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

255 homes

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NEW 7 HRS AGO

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

NEW 8 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Two - family home in the City of Poughkeepsie producing $2500/month in rental income. This basic duplex features separate units and a functional layout. - Conveniently located downtown, near public transportation and major highways. - Suitable for owner-occupant or investor.

$325,000

2 beds1 bath1,226 sq ft

101 N Clinton St, Poughkeepsie, NY 12601

Two family home • Separate units • Functional layout

Listing by KW MidHudson

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to this 4 bedroom 2 bathroom ranch in the Town of Hyde Park. The home features a new roof, new paint and flooring throughout. This home while in Hyde Park is closer Pleasant Valley or Arlington as it sits right off Salt Point Turnpike making it a commuters dream. Hyde Park offers open space like no other municipality in Dutchess County with public access to the Hudson River, FDR Estate, Vanderbilt Mansions and Mills/Norrie State Parks. This home is ready for immediate occupancy. Buyers agents please read agent only remarks for offer submission instructions.

$394,900

4 beds2 baths1,598 sq ft

3 Glade Rd, Poughkeepsie, NY 12601

Open space • New flooring • New paint

Listing by Century 21 Hudson Valley Rlty.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Fixer upper 1st row from the lake with private lake rights to Sylvan Lake! This seasonal home, managed from April-November, is perfect for those looking for a weekend getaway or for 'Snowbirds' looking for a place to call home in NY. You will not be disappointed with this home. Though this home is in need of updating the proximity to the lake and the unobstructed hilltop views make this home a must see. Enjoy your private beach on Sylvan Lake, take a swim, enjoy some beautiful sunsets, barbecue at one of the beachfront barbecue pits or just sit and Dip the hook for some great freshwater fishing, kayaking and or manual/electric boat!

$37,500

0 beds1 bath500 sq ft

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

Private lake rights • Private beach • Freshwater fishing

Listing by Houlihan Lawrence Inc.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
This charming home sits on nearly an acre of level property and offers 2,225 sq ft of comfortable living space. With 3 bedrooms and 3 full bathrooms, it’s ready to warmly welcome its new owners. The main level features a spacious living room, with the dining room just across the way. An updated kitchen with granite counter tops and stainless-steel appliances and has a walkout which provides access to both garages. You’ll love the expansive family room, complete with high ceilings, a wood-burning fireplace, and a walkout to the screened-in porch—perfect for relaxing or entertaining. A full bathroom completes the main level. Upstairs, you’ll find three generously sized

$565,000

3 beds3 baths2,225 sq ft

10 Helin Rd, Hopewell Junction, NY 12533

Screened in porch • Updated kitchen • Park like property

Listing by Coldwell Banker Realty

Property at 126 Curry Rd, Wappingers Falls, NY 12590, 3 beds, 2 baths

$323,000

3 beds2 baths2,514 sq ft

126 Curry Rd, Wappingers Falls, NY 12590

Listing by 1st Independent Realty Grp

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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 7 Duncan St, Beacon, NY 12508, 3 beds, 1 bath

$425,000

3 beds1 bath960 sq ft

7 Duncan St, Beacon, NY 12508

Listing by Century 21 Alliance Rlty Group

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 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 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 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 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 912-918 Hollow Rd, Salt Point, NY 12578, 5 beds, 5 baths

$1,200,000

5 beds5 baths4,851 sq ft

912-918 Hollow Rd, Salt Point, NY 12578

Listing by Century 21 Alliance Realty Grp

Property at 45 Baker Rd, Hopewell Junction, NY 12533, 3 beds, 2.5 baths

$449,888

3 beds2.5 baths1,632 sq ft

45 Baker Rd, Hopewell Junction, NY 12533

Listing by Real Broker NY LLC

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Based on information submitted to the MLS GRID as of Sat Dec 27 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 255 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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