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:
AMAZING OWNER OCCUPIED OR INVESTMENT OPPORTUNITY! In the heart of Stormville is a 2-story mixed-use Ranch style building-(ground floor warehouse, 2nd floor office and 1BR apartment) and an updated 2 BR cottage on four acres total spread over 2 parcels. Amazing location just off NY-52, less than 5mi to I-84. Currently all units are below-market rents, with Pro Forma NOI greater than $75,000. Warehouse/office is on a short-term lease and could vacate within 30 days, which presents an opportunity for a contractor (GC, HVAC, pest control, flooring, etc. ) to occupy the entire warehouse and utilize the large gravel lot for outdoor storage. Property is zoned R-2, and warehouse/storage is a contin

$875,000

3 beds2 baths6,468 sq ft

553 Hosner Mountain Rd, Stormville, NY 12582

Large gravel lot • Zoned r-2 • Updated cottage

Listing by KW MidHudson

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to 23 S Creek Rd – In the heart of Staatsburg, this well-maintained 4-bedroom, 2.5-bath farmhouse perfectly balances timeless charm with modern functionality — ideal for those seeking a live/work lifestyle in the heart of the Hudson Valley. The home’s curved wrap-around front porch and detailed trim work showcase its classic farmhouse character. Inside, natural light fills warm and inviting spaces designed for comfort and connection. The kitchen flows seamlessly into the dining and living areas, perfect for family gatherings or entertaining. Upstairs, four bedrooms provide room for everyone and don't miss the walk up attic — offering flexibility for a home of

$950,000

4 beds2.5 baths2,584 sq ft

23 S Creek Rd, Staatsburg, NY 12580

1.6 acre lot • 2 garage spots • Pool

Listing by Compass Greater NY, LLC

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Move right into this pristine, three bedroom, two-bathroom, recently renovated home where easy living becomes daily reality! With a beautiful, two-acre setting in the charming Hamlet of Wiccopee, this home typifies what country living is all about. It flaunts an open concept with exposed beams, gleaming hardwood floors, modern kitchen as well as a magnificent main bedroom suite with a walk-in closet. Big enough for a growing family and small enough if you're looking to downsize. A wood-burning stove makes this house a cozy, energy-efficient option that is conveniently located just minutes from I-84 and the Taconic State Parkway.

$525,000

3 beds2 baths1,652 sq ft

4 Pine Ln, Hopewell Junction, NY 12533

Open concept • Main bedroom suite • Two acre setting

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to 7 Phillips Road — a beautifully updated Cape Cod-style home in the Town of Poughkeepsie, offering comfort, charm, and modern living! This 3-bedroom, 2.5-bath home features a bright and inviting layout with gleaming hardwood floors, an updated kitchen with stainless steel appliances, and spacious living and dining areas perfect for entertaining. The first-floor primary suite offers a private retreat with a stand-up shower, while the two generously sized bedrooms upstairs provide plenty of space for family, guests, or a home office. Enjoy bright and open living spaces, a modern kitchen with a propane stove, stainless appliances, and a reverse osmosis water filter, perfect for

$450,000

3 beds2.5 baths1,880 sq ft

7 Phillips Rd, Poughkeepsie, NY 12603

Stand-up shower • Propane stove • Updated kitchen

Listing by Keller Williams Realty

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Tastefully updated and well maintained City of Poughkeepsie three family. Featuring two 3 bedroom units and unique 1 bedroom unit w/ cathedral ceiling & loft. Apartments featuring recent interior updates plus updated mechanicals including three newer gas boiler & three newer electric water heaters. Separate utilities, off street parking and spacious backyard. Central location with easy access to schools, shopping, dining, commuter routes, trains and Poughkeepsie waterfront. An exceptional investment opportunity.

