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:
Originally built by the developer of Simmons Drive as his personal home, this spacious Woodstock property offers a rare combination of Village convenience, mountain views, and a peaceful park-like setting. Situated on a quiet no-outlet street, it's just a five-minute stroll to Good Night restaurant, Tinker Street shopping, cafés, galleries, and everything the Village of Woodstock has to offer, all while enjoying a backyard shaded by mature trees and bordering Andy Lee Field, with no residential neighbors directly behind you. The home offers three bedrooms, though it lives comfortably as four, with plenty of additional flexible space. An enclosed porch and wood-burning stove add warmt

$625,000

3 beds1.5 baths1,814 sq ft

40 Simmons Dr, Woodstock, NY 12498

Wood-burning stove • Enclosed porch • Mountain views

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
Welcome to this spacious and character-filled home set on approximately 1.9 acres along the scenic Route 9W corridor in Saugerties. Offering over 1,800 square feet of living space, this property features 3 bedrooms, 1 full bath, and 1 half bath, providing a comfortable layout for everyday living. Inside, you'll find generously sized rooms, abundant natural light, and plenty of space to make your own. Outside, the expansive lot offers room to garden, entertain, or simply enjoy the peaceful surroundings. Conveniently located just minutes from the Village of Saugerties, the Hudson River, shopping, dining, and the NYS Thruway, this property provides easy access while maintaining a country feel.

$449,900

3 beds1.5 baths1,804 sq ft

4073 Route 9W, Saugerties, NY 12477

Expansive lot • Easy access • 1.9 acres

Listing by Hudson Valley Home Connection

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
Nestled in the charming Village of Saugerties, this 3-bedroom, 1-bath home presents an exciting opportunity for those with a vision. Whether you're an investor, contractor, or buyer looking to restore a home to its former glory, this property offers incredible potential in one of the Hudson Valley's most desirable communities. Enjoy the convenience of being just moments from Saugerties' vibrant Main Street, where you'll find local boutiques, restaurants, cafes, and year-round events. Outdoor enthusiasts will appreciate nearby access to the Hudson River, hiking trails, and popular destinations including the Saugerties Lighthouse and HITS. With easy access to Kingston, Woodstock, and the NYS

$215,000

3 beds1 bath1,260 sq ft

141 W Bridge St, Saugerties, NY 12477

Built 1880 • Listed 87 days

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
OPEN HOUSE SUNDAY 9/27/26 12 to 2pm This Spacious 3-bedroom, 2 full bath Brick Ranch set on a nicely landscaped 1 acre lot has a peaceful country feel yet is minutes to everything. A cozy living room is adjacent to an updated eat in kitchen with wood cabinets and quartz countertops. The island with a built-in sink and dishwasher gives you extra workspace and storage as well. The laundry room right off the kitchen is so convenient. A formal dining room opens up to a large family room with a floor to ceiling Stone Fireplace. A picture window looking out to the front gives this room great natural light. A French door leading from the kitchen to a gorgeous great room with a vaulted ceiling an

$469,900

3 beds2 baths2,126 sq ft

109 Main St, Lake Katrine, NY 12449

Large windows • Vaulted ceiling • Landscaped lot

ABOUT THIS HOME
Vintage Home for sale in Ulster County, NY:
This charming cottage in Olivebridge NY proves that great things really do come in small packages. Thoughtfully designed for easy living, it's the kind of home that lets you spend less time maintaining and more time enjoying everything the Hudson Valley has to offer. Inside, warm and inviting spaces feel instantly welcoming, while an airy loft provides the perfect spot for a home office, creative studio, or cozy reading nook. Whether you're working remotely or simply looking for a quiet place to unwind, this home offers just the right amount of space and versatility. Outside, the beautifully established gardens create a private retreat that bursts with seasonal color, offering plenty of roo

