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:
Welcome to 322 Old Route 22! Spacious, newly remodeled 2-family home is a great opportunity for owner-occupants, investors, or extended families. Great location just a few minutes from the heart of the Village of Pawling! Each unit features 2 bedrooms, a full bath, living room, dining area, kitchen and bright, enclosed sunporches, providing plenty of space and natural light throughout. Inside, both units are nicely remodeled, move-in ready with energy-efficient mini-split systems providing both heating and air conditioning. Outside is large backyard and detached garage, new blacktopped driveway. You'll find plenty of finished storage space in the walk-up attic & in unfinished basemen

$619,000

4 beds2 baths1,950 sq ft

322 Old Route 22, Pawling, NY 12564

Large backyard • Unfinished basement • Walk-up attic

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Highest and Best has been extended with a request from the seller, for No Escalation Clause offers now due Tuesday 11/3 at noon. Welcome Home! Nestled within the Wappingers Central School District, this adorable Cape Cod offers charm, comfort, and plenty of potential. Featuring 2 bedrooms and a full bath on the first floor, the third bedroom and full bath upstairs, this home provides a warm and inviting interior perfect for everyday living. The bonus room adds extra flexibility — ideal for a home office, playroom, or guest space — and the walk-up attic offers an additional space for future expansion. Step outside and enjoy the beautiful outdoor gathering areas, perfect for enter

$385,000

3 beds2 baths2,084 sq ft

39 Alda Dr, Poughkeepsie, NY 12603

0.41 acre lot • 2 garage spots • Built 1952

Listing by Houlihan Lawrence Inc.

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Charming Salt Point Ranch- Just outside the quaint hamlet of Salt Point, this well-maintained three-bedroom, two-bath ranch offers comfortable one-level living on a lovely corner lot. The remodeled kitchen opens to a spacious family room with vaulted ceilings and a fireplace, creating an inviting gathering space filled with natural light. A large living room with a second fireplace adds warmth and flexibility. Tastefully updated, the bright, open layout flows easily to a wraparound deck overlooking mature plantings and well-loved gardens—ideal for relaxing or entertaining. Beautifully cared for and move-in ready, this home combines convenience, comfort, and country charm with easy acc

$565,000

3 beds2 baths1,802 sq ft

2467 Salt Point Tpke, Clinton Corners, NY 12514

Move-in ready • Remodeled kitchen • Mature plantings

Listing by Four Seasons Sothebys Intl

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
MORE PHOTOS TO COME. .. PLEASE…BUT DON’T WAIT TO TOUR. THIS MIGHT BE GONE SOON! AMAZING DUPLEX OPPORTUNITY OFFERING ATTACHED TOWNHOUSE STYLE RESIDENCE THAT IS PERFECT FOR OWNER-OCCUPANTS OR INVESTORS ALIKE. EACH UNIT IS PRESENTLY UNDERGOING ITS INDIVIDUAL REFRESH AND UPDATES. ENJOY THE COMFORT OF HOME AND PRIVACY AS EACH UNIT IS OFFERING ITS OWN PRIVATE ENTRANCE, LIVING ROOM, DINING ROOM, KITCHEN, ENCLOSED PORCH FOR RELAXING ON THE FIRST FLOOR AND 3 BEDROOMS/FULL BATH ON THE SECOND FLOOR ACCESSIBLE TO A FULL SPACIOUS ATTIC. FOR ADDITIONAL STORAGE NEEDS THE FULL BASEMENT OFFERS AMPLE SPACE. THE RIGHT SIDE WILL BE DELIVERED WITH FULLY UPDATED WITH MODERN KITCHEN AND BATHROOM, LI

$469,000

6 beds2 baths2,708 sq ft

324-326 Church St, Poughkeepsie, NY 12601

4,792 sq ft lot • Built 1921 • Listed 35 days

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Beautifully maintained classic ranch — immaculate, move-in ready, and full of character with thoughtful updates throughout. This lovingly cared-for home features an open floor plan with gorgeous hardwood floors, an updated kitchen with granite countertops, island, breakfast bar, and abundant cabinet space. The spacious dining area flows seamlessly into a generous living room highlighted by a double-sided fireplace, crown molding, custom built-in cabinetry, and a picture window that fills the space with natural light. A cozy media room leads to the den or guest room, complete with French doors, fireplace, and closet. Patio doors from the kitchen open to an expansive composite deck over

