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

412 homes

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OPEN SAT, 2PM TO 5PM

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Some places have a way of finding a place in your heart. Set along beautiful Lake Dutchess, this contemporary two-bedroom, one-bath home is one of those rare places where the days seem to slow down, the views invite you to linger, and life feels a little more magical. Owned by architects James Evanson and Lisa Evanson, founders of Evanson Studios, this special lakefront retreat reflects a thoughtful connection between architecture and its natural surroundings. Beautiful lake views set the scene for serene morning coffees, afternoon daydreams, and evenings spent gathered around the firepit beneath a sky full of stars. A dock offers a front-row seat to lake life, whether you're heading out on

$599,000

2 beds1 bath1,034 sq ft

10 Dutchess Cv, Holmes, NY 12531

Lakefront retreat • Viking stove • Firepit

Listing by Compass Greater NY, LLC

NEW 14 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Unlock the true potential of this charming * * 2-bedroom, 1-bathroom ranch * * set on * * 3.6 pristine, scenic acres * * in the heart of Salt Point, New York. Situated in the highly sought-after * * Millbrook School District * * , this versatile property represents a rare canvas for a wide range of buyers. Whether you are an ambitious investor searching for your next high-value renovation, a homebuyer eager to customize a space and build substantial equity, or a city dweller seeking a peaceful weekend sanctuary away from the hustle, this home offers a foundation rich with opportunity. Step outside into an idyllic sanctuary where nature takes center stage. The gently rolling groun

$275,000

2 beds1 bath1,056 sq ft

5150 Route 82, Salt Point, NY 12578

Private sanctuary • Rolling grounds • Fire pit

Listing by eXp Realty

OPEN SUN, 12PM TO 2PM

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Tastefully updated 3 bedroom, 1.5 bath ranch situated on attractive park-like property. Remodeled kitchen w/ new cabinets, quartz counters & stainless appliances flows seamlessly to living room w/ stone fireplace. Three well proportioned bedrooms. Updated full bathroom plus half bathroom off mudroom, which also provides access to main level laundry room. Oversized one car garage and unfinished basement for abundant storage. New propane furnace, roof & driveway. Centrally located and just minutes from Village of Millbrook, Village of Rhinebeck, Taconic State Parkway & Poughkeepsie train station. One level living at its finest.

$399,000

3 beds1.5 baths1,300 sq ft

15 Balsam Rd, Hyde Park, NY 12538

New propane furnace • Remodeled kitchen • Unfinished basement

Listing by BHHS Hudson Valley Properties

NEW 14 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to your peaceful Hudson Valley retreat! This adorable and spacious 2-bedroom, 1-bathroom home at 1336 Route 343 offers the perfect blend of cozy charm, commuter convenience, and expansive privacy, nestled on over 7.5 pristine acres of land. Interior Highlights: • Bright & Airy Living: Enjoy a very spacious, light-filled layout boasting beautiful hardwood floors throughout. • Cozy Evenings: Gather around the warm and inviting fireplace, which serves as the centerpiece of the living space. Exterior & Land Features: • Outdoor Living: Step outside onto a wonderful, large deck designed for entertaining, relaxing, or enjoying your morning coffee. • Scenic V

$450,000

2 beds1 bath2,036 sq ft

1336 Route 343, Dover Plains, NY 12522

Large deck • Over 7.5 acres • Large 2 story barn

Listing by eXp Realty

NEW 19 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Discover this charming home with endless potential in the heart of Pleasant Valley, Dutchess County. This beautiful colonial-style residence offers timeless character, natural serenity, and a true indoor-outdoor lifestyle. With direct access to a tranquil creek from your backyard, this over 2,900 square feet home is perfect for unwinding in nature, listening to the soothing sounds of the water, or enjoying a peaceful evening by the fire pit under the stars. This light-filled 3-bedroom, 2-bath home features a flexible layout with a separate area ideal for guests. The open-concept design allows the main living spaces to flow seamlessly into one another, creating an inviting, airy feel that&rs