$399,000

1 bed1 bath1,000 sq ft

1906 County Road 3, Olivebridge, NY 12461

Low property taxes • Private retreat • Easy to manage lot

Property at 3 Dymond Rd, Kerhonkson, NY 12446, 1 bed, 1 bath

$225,000

1 bed1 bath472 sq ft

3 Dymond Rd, Kerhonkson, NY 12446

Property at 133 Fair St, Kingston, NY 12401, 6 beds, 2 baths

$775,000

6 beds2 baths2,536 sq ft

133 Fair St, Kingston, NY 12401

Listing by Corcoran Country Living

Property at 142 Railroad Ave, Kingston, NY 12401, 2 beds, 1.5 baths

$329,500

2 beds1.5 baths1,010 sq ft

142 Railroad Ave, Kingston, NY 12401

Listing by Serhant LLC

Property at 123 Tinker St, Woodstock, NY 12498, 2 beds, 2 baths

$449,000

2 beds2 baths1,284 sq ft

123 Tinker St, Woodstock, NY 12498

Property at 62 Appletree Dr, Saugerties, NY 12477, 3 beds, 1 bath

$379,900

3 beds1 bath1,414 sq ft

62 Appletree Dr, Saugerties, NY 12477

Property at 110 Greenkill Ave, Kingston, NY 12401, 3 beds, 1.5 baths

$449,000

3 beds1.5 baths1,386 sq ft

110 Greenkill Ave, Kingston, NY 12401

Listing by Howard Hanna Rand Realty

Property at 696 Sawkill Rd, Kingston, NY 12401, 5 beds, 3 baths

$594,000

5 beds3 baths— sq ft

696 Sawkill Rd, Kingston, NY 12401

Listing by Win Morrison Realty

Property at 322 Albany Ave, Kingston, NY 12401, 6 beds, 5.5 baths

$1,395,000

6 beds5.5 baths3,972 sq ft

322 Albany Ave, Kingston, NY 12401

Listing by The Kinderhook Group, Inc.

