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:
MOTIVATED SELLER! Welcome to the River View Inn, a distinctive homestead b & b revival in the heart of Roscoe. Built by hand in 1880 on a sturdy bluestone foundation, this iconic heritage homestead has been lovingly maintained by the same owners for generations. As one of the earliest pre-war homesteads in the Catskills, the 15-bedroom manor remains one of the last true "trophy properties" that has not yet been restored. Perched upon nearly 15 gently sloping acres, this historic four-level boarding house features a circular driveway ideal for valet parking and a separate driveway for guest parking. The interior unfolds with practical hospitality in mind: the primary level incl

$899,000

15 beds5 baths10,926 sq ft

2182 County Road 17, Roscoe, NY 12776

Bluestone foundation • Three-bedroom suite • Separate driveway

Listing by Boller Properties

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Some streets just have a feeling, and Chapel Street is one of them. Towering shade trees and classic homes line this beloved street in the Village of Jeffersonville, welcoming you to a timeless Victorian ready for its next chapter. Step inside to discover four bedrooms, two full bathrooms, and beautiful hardwood floors that speak to the craftsmanship of another era. Every room offers the opportunity to blend historic charm with your own personal style, creating a home that's uniquely yours. Outside, the magic continues. Gather around the outdoor fireplace on crisp Catskills evenings, host friends in the spacious backyard, or simply enjoy the peaceful surroundings beneath the mature trees th

$325,000

4 beds2 baths1,980 sq ft

8 Chapel St, Jeffersonville, NY 12748

Outdoor fireplace • Spacious backyard • Mature trees

Listing by Century 21 Geba Realty

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Welcome to 10 Church Road, where the comfort of home meets the freedom to dream bigger. Tucked away on 9.08 acres in the Hamlet Residence District of Mountaindale, this beautifully maintained property offers a rare combination of move in ready living and exceptional future potential. The charming 1,200 square foot home features two generously sized bedrooms, one full bathroom, soaring ceilings that create an open and airy feel, and thoughtful updates that make everyday living comfortable, including a recently installed heat pump for efficient year round heating and cooling. Step outside and you’ll quickly realize this property is something special. Meticulously maintained botanical ga

$474,900

2 beds1 bath1,220 sq ft

10 Church Rd, Mountain Dale, NY 12763

Dedicated greenhouse • Municipal water • 9.08 acres

Listing by KW Hudson Valley United

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Welcome to Lake View Hideaway at 34 Overlook Road—a proven, income-producing short-term rental perched above Lake Paradise in the heart of the Catskills. This renovated, fully furnished (optional) property is already operating as a successful year-round Airbnb, making it an exceptional turnkey opportunity for investors seeking immediate cash flow with upside. Set back from the road and surrounded by trees, the home offers the privacy and tranquil setting today’s short-term rental guests crave. Inside, rustic-chic design elements—wide-plank barnwood floors, sliding barn doors, and a wood-burning fireplace—create a warm, farmhouse aesthetic that photographs beautifully

$337,500

3 beds2 baths2,080 sq ft

34 Overlook Rd, Woodbourne, NY 12788

Chef's kitchen • Turnkey opportunity • 0.37 acre lot

Listing by Land and Water Realty LLC

ABOUT THIS HOME
Vintage Home for sale in Sullivan County, NY:
Public Remarks Welcome to the quintessential lake house in the storybook community of Smallwood. This charming four-season home immediately captivates with its outdoor setting; relax on your private deck to enjoy beautiful views of Mountain Lake while listening to the soothing sounds of White Lake Creek close by. It is an idyllic backdrop for morning coffee or evening relaxation. Inside, this three-bedroom, one-and-a-half-bath retreat perfectly captures the nostalgia of a classic getaway while offering rare, year-round comfort. The well-sized, light-filled rooms showcase beautiful vintage details, highlighted by a cozy working fireplace and classic hardwood floors that run throughou

