Vintage homes for sale & real estate in 12496, NY

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ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
Whether your search is for personal use or investment property, this Windham Farmhouse, just steps from the center of town, offers versatility and plenty of room for the whole family. A unique three floor layout allows for everyone to have their own space. The first and lowest level is the main living area: Kitchen, Dining, Living Room as well as a bedroom and full bath. The sunroom is an nice addition, expanding the living space and providing opportunity to enjoy the changing weather - the warmth of the sun, raindrops, snowflakes and all shades of the Windham sky. The second floor has another comfortable living area, a second bath and a large bedroom. Up one more flight of stairs are two b

$439,000

4 beds3 baths1,914 sq ft

17 Mitchell Hollow Rd, Windham, NY 12496

Attached garage • Three floor layout • Sunroom

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
Skiers and Hunters! 7 glorious acres 8 minutes to Windham Mountain! Charming Updated Home with mature trees, beautiful plantings and landscapes. Welcome to this inviting 3-bedroom, 1-bath home set on 7 beautiful acres offering privacy, space, and stunning natural surroundings. Located only 8 minutes from the local ski area, it's the perfect retreat for outdoor enthusiasts or anyone seeking a peaceful country setting with convenience. Inside, you'll find a home that blends comfort with thoughtful updates. The kitchen has been tastefully updated, featuring modern finishes and improved functionality, while the updated bath offers a clean, contemporary feel. The bedrooms are cozy, ideal for sim

$375,000

3 beds1 bath1,739 sq ft

477 Campbell Rd, Windham, NY 12407

7 acres • Updated bath • Updated kitchen

Listing by Century 21 Alliance Realty Grp

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
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!

$215,000

3 beds1.5 baths1,200 sq ft

384 Route 296, Windham, NY 12496

Mountain getaway • Hiking trails • 0.25 acre lot

Listing by Century 21 New West Properties

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
Welcome to this charming, freshly painted Cape-style farmhouse, where comfort and character meet. Inside, a warm and inviting living room with a wood-burning fireplace offers the perfect place to relax after a day of adventure. Step outside onto the back deck and soak in the tranquil wooded setting—ideal for morning coffee, evening sunsets, or simply enjoying nature's beauty. Perfectly situated just off Route 23, you're only 5 miles from Windham Mountain and 10 miles from Hunter Mountain, making this home a dream for outdoor enthusiasts and a peaceful retreat year-round. Don't miss your chance to make it yours—schedule a showing today!

$349,900

3 beds1.5 baths1,069 sq ft

28 Sutton Hollow Rd, Windham, NY 12496

Back deck • 0.36 acre lot • 2 garage spots

Listing by Venture Fox Realty Group LLC

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
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 meadows and fields. Also there sits a two acre pond and wooded area with a nice waterfall, beautiful mountain views from anywhere on the property. Five miles to Windham Village shops, restaurants, golf and Ski Windham. This property will not last long in this market.

$550,000

7 beds2.5 baths3,114 sq ft

804 Mitchell Hollow Rd, Windham, NY 12496

Large dining room • Large front porch • Large living room

Property at 5220 Route 23 #126, Windham, NY 12496, 1 bed, 1 bath

$170,000

1 bed1 bath423 sq ft

5220 Route 23 #126, Windham, NY 12496

Property at 28 Sutton Hollow Rd, Ashland, NY 12407, 3 beds, 1.5 baths

$349,900

3 beds1.5 baths1,069 sq ft

28 Sutton Hollow Rd, Ashland, NY 12407

Property at 769 Mitchell Hollow Rd, Windham, NY 12496, 4 beds, 3.5 baths

$779,000

4 beds3.5 baths2,100 sq ft

769 Mitchell Hollow Rd, Windham, NY 12496

Property at 25 Vets Road Rd, Windham, NY 12496, 4 beds, 4 baths

$499,000

4 beds4 baths2,374 sq ft

25 Vets Road Rd, Windham, NY 12496

Property at 20 Sutton Hollow Rd, Windham, NY 12496, 3 beds, 2.5 baths

$535,000

3 beds2.5 baths1,335 sq ft

20 Sutton Hollow Rd, Windham, NY 12496

Property at 5320 Route 23, Windham, NY 12496, 8 beds, 8 baths

$850,000

8 beds8 baths3,712 sq ft

5320 Route 23, Windham, NY 12496

Property at 5433 Ny-23, Windham, NY 12496, 5 beds, 3 baths

$1,999,999

5 beds3 baths3,409 sq ft

5433 Ny-23, Windham, NY 12496

Property at 5474 Route 23, Windham, NY 12496, 7 beds, 3 baths

$999,000

7 beds3 baths4,281 sq ft

5474 Route 23, Windham, NY 12496

Property at 689 Old Rd, Hensonville, NY 12439, 2 beds, 2 baths

$340,000

2 beds2 baths1,542 sq ft

689 Old Rd, Hensonville, NY 12439

Listing by Win Morrison Realty

Property at 689 Old Rd, Windham, NY 12496, 2 beds, 2 baths

$340,000

2 beds2 baths1,542 sq ft

689 Old Rd, Windham, NY 12496

Listing by Win Morrison Realty

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ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
Attention investors and DIY enthusiasts! Multiple exit strategies: finish this remodel then either flip, rent or move in! Home being sold as is. Cash preferred but will consider financed all offers. Seller is assisted by an Attorney in Fact. Do not knock on door or approach house without prior communication.

