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:
Charming 1800s Stone Colonial – Two-Family Residence in Poughkeepsie, Dutchess County. Discover a rare opportunity to own a beautifully maintained Stone Colonial built in the 1800s, offering timeless character paired with modern conveniences. This versatile two-family residence sits on a lovely yard and includes a detached 3-car garage, perfect for added storage or potential hobby space. Each apartment enjoys its own private outdoor area, ideal for relaxing or entertaining. First Floor Apartment: This spacious unit features 2 bedrooms and 1 bathroom, a large living room, and an eat-in kitchen. A new washer/dryer adds everyday convenience. Currently occupied with tenants under lease un

$429,000

3 beds2 baths2,322 sq ft

23 Musselman Dr, Poughkeepsie, NY 12601

0.7 acre lot • 3 garage spots • Built 1870

Listing by Exit Realty Connections

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Down this tree-lined street you will find this charming Southside Poughkeepsie storybook Cape Cod. Upon arrival you are greeted by the unique partial stone front. Open the front door into the living room featuring hardwood floor and a wonderful wood burning fireplace that is perfect for cozying up during a cold winter night. Cute as a button in style while offering classic traditional touches including multiple inviting archways and original hardwood floor throughout the first floor. The living room flows seamlessly in the dining room which is found adjacent to the kitchen highlighted by the newer stainless appliances and loads of cabinetry. The enclosed porch is perfect for relaxing and ca

$367,900

3 beds1 bath1,260 sq ft

46 Mitchell Ave, Poughkeepsie, NY 12603

7,405 sq ft lot • 2 garage spots • Built 1954

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Now is the time to own a very well maintained 2-family home. The first floor apartment offers a living room, dining room, 3 bedrooms, full bath & updated kitchen w/ a loft area. The second floor offers a living room, eat in kitchen, 3 bedrooms. Updates include roof (<4 yrs old), electric wall heaters, kitchens & baths, insulated basement & vinyl siding (level 1). The driveway allows for 4 car-parking and the level yard is great for gardening, outdoor enjoyment plus a shed to store bikes & outdoor furniture. All units responsible for their own water, sewer & electric. Enjoy everything the Hudson Valley has to offer; only a block away from The Walkway over t

$475,000

6 beds2 baths2,034 sq ft

26 Taylor Ave, Poughkeepsie, NY 12601

9,148 sq ft lot • 4 parking spots • Built 1900

Listing by Century 21 Alliance Rlty Group

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to this inviting ranch-style home nestled at the foot of Mount Beacon and lovingly cared for by the same family for nearly 40 years. This well-maintained 3-bedroom, 1-bath home offers the ease of one-level living, featuring hardwood floors, living room, a formal dining room or could be used as a comfortable family room, and a bright eat-in kitchen. A spacious screened-in porch provides a peaceful spot to unwind and enjoy the natural surroundings. The full unfinished basement offers excellent storage. With its warm character and ideal location close to Beacon’s trails, shops, and local amenities, this home is a wonderful opportunity.

$425,000

3 beds1 bath960 sq ft

7 Duncan St, Beacon, NY 12508

4,792 sq ft lot • Built 1950

Listing by Century 21 Alliance Rlty Group

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Renovated home minutes from college, shops, dining, large detached garage for cars and workshop, new kitchen cabinets, new windows, freshly painted throughout, welcome to your new home

$320,000

3 beds1.5 baths1,404 sq ft

191 Washington St, Poughkeepsie, NY 12601

Renovated home • New kitchen cabinets • New windows

Listing by Winwin Realty

Property at 17 Homer Pl, Poughkeepsie, NY 12603, 4 beds, 1.5 baths

$495,000

4 beds1.5 baths1,776 sq ft

17 Homer Pl, Poughkeepsie, NY 12603

Listing by HV Premier Properties Realty

Property at 2809 Route 9D, Wappingers Falls, NY 12590, 4 beds, 2 baths

$395,000

4 beds2 baths2,176 sq ft

2809 Route 9D, Wappingers Falls, NY 12590

Listing by Compass Greater NY, LLC

Property at 95 Market St, Wappingers Falls, NY 12590, 3 beds, 2 baths

$529,000

3 beds2 baths1,802 sq ft

95 Market St, Wappingers Falls, NY 12590

Listing by HV Premier Properties Realty

Property at 786 N Clove Rd, Verbank, NY 12585, 4 beds, 2.5 baths

$650,000

4 beds2.5 baths3,446 sq ft

786 N Clove Rd, Verbank, NY 12585

Listing by Houlihan Lawrence Inc.