$599,900

4 beds2.5 baths2,292 sq ft

69 Round Hill Rd, Poughkeepsie, NY 12603

Open floor plan • Updated kitchen • Granite countertops

Listing by BHHS Hudson Valley Properties

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 15 Paye Ave, Beacon, NY 12508, 5 beds, 2 baths

$650,000

5 beds2 baths2,028 sq ft

15 Paye Ave, Beacon, NY 12508

Listing by Compass Greater NY, LLC

Property at 111 S Hamilton St, Poughkeepsie, NY 12601, 4 beds, 1.5 baths

$415,000

4 beds1.5 baths1,895 sq ft

111 S Hamilton St, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 4335 Albany Post Rd, Hyde Park, NY 12538, 4 beds, 2 baths

$210,000

4 beds2 baths1,955 sq ft

4335 Albany Post Rd, Hyde Park, NY 12538

Listing by Grist Mill Real Estate

Property at 32 Lagrange Ave, Poughkeepsie, NY 12603, 4 beds, 2 baths

$417,000

4 beds2 baths2,025 sq ft

32 Lagrange Ave, Poughkeepsie, NY 12603

Property at 77 Brothers Rd, Wappingers Falls, NY 12590, 4 beds, 2.5 baths

$499,999

4 beds2.5 baths2,176 sq ft

77 Brothers Rd, Wappingers Falls, NY 12590

Listing by River Realty Services, 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 1665 Bulls Head Rd, Clinton Corners, NY 12514, 3 beds, 3 baths

$560,000

3 beds3 baths2,404 sq ft

1665 Bulls Head Rd, Clinton Corners, NY 12514

Listing by Fraleigh & Rakow Realty, LLC

Property at 61 Delafield St, Poughkeepsie, NY 12601, 4 beds, 2 baths

$349,900

4 beds2 baths2,659 sq ft

61 Delafield St, Poughkeepsie, NY 12601

Listing by Century 21 Alliance Realty Grp

Property at 416 Hapeman Hill Rd, Red Hook, NY 12571, 4 beds, 2.5 baths

$2,950,000

4 beds2.5 baths4,192 sq ft

416 Hapeman Hill Rd, Red Hook, NY 12571

Property at 31 Weston Ave, Fishkill, NY 12524, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths1,520 sq ft

31 Weston Ave, Fishkill, NY 12524

Listing by Keller Williams Realty Partner

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 60 Cherry Ln, Stormville, NY 12582, 2 beds, 1 bath

