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:
Fully available. .. . Three family home located on a quiet street in the desirable South Side of Poughkeepsie. This home is in good condition and has been nicely maintained throughout the years. Improvements include replacement windows, exterior & interior painting, and new floors in some rooms. Gas boilers, municipal water and sewer. The heating systems and electric meters are fully separated for each unit so the tenant pays their own utilities. Rents are $1,550 + $1,650 + $1,750. Bedroom splits are 3 / 3 / 4. Invest in your future and come take a look at 77 Carroll Street! (Note : Photos are from a older listing and actual condition could be different than what is shown) Price is

$460,000

10 beds3 baths3,052 sq ft

77 Carroll St, Poughkeepsie, NY 12601

New floors • Municipal water • Interior painting

Listing by eXp Realty

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Rare redevelopment opportunity in newly established Campus Development zoning district, providing areas for educational, research and development and health care uses. Corner lot situated adjacent to Route 9 exit ramp for easy access to and from Route 9. Exceptional location with neighboring properties consisting of Vassar Hospital and Optum Medical. Permitted uses include medical, office, studio for performing arts, single family, multi-family or townhouses. Don't miss this opportunity in the thriving City of Poughkeepsie market. Cash offers only.

$275,000

3 beds1 bath1,350 sq ft

20 Columbia St, Poughkeepsie, NY 12601

Easy access • Corner lot • 3,920 sq ft lot

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Welcome to your private equestrian retreat, just 4 miles from the Harlem–Valley Wingdale Train Station, 4 miles to charming Kent, CT, a mile away to the Appalachian Trail & easy access to Route 7 & Route 22. Set on a secluded private road off Lake Ellis, this property offers both convenience & privacy. Equestrian amenities include a main barn with 6 (12x10) stalls w/ hay loft, heated wash stall, & tack room, plus a 3-stall shed row barn, four paddocks, & a fully fenced in 180’ x 90’ outdoor riding arena. A heated workshop w/ car lift, air compressor & ability to install work benches, along w/ a pristine 2-car garage featuring epoxy floorin

$899,000

4 beds3 baths1,850 sq ft

73 Lake Ellis Rd, Wingdale, NY 12594

8.92 acre lot • 2 garage spots • Built 1941

Listing by Keller Williams NY Realty

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Nestled in between trees and rocks, privacy abounds in this Contemporary Colonial style dwelling with numerous upgrades. A down to the studs remodel in 2016, the home boasts generous open concept living, dining and kitchen areas all with recessed lighting. Kitchen includes butcherblock counter tops and stainless-steel appliances. Entry nook convenient for coats, purses, backpacks and shoes. First floor en suite perfect for in home office with separate entrance to meet clients right at home - doubles as extra guest space. 2nd floor, naturally bright Family Room with hardwood floors, ceiling fan and vaulted ceiling. Sliding glass door to large deck, existing hookups for the possibility of a h

$537,500

3 beds3.5 baths2,106 sq ft

101 Bundy Hill Rd, Holmes, NY 12531

First floor en suite • Entry nook • 0.5 acre lot

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Dutchess County, NY:
Built circa 1790, this idyllic, 3193 square foot home is the country oasis you have been seeking. Only 1 3/4 hours from NYC, swim in your private pond, stroll through your private woods and relax in the peacefulness of this charming Hudson Valley homestead. With 3 (possibly 4) bedrooms, 2 1/2 bathrooms, a formal dining room and the very large, original timber-beamed living room with a large 18th century, wood-burning fireplace. Features include gorgeous wide-board floors, original moldings and high ceilings throughout both floors. There is a half-bath on the first floor as well as another room which could easily be used as a bedroom. There are 2 full baths on the second floor as well as a

$1,500,000

3 beds2.5 baths3,193 sq ft

1606 Bulls Head Rd, Stanfordville, NY 12581

Private woods • Private pond • Original moldings

Property at 25 Garfield Pl, Poughkeepsie, NY 12601, 4 beds, 2.5 baths

$649,900

4 beds2.5 baths3,042 sq ft

25 Garfield Pl, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 50 Glanhope Rd #23, Hopewell Junction, NY 12533, 1 bed, 1 bath

$49,999

1 bed1 bath750 sq ft

50 Glanhope Rd #23, Hopewell Junction, NY 12533

Listing by Houlihan Lawrence Inc.

