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

413 homes

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OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Set along the back of the waterfall on Fishkill Creek, this move-in ready Beacon farmhouse combines historic character with thoughtful modern updates. The home welcomes you with a classic rocking-chair front porch and two convenient entrances. Inside, classic details like wainscoting walls and rooms with original hardwood floors preserve its charm, while major updates including new energy efficient windows, septic system, updated plumbing, newer roof and furnace add modern improvements. The spacious kitchen is the heart of the home, showcasing quartz countertops, stainless steel appliances, and abundant cabinetry. The adjacent dining room offers a lovely mantle and views of the patio and ba

$585,000

2 beds2 baths1,513 sq ft

594 Washington Ave, Beacon, NY 12508

Quartz countertops • Newer roof • Spacious kitchen

Listing by Compass Greater NY, LLC

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
A covered front porch, bold blue siding and the convenience of nearby shops and restaurants make 7 Lewis Avenue worth a closer look. Renovated within the past few years, this three-bedroom, one-and-a-half-bath home pairs classic character with an updated kitchen, bathroom and flooring. Start the day with coffee on the front porch or unwind on the rear deck. A detached one-car garage, useable attic space, and full unfinished basement provide plenty of room for storage and more. Set in the Arlington School District and within walking distance of local restaurants, stores, and public transportation, this home brings everyday conveniences close to your doorstep. Showings begin October 16, 2026.

$350,000

3 beds1.5 baths1,308 sq ft

7 Lewis Ave, Poughkeepsie, NY 12603

Covered front porch • Updated kitchen • Updated flooring

Listing by Legacy Land & Homes LLC

OPEN SAT, 12PM TO 2PMVIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Single-Level Living on 0.77 Acres in Wappingers Schools – Spacious Kitchen & Room to Grow, a classic ranch on a generous lot in the heart of Dutchess County. This 2 bedrooms, 1 bath on one level, offers easy, low-maintenance living and a setting that's increasingly hard to find. The kitchen is the heart of the home, with abundant cabinetry, generous counter space, a counter seating area and a new range, ready for everyday cooking and casual gatherings. Two comfortably sized bedrooms and a new washing machine round out the main level. Below, a full basement with walk-out Bilco door access provides valuable storage and utility space, and pull-down attic stairs add even more storag

$325,000

2 beds1 bath990 sq ft

214 Old Hopewell Rd, Wappingers Falls, NY 12590

Functional kitchen • Covered porch • Partial basement

Listing by Howard Hanna Rand Realty

OPEN SAT, 12PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
BEAUTIFULLY RENOVATED CAPE COD IN THE HEART OF HYDE PARK! Old-world charm meets modern elegance in this beautifully renovated 4-bedroom, 2-full-bath Cape Cod, nestled in a desirable neighborhood in the heart of Historic Hyde Park - one of the favorite neighborhoods in all of Hyde Park for Halloween fun and trick-or-treaters! From the moment you enter, you'll appreciate the timeless character, charming arched entryways, gleaming refinished original oak floors, and thoughtful updates throughout. The stunning, completely renovated kitchen is truly a showstopper! Sunlight pours through the windows, illuminating gorgeous quartz countertops, a striking backsplash, new waterproof luxury vinyl fl

$429,900

4 beds2 baths1,231 sq ft

23 Mansion Dr, Hyde Park, NY 12538

Brick fireplace • Renovated kitchen • 0.24 acre lot

Listing by K. Fortuna Realty, Inc.

NEW 5 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
A true treasure and piece of Pine Plains history, this elegant circa-1903 residence offers an exceptional blend of historic character, architectural detail, and extraordinary potential. Boasting over 3,000 square feet, four bedrooms, and 1.5 baths, the home showcases generously proportioned rooms, soaring ceilings, original woodwork, pastel tile and classic period trim that speak to its enduring charm. Once home to the village pharmacy and library, this remarkable property carries a unique legacy, ready to be thoughtfully restored and elevated. Set on approximately 0.47 acres, the grounds include a lofted barn offering a wealth of possibilities for a studio, workshop, or additional storage

$425,000

4 beds1.5 baths3,072 sq ft

7786 S Main St, Pine Plains, NY 12567

Architectural detail • Fenced yard • Historic character

Listing by Mondello Upstate Properties

Property at 19 Greentree Dr S, Hyde Park, NY 12538, 3 beds, 1 bath

$355,000

3 beds1 bath1,308 sq ft

19 Greentree Dr S, Hyde Park, NY 12538

Listing by Dixon Smith Realty

Property at 10 Barrett Dr, Hopewell Junction, NY 12533, 1.5 baths

$589,000

Studio1.5 baths2,224 sq ft

10 Barrett Dr, Hopewell Junction, NY 12533

Listing by Century 21 Alliance Rlty Group

Property at 201 Bower Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$395,000

