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

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ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
Few properties embody the history, architecture, and landscape of Woodstock as completely as the Lewis House. On the side of Overlook Mountain, at the very top of Lewis Hollow Road, and surrounded by thousands of acres of protected forest on Overlook Mountain, this remarkable property has evolved over more than 220 years while retaining the quiet character that makes it truly timeless. The original quarry house, dating to 1805, forms the heart of the current home, with what are now the living room and library serving as its earliest rooms and bedrooms above. Successive stewards thoughtfully expanded the residence rather than reinventing it, allowing each generation to contribute its own cha

$2,300,000

3 beds3 baths2,515 sq ft

190 Lewis Hollow Rd, Woodstock, NY 12498

In-ground pool • Ancient stone walls • Complete privacy

Listing by Compass Greater NY, LLC

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
Set just off Malden Turnpike, this versatile 6-bedroom, 5.5-bath multi-family ranch sits on 17 acres (15 acres are from adjacent lot) with beautiful mountain views and offers a rare combination of strong existing rental income and exceptional development or expansion potential. The property includes four well-proportioned units, each with its own meter and designated parking: Studio with full bath — long-term tenant in place 2BR / 1.5BA unit — tenant in place 2BR / 2BA duplex — tenant in place 1BR / 1BA landlord suite — includes a generous living room (usable as a second bedroom or lounge) with a concrete patio walkout, plus a nicely sized kitchen/dining area. With

$695,000

6 beds6 baths3,200 sq ft

266 Malden Tpke, Saugerties, NY 12477

20 year leach field • Designated parking • Mountain views

Listing by Redfin Real Estate

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
Step into a piece of Hudson Valley history. This remarkable estate spans 6.7 private acres, home to a beautifully preserved historic residence. Pass through the gated entrance and follow a private, stone wall-lined drive as it winds toward this testament to early American craftsmanship. Built in 1775 by Jonas Freer Jr. - grandson of Hugo Freer, one of the twelve original New Paltz patentees - this stone house remained in the same family through the 1880s, passing from Jonas to his son Elias, and then to his grandson Stephen. The 1,828-square-foot residence displays authentic period living at its finest: gorgeous wide plank floors that have weathered generations, exposed wood beams overhead,

$999,000

4 beds2.5 baths1,828 sq ft

100 Shivertown Rd, New Paltz, NY 12561

Historic residence • Serene pond • Stone patio

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
Bring your vision to this spacious 3-bedroom, 2½-bath home offering approximately 1,915 square feet in desirable Midtown Kingston. With generous living space, classic hardwood floors, and an abundance of storage, this property offers a solid foundation for those looking to add their personal touch. The spacious family room provides plenty of room to gather, while the three-season back porch and rear deck create additional spaces to relax and enjoy the outdoors. The fully vinyl-fenced backyard offers privacy and versatility for entertaining, gardening, pets, or play. Additional features include two garages, an on-demand tankless hot water heater, a walk-up attic, and a full basement,

$349,900

3 beds2.5 baths1,915 sq ft

94 Oneil St, Kingston, NY 12401

Full basement • Rear deck • Walk-up attic

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
RARE HUDSON VALLEY COMPOUND OPPORTUNITY AT BINNEWATER LAKES! Discover the ultimate vision with this unique two-parcel package just minutes from Kingston and the iconic Rosendale Trestle, with Fourth Lake a 3-minute stroll away for kayaking, paddle boarding, and swimming. The main residence at 18 Lake Hill Rd was totally overhauled in 2023 to offer turn-key, sunlit luxury framed by expansive custom Marvin windows, main-level hardwoods, and lower-level concrete floors. Modern mechanical upgrades include a high-efficiency heat pump system, spray foam insulation, UV water filtration, and upgraded electrical and plumbing. An open-concept main level flows out to multi-level decking for al fresco

$729,900

3 beds3 baths1,650 sq ft

14 & 18 Lake Hill Rd, Kingston, NY 12401

Private deck • 1930s bungalow • 3 minute stroll

Listing by Compass Greater NY, LLC

Property at 8 S Ohioville Rd, New Paltz, NY 12561, 2 beds, 1 bath

$415,000

2 beds1 bath1,304 sq ft

8 S Ohioville Rd, New Paltz, NY 12561

Listing by Edwards Properties

Property at 388-390 Wittenberg Rd, Bearsville, NY 12409, 5 beds, 4 baths

$1,195,000

5 beds4 baths3,475 sq ft

388-390 Wittenberg Rd, Bearsville, NY 12409

Listing by Coldwell Banker Village Green

Property at 403 County Road 2, Accord, NY 12404, 3 beds, 2 baths

$979,000

3 beds2 baths1,700 sq ft

403 County Road 2, Accord, NY 12404

Property at 125 Vineyard Ave, Highland, NY 12528, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,458 sq ft

