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:
Multi-generational housing opportunity with 3 individual homes on one property. 3 distinct home styles with plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well. Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with abundant light, Formal Dining Room with chair rail accent and beautiful chandelier. Eat in Kitchen with center island, Bosch oven, stainless steel appliances with breakfast nook and bay window. Convenient First floor laundry with 2nd laundry on lower level. Sunroom with tile floor and fireplace. Primary B

$1,400,000

11 beds8 baths— sq ft

750 Route 292, Holmes, NY 12531

Distinct home styles • Formal dining room • Eat in kitchen

Listing by BHHS Hudson Valley Properties

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ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to 31 Blueberry Lane in Stormville, a unique estate offering two homes and a guest studio on over 17 private acres with stunning natural features, including two ponds and an inground pool. The primary residence is a 3-bedroom, 3-bathroom home designed for comfort and entertaining, featuring a large living area with modern windows and exterior doors, an efficient heating and cooling system with a heat pump and mini splits, a rebuilt chimney, and the convenience of a standby generator. Overlooking its own serene 2-acre pond, this home also offers an inground pool complete with an updated pump and filter for effortless summer enjoyment. The secondary home is a well-appointed 2-bedroom,

$1,495,000

3 beds3 baths1,723 sq ft

31 Blueberry Ln, Stormville, NY 12582

Large living area • Guest studio • Two ponds

Listing by Serhant LLC

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
PRICE REDUCTION. .. .Welcome to this 3 bedroom with a den/office and 1.5 bath home located in the Town of Poughkeepsie, Arlington School District. The eat in kitchen features high ceilings with skylights, plenty of counter space and a large pantry. A cozy living room with a pelot stove for those cold nights. Stackable washer and dryer in the upstairs bathroom closet. Fully fenced in backyard with a nice size deck for entertaining and a shed for extra storage. A detached one car garage with spacious driveway. City water and Sewer. A must see. .. ..

$424,900

3 beds1.5 baths1,655 sq ft

18 Peckham Rd, Poughkeepsie, NY 12603

Cozy living room • Eat in kitchen • Large pantry

Listing by Exit Realty Connections

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Originally built in 1836, this beautifully restored Greek Revival Center Hall welcomes you with timeless charm and thoughtful updates. Set on over four acres with Willow Brook gently winding through the property, it offers a warm, peaceful retreat where historic character and modern comfort come together to create a truly special place to call home. Inside, original wide board floors, exposed hardwood beams, and intricate molding and trim work highlight the home's craftsmanship. The center hall layout leads to a stunning double parlor with two fireplaces and original pocket doors, as well as an open dining and living room boasting two additional fireplaces, perfect for gatherings both intim

$1,399,000

4 beds4.5 baths3,090 sq ft

36 Market Ln, Clinton Corners, NY 12514

Center hall layout • Double parlor • Over four acres

Listing by Patricia A. Hinkein Realty

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Discover the ideal investment opportunity or live-in-and-rent scenario with this well-maintained two-family home. Offering reliable cash flow and a prime location, this property is perfect for savvy investors or those looking to offset their mortgage with rental income. This home consists of one - 2 bedroom apartment and a studio. Previously a three family there is an additional area that used to be residential but the Hamlet Zoning allows for a business and/or and office on this high visibility Rt 82 location. There is a detached 2- car garage, currently being rented as a workshop. This listing is part of 3 house portfolio, also listed as MLS 925249 & 925245, all congruent to each ot

$445,000

2 beds— baths— sq ft

3406 Route 82, Verbank, NY 12585

Two-family home • Prime location • 2 acre lot

Listing by Houlihan Lawrence Inc.

