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

401 homes

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NEW 15 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
* * Charming, affordable, and full of potential! * * This inviting 2-bedroom bungalow in Poughkeepsie offers a great opportunity to own a home with character and make it your own. Partially renovated and ready for your finishing touches, the home features new vinyl plank flooring throughout and a surprisingly spacious interior. The comfortable living room features a unique spiral staircase leading to a versatile loft area, complete with additional attic storage. A formal dining room sits conveniently adjacent to the kitchen, while an enclosed porch/mudroom provides easy access to the driveway, making everyday tasks like bringing in groceries a breeze. Two bedrooms and a full bathroom com

$210,000

2 beds1 bath972 sq ft

34 Mckinley Ln, Poughkeepsie, NY 12601

Level backyard • Enclosed porch • Fenced front yard

Listing by Howard Hanna Rand Realty

NEW 3 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
A rare opportunity to enjoy the best of village living, this beautifully maintained and thoughtfully renovated Millbrook property pairs timeless character with modern convenience and exceptional versatility. The three-bedroom, two-bath main residence offers 2,132 square feet of comfortable living space. A charming carriage house features a one-bedroom, one-bath apartment, built in 2018, encompassing approximately 1,000 additional square feet. There is also a gym, and a 2 car garage. Rich in potential, the carriage house offers an ideal setting for guests, extended family, or rental income, adding a valuable layer of flexibility to this distinctive offering. Originally built in 1920, the mai

$1,225,000

4 beds3 baths3,068 sq ft

3311 Franklin Ave, Millbrook, NY 12545

Bluestone patios • 9,148 sq ft lot • 2 garage spots

Listing by Compass Greater NY, LLC

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Renovation opportunity in a convenient Poughkeepsie location! This single-level ranch offers 4 bedrooms, 1 full bath, and a nearly level quarter-acre lot with mature trees, driveway parking, and a large storage shed. The home requires significant work and is being offered strictly as-is. Natural gas service has been shut off, and the property currently has no heat or hot water. The location offers convenient access to the Hudson River, Walkway Over the Hudson, Vassar College, Marist University, Dutchess Community College, and the Culinary Institute of America. An opportunity for an investor, contractor, or buyer ready to take on a renovation project and create value. Bring your vision and e

$270,000

4 beds1 bath1,196 sq ft

158 Violet Ave, Poughkeepsie, NY 12601

Single-level ranch • Quarter-acre lot • Large storage shed

Listing by Berkshire Hathaway HS NY Prop

NEW 20 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to 182 Mill Street, a beautifully renovated two-family home offering an exceptional opportunity for an owner-occupant or investor. Each unit features 3 bedrooms and 1 full bathroom, providing spacious and versatile living arrangements. The property has been completely gutted and renovated within the past two years, leaving little for a new owner to worry about. Updates include quartz countertops, stainless steel appliances, updated kitchens and bathrooms, new plumbing and electrical wiring, updated heating systems and hot water, furnaces, and much more. The extensive renovations offer the peace of mind of owning a property where the major systems have already been addressed. Another

$499,000

6 beds2 baths2,360 sq ft

182 Mill St, Poughkeepsie, NY 12601

Quartz countertops • New plumbing • Updated bathrooms

Listing by KW MidHudson

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
* * * Note that the list price is NOT indicative of the seller's final reserve amount; it is just the starting auction bid amount * * * This 2345 SF ranch home sits on an 1.32 acre lot. This property is eligible under the Freddie Mac First Look Initiative through 10/27/2026. It is sold only to owner-occupants, non-profit organizations, and government entities during the First Look period. This property is part of an online bidding event; please visit the Auction company's website to place a bid and contact your real estate agent for auction bidding instructions. Inspections of this property and contact with occupants are strictly prohibited. Property is sold "as is" with NO i

$275,000

3 beds2 baths2,345 sq ft

300 W Market St, Red Hook, NY 12571

1.32 acre lot • 3 garage spots • Pool

Listing by Rising Star Realty

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 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

Property at 26 Oakwood Blvd, Poughkeepsie, NY 12603, 3 beds, 1.5 baths

$360,000

3 beds1.5 baths2,028 sq ft

26 Oakwood Blvd, Poughkeepsie, NY 12603

Listing by KW Hudson Valley United

Property at 30 Old Post Rd, Red Hook, NY 12571, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths3,424 sq ft

30 Old Post Rd, Red Hook, NY 12571

Listing by Mondello Upstate Properties

Property at 10 Robinson St, Beacon, NY 12508, 3 beds, 3 baths

$795,000

3 beds3 baths1,600 sq ft

10 Robinson St, Beacon, NY 12508

Listing by KW MidHudson

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 11 Bloomer Rd, Lagrangeville, NY 12540, 3 beds, 2 baths

$449,000

3 beds2 baths1,866 sq ft

11 Bloomer Rd, Lagrangeville, NY 12540

Listing by KW MidHudson

Property at 3 Liss Rd, Wappingers Falls, NY 12590, 3 beds, 1 bath

$445,000

3 beds1 bath1,420 sq ft

3 Liss Rd, Wappingers Falls, NY 12590

Listing by KW MidHudson

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

$599,000

5 beds3 baths3,375 sq ft

5 Douglas Dr, Wappingers Falls, NY 12590

Listing by KW Hudson Valley North

Property at 21 Meads Ln, Stormville, NY 12582, 3 beds, 1.5 baths

$550,000

3 beds1.5 baths1,824 sq ft

21 Meads Ln, Stormville, NY 12582

Listing by KW Hudson Valley United

Property at 669 Vassar Rd, Poughkeepsie, NY 12603, 3 beds, 2 baths

$479,999

3 beds2 baths1,573 sq ft

669 Vassar Rd, Poughkeepsie, NY 12603

Listing by William Raveis Real Estate

Property at 13 Kirchner Ave, Hyde Park, NY 12538, 4 beds, 1.5 baths

$529,500

4 beds1.5 baths1,597 sq ft

13 Kirchner Ave, Hyde Park, NY 12538

Listing by K. Fortuna Realty, Inc.