3 beds1 bath1,308 sq ft

201 Bower Rd, Poughkeepsie, NY 12603

Listing by Coldwell Banker Realty

Property at 25 Rymph Blvd, Poughkeepsie, NY 12601, 2 beds, 1 bath

$329,900

2 beds1 bath902 sq ft

25 Rymph Blvd, Poughkeepsie, NY 12601

Listing by McNiff Real Estate LTD

Property at 943 Main St, Fishkill, NY 12524, 4 beds, 2 baths

$500,000

4 beds2 baths1,808 sq ft

943 Main St, Fishkill, NY 12524

Listing by BHHS Hudson Valley Properties

Property at 41 Antler Club Rd, Pine Plains, NY 12567, 4 beds, 2.5 baths

$679,000

4 beds2.5 baths1,809 sq ft

41 Antler Club Rd, Pine Plains, NY 12567

Listing by Thomas Zengen

Property at 156 Red Schoolhouse Rd, Fishkill, NY 12524, 3 beds, 3 baths

$649,500

3 beds3 baths2,123 sq ft

156 Red Schoolhouse Rd, Fishkill, NY 12524

Listing by KW MidHudson

Property at 34 Mckinley Ln, Poughkeepsie, NY 12601, 2 beds, 1 bath

$210,000

2 beds1 bath972 sq ft

34 Mckinley Ln, Poughkeepsie, NY 12601

Listing by Howard Hanna Rand Realty

Property at 389 Route 199, Red Hook, NY 12571, 3 beds, 1 bath

$449,000

3 beds1 bath1,792 sq ft

389 Route 199, Red Hook, NY 12571

Listing by Houlihan Lawrence Inc.

Property at 19 Russell Ave, Rhinebeck, NY 12572, 3 beds, 3 baths

$800,000

3 beds3 baths2,154 sq ft

19 Russell Ave, Rhinebeck, NY 12572

Property at 125 Jackson St, Fishkill, NY 12524, 2 beds, 1.5 baths

$349,500

2 beds1.5 baths1,342 sq ft

125 Jackson St, Fishkill, NY 12524

Listing by K. Fortuna Realty, Inc.

Property at 12 Gary Dr, Hyde Park, NY 12538, 4 beds, 2 baths

$299,000

4 beds2 baths— sq ft

12 Gary Dr, Hyde Park, NY 12538

Listing by K. Fortuna Realty, Inc.

Property at 20 Memory Ln, Poughkeepsie, NY 12603, 4 beds, 2.5 baths

$445,000

4 beds2.5 baths1,729 sq ft

20 Memory Ln, Poughkeepsie, NY 12603

Listing by eXp Realty

Property at 23 Lake Dr, Holmes, NY 12531, 1 bed, 1 bath

$374,999

1 bed1 bath768 sq ft

23 Lake Dr, Holmes, NY 12531

Listing by eRealty Advisors, Inc

Property at 158 Violet Ave, Poughkeepsie, NY 12601, 4 beds, 1 bath

$270,000

4 beds1 bath1,196 sq ft

158 Violet Ave, Poughkeepsie, NY 12601

Listing by Berkshire Hathaway HS NY Prop

Property at 5829 Route 22, Millerton, NY 12546, 3 beds, 2.5 baths

$514,999

3 beds2.5 baths2,880 sq ft

5829 Route 22, Millerton, NY 12546

Listing by eXp Realty

Property at 206 Old Route 22, Wassaic, NY 12592, 3 beds, 1 bath

$279,000

3 beds1 bath1,360 sq ft

206 Old Route 22, Wassaic, NY 12592

Listing by BHHS Hudson Valley Properties

Property at 173 Milltown Rd, Holmes, NY 12531, 2 beds, 2 baths

$585,000

2 beds2 baths2,431 sq ft

173 Milltown Rd, Holmes, NY 12531

Listing by Briante Realty Group, LLC

Property at 46 Old Post Rd, Staatsburg, NY 12580, 4 beds, 3 baths

$499,000

4 beds3 baths2,058 sq ft

46 Old Post Rd, Staatsburg, NY 12580

Listing by Jeff S. Colton

Property at 256 E Main St, Beacon, NY 12508, 3 beds, 2 baths

$799,000

3 beds2 baths1,696 sq ft

256 E Main St, Beacon, NY 12508

Listing by Compass Greater NY, LLC

Property at 19 Russell Ave, Rhinecliff, NY 12574, 3 beds, 3 baths

$800,000

3 beds3 baths2,154 sq ft

19 Russell Ave, Rhinecliff, NY 12574

Listing by Corcoran Country Living

Property at 23 S Creek Rd, Staatsburg, NY 12580, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,584 sq ft