$399,000

3 beds1.5 baths1,234 sq ft

628 Lakeshore Dr, Smallwood, NY 12778

Private deck • Extra lot • Working fireplace

Property at 184 Yankee Lake Rd, Wurtsboro, NY 12790, 4 beds, 1.5 baths

$349,900

4 beds1.5 baths1,386 sq ft

184 Yankee Lake Rd, Wurtsboro, NY 12790

Listing by J. Morreale, LTD

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 32 Brookside Dr, Neversink, NY 12788, 4 beds, 2 baths

$145,000

4 beds2 baths832 sq ft

32 Brookside Dr, Neversink, NY 12788

Listing by Resort 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 97 Rauch Rd, Lake Huntington, NY 12726, 5 beds, 2 baths

$399,000

5 beds2 baths— sq ft

97 Rauch Rd, Lake Huntington, NY 12726

Listing by Century 21 Geba Realty

Property at 223 Yulan-barryville Rd, Barryville, NY 12719, 1 bed, 1 bath

$180,000

1 bed1 bath777 sq ft

223 Yulan-barryville Rd, Barryville, NY 12719

Listing by KW Hudson Valley United

Property at 31 Cottage St, Monticello, NY 12701, 4 beds, 2 baths

$425,000

4 beds2 baths— sq ft

31 Cottage St, Monticello, NY 12701

Listing by Resort Realty

Property at 3565 State Route 55, Bethel, NY 12720, 3 beds, 2.5 baths

$873,000

3 beds2.5 baths2,108 sq ft

3565 State Route 55, Bethel, NY 12720

Listing by Malek Properties

Property at 6197 Route 42 RTE, Woodbourne, NY 12788, 3 beds, 2 baths

$375,000

3 beds2 baths— sq ft

6197 Route 42 RTE, Woodbourne, NY 12788

Property at 24 N Mohican Trl, Smallwood, NY 12778, 2 beds, 1 bath

$155,000

2 beds1 bath672 sq ft

24 N Mohican Trl, Smallwood, NY 12778

Listing by Malek Properties

Property at 5033 Main St, South Fallsburg, NY 12779, 3 beds, 1 bath

$420,000

3 beds1 bath1,020 sq ft

5033 Main St, South Fallsburg, NY 12779

Listing by Keller Williams Realty

Property at 171 Winterton Rd, Bloomingburg, NY 12721, 3 beds, 3.5 baths

$3,500,000

3 beds3.5 baths2,535 sq ft

171 Winterton Rd, Bloomingburg, NY 12721

Listing by Rieber Realty Inc

Property at 3019 Rt 17b, Cochecton, NY 12726, 4 beds, 2 baths

$435,000

4 beds2 baths2,581 sq ft

3019 Rt 17b, Cochecton, NY 12726

Listing by Resort Realty

Property at 118 Old Roosa Gap Rd, Bloomingburg, NY 12721, 4 beds, 2 baths

$579,000

4 beds2 baths2,533 sq ft

118 Old Roosa Gap Rd, Bloomingburg, NY 12721

Listing by Real Estate Circuit Inc

Property at 1132 Old Route 17, Ferndale, NY 12734, 3 beds, 1 bath

$399,900

3 beds1 bath850 sq ft

1132 Old Route 17, Ferndale, NY 12734

Listing by The Maxx Group LLC

Property at 18 York Ave, Highland Falls, NY 12701, 3 beds, 2 baths

$241,777

3 beds2 baths1,396 sq ft

18 York Ave, Highland Falls, NY 12701

Listing by Portillo Realty Corp

Property at 407 Yankee Lake Rd, Wurtsboro, NY 12790, 2 beds, 2 baths

$585,000

2 beds2 baths1,392 sq ft

407 Yankee Lake Rd, Wurtsboro, NY 12790

Listing by Stepping Stone Realty

Property at 2794 Cty Rte 55, Bethel, NY 12720, 9 beds, 4 baths

$775,000

9 beds4 baths2,968 sq ft

2794 Cty Rte 55, Bethel, NY 12720

Listing by KW Hudson Valley United

Property at 21 Hillside Ave, Woodbourne, NY 12788, 2 beds, 1 bath

$225,000

2 beds1 bath924 sq ft

21 Hillside Ave, Woodbourne, NY 12788

