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

251 homes

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ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Once in a generation does a home like this come available. Meticulously cared for by the previous family; this Red Hook gem features a fabulous floor plan. One level easy living and a full finished basement with room for so much expansion. Walk in through the breezeway with blue stone floors and walls of windows, perfect for a grand entry way or lounge area to have a sunlight morning cup of coffee and relax. Two car attached garage with room for storage or work shop off one way of the room and enter into the home off the other side to the country Kitchen with handsome details and large windows overlooking the lovely, resort level backyard, half Bath powder room off kitchen perfect for guest

$499,000

4 beds1.5 baths1,362 sq ft

201 Linden Ave, Red Hook, NY 12571

Country kitchen • Gunite pool • Finished basement

Listing by Mondello Upstate Properties

NEW 15 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
This charming, recently updated home is ideally situated on a quiet dead-end street, offering a serene escape without sacrificing convenience. The location provides easy access to local amenities and transportation options. Step inside to discover a freshly revitalized interior featuring new flooring and paint throughout, creating a bright and welcoming atmosphere. The spacious living area is bathed in natural light and anchored by a cozy fireplace, perfect for relaxing evenings. The heart of the home, the kitchen, has been thoughtfully updated with sleek quartz countertops, stylish subway tile backsplash, and modern finishes. The flexible layout offers two generously sized bedrooms and a f

$485,000

4 beds3 baths2,517 sq ft

3 Pond Rd, Poughkeepsie, NY 12601

New flooring • New paint • Cozy fireplace

Listing by Exit Realty Connections

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to one level living in this well-maintained charming ranch on 1.7 acres. 3 bedroom 1 bath functional ranch offers comfortable and cozy living with a fireplace in the living room, dining room, hardwood floors. Central air, large clean basement for storage and laundry. Back yard is level ideal for entertaining, gardening and pets. Enclosed heated breezeway with front and rear access sliding glass doors. Oversized one car garage and driveway with plenty of room for parking. Solid home well located near Route 9 for shopping, medical, entertainment and close to all commuter routes. Welcome to one level living in this well-maintained charming ranch on 1.7 acres. The home is in need of a l

$389,000

3 beds1 bath1,173 sq ft

276 Old Hopewell Rd, Wappingers Falls, NY 12590

Well maintained • One level living • Level back yard

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
In The Historic District, Bordering On The Southside, Is This Freshly Painted And Updated Four Bedroom, Two Bath Home Available For Immediate Occupancy. This As Is Bi-Level Offers An Open Floor Plan Lower Level With Bedroom And Bath. Second Landing Allows Three Additional Bedrooms, Bathroom And A Bonus Room For A Possible Walk In Closet, Office. .. .. .Your Choice. The Convenience Of Being Close To Transportation, Hospitals, Shopping, Major Routes, Restaurants, The Arts, Could Make This Home's Purchase Ideal. Agents, Please See Other Remarks.

$329,900

4 beds2 baths1,312 sq ft

92 Academy St, Poughkeepsie, NY 12601

Open floor plan • Close to hospitals • Bonus room

Listing by Century 21 Hudson Valley Rlty.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Charming Cape nestled on a quiet cul-de-sac. The sun-filled living room with fireplace flows seamlessly into the dining room, featuring a bay window overlooking the level backyard. The kitchen opens to the dining room, making it ideal for entertaining. The main level offers a bedroom, den/guest room, and a beautifully updated full bath. Upstairs, you’ll find a spacious primary bedroom with a sitting area, a large third bedroom, and a full bath. Laundry is located in the full unfinished basement with Bilco doors. A one-car garage is conveniently located off the kitchen. Enjoy outdoor living under the large covered patio—perfect for BBQs and relaxing. Gleaming hardwood floors high

$435,000

3 beds2 baths1,764 sq ft

22 Wendover Dr, Poughkeepsie, NY 12601

Living room • Level backyard • Bay window

Listing by BHHS Hudson Valley Properties

Property at 101 N Clinton St, Poughkeepsie, NY 12601, 2 beds, 1 bath

$325,000

2 beds1 bath1,226 sq ft

101 N Clinton St, Poughkeepsie, NY 12601

Listing by KW MidHudson

Property at 3 Glade Rd, Poughkeepsie, NY 12601, 4 beds, 2 baths

$394,900

4 beds2 baths1,598 sq ft

3 Glade Rd, Poughkeepsie, NY 12601

Listing by Century 21 Hudson Valley Rlty.

