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

303 homes

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ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Move-In Ready & Fully Renovated! Welcome to worry-free living in this beautifully renovated home, featuring a stunning brand-new kitchen with modern appliances, fresh flooring throughout, and fully updated bathrooms. Additional upgrades—including a new roof and new windows—bring enhanced comfort and fill every room with natural light. The main level offers a bright, open layout with the kitchen flowing into a welcoming dining area and then into a spacious living room—perfect for everyday living and entertaining. Step out onto the deck just off the kitchen and enjoy the fenced-in backyard, ideal for pets, play, gardening, or simply relaxing outdoors. Upstairs, you&rs

$349,000

2 beds1.5 baths1,045 sq ft

34 Wilmar Ter, Poughkeepsie, NY 12601

Finished basement • Updated bathrooms • Brand-new kitchen

Listing by K. Fortuna Realty, Inc.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Great investment opportunity. Fantastic location surrounded by well maintained homes. Three bedrooms, one full bathroom, hardwood floors, brick fireplace, large living room and dining room, laundry room with plumbing for half bath. Mature landscape, front porch, patio off kitchen. Full unfinished basement. One car garage under. Close to Marist College. Metro North. Shopping and schools.

$280,000

3 beds1 bath1,513 sq ft

88 Buckingham Ave, Poughkeepsie, NY 12601

Brick fireplace • Laundry room • Large living room

Listing by Houlihan Lawrence Inc.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Adorable Craftsman Cottage in a Quiet, Tree-Lined Neighborhood Charming and move-in ready, this delightful 2-bedroom, 1-bath Craftsman-style cottage offers comfort, character, and thoughtful updates throughout. The home features a welcoming screened porch and a three-season sun porch, perfect for relaxing or entertaining. Inside, the open-concept kitchen, dining, and living area centers around a cozy wood-burning fireplace, creating a warm and inviting gathering space. Beautiful custom built-ins and solid wood interior panel doors showcase classic craftsmanship, while the updated bathroom includes a custom vanity. The kitchen boasts stainless steel appliances and a 3-year-old stove. Practic

$329,000

2 beds1 bath1,017 sq ft

39 W Pine Rd, Staatsburg, NY 12580

0.33 acre lot • 4 parking spots • Built 1938

Listing by K. Fortuna Realty, Inc.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
This 4 bedroom 2 full bathroom classic Cape Cod is located in historic Hyde Park, NY, a charming Hudson Valley river town steeped in American history. The town also features the FDR Presidential Library and Home, the Vanderbilt Mansion, and the Mills Estate which are open to the public on the banks of the Hudson River. Hyde Park boasts scenic views, wooded trails along the rivers edge, and a peaceful, suburban atmosphere. It’s home to the prestigious Culinary Institute of America, drawing food lovers to its world-class restaurants. With a blend of natural beauty, cultural richness, and small-town warmth, Hyde Park is a destination for history buffs, outdoor enthusiasts, and culinary e

$379,900

4 beds2 baths1,539 sq ft

1 Abbie Ln, Hyde Park, NY 12538

Vanderbilt mansion • Historic hyde park • Scenic views

Listing by Century 21 Hudson Valley Rlty.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to the Historic Town of Pine Plains! This completely renovated three bedroom home on a quiet country road will delight and intrigue you. The home dates back to the early 1900's and some of the original characteristics have been left in tact. This is most assuredly Old World Charm meets Modern Convenience. One bedroom on the first floor attached to the Sunroom, will work for a great Flex space, while the Primary bedroom upstairs with the large walk in closet is situated nicely near the additional upstairs bedroom. The hard wood floors, rustic ceiling beams and details of the handrail and doorknobs meld beautifully with the updated kitchen and bath finishes this builder has chosen. Th

$490,000

3 beds2 baths1,298 sq ft

30 Myrtle Ave, Pine Plains, NY 12567

Hard wood floors • Rustic ceiling beams • Flex space

Listing by Houlihan Lawrence Inc.

Property at 85 W Hook Rd, Hopewell Junction, NY 12533, 2 beds, 1 bath

$349,999

2 beds1 bath1,412 sq ft

85 W Hook Rd, Hopewell Junction, NY 12533

Listing by K. Fortuna Realty, Inc.