$600,000

7 beds3 baths2,844 sq ft

18 S Clinton St, Poughkeepsie, NY 12601

Loft • Newer gas boiler • Updated mechanicals

Listing by BHHS Hudson Valley Properties

Property at 671 Noxon Rd, Poughkeepsie, NY 12603, 4 beds, 4.5 baths

$649,000

4 beds4.5 baths3,030 sq ft

671 Noxon Rd, Poughkeepsie, NY 12603

Listing by Hudson Modern Co

Property at 191 White Schoolhouse Rd, Rhinebeck, NY 12572, 3 beds, 2.5 baths

$1,495,000

3 beds2.5 baths1,871 sq ft

191 White Schoolhouse Rd, Rhinebeck, NY 12572

Listing by Staley Real Estate, LLC

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

$280,000

3 beds1.5 baths1,162 sq ft

17 Fishkill Hook Rd, Hopewell Junction, NY 12533

Listing by BHHS Hudson Valley Properties

Property at 4 Railroad Ave, Staatsburg, NY 12580, 4 beds, 2 baths

$729,000

4 beds2 baths2,450 sq ft

4 Railroad Ave, Staatsburg, NY 12580

Listing by Corcoran Country Living

Property at 2 Haggerty Hill Rd, Rhinebeck, NY 12572, 2 beds, 2 baths

$559,500

2 beds2 baths1,550 sq ft

2 Haggerty Hill Rd, Rhinebeck, NY 12572

Listing by BHHS Hudson Valley Properties

Property at 32 Greentree Dr N, Hyde Park, NY 12538, 3 beds, 2 baths

$429,500

3 beds2 baths1,543 sq ft

32 Greentree Dr N, Hyde Park, NY 12538

Listing by Realty Center Hudson Valley

Property at 35 Rapalje Rd, Fishkill, NY 12524, 4 beds, 3 baths

$619,000

4 beds3 baths2,350 sq ft

35 Rapalje Rd, Fishkill, NY 12524

Listing by OXM Realty Group LLC

Property at 18 Hummingbird Way, Staatsburg, NY 12580, 3 beds, 1 bath

$372,500

3 beds1 bath1,387 sq ft

18 Hummingbird Way, Staatsburg, NY 12580

Listing by BHHS Hudson Valley Properties

Property at 84 North Rd, Red Hook, NY 12571, 3 beds, 1 bath

$325,000

3 beds1 bath1,440 sq ft

84 North Rd, Red Hook, NY 12571

Listing by Mondello Upstate Properties

Property at 27 Peckham Rd, Poughkeepsie, NY 12603, 2 beds, 1 bath

$260,000

2 beds1 bath848 sq ft

27 Peckham Rd, Poughkeepsie, NY 12603

Listing by Keller Williams Hudson Valley

Property at 30 Old Post Rd N, Red Hook, NY 12571, 5 beds, 2.5 baths

$874,000

5 beds2.5 baths3,424 sq ft

30 Old Post Rd N, Red Hook, NY 12571

Listing by RE/MAX Town & Country

Property at 33 Thompson St, Red Hook, NY 12571, 3 beds, 1 bath

$369,000

3 beds1 bath1,496 sq ft

33 Thompson St, Red Hook, NY 12571

Listing by Mondello Upstate Properties

Property at 121-125 Butts Hollow Rd, Millbrook, NY 12545, 9 beds, 9.5 baths

$11,995,000

9 beds9.5 baths13,737 sq ft

121-125 Butts Hollow Rd, Millbrook, NY 12545

Listing by Douglas Elliman Real Estate

Property at 71 Honeywell Ln, Hyde Park, NY 12538, 3 beds, 1 bath

$295,000

3 beds1 bath868 sq ft

71 Honeywell Ln, Hyde Park, NY 12538

Listing by K. Fortuna Realty, Inc.

Property at 35 Seitz Ter, Poughkeepsie, NY 12603, 4 beds, 2 baths

$410,000

4 beds2 baths1,510 sq ft

35 Seitz Ter, Poughkeepsie, NY 12603

Listing by Exit Realty Connections

Property at 18 Cambridge Dr, Red Hook, NY 12571, 3 beds, 1 bath

$349,900

3 beds1 bath1,054 sq ft

18 Cambridge Dr, Red Hook, NY 12571

Listing by BHHS Hudson Valley Properties

Property at 11 Franklin St, Poughkeepsie, NY 12601, 8 beds, 4 baths

$690,000

8 beds4 baths5,520 sq ft

11 Franklin St, Poughkeepsie, NY 12601

Listing by RE/MAX Town & Country

Property at 84 Fairview Ave, Poughkeepsie, NY 12601, 4 beds, 1 bath

$325,000

4 beds1 bath1,176 sq ft

84 Fairview Ave, Poughkeepsie, NY 12601

Listing by RMB & Associates

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 13 Garfield Pl, Poughkeepsie, NY 12601, 4 beds, 3.5 baths

