Vintage homes for sale & real estate in Sullivan County, NY

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ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Classic Livingston Manor Four Square – Timeless Charm in the Heart of the Catskills Step into a piece of Livingston Manor history with this beautifully maintained Four Square home, where original character and modern-day possibilities come together. Rich in warmth and authenticity, the home retains its original woodwork throughout, showcasing the craftsmanship and charm that are increasingly hard to find and only a short walk to Main Street. For the fly-fishing enthusiast, this location is hard to beat. Just minutes from some of the most celebrated trout waters in the Catskills, you'll have easy access to the legendary Willowemoc and Beaverkill rivers. With its spacious layout, inviti

$374,500

3 beds1.5 baths1,300 sq ft

532 Old Route 17, Livingston Manor, NY 12758

Original wood trim • Natural light • Original woodwork

Listing by Carole Edwards Realty

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Charming , light, bright, well maintained 3 unit property with lots of history, located in downtown Kauneonga Lake. 3 miles from Bethel Woods Performing Arts Center. Breathtaking lake views. Walk to restaurants and shops. Enjoy over 1 acre of property, both cleared and wooded. Can be used as commercial or residential space. Washer dryer for each unit.

$575,000

5 beds4 baths— sq ft

3568 State Route 55, Swan Lake, NY 12783

3 unit property • Built 1950 • Listed 82 days

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Nestled in a peaceful neighborhood, this charming fully furnished home offers an incredible opportunity for both personal enjoyment and investment. Conveniently located just minutes from Route 17, the property provides easy access to major transportation routes and is approximately 1.5 hours from NYC. Thoughtfully remodeled nine years ago with custom touches throughout, this home has been successfully operated as a short-term rental, making it an attractive turnkey investment for those looking to continue its rental potential. The home is being offered fully furnished, allowing a new owner to seamlessly continue hosting guests from day one. The home features four spacious bedrooms, includin

$450,000

4 beds2 baths2,647 sq ft

158 Harris Rd, Harris, NY 12742

Propane fireplace • Custom touches • Fully furnished

Listing by Land and Water Realty LLC

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Welcome to your private Sullivan County sanctuary, tucked away in the scenic heart of the Upper Delaware River Valley. This beautifully 3-bedroom, 2-bathroom ranch blends classic mid-century structure with modern comfort, offering 2,050 square feet of bright, inviting living space. The crown jewel of the home is the expansive three-season sunroom—the absolute perfect spot for your morning coffee or winding down after a day on the water, offering sweeping views of the Pennsylvania mountains and a seasonal glimpse of the Delaware River. Inside, gleaming original hardwood floors flow seamlessly through a bright, functional layout complemented by a well-appointed kitchen with abundant sto

$325,000

3 beds2 baths2,050 sq ft

24 Andrew Paye Rd, Pond Eddy, NY 12770

Three-season sunroom • 0.83 acre lot • Garage

Listing by KW Hudson Valley United

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Motivated seller! Get ready to fall in love with this charming New England style farmhouse in a most desirable location. Beautifully arranged with plenty of room for entertainment and relaxation this is a real treat. Well-appointed interior with wood floors and warm original details offers space for everyone to spread out and enjoy. The large eat-in kitchen boasts an island and granite counters with cabinets galore and upscale appliances. French doors open to formal living room with gas fireplace, and the cozy formal dining room is just around the corner. Sitting room/ den leads to the glorious sunroom which overlooks the peaceful meadow view. Upstairs offers three bedrooms and full bath wi

$435,000

3 beds3 baths2,592 sq ft

237 Best Rd, Swan Lake, NY 12783

Large eat-in kitchen • Gas fireplace • Upscale appliances

Listing by Malek Properties

Property at 360 Laurel Ave, Fallsburg, NY 12733, 4 beds, 3 baths

$579,000

4 beds3 baths1,752 sq ft

360 Laurel Ave, Fallsburg, NY 12733

Listing by eRealty Advisors, Inc

Property at 60 Haddock Rd, Monticello, NY 12701, 6 beds, 2 baths

$399,000

6 beds2 baths1,456 sq ft

60 Haddock Rd, Monticello, NY 12701

Listing by eRealty Advisors, Inc

Property at 25 Canal Rd, Wurtsboro, NY 12790, 3 beds, 2 baths

$399,900

3 beds2 baths1,398 sq ft

25 Canal Rd, Wurtsboro, NY 12790

Listing by J. Morreale, LTD

Property at 64 & 68 Mineral Springs Rd, Livingston Manor, NY 12758, 4 beds, 2 baths