Property at 10 Helin Rd, Hopewell Junction, NY 12533, 3 beds, 3 baths

$565,000

3 beds3 baths2,225 sq ft

10 Helin Rd, Hopewell Junction, NY 12533

Listing by Coldwell Banker Realty

Property at 34 Adriance Ave, Poughkeepsie, NY 12601, 4 beds, 2.5 baths

$515,000

4 beds2.5 baths2,374 sq ft

34 Adriance Ave, Poughkeepsie, NY 12601

Listing by eXp Realty

Property at 106 New Hamburg Rd, Wappingers Falls, NY 12590, 3 beds, 2 baths

$399,999

3 beds2 baths1,359 sq ft

106 New Hamburg Rd, Wappingers Falls, NY 12590

Listing by Century 21 Alliance Rlty Group

Property at 15 Valley View Rd, Hyde Park, NY 12538, 3 beds, 2 baths

$399,999

3 beds2 baths2,185 sq ft

15 Valley View Rd, Hyde Park, NY 12538

Listing by KFortuna All Aspects Realty

Property at 266 Sylvan Lake Rd Unit A-13, Hopewell Junction, NY 12533, 1 bath

$29,999

0 beds1 bath500 sq ft

266 Sylvan Lake Rd Unit A-13, Hopewell Junction, NY 12533

Listing by Houlihan Lawrence Inc.

Property at 69 Beacon St, Beacon, NY 12508, 2 beds, 1 bath

$475,000

2 beds1 bath1,136 sq ft

69 Beacon St, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 95 Smithtown Rd, Fishkill, NY 12524, 3 beds, 2 baths

$499,000

3 beds2 baths1,400 sq ft

95 Smithtown Rd, Fishkill, NY 12524

Listing by Howard Hanna Rand Realty

Property at 28 S Brett St, Beacon, NY 12508, 3 beds, 2 baths

$750,000

3 beds2 baths1,930 sq ft

28 S Brett St, Beacon, NY 12508

Listing by Compass Greater NY, LLC

Property at 21 Harvey St, Hyde Park, NY 12538, 3 beds, 2.5 baths

$329,000

3 beds2.5 baths1,652 sq ft

21 Harvey St, Hyde Park, NY 12538

Listing by KW MidHudson

Property at 137 S Highland Rd, Wappingers Falls, NY 12590, 3 beds, 1 bath

$483,976

3 beds1 bath2,094 sq ft

137 S Highland Rd, Wappingers Falls, NY 12590

Listing by Locqube New York, Inc.

Property at 91 Clove Branch Rd, Hopewell Junction, NY 12533, 3 beds, 1 bath

$375,000

3 beds1 bath1,593 sq ft

91 Clove Branch Rd, Hopewell Junction, NY 12533

Listing by River Realty Services, Inc.

Property at 83 Marple Road Ext, Poughkeepsie, NY 12603, 4 beds, 2 baths

$489,900

4 beds2 baths1,766 sq ft

83 Marple Road Ext, Poughkeepsie, NY 12603

Property at 6 Liss Rd, Wappingers Falls, NY 12590, 3 beds, 1.5 baths

$400,000

3 beds1.5 baths1,442 sq ft

6 Liss Rd, Wappingers Falls, NY 12590

Listing by Epique Realty

Property at 703 Butts Hollow Rd, Dover Plains, NY 12522, 5 beds, 3 baths

$319,999

5 beds3 baths— sq ft

703 Butts Hollow Rd, Dover Plains, NY 12522

Listing by Newman Realty Inc

Property at 67 Dutchess Ter, Beacon, NY 12508, 4 beds, 3 baths

$599,000

4 beds3 baths1,926 sq ft

67 Dutchess Ter, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 354 Van Wagner Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$385,000

3 beds1 bath1,841 sq ft

354 Van Wagner Rd, Poughkeepsie, NY 12603

Listing by REO Edge LLC

Property at 27 Spruce St, Poughkeepsie, NY 12601, 4 beds, 2 baths

$389,000

4 beds2 baths1,501 sq ft

27 Spruce St, Poughkeepsie, NY 12601

Listing by eXp Realty

Property at 28 Red Oaks Mill Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$425,000

3 beds1 bath1,302 sq ft

28 Red Oaks Mill Rd, Poughkeepsie, NY 12603

Listing by K. Fortuna Realty, Inc.