Property at 101-113 Glenerie Blvd, Saugerties, NY 12477, 12 beds, 5 baths

$1,349,999

12 beds5 baths10,000 sq ft

101-113 Glenerie Blvd, Saugerties, NY 12477

Listing by eXp Realty

Property at 4230-4257 Atwood Rd, Stone Ridge, NY 12484, 5 beds, 3 baths

$958,000

5 beds3 baths3,914 sq ft

4230-4257 Atwood Rd, Stone Ridge, NY 12484

Listing by BHHS Nutshell Realty

Property at 140 Station Rd, Kingston, NY 12401, 4 beds, 3 baths

$1,200,000

4 beds3 baths3,335 sq ft

140 Station Rd, Kingston, NY 12401

Listing by KW Hudson Valley United

Property at 342 State Route 375, West Hurley, NY 12491, 3 beds, 2 baths

$620,000

3 beds2 baths1,323 sq ft

342 State Route 375, West Hurley, NY 12491

Property at 27 Old Mill Rd, Esopus, NY 12429, 4 beds, 2 baths

$449,999

4 beds2 baths1,545 sq ft

27 Old Mill Rd, Esopus, NY 12429

Listing by KW Hudson Valley United

Property at 393 Ny-375, West Hurley, NY 12491, 4 beds

$400,000

4 beds— baths2,532 sq ft

393 Ny-375, West Hurley, NY 12491

Property at 280 Cottekill Rd, Cottekill, NY 12419, 2 beds, 2 baths

$394,900

2 beds2 baths1,320 sq ft

280 Cottekill Rd, Cottekill, NY 12419

Property at 28-30 Wallkill Ave, Tillson, NY 12486, 3 beds, 2 baths

$475,000

3 beds2 baths1,430 sq ft

28-30 Wallkill Ave, Tillson, NY 12486

Property at 452 Vineyard Ave, Highland, NY 12528, 3 beds, 3 baths

$524,900

3 beds3 baths2,050 sq ft

452 Vineyard Ave, Highland, NY 12528

Listing by Greene Realty Group

Property at 39 Marys Ave, Kingston, NY 12401, 1 bed, 1 bath

$299,900

1 bed1 bath650 sq ft

39 Marys Ave, Kingston, NY 12401

Property at 55 Partition St, Saugerties, NY 12477, 4 beds, 2 baths

$399,900

4 beds2 baths— sq ft

55 Partition St, Saugerties, NY 12477

Listing by Rand Commercial

Property at 1389 Route 212, Saugerties, NY 12477, 4 beds, 5 baths

$6,900,000

4 beds5 baths6,923 sq ft

1389 Route 212, Saugerties, NY 12477

Listing by Coldwell Banker Village Green

Property at 43 Augustine Rd, Saugerties, NY 12477, 3 beds, 4.5 baths

$1,499,000

3 beds4.5 baths5,999 sq ft

43 Augustine Rd, Saugerties, NY 12477

Listing by BHHS Hudson Valley Properties

Property at 67 Katzman Rd, Ellenville, NY 12428, 1 bed, 1 bath

$199,000

1 bed1 bath406 sq ft

67 Katzman Rd, Ellenville, NY 12428

Listing by Compass Greater NY, LLC

Property at 4868 Ny-212, Willow, NY 12495, 4 beds, 3 baths

$795,000

4 beds3 baths2,044 sq ft

4868 Ny-212, Willow, NY 12495

Property at 212 Market St, Saugerties, NY 12477, 3 beds, 2 baths

$649,000

3 beds2 baths1,616 sq ft

212 Market St, Saugerties, NY 12477

Property at 156 Hurley Ave, Kingston, NY 12401, 4 beds, 1.5 baths

$499,000

4 beds1.5 baths1,980 sq ft

156 Hurley Ave, Kingston, NY 12401

Property at 850-872 Oliverea Rd, Big Indian, NY 12410, 26 beds, 16 baths

$975,000

26 beds16 baths6,300 sq ft

850-872 Oliverea Rd, Big Indian, NY 12410

Property at 281 Cold Brook Rd, Bearsville, NY 12409, 1 bath

$399,000

Studio1 bath1,000 sq ft

281 Cold Brook Rd, Bearsville, NY 12409

Listing by Century 21 Alliance Rlty Group

Property at 845 Lucas Avenue Ext, Hurley, NY 12443, 2 beds, 2 baths

$399,900

2 beds2 baths1,680 sq ft

845 Lucas Avenue Ext, Hurley, NY 12443

Listing by Living Structures

Property at 11-13 Wiltwyck Ave, Kingston, NY 12401, 3 beds, 3 baths

$495,000

3 beds3 baths— sq ft

11-13 Wiltwyck Ave, Kingston, NY 12401

Listing by Compass Greater NY, LLC

Property at 25-29 Mink Hollow Rd, Lake Hill, NY 12448, 4 beds, 3 baths

$858,000

4 beds3 baths2,410 sq ft

25-29 Mink Hollow Rd, Lake Hill, NY 12448

Listing by Realty One Group Key

Property at 140 First St, Esopus, NY 12429, 5 beds

$3,400,000

5 beds— baths3,283 sq ft

140 First St, Esopus, NY 12429

Property at 29 Saugerties Manor Rd, Saugerties, NY 12477, 2 beds, 1.5 baths

$334,000

2 beds1.5 baths1,300 sq ft

29 Saugerties Manor Rd, Saugerties, NY 12477

Listing by Howard Hanna Rand Realty

Property at 175-177 Tinker St, Woodstock, NY 12498, 5 beds, 4.5 baths

$2,400,000

5 beds4.5 baths2,978 sq ft

175-177 Tinker St, Woodstock, NY 12498

Property at 215 Maple Ave, Kerhonkson, NY 12446, 5 beds, 2 baths

$314,900

5 beds2 baths1,920 sq ft

215 Maple Ave, Kerhonkson, NY 12446

Listing by HomeSmart Homes & Estates

Property at 39 N Chestnut St, New Paltz, NY 12561, 9 beds, 4 baths

$999,999

9 beds4 baths3,273 sq ft

39 N Chestnut St, New Paltz, NY 12561

Listing by eXp Realty

Property at 5813 Route 44/55, Kerhonkson, NY 12446, 3 beds, 1 bath

$359,000

3 beds1 bath1,250 sq ft

5813 Route 44/55, Kerhonkson, NY 12446

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Based on information submitted to the MLS GRID as of Mon Oct 26 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 401 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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