Property at 20 Hillcrest Ln, Rhinebeck, NY 12572, 3 beds, 2 baths

$395,000

3 beds2 baths1,615 sq ft

20 Hillcrest Ln, Rhinebeck, NY 12572

Listing by BHHS Hudson Valley Properties

Property at 275 Osborne Hill Rd, Fishkill, NY 12524, 3 beds, 1.5 baths

$519,000

3 beds1.5 baths1,512 sq ft

275 Osborne Hill Rd, Fishkill, NY 12524

Listing by Exit Realty Connections

Property at 76 Church St, Beacon, NY 12508, 3 beds, 1 bath

$497,000

3 beds1 bath1,296 sq ft

76 Church St, Beacon, NY 12508

Listing by Exit Realty Connections

Property at 9 Maple St, Glenham, NY 12527, 2 beds, 1.5 baths

$575,000

2 beds1.5 baths1,100 sq ft

9 Maple St, Glenham, NY 12527

Listing by BHHS Hudson Valley Properties

Property at 86 Vassar Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$440,000

3 beds1 bath1,773 sq ft

86 Vassar Rd, Poughkeepsie, NY 12603

Listing by K. Fortuna Realty, Inc.

Property at 88 Innis Ave, Poughkeepsie, NY 12601, 3 beds, 2.5 baths

$450,000

3 beds2.5 baths1,500 sq ft

88 Innis Ave, Poughkeepsie, NY 12601

Listing by Dixon Smith Realty

Property at 113 Hooker Ave, Poughkeepsie, NY 12601, 5 beds, 5.5 baths

$599,000

5 beds5.5 baths4,800 sq ft

113 Hooker Ave, Poughkeepsie, NY 12601

Listing by Keller Williams Hudson Valley

Property at 195 Hooker Ave, Poughkeepsie, NY 12603, 3 beds, 1.5 baths

$425,000

3 beds1.5 baths1,420 sq ft

195 Hooker Ave, Poughkeepsie, NY 12603

Listing by Weichert Realtors

Property at 6 Laurel Dr, Holmes, NY 12531, 5 beds, 4 baths

$299,900

5 beds4 baths— sq ft

6 Laurel Dr, Holmes, NY 12531

Listing by AI Realty Brokerage LLC

Property at 37 E Market St, Hyde Park, NY 12538

$249,000

0 beds— baths2,956 sq ft

37 E Market St, Hyde Park, NY 12538

Listing by Coldwell Banker Realty

Property at 10 Meier Rd, Poughkeepsie, NY 12603, 3 beds, 2 baths

$410,000

3 beds2 baths1,562 sq ft

10 Meier Rd, Poughkeepsie, NY 12603

Listing by Houlihan Lawrence Inc.

Property at 95 Washington Ave, Beacon, NY 12508, 3 beds, 3 baths

$725,000

3 beds3 baths1,630 sq ft

95 Washington Ave, Beacon, NY 12508

Listing by Houlihan Lawrence 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 65 Worrall Ave, Poughkeepsie, NY 12603, 4 beds, 2 baths

$399,000

4 beds2 baths1,350 sq ft

65 Worrall Ave, Poughkeepsie, NY 12603

Listing by United RE Hudson Valley Edge

Property at 10 Albertson St, Hyde Park, NY 12538, 2 beds, 1.5 baths

$300,000

2 beds1.5 baths1,256 sq ft

10 Albertson St, Hyde Park, NY 12538

Listing by HomeSmart Homes & Estates

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 29 Wedgewood Rd, Fishkill, NY 12524, 3 beds, 1.5 baths

$475,000

3 beds1.5 baths1,386 sq ft

29 Wedgewood Rd, Fishkill, NY 12524

Listing by BHHS Hudson Valley Properties

Property at 15 Franklin Rd, Hyde Park, NY 12538, 4 beds, 2 baths

$389,000

4 beds2 baths1,834 sq ft

15 Franklin Rd, Hyde Park, NY 12538

Listing by KW MidHudson

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 34 Wilmar Ter, Poughkeepsie, NY 12601, 2 beds, 1.5 baths

$349,000

2 beds1.5 baths1,045 sq ft

34 Wilmar Ter, Poughkeepsie, NY 12601

Listing by K. Fortuna Realty, Inc.

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 284 S Quaker Ln, Hyde Park, NY 12538, 4 beds, 2 baths

$399,900

4 beds2 baths1,370 sq ft

284 S Quaker Ln, Hyde Park, NY 12538

Listing by BHHS Hudson Valley Properties

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 14 Ruppert Rd, Poughkeepsie, NY 12603, 2 beds, 1 bath

$330,000

2 beds1 bath918 sq ft

14 Ruppert Rd, Poughkeepsie, NY 12603

Listing by Keller Williams Realty

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 30 Myrtle Ave, Pine Plains, NY 12567, 3 beds, 2 baths

$490,000

3 beds2 baths1,298 sq ft

30 Myrtle Ave, Pine Plains, NY 12567

Listing by Houlihan Lawrence Inc.

Property at 107 Noxon Rd, Poughkeepsie, NY 12603, 3 beds, 2 baths

$399,000

3 beds2 baths1,738 sq ft

107 Noxon Rd, Poughkeepsie, NY 12603

Listing by eXp Realty

Property at 15 Milano Dr, Poughkeepsie, NY 12603, 3 beds, 2 baths

$499,900

3 beds2 baths2,700 sq ft

15 Milano Dr, Poughkeepsie, NY 12603

Listing by eXp Realty

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 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 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 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

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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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