Property at 29 Kelsey Rd, Poughkeepsie, NY 12601, 3 beds, 1.5 baths

$440,000

3 beds1.5 baths1,700 sq ft

29 Kelsey Rd, Poughkeepsie, NY 12601

Listing by KW MidHudson

Property at 412 Ruskey Ln, Hyde Park, NY 12538, 6 beds, 3.5 baths

$979,000

6 beds3.5 baths4,400 sq ft

412 Ruskey Ln, Hyde Park, NY 12538

Listing by Carole Edwards Realty

Property at 148 Rowe Rd, Red Hook, NY 12571, 5 beds, 6.5 baths

$1,250,000

5 beds6.5 baths8,925 sq ft

148 Rowe Rd, Red Hook, NY 12571

Listing by William Pitt Sotheby's

Property at 89 S Cherry St, Poughkeepsie, NY 12601, 6 beds, 2 baths

$479,999

6 beds2 baths5,016 sq ft

89 S Cherry St, Poughkeepsie, NY 12601

Listing by Find Real Estate LLC

Property at 262 Cream St, Poughkeepsie, NY 12601, 4 beds, 2.5 baths

$999,900

4 beds2.5 baths3,153 sq ft

262 Cream St, Poughkeepsie, NY 12601

Listing by Howard Hanna Rand Realty

Property at 729 Cold Spring Rd, Stanfordville, NY 12581, 6 beds, 5 baths

$2,290,000

6 beds5 baths3,352 sq ft

729 Cold Spring Rd, Stanfordville, NY 12581

Listing by William Pitt Sothebys Int Rlty

Property at 7441 S Broadway, Red Hook, NY 12571, 5 beds, 3.5 baths

$899,000

5 beds3.5 baths2,500 sq ft

7441 S Broadway, Red Hook, NY 12571

Listing by BHHS Hudson Valley Properties

Property at 24 Jewett Ave, Poughkeepsie, NY 12601, 7 beds, 3 baths

$499,900

7 beds3 baths— sq ft

24 Jewett Ave, Poughkeepsie, NY 12601

Listing by Fathom Realty NY LLC

Property at 4354-4356 Albany Post Rd, Hyde Park, NY 12538, 4 beds, 3.5 baths

$875,000

4 beds3.5 baths3,911 sq ft

4354-4356 Albany Post Rd, Hyde Park, NY 12538

Listing by Century 21 Alliance Realty Grp

Property at 12-19 Goose Pond Ln, Millerton, NY 12546, 9 beds, 5 baths

$1,600,000

9 beds5 baths2,560 sq ft

12-19 Goose Pond Ln, Millerton, NY 12546

Listing by Elyse Harney Real Estate

Property at 15 Thompson St, Poughkeepsie, NY 12601, 3 beds, 2 baths

$360,000

3 beds2 baths3,145 sq ft

15 Thompson St, Poughkeepsie, NY 12601

Listing by Valley Palms Real Estate Inc

Property at 70 Taft Ave, Poughkeepsie, NY 12603, 6 beds, 2.5 baths

$450,000

6 beds2.5 baths1,880 sq ft

70 Taft Ave, Poughkeepsie, NY 12603

Property at 75 Midway Ave, Amenia, NY 12501, 4 beds, 3 baths

$369,000

4 beds3 baths1,560 sq ft

75 Midway Ave, Amenia, NY 12501

Listing by William Pitt Sothebys Int Rlty

Property at 148 N Creek Rd, Staatsburg, NY 12580, 5 beds, 2 baths

$1,999,999

5 beds2 baths2,618 sq ft

148 N Creek Rd, Staatsburg, NY 12580

Listing by BHHS Hudson Valley Properties

Property at 11 Brown Rd, Pleasant Valley, NY 12569, 6 beds, 3.5 baths

$1,600,000

6 beds3.5 baths4,248 sq ft

11 Brown Rd, Pleasant Valley, NY 12569

Listing by Skyler Realty LLC

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

$499,000

4 beds1.5 baths3,072 sq ft

7786 S Main St, Pine Plains, NY 12567

Listing by Houlihan Lawrence Inc.

Property at 11 Hibiscus Cir #11, Hopewell Junction, NY 12533, 1 bed, 1 bath

$48,000

1 bed1 bath400 sq ft

11 Hibiscus Cir #11, Hopewell Junction, NY 12533

Listing by Houlihan Lawrence Inc.