$474,999

4 beds3.5 baths3,354 sq ft

13 Garfield Pl, Poughkeepsie, NY 12601

Listing by BHHS River Towns Real Estate

Property at 162 Spring Valley St, Beacon, NY 12508, 3 beds, 1.5 baths

$610,000

3 beds1.5 baths1,250 sq ft

162 Spring Valley St, Beacon, NY 12508

Listing by OXM Realty Group LLC

Property at 1 Essex Rd, Poughkeepsie, NY 12601, 3 beds, 2.5 baths

$384,900

3 beds2.5 baths1,248 sq ft

1 Essex Rd, Poughkeepsie, NY 12601

Listing by Century 21 Alliance Rlty Group

Property at 2261 Salt Point Tpke, Clinton Corners, NY 12514, 6 beds, 6.5 baths

$754,000

6 beds6.5 baths5,885 sq ft

2261 Salt Point Tpke, Clinton Corners, NY 12514

Listing by Grist Mill Real Estate

Property at 106 Skidmore Rd, Lagrangeville, NY 12540, 4 beds, 2 baths

$399,000

4 beds2 baths1,908 sq ft

106 Skidmore Rd, Lagrangeville, NY 12540

Listing by Houlihan Lawrence Inc.

Property at 34 Mountain View Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$375,000

3 beds1 bath1,558 sq ft

34 Mountain View Rd, Poughkeepsie, NY 12603

Listing by Compass Greater NY, LLC

Property at 750 Route 292, Holmes, NY 12531, 11 beds, 8 baths

$1,400,000

11 beds8 baths— sq ft

750 Route 292, Holmes, NY 12531

Listing by BHHS Hudson Valley Properties

Property at 175 Washington St, Poughkeepsie, NY 12601, 8 beds, 2 baths

$450,000

8 beds2 baths2,460 sq ft

175 Washington St, Poughkeepsie, NY 12601

Listing by KW MidHudson

Property at 108 Wey Rd, Rhinebeck, NY 12572, 4 beds, 2 baths

$1,800,000

4 beds2 baths3,167 sq ft

108 Wey Rd, Rhinebeck, NY 12572

Listing by Rouse + Co Real Estate LLC

Property at 32 Balding Ave, Poughkeepsie, NY 12601, 4 beds, 2 baths

$410,000

4 beds2 baths2,452 sq ft

32 Balding Ave, Poughkeepsie, NY 12601

Listing by Keller Williams Hudson Valley

Property at 31 Old Route 22, Wassaic, NY 12592, 4 beds

$229,000

4 beds— baths— sq ft

31 Old Route 22, Wassaic, NY 12592

Listing by Compass Greater NY, LLC

Property at 146 Forest Dr, Hyde Park, NY 12538, 3 beds, 2.5 baths

$725,000

3 beds2.5 baths2,183 sq ft

146 Forest Dr, Hyde Park, NY 12538

Listing by Compass Greater NY, LLC

Property at 11 Tree Top Ln, Poughkeepsie, NY 12603, 3 beds, 2 baths

$519,900

3 beds2 baths2,298 sq ft

11 Tree Top Ln, Poughkeepsie, NY 12603

Listing by Century 21 Alliance Rlty Group

Property at 10 Stagecoach Ln, Amenia, NY 12501, 4 beds, 1.5 baths

$675,000

4 beds1.5 baths3,624 sq ft

10 Stagecoach Ln, Amenia, NY 12501

Listing by RE/MAX Town & Country

Property at 21 Lent St, Poughkeepsie, NY 12601, 4 beds, 2 baths

$459,000

4 beds2 baths— sq ft

21 Lent St, Poughkeepsie, NY 12601

Listing by Clarke Realty & Associates LLC

Property at 404 Gretna Rd, Hyde Park, NY 12538, 5 beds, 3 baths

$650,000

5 beds3 baths3,000 sq ft

404 Gretna Rd, Hyde Park, NY 12538

Listing by BHHS Hudson Valley Properties

Property at 73 Lake Ellis Rd, Wingdale, NY 12594, 4 beds, 3 baths

$899,000

4 beds3 baths1,850 sq ft

73 Lake Ellis Rd, Wingdale, NY 12594

Listing by Keller Williams NY 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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