Property at 1258 North Ave, Beacon, NY 12508, 6 beds, 3 baths

$649,900

6 beds3 baths2,501 sq ft

1258 North Ave, Beacon, NY 12508

Listing by Berkshire Hathaway HS NY Prop

Property at 121 Butts Hollow Rd, Millbrook, NY 12545, 9 beds, 9.5 baths

$11,995,000

9 beds9.5 baths13,737 sq ft

121 Butts Hollow Rd, Millbrook, NY 12545

Property at 37 S Bridge St, Poughkeepsie, NY 12601, 3 beds, 3 baths

$595,000

3 beds3 baths2,880 sq ft

37 S Bridge St, Poughkeepsie, NY 12601

Listing by KW MidHudson

Property at 51 Ward Pl, Fishkill, NY 12524, 3 beds, 1 bath

$509,000

3 beds1 bath1,632 sq ft

51 Ward Pl, Fishkill, NY 12524

Listing by eXp Realty

Property at 36 Spruce St, Poughkeepsie, NY 12601, 2 beds, 1 bath

$275,000

2 beds1 bath1,232 sq ft

36 Spruce St, Poughkeepsie, NY 12601

Listing by KW MidHudson

Property at 60 Hibiscus Cir #60, Hopewell Junction, NY 12533, 1 bed, 1 bath

$37,000

1 bed1 bath462 sq ft

60 Hibiscus Cir #60, Hopewell Junction, NY 12533

Listing by RE/MAX Town & Country

Property at 352-354 Ruskey Ln, Hyde Park, NY 12538, 4 beds, 2 baths

$875,000

4 beds2 baths2,160 sq ft

352-354 Ruskey Ln, Hyde Park, NY 12538

Listing by Houlihan Lawrence Inc.

Property at 29 Lewis Ave, Poughkeepsie, NY 12603, 4 beds, 1.5 baths

$354,999

4 beds1.5 baths1,251 sq ft

29 Lewis Ave, Poughkeepsie, NY 12603

Listing by VYLLA Home

Property at 85 Overocker Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$375,000

3 beds1 bath1,602 sq ft

85 Overocker Rd, Poughkeepsie, NY 12603

Listing by eXp Realty

Property at 32 Old Glenham Rd, Beacon, NY 12508, 5 beds, 3 baths

$935,000

5 beds3 baths5,002 sq ft

32 Old Glenham Rd, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 57 Kingwood Dr, Poughkeepsie, NY 12601, 5 beds, 2.5 baths

$885,000

5 beds2.5 baths3,707 sq ft

57 Kingwood Dr, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 252 Route 199, Red Hook, NY 12571, 4 beds, 1.5 baths

$449,000

4 beds1.5 baths1,854 sq ft

252 Route 199, Red Hook, NY 12571

Listing by Coldwell Banker Village Green

Property at 4865 South St, Amenia, NY 12501, 2 beds, 1 bath

$299,000

2 beds1 bath816 sq ft

4865 South St, Amenia, NY 12501

Listing by Havens Real Estate

Property at 33 Virginia Ave, Poughkeepsie, NY 12601, 4 beds, 4 baths

$620,000

4 beds4 baths5,055 sq ft

33 Virginia Ave, Poughkeepsie, NY 12601

Listing by Joseph Baratta Company Realty

Property at 671 Noxon Rd, Poughkeepsie, NY 12603, 4 beds, 4.5 baths

$649,000

4 beds4.5 baths3,030 sq ft

671 Noxon Rd, Poughkeepsie, NY 12603

Listing by Hudson Modern Co

Property at 102 Cedar Ave, Poughkeepsie, NY 12603, 4 beds, 2.5 baths

$575,000

4 beds2.5 baths2,400 sq ft

102 Cedar Ave, Poughkeepsie, NY 12603

Listing by K. Fortuna Realty, Inc.

Property at 145 Drake Rd, Pleasant Valley, NY 12569, 2 beds, 1.5 baths

$650,000

2 beds1.5 baths1,368 sq ft

145 Drake Rd, Pleasant Valley, NY 12569

Listing by George T Whalen Real Estate

Property at 37 Shady Creek Rd, Pleasant Valley, NY 12569, 3 beds, 1 bath

$275,000

3 beds1 bath904 sq ft

37 Shady Creek Rd, Pleasant Valley, NY 12569

Listing by Corcoran Country Living

Property at 108 Winnikee Ave, Poughkeepsie, NY 12601, 9 beds, 3 baths

$600,000

9 beds3 baths4,188 sq ft

108 Winnikee Ave, Poughkeepsie, NY 12601

Listing by Century 21 Hudson Valley Rlty.