$49,900

4 beds1 bath2,451 sq ft

3673 Route 20, Durham, NY 12418

1 acre lot • Built 1900

Listing by The Greene Realty Group

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
Welcome to your cozy retreat in the heart of Ashland, NY. Nestled on 1.8 scenic acres between Windham and Hunter Mountains, this inviting property offers two charming homes, stunning mountain views, and a tranquil setting surrounded by nature and neighboring horse pastures. This stunning property has undergone a full transformation within the last 3 years — rebuilt from the ground up with quality craftsmanship and attention to detail. Every element is new, including electrical, HVAC, roofs, appliances, floors and finishes. Enjoy the peace of mind of a brand-new home with the charm of an established location. The main cottage is approx. 1,100 sq ft. and features 3 bedrooms (1 primary w

$460,000

4 beds3 baths1,510 sq ft

12295 State Highway 23, Ashland, NY 12407

1.8 acre lot • 8 parking spots • Built 1951

Listing by Berkshire Hathaway Home Services Blake

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
What an investment opportunity to finish the renovations and own a two-family home. The downstairs unit is ready to go and offers 3 Bedrooms and one full bath. Wood floors throughout and a cozy wood stove. Upstairs will need to be a rehab project. New windows throughout and newer metal roof. Lovely older country home with front porch and ramp access in the back. Come and take a look and get your hammer ready to finish the upstairs.

$164,500

3 beds1 bath2,431 sq ft

1289 990v, Gilboa, NY 12076

Cozy wood stove • Wood floors • Front porch

Listing by Howard Hanna Capital, Inc.

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
Welcome to this hidden gem nestled on an acre of picturesque land in Jewett, NY. This ranch-style home offers a unique opportunity for those seeking a tranquil escape with breathtaking mountain views. Conveniently located in close proximity to the renowned ski slopes of Hunter and Windham Mountains. Perfect for avid skiers or those looking to enjoy the cozy ambiance of mountain resort. Delight in local shops, restaurants, and community events, which is just a short drive away from the charming villages of Windham, Hunter, and Tannersville. This property provides a perfect blend of seclusion and accessibility. Enjoy the stunning backdrop of mountain views that change with the seasons. Nature

$250,000

2 beds1 bath844 sq ft

49 Ryan Rd, Jewett, NY 12444

Serene creeks • Ski slopes • Hiking trails

Listing by RE/MAX ELITE

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
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 refl

$2,495,000

8 beds3.5 baths3,350 sq ft

3 Leon Macglashan Rd, Windham, NY 12496

10 bedroom farmhouse • Mature forests • 210 acres

Listing by Serhant LLC

ABOUT THIS HOME
Vintage Home for sale in 12496, NY:
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 ref

$2,495,000

8 beds3.5 baths6,700 sq ft

3 Leon Macglashan Rd, Windham, NY 12496

10 bedroom farmhouse • 210 acres • 210 acre lot

Property at 161 Beaver Hill Dr, Gilboa, NY 12076, 6 beds, 3 baths

$935,000

6 beds3 baths3,423 sq ft

161 Beaver Hill Dr, Gilboa, NY 12076

Listing by Four Seasons Sotheby's International Realty

Property at 436 Big Hollow Rd, Windham, NY 12496, 3 beds, 2 baths

$399,000

3 beds2 baths1,400 sq ft

436 Big Hollow Rd, Windham, NY 12496

Property at 934 Route 296, Jewett, NY 12444, 4 beds, 2 baths

$385,000

4 beds2 baths1,582 sq ft

934 Route 296, Jewett, NY 12444

Property at 169 Rt. 4, Prattsville, NY 12468, 2 beds, 1 bath

$429,900

2 beds1 bath1,618 sq ft

169 Rt. 4, Prattsville, NY 12468

Property at 293 Carl Rd, Jewett, NY 12444, 6 beds, 2 baths

$799,000

6 beds2 baths4,294 sq ft

293 Carl Rd, Jewett, NY 12444

Listing by EXIT Realty Premier

Property at 1232 Route 990 V, Gilboa, NY 12076, 3 beds, 1 bath

$274,000

3 beds1 bath1,036 sq ft

1232 Route 990 V, Gilboa, NY 12076

Listing by Coldwell Banker Village Green

Property at 12112 State Highway 23, Ashland, NY 12468, 5 beds, 3 baths

$425,000

5 beds3 baths2,160 sq ft

12112 State Highway 23, Ashland, NY 12468

Listing by Find Advisors

Based on information submitted to the MLS GRID as of Thu Nov 27 2025. 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.

Vintage Homes for Sale in 12496

There are currently 15 vintage homes for sale in 12496 at a median listing price of $725K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 12496 stay on the market for 130 days. This map is refreshed with the newest listings in 12496 every 15 minutes.

In the past month, 5 homes have been sold in 12496. In addition to houses in 12496, there were also 6 condos, 1 townhouse, and 1 multi-family unit for sale in 12496 last month. Find your dream home in 12496 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 12496 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 12496. If you're looking to sell your home in the 12496 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 12496 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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