lot in Boulder Brook has been thoughtfully designed with ample space, natural beauty, and easy access in mind. Whether you're planning a cozy weekend getaway, a

Kyla Thomas Howard Hanna Rand Realty

TBD Boulder Brook Lot 11 Rd, Windham, NY 12496

New York Greene County

Home Prices in Windham, NY

The median home sale price in Windham, NY is $715,000, up 38% year-over-year. Homes in Windham sell in 129 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $715,000	Median Single Family Sale Price $685,000
Median Townhouse Sale Price $399,000	Median 2 Bedroom Sale Price $310,000
Median 1 Bedroom Sale Price $158,000	Average Price Per Sq Ft $351
Number of Homes for Sale 78	Last 12 months Home Sales 91
Months of Supply 10.30	Median List Price $725,000
Median Change From 1st List Price 6%	Median Home Sale Price YoY Change 38%

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