125 Vineyard Ave, Highland, NY 12528

Listing by BHHS Hudson Valley Properties

Property at 403 County Route 2, Accord, NY 12404, 3 beds, 2 baths

$979,000

3 beds2 baths1,700 sq ft

403 County Route 2, Accord, NY 12404

Listing by Coldwell Banker Village Green

Property at 145 Tinker St, Woodstock, NY 12498, 3 beds, 2 baths

$749,000

3 beds2 baths1,553 sq ft

145 Tinker St, Woodstock, NY 12498

Listing by Halter Associates Realty Inc

Property at 26 Reservoir Rd, Highland, NY 12528, 3 beds, 2 baths

$439,000

3 beds2 baths1,382 sq ft

26 Reservoir Rd, Highland, NY 12528

Listing by Edwards Properties

Property at 21-23 Library Ln, Woodstock, NY 12498, 7 beds, 4 baths

$3,950,000

7 beds4 baths3,948 sq ft

21-23 Library Ln, Woodstock, NY 12498

Property at 120 Sherman Rd, Kingston, NY 12401, 3 beds, 1 bath

$475,000

3 beds1 bath1,351 sq ft

120 Sherman Rd, Kingston, NY 12401

Listing by Howard Hanna Rand Realty

Property at 5 Dewitt St, Ellenville, NY 12428, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths1,904 sq ft