$400,000

3 beds1.5 baths2,992 sq ft

1675 Main St, Pleasant Valley, NY 12569

Sunlit room • Park-like setting • 0.56 acre lot

Listing by RE/MAX Town & Country

Property at 21 Fishkill Rd, Hopewell Junction, NY 12533, 8 beds, 2 baths

$519,000

8 beds2 baths3,388 sq ft

21 Fishkill Rd, Hopewell Junction, NY 12533

Listing by Joncar Realty Inc

Property at 594 Washington Ave, Beacon, NY 12508, 2 beds, 2 baths

$585,000

2 beds2 baths1,513 sq ft

594 Washington Ave, Beacon, NY 12508

Listing by Compass Greater NY, LLC

Property at 214 Old Hopewell Rd, Wappingers Falls, NY 12590, 2 beds, 1 bath

$325,000

2 beds1 bath990 sq ft

214 Old Hopewell Rd, Wappingers Falls, NY 12590

Listing by Howard Hanna Rand Realty

Property at 943 Main St, Fishkill, NY 12524, 4 beds, 2 baths

$500,000

4 beds2 baths1,808 sq ft

943 Main St, Fishkill, NY 12524

Listing by BHHS Hudson Valley Properties

Property at 156 Red Schoolhouse Rd, Fishkill, NY 12524, 3 beds, 3 baths

$649,500

3 beds3 baths2,123 sq ft

156 Red Schoolhouse Rd, Fishkill, NY 12524

Listing by KW MidHudson

Property at 143 Hooker Ave, Poughkeepsie, NY 12601, 3 beds, 1.5 baths

$499,000

3 beds1.5 baths2,092 sq ft

143 Hooker Ave, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 41 Antler Club Rd, Pine Plains, NY 12567, 4 beds, 2.5 baths

$679,000

4 beds2.5 baths1,809 sq ft

41 Antler Club Rd, Pine Plains, NY 12567

Listing by Thomas Zengen

Property at 177 White Schoolhouse Rd, Rhinebeck, NY 12572, 2 beds, 2 baths

$685,000

2 beds2 baths1,632 sq ft

177 White Schoolhouse Rd, Rhinebeck, NY 12572

Listing by Atelier WM LLC

Property at 389 Route 199, Red Hook, NY 12571, 3 beds, 1 bath

$449,000

3 beds1 bath1,792 sq ft

389 Route 199, Red Hook, NY 12571

Listing by Houlihan Lawrence Inc.

Property at 195 Drake Rd, Pleasant Valley, NY 12569, 3 beds, 3 baths

$799,000

3 beds3 baths3,139 sq ft

195 Drake Rd, Pleasant Valley, NY 12569

Listing by Corcoran Country Living

Property at 20 Memory Ln, Poughkeepsie, NY 12603, 4 beds, 2.5 baths

$445,000

4 beds2.5 baths1,729 sq ft

20 Memory Ln, Poughkeepsie, NY 12603

Listing by eXp Realty

Property at 19 Russell Ave, Rhinebeck, NY 12572, 3 beds, 3 baths

$800,000

3 beds3 baths2,154 sq ft

19 Russell Ave, Rhinebeck, NY 12572

Property at 23 Mansion Dr, Hyde Park, NY 12538, 4 beds, 2 baths

$429,900

4 beds2 baths1,231 sq ft

23 Mansion Dr, Hyde Park, NY 12538

Listing by K. Fortuna Realty, Inc.

Property at 10 Barrett Dr, Hopewell Junction, NY 12533, 1.5 baths

$589,000

Studio1.5 baths2,224 sq ft

10 Barrett Dr, Hopewell Junction, NY 12533

Listing by Century 21 Alliance Rlty Group

Property at 12 Gary Dr, Hyde Park, NY 12538, 4 beds, 2 baths

$299,000

4 beds2 baths— sq ft

12 Gary Dr, Hyde Park, NY 12538

Listing by K. Fortuna Realty, Inc.

Property at 7786 S Main St, Pine Plains, NY 12567, 4 beds, 1.5 baths

$425,000

4 beds1.5 baths3,072 sq ft

7786 S Main St, Pine Plains, NY 12567

Listing by Mondello Upstate Properties

Property at 7 Lewis Ave, Poughkeepsie, NY 12603, 3 beds, 1.5 baths

$350,000

3 beds1.5 baths1,308 sq ft

7 Lewis Ave, Poughkeepsie, NY 12603

Listing by Legacy Land & Homes LLC

Property at 25 Rymph Blvd, Poughkeepsie, NY 12601, 2 beds, 1 bath

$329,900

2 beds1 bath902 sq ft

25 Rymph Blvd, Poughkeepsie, NY 12601

Listing by McNiff Real Estate LTD

Property at 206 Old Route 22, Wassaic, NY 12592, 3 beds, 1 bath

$279,000

3 beds1 bath1,360 sq ft

206 Old Route 22, Wassaic, NY 12592

Listing by BHHS Hudson Valley Properties

Property at 23 Lake Dr, Holmes, NY 12531, 1 bed, 1 bath

$374,999

1 bed1 bath768 sq ft

23 Lake Dr, Holmes, NY 12531

Listing by eRealty Advisors, Inc

Property at 23 S Creek Rd, Staatsburg, NY 12580, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths2,584 sq ft