Property at 2117 Route 82, Lagrangeville, NY 12540, 3 beds, 3.5 baths

$699,999

3 beds3.5 baths4,400 sq ft

2117 Route 82, Lagrangeville, NY 12540

Listing by McGrath Realty Inc

Property at 107 Marshall Rd, Salt Point, NY 12578, 4 beds, 2.5 baths

$475,000

4 beds2.5 baths2,016 sq ft

107 Marshall Rd, Salt Point, NY 12578

Listing by Rich Brenner Realty, LLC

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 1680 Main St, Pleasant Valley, NY 12569, 3 beds, 1 bath

$289,500

3 beds1 bath1,384 sq ft

1680 Main St, Pleasant Valley, NY 12569

Listing by Next Level Property Management

Property at 181 Union St, Poughkeepsie, NY 12601, 5 beds, 3.5 baths

$699,900

5 beds3.5 baths3,640 sq ft

181 Union St, Poughkeepsie, NY 12601

Listing by Rural Connection Inc.

Property at 1035 Noxon Rd, Lagrangeville, NY 12540, 5 beds, 3.5 baths

$995,000

5 beds3.5 baths4,356 sq ft

1035 Noxon Rd, Lagrangeville, NY 12540

Listing by BHHS Hudson Valley Properties

Property at 83-85 Old Post Rd, Staatsburg, NY 12580, 5 beds, 4 baths

$650,000

5 beds4 baths3,384 sq ft

83-85 Old Post Rd, Staatsburg, NY 12580

Listing by Serhant LLC

Property at 7 Ferris Ln, Poughkeepsie, NY 12601, 5 beds, 3 baths

$825,000

5 beds3 baths4,100 sq ft

7 Ferris Ln, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 14 SE Mountain Rd, Wingdale, NY 12594, 3 beds, 1 bath

$169,000

3 beds1 bath1,092 sq ft

14 SE Mountain Rd, Wingdale, NY 12594

Listing by Voro LLC

Property at 40 N Elm St, Beacon, NY 12508, 2 beds, 1 bath

$525,000

2 beds1 bath1,062 sq ft

40 N Elm St, Beacon, NY 12508

Listing by Coldwell Banker Realty

Property at 49 Lakeview Dr, Holmes, NY 12531, 2 beds, 3 baths

$425,000

2 beds3 baths2,140 sq ft

49 Lakeview Dr, Holmes, NY 12531

Listing by BHHS Hudson Valley Properties

Property at 22 Beilke Rd, Millerton, NY 12546, 3 beds, 2 baths

$125,000

3 beds2 baths2,000 sq ft

22 Beilke Rd, Millerton, NY 12546

Listing by BHHS Hudson Valley Properties

Property at 148 Bower Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$399,900

3 beds1 bath1,200 sq ft

148 Bower Rd, Poughkeepsie, NY 12603

Listing by Serhant LLC

Property at 334 Lake Dr, Rhinebeck, NY 12572, 3 beds, 2.5 baths

$1,345,000

3 beds2.5 baths2,900 sq ft

334 Lake Dr, Rhinebeck, NY 12572

Listing by BHHS Hudson Valley Properties

Property at 7679 Albany Post Rd, Red Hook, NY 12571, 3 beds, 1 bath

$298,000

3 beds1 bath1,831 sq ft

7679 Albany Post Rd, Red Hook, NY 12571

Listing by Upstate Down

Property at 11 Cambridge Dr, Red Hook, NY 12571, 3 beds, 1 bath

$409,900

3 beds1 bath1,400 sq ft

11 Cambridge Dr, Red Hook, NY 12571

Listing by Margaret Mondello Real Estate

Property at 27 Osborne Hill Rd, Wappingers Falls, NY 12590, 4 beds, 1.5 baths

$499,000

4 beds1.5 baths1,296 sq ft

27 Osborne Hill Rd, Wappingers Falls, NY 12590

Listing by BHHS Hudson Valley Properties

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 22 Old Mill Rd, Poughkeepsie, NY 12603, 4 beds, 3 baths

$449,900

4 beds3 baths3,156 sq ft

22 Old Mill Rd, Poughkeepsie, NY 12603

Listing by BHHS Hudson Valley Properties

Property at 94 South Ave, Poughkeepsie, NY 12601, 7 beds, 3 baths

$329,900

7 beds3 baths2,200 sq ft

94 South Ave, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 13 Hooker Ave, Poughkeepsie, NY 12601, 2 beds, 2 baths

$309,000

2 beds2 baths— sq ft

13 Hooker Ave, Poughkeepsie, NY 12601

Listing by K. Fortuna Realty, Inc.