Listing by Keller Williams Hudson Valley

Property at 33 Pearl St, Livingston Manor, NY 12758, 4 beds, 1.5 baths

$300,000

4 beds1.5 baths5,200 sq ft

33 Pearl St, Livingston Manor, NY 12758

Listing by Exit Realty Connections

Property at 20 Maple Ave, Kauneonga Lake, NY 12749, 3 beds, 2 baths

$420,000

3 beds2 baths1,500 sq ft

20 Maple Ave, Kauneonga Lake, NY 12749

Property at 143 State Route 55, Barryville, NY 12719, 1 bath

$159,900

Studio1 bath1,312 sq ft

143 State Route 55, Barryville, NY 12719

Listing by Rural Connection Inc.

Property at 4 Tow Path Rd, Barryville, NY 12719, 2 beds, 1 bath

$850,000

2 beds1 bath2,948 sq ft

4 Tow Path Rd, Barryville, NY 12719

Listing by Caroline Akt Realty LLC

Property at 3 Perry Rd, Barryville, NY 12719, 2 beds, 1 bath

$409,000

2 beds1 bath828 sq ft

3 Perry Rd, Barryville, NY 12719

Listing by The Sunshine Group Real Estate

Property at 80 Beaver Brook Rd, Yulan, NY 12764, 2 beds, 1 bath

$405,000

2 beds1 bath1,300 sq ft

80 Beaver Brook Rd, Yulan, NY 12764

Listing by Eagle Valley Realty

Property at 48-50 Horseshoe Lake Rd, Kauneonga Lake, NY 12749, 6 beds, 5 baths

$599,000

6 beds5 baths3,400 sq ft

48-50 Horseshoe Lake Rd, Kauneonga Lake, NY 12749

Listing by Catskills Home Services

Property at 105 Cold Spring Rd, Liberty, NY 12754, 3 beds, 2 baths

$369,000

3 beds2 baths1,728 sq ft

105 Cold Spring Rd, Liberty, NY 12754

Listing by Joy Romano Realty

Property at 7 North Rd, Bloomingburg, NY 12721, 3 beds, 1.5 baths

$649,900

3 beds1.5 baths1,056 sq ft

7 North Rd, Bloomingburg, NY 12721

Listing by DiMatteo Realty LLC

Property at 40 Kelly Ave, Liberty, NY 12754, 4 beds, 1.5 baths

$399,000

4 beds1.5 baths1,523 sq ft

40 Kelly Ave, Liberty, NY 12754

Listing by KW Hudson Valley United

Property at 13 Third St, Woodridge, NY 12789, 2 beds, 2 baths

$375,000

2 beds2 baths1,346 sq ft

13 Third St, Woodridge, NY 12789

Listing by Resort Realty

Property at 6641 Narrowsburg Rd, Lake Huntington, NY 12752, 7 beds, 5 baths

$799,000

7 beds5 baths5,032 sq ft

6641 Narrowsburg Rd, Lake Huntington, NY 12752

Listing by Compass Greater NY, LLC

Property at 13 Sycamore Trl, Wurtsboro, NY 12790, 1 bed, 1 bath

$185,250

1 bed1 bath630 sq ft

13 Sycamore Trl, Wurtsboro, NY 12790

Listing by Century 21 Geba Realty

Property at 59 2nd Ave, Narrowsburg, NY 12764, 4 beds, 1.5 baths

$599,000

4 beds1.5 baths1,536 sq ft

59 2nd Ave, Narrowsburg, NY 12764

Listing by Land and Water Realty LLC

Property at 5 Steges Rd, Eldred, NY 12743, 3 beds, 1 bath

$249,000

3 beds1 bath1,008 sq ft

5 Steges Rd, Eldred, NY 12743

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 238 Trout Brook Rd, Roscoe, NY 12776, 3 beds, 2 baths

$429,000

3 beds2 baths1,980 sq ft

238 Trout Brook Rd, Roscoe, NY 12776

Listing by Land and Water Realty LLC

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Based on information submitted to the MLS GRID as of Sat Oct 24 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 316 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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