Property at 1282 Route 82, Hopewell Junction, NY 12533, 4 beds, 2 baths

$548,888

4 beds2 baths2,719 sq ft

1282 Route 82, Hopewell Junction, NY 12533

Listing by Coldwell Banker Realty

Property at 20 Smithfield Way, Amenia, NY 12501, 7 beds, 4 baths

$5,500,000

7 beds4 baths6,019 sq ft

20 Smithfield Way, Amenia, NY 12501

Listing by Houlihan Lawrence Inc.

Property at 1598 Jackson Corners Rd, Red Hook, NY 12571, 5 beds, 3.5 baths

$1,499,000

5 beds3.5 baths4,176 sq ft

1598 Jackson Corners Rd, Red Hook, NY 12571

Listing by BHHS Hudson Valley Properties

Property at 6 Byrds Hill Rd, Pawling, NY 12564, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths3,035 sq ft

6 Byrds Hill Rd, Pawling, NY 12564

Listing by William Pitt Sothebys Int Rlty

Property at 101 Drake Rd, Pleasant Valley, NY 12569, 3 beds, 2.5 baths

$1,395,000

3 beds2.5 baths2,820 sq ft

101 Drake Rd, Pleasant Valley, NY 12569

Listing by Corcoran Country Living

Property at 27 Hooker Ave, Poughkeepsie, NY 12601, 6 beds, 3 baths

$610,000

6 beds3 baths— sq ft

27 Hooker Ave, Poughkeepsie, NY 12601

Listing by K. Fortuna Realty, Inc.

Property at 360 Old State Route 22, Dover Plains, NY 12522, 4 beds, 4.5 baths

$825,000

4 beds4.5 baths2,234 sq ft

360 Old State Route 22, Dover Plains, NY 12522

Listing by BHHS Hudson Valley Properties

Property at 2277 Route 52, Hopewell Junction, NY 12533, 3 beds, 1 bath

$775,000

3 beds1 bath2,259 sq ft

2277 Route 52, Hopewell Junction, NY 12533

Listing by Tassone Realty Corp.

Property at 2-4 Hunns Lake Rd, Stanfordville, NY 12581, 7 beds, 5 baths

$699,000

7 beds5 baths4,353 sq ft

2-4 Hunns Lake Rd, Stanfordville, NY 12581

Listing by Compass Greater NY, LLC

Property at 618 Quaker Hill Rd, Pawling, NY 12564, 17 beds, 11 baths

$5,500,000

17 beds11 baths15,000 sq ft

618 Quaker Hill Rd, Pawling, NY 12564

Listing by Douglas Elliman Real Estate

Property at 22 Hunns Lake Rd, Stanfordville, NY 12581, 5 beds, 2 baths

$525,000

5 beds2 baths2,304 sq ft

22 Hunns Lake Rd, Stanfordville, NY 12581

Listing by Hudson Valley Home Connection

Property at 58 Lincoln Ave, Poughkeepsie, NY 12601, 9 beds, 3 baths

$525,000

9 beds3 baths3,576 sq ft

58 Lincoln Ave, Poughkeepsie, NY 12601

Listing by Legacy Land & Homes LLC

Property at 42 Blackstone Rdg, Holmes, NY 12531, 3 beds, 2.5 baths

$830,000

3 beds2.5 baths2,016 sq ft

42 Blackstone Rdg, Holmes, NY 12531

Listing by William Raveis Real Estate

Property at 16 Trinity Pl, Rhinebeck, NY 12572, 3 beds, 3 baths

$795,000

3 beds3 baths1,777 sq ft

16 Trinity Pl, Rhinebeck, NY 12572

Property at 126 Old Route 55, Pawling, NY 12564, 4 beds, 4.5 baths

$598,500

4 beds4.5 baths2,361 sq ft

126 Old Route 55, Pawling, NY 12564

Listing by HomeSmart Homes & Estates

Property at 570 Pumpkin Ln, Clinton Corners, NY 12514, 6 beds, 4.5 baths

$4,250,000

6 beds4.5 baths4,208 sq ft

570 Pumpkin Ln, Clinton Corners, NY 12514

Listing by Corcoran Country Living

Property at 465 Shunpike, Millbrook, NY 12545, 6 beds, 8 baths

$5,900,000

6 beds8 baths8,117 sq ft

465 Shunpike, Millbrook, NY 12545

Listing by Corcoran Country Living

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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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