$199,900

2 beds1 bath861 sq ft

60 Cherry Ln, Stormville, NY 12582

Listing by BHHS Hudson Valley Properties

Property at 12 State Line Rd, Millerton, NY 12546, 3 beds, 2 baths

$449,500

3 beds2 baths1,771 sq ft

12 State Line Rd, Millerton, NY 12546

Listing by KW MidHudson

Property at 65 Greenwood Dr, Beacon, NY 12508, 2 beds, 1 bath

$499,500

2 beds1 bath1,397 sq ft

65 Greenwood Dr, Beacon, NY 12508

Listing by Century 21 Alliance Rlty Group

Property at 207 Horns Park S, Hyde Park, NY 12538, 4 beds, 2 baths

$324,900

4 beds2 baths2,092 sq ft

207 Horns Park S, Hyde Park, NY 12538

Listing by RE/MAX Town & Country

Property at 660 Wheeler Hill Rd, Wappingers Falls, NY 12590, 2 beds, 2 baths

$2,200,000

2 beds2 baths2,290 sq ft

660 Wheeler Hill Rd, Wappingers Falls, NY 12590

Listing by BHHS Hudson Valley Properties

Property at 54 Oakwood Blvd, Poughkeepsie, NY 12603, 2 beds, 1 bath

$408,880

2 beds1 bath1,556 sq ft

54 Oakwood Blvd, Poughkeepsie, NY 12603

Listing by BHHS Hudson Valley Properties

Property at 60 Lent St, Poughkeepsie, NY 12601, 5 beds, 3 baths

$350,000

5 beds3 baths— sq ft

60 Lent St, Poughkeepsie, NY 12601

Listing by Exit Realty Connections

Property at 19 Ridgeview Rd, Poughkeepsie, NY 12603, 4 beds, 3.5 baths

$749,100

4 beds3.5 baths4,208 sq ft

19 Ridgeview Rd, Poughkeepsie, NY 12603

Listing by Houlihan Lawrence Inc.

Property at 105 E Market St, Rhinebeck, NY 12572, 3 beds, 2 baths

$675,000

3 beds2 baths2,263 sq ft

105 E Market St, Rhinebeck, NY 12572

Listing by Corcoran Country Living

Property at 107 E Market St, Rhinebeck, NY 12572, 4 beds, 2.5 baths

$750,000

4 beds2.5 baths2,102 sq ft

107 E Market St, Rhinebeck, NY 12572

Listing by Corcoran Country Living

Property at 134-144 Tinkertown Rd, Salt Point, NY 12578, 1 bed, 1 bath

$175,000

1 bed1 bath476 sq ft

134-144 Tinkertown Rd, Salt Point, NY 12578

Listing by BHHS Hudson Valley Properties

Property at 565 Route 308, Rhinebeck, NY 12572, 5 beds, 3 baths

$2,250,000

5 beds3 baths3,140 sq ft

565 Route 308, Rhinebeck, NY 12572

Listing by Rouse + Co Real Estate LLC

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 8 Walker Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$400,000

3 beds1 bath1,412 sq ft

8 Walker Rd, Poughkeepsie, NY 12603

Listing by Weichert Realtors

Property at 28 On The Grn, Verbank, NY 12585, 5 beds

$625,000

5 beds— baths— sq ft

28 On The Grn, Verbank, NY 12585

Listing by Houlihan Lawrence Inc.

Property at 1 Hoyt Rd, Wingdale, NY 12594, 2 beds, 3 baths

$450,000

2 beds3 baths1,939 sq ft

1 Hoyt Rd, Wingdale, NY 12594

Listing by RE/MAX Classic Realty

Property at 3406 Route 82, Verbank, NY 12585, 2 beds

$445,000

2 beds— baths— sq ft

3406 Route 82, Verbank, NY 12585

Listing by Houlihan Lawrence Inc.

Property at 25 On The Grn, Verbank, NY 12585, 2 beds

$485,000

2 beds— baths— sq ft

25 On The Grn, Verbank, NY 12585

Listing by Houlihan Lawrence Inc.

Property at 1668 Route 9 Unit 3C, Wappingers Falls, NY 12590, 1 bed, 1 bath

$195,000

1 bed1 bath800 sq ft

1668 Route 9 Unit 3C, Wappingers Falls, NY 12590

Listing by eXp Realty

Property at 9 Greenbush Dr, Poughkeepsie, NY 12601, 3 beds, 1 bath

$325,000

3 beds1 bath951 sq ft

9 Greenbush Dr, Poughkeepsie, NY 12601

Listing by Compass Greater NY, LLC

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

$469,900

3 beds2 baths2,018 sq ft

10 Benton Rd, Poughkeepsie, NY 12603

Listing by Sams Realty

Property at 18 Blue Heron Ln Unit 18,20,21,26, Staatsburg, NY 12580, 4 beds, 4 baths

$460,000

4 beds4 baths— sq ft

18 Blue Heron Ln Unit 18,20,21,26, Staatsburg, NY 12580

Listing by BHHS Hudson Valley Properties

Property at 12 S Parsonage St, Rhinebeck, NY 12572, 5 beds, 4 baths

$730,000

5 beds4 baths3,444 sq ft

12 S Parsonage St, Rhinebeck, NY 12572

Listing by Century 21 Alliance Realty Grp

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

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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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