Property at 29 Red Barn Rd, Hyde Park, NY 12538, 3 beds, 1 bath

$290,000

3 beds1 bath1,411 sq ft

29 Red Barn Rd, Hyde Park, NY 12538

Listing by K. Fortuna Realty, Inc.

Property at 1 Dean Ave, Wappingers Falls, NY 12590, 3 beds, 1 bath

$399,900

3 beds1 bath1,387 sq ft

1 Dean Ave, Wappingers Falls, NY 12590

Listing by K. Fortuna Realty, Inc.

Property at 54 Midway Ave, Amenia, NY 12501, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,344 sq ft

54 Midway Ave, Amenia, NY 12501

Listing by eXp Realty

Property at 39 Alda Dr, Poughkeepsie, NY 12603, 3 beds, 2 baths

$385,000

3 beds2 baths2,084 sq ft

39 Alda Dr, Poughkeepsie, NY 12603

Listing by Houlihan Lawrence Inc.

Property at 2123 New Hackensack Rd, Poughkeepsie, NY 12603, 3 beds, 1.5 baths

$484,000

3 beds1.5 baths1,824 sq ft

2123 New Hackensack Rd, Poughkeepsie, NY 12603

Listing by Realty Center Hudson Valley

Property at 12 Russell Rd, Wappingers Falls, NY 12590, 3 beds, 1 bath

$499,900

3 beds1 bath1,366 sq ft

12 Russell Rd, Wappingers Falls, NY 12590

Listing by Coldwell Banker Realty

Property at 228 Dog Tail Corners Rd, Wingdale, NY 12594, 2 beds, 1 bath

$350,000

2 beds1 bath1,296 sq ft

228 Dog Tail Corners Rd, Wingdale, NY 12594

Listing by McGrath Realty Inc

Property at 123 Creamery Rd, Hopewell Junction, NY 12533, 3 beds, 2 baths

$550,000

3 beds2 baths1,988 sq ft

123 Creamery Rd, Hopewell Junction, NY 12533

Listing by BHHS River Towns Real Estate

Property at 34 Smith St, Poughkeepsie, NY 12601, 3 beds, 2 baths

$346,000

3 beds2 baths2,200 sq ft

34 Smith St, Poughkeepsie, NY 12601

Listing by eXp Realty

Property at 19 Grove St, Beacon, NY 12508, 4 beds, 2 baths

$639,000

4 beds2 baths1,894 sq ft

19 Grove St, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 30 Old Post Rd N, Red Hook, NY 12571, 5 beds, 2.5 baths

$874,000

5 beds2.5 baths3,424 sq ft

30 Old Post Rd N, Red Hook, NY 12571

Listing by RE/MAX Town & Country

Property at 379 S White Rock Rd, Holmes, NY 12531, 3 beds, 2 baths

$720,000

3 beds2 baths1,822 sq ft

379 S White Rock Rd, Holmes, NY 12531

Listing by Coldwell Banker Realty

Property at 212 Church St, Poughkeepsie, NY 12601, 6 beds, 3 baths

$299,900

6 beds3 baths1,672 sq ft

212 Church St, Poughkeepsie, NY 12601

Listing by Century 21 Hudson Valley Rlty.

Property at 461 White Schoolhouse Rd, Rhinebeck, NY 12572, 3 beds, 1 bath

$725,000

3 beds1 bath1,104 sq ft

461 White Schoolhouse Rd, Rhinebeck, NY 12572

Listing by BHHS Hudson Valley Properties

Property at 6099 Route 82, Stanfordville, NY 12581, 3 beds, 2 baths

$299,900

3 beds2 baths3,841 sq ft

6099 Route 82, Stanfordville, NY 12581

Listing by Mondello Upstate Properties

Property at 214 Church St, Poughkeepsie, NY 12601, 4 beds, 3 baths

$399,900

4 beds3 baths2,000 sq ft

214 Church St, Poughkeepsie, NY 12601

Listing by Century 21 Hudson Valley Rlty.

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Based on information submitted to the MLS GRID as of Sun Nov 30 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 Dutchess County

There are currently 303 vintage homes for sale in Dutchess County at a median listing price of $547K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Dutchess County stay on the market for 55 days and receive 4 offers. This map is refreshed with the newest listings in Dutchess County every 15 minutes.

In the past month, 261 homes have been sold in Dutchess County. In addition to houses in Dutchess County, there were also 98 condos, 2 townhouses, and 71 multi-family units for sale in Dutchess County last month. Find your dream home in Dutchess 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 Dutchess County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Dutchess County. If you're looking to sell your home in the Dutchess County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Dutchess 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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