23 S Creek Rd, Staatsburg, NY 12580

Listing by Compass Greater NY, LLC

Property at 256 E Main St, Beacon, NY 12508, 3 beds, 2 baths

$799,000

3 beds2 baths1,696 sq ft

256 E Main St, Beacon, NY 12508

Listing by Compass Greater NY, LLC

Property at 5829 Route 22, Millerton, NY 12546, 3 beds, 2.5 baths

$514,999

3 beds2.5 baths2,880 sq ft

5829 Route 22, Millerton, NY 12546

Listing by eXp Realty

Property at 19 Russell Ave, Rhinecliff, NY 12574, 3 beds, 3 baths

$800,000

3 beds3 baths2,154 sq ft

19 Russell Ave, Rhinecliff, NY 12574

Listing by Corcoran Country Living

Property at 46 Old Post Rd, Staatsburg, NY 12580, 4 beds, 3 baths

$499,000

4 beds3 baths2,058 sq ft

46 Old Post Rd, Staatsburg, NY 12580

Listing by Jeff S. Colton

Property at 19 Greentree Dr S, Hyde Park, NY 12538, 3 beds, 1 bath

$355,000

3 beds1 bath1,308 sq ft

19 Greentree Dr S, Hyde Park, NY 12538

Listing by Dixon Smith Realty

Property at 17 N Clover St, Poughkeepsie, NY 12601, 5 beds, 3 baths

$499,000

5 beds3 baths— sq ft

17 N Clover St, Poughkeepsie, NY 12601

Listing by Clarke Realty & Associates LLC

Property at 16 Hanna Ln, Beacon, NY 12508, 7 beds, 9 baths

$2,800,000

7 beds9 baths8,000 sq ft

16 Hanna Ln, Beacon, NY 12508

Listing by McGrath Realty Inc

Property at 2676 W Main St, Wappingers Falls, NY 12590

$649,000

Studio— baths3,465 sq ft

2676 W Main St, Wappingers Falls, NY 12590

Listing by Sams Realty

Property at 201 Bower Rd, Poughkeepsie, NY 12603, 3 beds, 1 bath

$395,000

3 beds1 bath1,308 sq ft

201 Bower Rd, Poughkeepsie, NY 12603

Listing by Coldwell Banker Realty

Property at 3311 Franklin Ave, Millbrook, NY 12545, 4 beds, 3 baths

$1,225,000

4 beds3 baths3,068 sq ft

3311 Franklin Ave, Millbrook, NY 12545

Listing by Compass Greater NY, LLC

Property at 360 Old State Route 22, Dover Plains, NY 12522, 4 beds, 4 baths

$775,000

4 beds4 baths2,234 sq ft

360 Old State Route 22, Dover Plains, NY 12522

Listing by BHHS Hudson Valley Properties

Property at 300 W Market St, Red Hook, NY 12571, 3 beds, 2 baths

$275,000

3 beds2 baths2,345 sq ft

300 W Market St, Red Hook, NY 12571

Listing by Rising Star Realty

Property at 34 Mckinley Ln, Poughkeepsie, NY 12601, 2 beds, 1 bath

$210,000

2 beds1 bath972 sq ft

34 Mckinley Ln, Poughkeepsie, NY 12601

Listing by Howard Hanna Rand 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 158 Violet Ave, Poughkeepsie, NY 12601, 4 beds, 1 bath

$270,000

4 beds1 bath1,196 sq ft

158 Violet Ave, Poughkeepsie, NY 12601

Listing by Berkshire Hathaway HS NY Prop

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Based on information submitted to the MLS GRID as of Tue Oct 20 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 412 vintage homes for sale in Dutchess County at a median listing price of $560K. 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, 226 homes have been sold in Dutchess County. In addition to houses in Dutchess County, there were also 112 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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