Property at 17 Garden St, Red Hook, NY 12571, 3 beds, 2.5 baths

$875,000

3 beds2.5 baths1,887 sq ft

17 Garden St, Red Hook, NY 12571

Listing by Rouse + Co Real Estate LLC

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 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 70 E Main St, Wappingers Falls, NY 12590, 6 beds, 2 baths

$4,200,000

6 beds2 baths9,052 sq ft

70 E Main St, Wappingers Falls, NY 12590

Listing by Tactical Realty LLC

Property at 3346 Route 343, Amenia, NY 12501, 8 beds, 4 baths

$699,000

8 beds4 baths2,304 sq ft

3346 Route 343, Amenia, NY 12501

Listing by eXp Realty

$799,000

4 beds2.5 baths2,584 sq ft

23 S Creek Rd, Staatsburg, NY 12580

$649,000

Studio— baths3,465 sq ft

2676 W Main St, Wappingers Falls, NY 12590

Listing by Sams 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 43 Laffin Ln, Poughkeepsie, NY 12603, 5 beds, 2 baths

$484,000

5 beds2 baths2,256 sq ft

43 Laffin Ln, Poughkeepsie, NY 12603

Listing by BHHS Hudson Valley Properties

Property at 1 Norah Ln, Hyde Park, NY 12538, 3 beds, 1.5 baths

$419,900

3 beds1.5 baths2,370 sq ft

1 Norah Ln, Hyde Park, NY 12538

Listing by HomeSmart Homes & Estates

Property at 64 North Rd, Tivoli, NY 12583, 2 beds, 1 bath

$479,000

2 beds1 bath1,416 sq ft

64 North Rd, Tivoli, NY 12583

Listing by Houlihan Lawrence Inc.

Property at 15 S Walnut St, Beacon, NY 12508, 2 beds, 2 baths

$499,900

2 beds2 baths1,074 sq ft

15 S Walnut St, Beacon, NY 12508

Listing by Sams Realty

Property at 121 First Rd, Wappingers Falls, NY 12590, 4 beds, 1 bath

$399,999

4 beds1 bath1,290 sq ft

121 First Rd, Wappingers Falls, NY 12590

Listing by Exit Realty Connections

Property at 295 Baxtertown Rd, Fishkill, NY 12524, 3 beds, 2 baths

$500,000

3 beds2 baths2,005 sq ft

295 Baxtertown Rd, Fishkill, NY 12524

Listing by RE/MAX Benchmark Realty Group

Property at 9 Horns Park Rd, Hyde Park, NY 12538, 3 beds, 2 baths

$425,000

3 beds2 baths2,207 sq ft

9 Horns Park Rd, Hyde Park, NY 12538

Listing by eXp Realty

Property at 6 Woods Rd, Rhinebeck, NY 12572, 2 beds, 1 bath

$319,000

2 beds1 bath968 sq ft

6 Woods Rd, Rhinebeck, NY 12572

Listing by Real Broker NY LLC

Property at 15 Merry Hill Rd, Poughkeepsie, NY 12603, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths1,891 sq ft

15 Merry Hill Rd, Poughkeepsie, NY 12603

Listing by RE/MAX Town & Country

Property at 136 Bundy Hill Rd, Holmes, NY 12531, 2 beds, 2 baths

$395,000

2 beds2 baths920 sq ft

136 Bundy Hill Rd, Holmes, NY 12531

Listing by Compass Greater NY, LLC

Property at 32 Fairview Rd, Beacon, NY 12508, 2 beds, 1 bath

$395,000

2 beds1 bath1,312 sq ft

32 Fairview Rd, Beacon, NY 12508

Listing by BHHS Hudson Valley Properties

Property at 280 Noxon Rd, Lagrangeville, NY 12603, 3 beds, 2 baths

$399,999

3 beds2 baths1,345 sq ft

280 Noxon Rd, Lagrangeville, NY 12603

Listing by eXp Realty

Property at 5 Vail Rd, Poughkeepsie, NY 12603, 5 beds, 3.5 baths

$729,900

5 beds3.5 baths2,628 sq ft

5 Vail Rd, Poughkeepsie, NY 12603

Listing by Houlihan Lawrence Inc.

Property at 13 East St, Beacon, NY 12508, 3 beds, 2.5 baths

$879,900

3 beds2.5 baths2,590 sq ft

13 East St, Beacon, NY 12508

Listing by Century 21 Alliance Rlty Group

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Based on information submitted to the MLS GRID as of Tue Oct 13 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 401 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 113 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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