Property at 2101 Bruzgul Rd, Lagrangeville, NY 12540, 5 beds, 2.5 baths

$950,000

5 beds2.5 baths3,644 sq ft

2101 Bruzgul Rd, Lagrangeville, NY 12540

Listing by BHHS Hudson Valley Properties

Property at 5 Douglas, Wappingers Falls, NY 12590, 5 beds, 3 baths

$799,900

5 beds3 baths3,600 sq ft

5 Douglas, Wappingers Falls, NY 12590

Listing by K. Fortuna Realty, Inc.

Property at 5846 S Elm Ave, Millerton, NY 12546, 4 beds, 2 baths

$299,000

4 beds2 baths2,304 sq ft

5846 S Elm Ave, Millerton, NY 12546

Listing by Havens Real Estate

Property at 45 Hitchcock Ln, Millbrook, NY 12545, 10 beds, 7 baths

$65,000,000

10 beds7 baths14,706 sq ft

45 Hitchcock Ln, Millbrook, NY 12545

Listing by William Pitt Sothebys Int Rlty

Property at 645 Tyrrel Rd, Millbrook, NY 12545, 5 beds, 4 baths

$1,525,000

5 beds4 baths4,410 sq ft

645 Tyrrel Rd, Millbrook, NY 12545

Listing by William Pitt Sothebys Int Rlty

Property at 320 Mansion St, Poughkeepsie, NY 12601, 5 beds, 2 baths

$335,000

5 beds2 baths2,272 sq ft

320 Mansion St, Poughkeepsie, NY 12601

Listing by HomeSmart Homes & Estates

Property at 57 E Main St, Beacon, NY 12508, 1 bath

$1,599,000

0 beds1 bath6,052 sq ft

57 E Main St, Beacon, NY 12508

Listing by Compass Greater NY, LLC

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 10 Memory Ln, Poughkeepsie, NY 12603, 3 beds, 1.5 baths

$425,000

3 beds1.5 baths1,534 sq ft

10 Memory Ln, Poughkeepsie, NY 12603

Listing by Coldwell Banker Realty

Property at 47 Main St, Wappingers Falls, NY 12590, 5 beds, 3 baths

$650,000

5 beds3 baths2,808 sq ft

47 Main St, Wappingers Falls, NY 12590

Listing by Staley Real Estate, LLC

Property at 25 Carroll St #25, Poughkeepsie, NY 12601, 2 beds, 3 baths

$499,000

2 beds3 baths2,100 sq ft

25 Carroll St #25, Poughkeepsie, NY 12601

Listing by Dixon Smith Realty

Property at 10 Vail Ave, Beacon, NY 12508, 3 beds, 1.5 baths

$598,700

3 beds1.5 baths1,472 sq ft

10 Vail Ave, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 1388 Route 83, Pine Plains, NY 12567, 4 beds, 4.5 baths

$840,000

4 beds4.5 baths3,000 sq ft

1388 Route 83, Pine Plains, NY 12567

Listing by Houlihan Lawrence Inc.

Property at 7668 Route 82, Pine Plains, NY 12567, 4 beds, 1.5 baths

$875,000

4 beds1.5 baths2,709 sq ft

7668 Route 82, Pine Plains, NY 12567

Listing by George T Whalen Real Estate

Property at 198 Tinkertown Rd, Salt Point, NY 12578, 2 beds, 1 bath

$315,000

2 beds1 bath1,186 sq ft

198 Tinkertown Rd, Salt Point, NY 12578

Listing by BHHS Hudson Valley Properties

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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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