23 S Creek Rd, Staatsburg, NY 12580

Listing by Compass Greater NY, LLC

Property at 16 Hanna Ln, Beacon, NY 12508, 7 beds, 9 baths

$2,800,000

7 beds9 baths8,000 sq ft

16 Hanna Ln, Beacon, NY 12508

Listing by McGrath Realty Inc

Property at 17 N Clover St, Poughkeepsie, NY 12601, 5 beds, 3 baths

$499,000

5 beds3 baths— sq ft

17 N Clover St, Poughkeepsie, NY 12601

Listing by Clarke Realty & Associates LLC

Property at 17 N Brett St, Beacon, NY 12508, 3 beds, 2 baths

$950,000

3 beds2 baths2,048 sq ft

17 N Brett St, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 182 Mill St, Poughkeepsie, NY 12601, 6 beds, 2 baths

$499,000

6 beds2 baths2,360 sq ft

182 Mill St, Poughkeepsie, NY 12601

Listing by KW MidHudson

Property at 75 College Ave, Poughkeepsie, NY 12603, 5 beds, 2.5 baths

$399,000

5 beds2.5 baths1,912 sq ft

75 College Ave, Poughkeepsie, NY 12603

Listing by HV Premier Properties Realty

Property at 320 Church St, Poughkeepsie, NY 12601, 4 beds, 2 baths

$425,000

4 beds2 baths2,151 sq ft

320 Church St, Poughkeepsie, NY 12601

Listing by Keller Williams Realty Partner

Property at 2676 W Main St, Wappingers Falls, NY 12590

$649,000

Studio— baths3,465 sq ft

2676 W Main St, Wappingers Falls, NY 12590

Listing by Sams Realty

Property at 360 Old State Route 22, Dover Plains, NY 12522, 4 beds, 4 baths

$775,000

4 beds4 baths2,234 sq ft

360 Old State Route 22, Dover Plains, NY 12522

Listing by BHHS Hudson Valley Properties

Property at 3311 Franklin Ave, Millbrook, NY 12545, 4 beds, 3 baths

$1,225,000

4 beds3 baths3,068 sq ft

3311 Franklin Ave, Millbrook, NY 12545

Listing by Compass Greater NY, LLC

Property at 300 W Market St, Red Hook, NY 12571, 3 beds, 2 baths

$275,000

3 beds2 baths2,345 sq ft

300 W Market St, Red Hook, NY 12571

Listing by Rising Star Realty

Property at 44 Degarmo Hills Rd, Wappingers Falls, NY 12590, 4 beds, 2.5 baths

$499,000

4 beds2.5 baths2,034 sq ft

44 Degarmo Hills Rd, Wappingers Falls, NY 12590

Listing by Real Broker NY LLC

Property at 262 Stissing Rd, Stanfordville, NY 12581, 4 beds, 2.5 baths

$720,000

4 beds2.5 baths2,464 sq ft

262 Stissing Rd, Stanfordville, NY 12581

Listing by Corcoran Country Living

Property at 17 Whitehouse Ave, Poughkeepsie, NY 12601, 5 beds, 4 baths

$625,000

5 beds4 baths5,400 sq ft

17 Whitehouse Ave, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 1408 Route 83, Pine Plains, NY 12567, 2 beds, 2 baths

$685,000

2 beds2 baths1,406 sq ft

1408 Route 83, Pine Plains, NY 12567

Listing by Corcoran Country Living

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Based on information submitted to the MLS GRID as of Fri Oct 16 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 Dutchess County

There are currently 413 vintage homes for sale in Dutchess County at a median listing price of $565K. 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 62 days and receive 3 offers. This map is refreshed with the newest listings in Dutchess County every 15 minutes.

In the past month, 225 homes have been sold in Dutchess County. In addition to houses in Dutchess County, there were also 112 condos, 2 townhouses, and 77 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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