$489,000

4 beds2 baths1,772 sq ft

64 & 68 Mineral Springs Rd, Livingston Manor, NY 12758

Listing by Century 21 Geba Realty

Property at 77 Rockland Rd, Roscoe, NY 12776, 3 beds, 1.5 baths

$269,000

3 beds1.5 baths1,456 sq ft

77 Rockland Rd, Roscoe, NY 12776

Listing by Land and Water Realty LLC

Property at 91 Old Hankins Rd, Callicoon, NY 12723, 6 beds, 4 baths

$1,200,000

6 beds4 baths4,080 sq ft

91 Old Hankins Rd, Callicoon, NY 12723

Listing by Country House Realty Inc

Property at 86 Plank Rd, Mongaup Valley, NY 12762, 2 beds, 2 baths

$279,900

2 beds2 baths1,090 sq ft

86 Plank Rd, Mongaup Valley, NY 12762

Listing by River Realty Services, Inc.

Property at 28 Upper Main St, Callicoon, NY 12723, 7 beds, 3 baths

$674,000

7 beds3 baths4,900 sq ft

28 Upper Main St, Callicoon, NY 12723

Listing by BERKSHIRE HATHAWAY

Property at 299-301 Stump Pond Rd, Livingston Manor, NY 12758, 6 beds, 2 baths

$444,500

6 beds2 baths2,174 sq ft

299-301 Stump Pond Rd, Livingston Manor, NY 12758

Listing by Malek Properties

Property at 12 Winthrop Ave, Liberty, NY 12754, 2 beds, 1 bath

$199,900

2 beds1 bath1,107 sq ft

12 Winthrop Ave, Liberty, NY 12754

Listing by The Maxx Group LLC

Property at 530 Sackett Lake Rd, Monticello, NY 12701, 4 beds, 3 baths

$395,000

4 beds3 baths2,452 sq ft

530 Sackett Lake Rd, Monticello, NY 12701

Listing by Resort Realty

Property at 64 Moon Manor Rd #3, Monticello, NY 12701, 3 beds, 1.5 baths

$165,000

3 beds1.5 baths1,464 sq ft

64 Moon Manor Rd #3, Monticello, NY 12701

Listing by Exit Realty First Choice

Property at 24 Eldridge St S, Smallwood, NY 12778, 2 beds, 1 bath

$229,000

2 beds1 bath721 sq ft

24 Eldridge St S, Smallwood, NY 12778

Listing by Malek Properties

Property at 12 Railroad St, Long Eddy, NY 12760, 6 beds, 2.5 baths

$650,000

6 beds2.5 baths2,674 sq ft

12 Railroad St, Long Eddy, NY 12760

Listing by Matthew J Freda Real Estate

Property at 179 W Mohican Trl, Glen Spey, NY 12737, 1 bed, 1 bath

$269,000

1 bed1 bath576 sq ft

179 W Mohican Trl, Glen Spey, NY 12737

Listing by Century 21 Geba Realty

Property at 23 Cooley Rd, Parksville, NY 12768

$550,000

Studio— baths— sq ft

23 Cooley Rd, Parksville, NY 12768

Listing by Keller Williams Realty

Property at 623 Wurtsboro Mtn Rd, Wurtsboro, NY 12790, 3 beds, 2.5 baths

$295,000

3 beds2.5 baths1,288 sq ft

623 Wurtsboro Mtn Rd, Wurtsboro, NY 12790

Listing by Eagle Valley Realty

Property at 220 Mail Rd, Barryville, NY 12719, 3 beds, 1.5 baths

$339,000

3 beds1.5 baths1,252 sq ft

220 Mail Rd, Barryville, NY 12719

Listing by NexLvl Real Estate Inc.