Property at 46 Mitchell Ave, Poughkeepsie, NY 12603, 3 beds, 1 bath

$367,900

3 beds1 bath1,260 sq ft

46 Mitchell Ave, Poughkeepsie, NY 12603

Listing by BHHS Hudson Valley Properties

Property at 19 Ann St, Poughkeepsie, NY 12603, 3 beds, 1 bath

$379,000

3 beds1 bath1,100 sq ft

19 Ann St, Poughkeepsie, NY 12603

Listing by K. Fortuna Realty, Inc.

Property at 162 Osborne Hill Rd, Fishkill, NY 12524, 2 beds, 1 bath

$299,900

2 beds1 bath988 sq ft

162 Osborne Hill Rd, Fishkill, NY 12524

Listing by River Realty Services, Inc.

Property at 445 N Quaker Ln, Hyde Park, NY 12538, 3 beds, 2 baths

$430,000

3 beds2 baths1,440 sq ft

445 N Quaker Ln, Hyde Park, NY 12538

Listing by Coldwell Banker Realty

Property at 7432 S Broadway, Red Hook, NY 12571, 4 beds, 3 baths

$639,000

4 beds3 baths2,559 sq ft

7432 S Broadway, Red Hook, NY 12571

Listing by Coldwell Banker Village Green

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 29 Dinan St, Beacon, NY 12508, 2 beds, 1 bath

$650,000

2 beds1 bath894 sq ft

29 Dinan St, Beacon, NY 12508

Listing by Greene Realty Group

Property at 173 N Grand Ave, Poughkeepsie, NY 12603, 3 beds, 2 baths

$498,000

3 beds2 baths1,660 sq ft

173 N Grand Ave, Poughkeepsie, NY 12603

Listing by Houlihan Lawrence Inc.

Property at 565 Old Hopewell Rd, Hopewell Junction, NY 12533, 2 beds, 1.5 baths

$390,000

2 beds1.5 baths1,072 sq ft

565 Old Hopewell Rd, Hopewell Junction, NY 12533

Listing by Serhant LLC

Property at 104 S Quaker Ln, Hyde Park, NY 12538, 3 beds, 2 baths

$750,000

3 beds2 baths1,548 sq ft

104 S Quaker Ln, Hyde Park, NY 12538

Listing by Schunk Realty Group

Property at 17 Fishkill Hook Rd, Hopewell Junction, NY 12533, 3 beds, 1.5 baths

$278,000

3 beds1.5 baths1,162 sq ft

17 Fishkill Hook Rd, Hopewell Junction, NY 12533

Listing by BHHS Hudson Valley Properties

Property at 29 Delano St, Poughkeepsie, NY 12601, 5 beds, 2 baths

$449,900

5 beds2 baths— sq ft

29 Delano St, Poughkeepsie, NY 12601

Listing by K. Fortuna Realty, Inc.

Property at 13 Hammersley Ave, Poughkeepsie, NY 12601, 8 beds, 3 baths

$445,000

8 beds3 baths3,360 sq ft

13 Hammersley Ave, Poughkeepsie, NY 12601

Listing by Century 21 Alliance Rlty Group

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 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 1370 Route 55, Lagrangeville, NY 12540, 2 beds, 2 baths

$449,000

2 beds2 baths3,072 sq ft

1370 Route 55, Lagrangeville, NY 12540

Listing by BHHS Hudson Valley Properties

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Based on information submitted to the MLS GRID as of Tue Dec 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 251 vintage homes for sale in Dutchess County at a median listing price of $540K. 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 65 days and receive 3 offers. This map is refreshed with the newest listings in Dutchess County every 15 minutes.

In the past month, 200 homes have been sold in Dutchess County. In addition to houses in Dutchess County, there were also 88 condos, 1 townhouse, and 63 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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