5 Dewitt St, Ellenville, NY 12428

Listing by BHHS Nutshell Realty

Property at 583 Swartekill Rd, New Paltz, NY 12561, 3 beds, 1.5 baths

$750,000

3 beds1.5 baths2,588 sq ft

583 Swartekill Rd, New Paltz, NY 12561

Listing by Howard Hanna Rand Realty

Property at 5 Wilbur Ave, Kingston, NY 12401, 4 beds, 2 baths

$299,900

4 beds2 baths2,000 sq ft

5 Wilbur Ave, Kingston, NY 12401

Listing by Berardi Realty

Property at 153 Glenerie Blvd, Saugerties, NY 12477, 2 beds, 1 bath

$164,999

2 beds1 bath1,440 sq ft

153 Glenerie Blvd, Saugerties, NY 12477

Listing by Keller Williams Realty

Property at 234 Sawmill Rd, Lake Katrine, NY 12449, 3 beds, 3 baths

$618,000

3 beds3 baths2,900 sq ft

234 Sawmill Rd, Lake Katrine, NY 12449

Listing by Howard Hanna Rand Realty

Property at 16 Cottage St, Wallkill, NY 12589, 3 beds, 1 bath

$269,000

3 beds1 bath936 sq ft

16 Cottage St, Wallkill, NY 12589

Listing by Rita Levine Real Estate

Property at 1693 Route 32, Saugerties, NY 12477, 3 beds, 2 baths

$695,000

3 beds2 baths2,754 sq ft

1693 Route 32, Saugerties, NY 12477

Listing by Compass Greater NY, LLC

Property at 2220 Bruynswick Rd, Wallkill, NY 12589, 3 beds, 1 bath

$337,000

3 beds1 bath1,269 sq ft

2220 Bruynswick Rd, Wallkill, NY 12589

Listing by Century 21 Geba Realty

Property at 47 Baker Rd, Bearsville, NY 12409, 1 bed, 1 bath

$365,000

1 bed1 bath660 sq ft

47 Baker Rd, Bearsville, NY 12409

Property at 31 Stuyvesant St, Kingston, NY 12401, 4 beds, 2.5 baths

$825,000

4 beds2.5 baths1,658 sq ft

31 Stuyvesant St, Kingston, NY 12401

Listing by The Machree Group, LLC

Property at 112 Glen St, Kingston, NY 12401, 2 beds, 2 baths

$399,900

2 beds2 baths1,665 sq ft

112 Glen St, Kingston, NY 12401

Listing by Corcoran Country Living

Property at 18 Lake Hill Rd, Kingston, NY 12401, 2 beds, 2 baths

$569,900

2 beds2 baths897 sq ft

18 Lake Hill Rd, Kingston, NY 12401

Listing by Compass Greater NY, LLC

Property at 98 Dellay Ave, Kingston, NY 12401, 3 beds, 1 bath

$290,000

3 beds1 bath1,331 sq ft

98 Dellay Ave, Kingston, NY 12401

Listing by eXp Realty

Property at 2323 Glasco Tpke, Woodstock, NY 12498, 3 beds, 2 baths

$749,000

3 beds2 baths1,562 sq ft

2323 Glasco Tpke, Woodstock, NY 12498

Property at 2673 Glasco Tpke, Woodstock, NY 12498, 2 beds, 2 baths

$2,600,000

2 beds2 baths1,511 sq ft

2673 Glasco Tpke, Woodstock, NY 12498

Property at 371 Crescent Ave, Plattekill, NY 12528, 3 beds, 2 baths

$440,000

3 beds2 baths1,352 sq ft

371 Crescent Ave, Plattekill, NY 12528

Listing by eXp Realty

Property at 203 Samsonville Rd, Kerhonkson, NY 12446, 3 beds, 2.5 baths

$1,695,000

3 beds2.5 baths3,504 sq ft

203 Samsonville Rd, Kerhonkson, NY 12446

Listing by BHHS Nutshell Realty

Property at 34 Tillson Rd, Rosendale, NY 12486, 3 beds, 1.5 baths

$445,000

3 beds1.5 baths1,368 sq ft

34 Tillson Rd, Rosendale, NY 12486

Listing by Coldwell Banker Village Green

Property at 126 Glenerie Blvd, Saugerties, NY 12477, 3 beds, 2 baths

$849,000

3 beds2 baths1,518 sq ft

126 Glenerie Blvd, Saugerties, NY 12477

Listing by eXp Realty

Property at 16 Esopus Ave, Kingston, NY 12401, 2 beds, 1 bath

$259,000

2 beds1 bath882 sq ft

16 Esopus Ave, Kingston, NY 12401

Listing by Compass Greater NY, LLC

Property at 15 Esopus Ave, Kingston, NY 12401, 4 beds, 2 baths

$495,000

4 beds2 baths— sq ft

15 Esopus Ave, Kingston, NY 12401

Listing by Compass Greater NY, LLC

Property at 18 Rock City Road Rd Unit A,B,C, Woodstock, NY 12498, 5 beds, 5 baths

$1,095,000

5 beds5 baths2,708 sq ft

18 Rock City Road Rd Unit A,B,C, Woodstock, NY 12498

Property at 22 Bridge St, Wallkill, NY 12589, 5 beds, 3 baths

$537,000

5 beds3 baths2,550 sq ft

22 Bridge St, Wallkill, NY 12589

Listing by BHHS Nutshell Realty

Property at 64 Manor Pl, Kingston, NY 12401, 0.5 baths

$375,000

— beds0.5 baths2,898 sq ft

64 Manor Pl, Kingston, NY 12401

Property at 736 Sundown Rd, Sundown, NY 12740, 3 beds, 1 bath

$349,000

3 beds1 bath1,181 sq ft

736 Sundown Rd, Sundown, NY 12740

Listing by BHHS Nutshell Realty

Property at 166 Ulster Landing Rd, Kingston, NY 12401, 5 beds, 3 baths

$3,750,000

5 beds3 baths3,774 sq ft

166 Ulster Landing Rd, Kingston, NY 12401

Listing by Staley Real Estate, LLC

Property at 103 E Chester St, Kingston, NY 12401, 3 beds, 3 baths

$455,000

3 beds3 baths1,943 sq ft

103 E Chester St, Kingston, NY 12401

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Based on information submitted to the MLS GRID as of Thu Oct 29 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 Ulster County

There are currently 402 vintage homes for sale in Ulster County at a median listing price of $569K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Ulster County stay on the market for 65 days and receive 3 offers. This map is refreshed with the newest listings in Ulster County every 15 minutes.

In the past month, 170 homes have been sold in Ulster County. In addition to houses in Ulster County, there were also 36 condos, 12 townhouses, and 82 multi-family units for sale in Ulster County last month. Find your dream home in Ulster 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 Ulster County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Ulster County. If you're looking to sell your home in the Ulster County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Ulster 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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