Property at 302 Todd Rd Unit T, Woodbourne, NY 12788, 2 beds, 1 bath

$110,000

2 beds1 bath1,551 sq ft

302 Todd Rd Unit T, Woodbourne, NY 12788

Listing by KW Hudson Valley United

Property at 12 Henderson Rd, Fremont, NY 12741, 4 beds, 1 bath

$219,000

4 beds1 bath1,700 sq ft

12 Henderson Rd, Fremont, NY 12741

Listing by Matthew J Freda Real Estate

Property at 26 Maple AVE, White Lake, NY 12786, 5 beds, 3 baths

$599,000

5 beds3 baths1,540 sq ft

26 Maple AVE, White Lake, NY 12786

Property at 22 Ballard St, Smallwood, NY 12778, 4 beds, 3 baths

$340,000

4 beds3 baths1,560 sq ft

22 Ballard St, Smallwood, NY 12778

Listing by Resort Realty

Property at 242 High Rd, Glen Spey, NY 12737, 3 beds, 2 baths

$888,000

3 beds2 baths2,576 sq ft

242 High Rd, Glen Spey, NY 12737

Listing by Payne Team LLC

Property at 194 Canal Rd, Wurtsboro, NY 12790, 4 beds, 2 baths

$699,900

4 beds2 baths1,688 sq ft

194 Canal Rd, Wurtsboro, NY 12790

Listing by J. Morreale, LTD

Property at 1193 South Rd, Wurtsboro, NY 12790, 2 beds, 1 bath

$449,000

2 beds1 bath1,120 sq ft

1193 South Rd, Wurtsboro, NY 12790

Listing by Stepping Stone Realty

Property at 1 Hammond St, Monticello, NY 12701, 3 beds, 1.5 baths

$325,000

3 beds1.5 baths1,575 sq ft

1 Hammond St, Monticello, NY 12701

Listing by Resort Realty

Property at 00 Gold Dan Rd Unit c, Swan Lake, NY 12783, 3 beds, 2 baths

$165,000

3 beds2 baths1,600 sq ft

00 Gold Dan Rd Unit c, Swan Lake, NY 12783

Listing by Malek Properties

Property at 34 Overlook Rd, Woodbourne, NY 12788, 3 beds, 2 baths

$337,500

3 beds2 baths2,080 sq ft

34 Overlook Rd, Woodbourne, NY 12788

Listing by Land and Water Realty LLC

Property at 5 Washington, Liberty, NY 12754, 3 beds, 1 bath

$110,000

3 beds1 bath1,254 sq ft

5 Washington, Liberty, NY 12754

Listing by Resort Realty

Property at 238 Lakeview Drive Rd, Highland Lake, NY 12743, 11 beds, 7 baths

$900,000

11 beds7 baths4,762 sq ft

238 Lakeview Drive Rd, Highland Lake, NY 12743

Listing by KW Hudson Valley United

Property at 628 Lake Shore Dr, Smallwood, NY 12778, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths1,234 sq ft

628 Lake Shore Dr, Smallwood, NY 12778

Listing by Malek Properties

Property at 37 Nober Strunk Rd, Narrowsburg, NY 12764, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths2,000 sq ft

37 Nober Strunk Rd, Narrowsburg, NY 12764

Listing by BERKSHIRE HATHAWAY

Property at 3 Rennenberg Rd, Highland Lake, NY 12743, 2 beds, 1 bath

$385,000

2 beds1 bath1,092 sq ft

3 Rennenberg Rd, Highland Lake, NY 12743

Listing by Century 21 Geba Realty

Property at 286 Dingle Daisy Rd, Monticello, NY 12701, 2 beds, 1 bath

$299,000

2 beds1 bath1,190 sq ft

286 Dingle Daisy Rd, Monticello, NY 12701

Listing by Joy Romano Realty

Property at 5 Liberty Pl N, Smallwood, NY 12778, 2 beds, 1.5 baths

$239,000

2 beds1.5 baths676 sq ft

5 Liberty Pl N, Smallwood, NY 12778

Listing by Caroline Akt Realty LLC

Property at 2182 County Road 17, Roscoe, NY 12776, 15 beds, 5 baths

$899,000

15 beds5 baths10,926 sq ft

2182 County Road 17, Roscoe, NY 12776

Listing by Boller Properties

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Based on information submitted to the MLS GRID as of Wed Oct 21 2026. 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 Sullivan County

There are currently 314 vintage homes for sale in Sullivan County at a median listing price of $425K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Sullivan County stay on the market for 105 days and receive 1 offers. This map is refreshed with the newest listings in Sullivan County every 15 minutes.

In the past month, 75 homes have been sold in Sullivan County. In addition to houses in Sullivan County, there were also 12 condos, 2 townhouses, and 29 multi-family units for sale in Sullivan County last month. Find your dream home in Sullivan County 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 Sullivan County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Sullivan County. If you're looking to sell your home in the Sullivan County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Sullivan County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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