Vintage homes for sale & real estate in Downtown Poughkeepsie, NY

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ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, 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

ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, NY:
Spacious Five Bedroom, Two Full Bath Home For Sale Displaying Hardwood And Ceramic Tiles Floors, Kitchen With Range, Refrigerator And Washer/Dryer Hookups, Full/Unfinished Basement Driveway And Parking In Back Of Building. This Two Story Home Is Located Nearby Shopping, Restaurants, On Bus Route And Not Far From Colleges, Hospitals And Train Station. Property To Be Sold "As Is" With Present Certificate Of Occupancy In Place; Can Also Be Delivered Vacant. Agents, Please See Other Remarks For More Information * * * Prior Day's Notice For All Showings * * *

$329,900

5 beds2 baths2,208 sq ft

257 Church St, Poughkeepsie, NY 12601

Driveway and parking • Kitchen with range • On bus route

Listing by Century 21 Hudson Valley Rlty.

$650,000

0 beds— baths6,968 sq ft

350 Main St, Poughkeepsie, NY 12601

3,049 sq ft lot • Built 1900 • Listed 289 days

Listing by Houlihan Lawrence Inc.

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ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, NY:
MORE PHOTOS TO COME. .. PLEASE…BUT DON’T WAIT TO TOUR. THIS MIGHT BE GONE SOON! AMAZING DUPLEX OPPORTUNITY OFFERING ATTACHED TOWNHOUSE STYLE RESIDENCE THAT IS PERFECT FOR OWNER-OCCUPANTS OR INVESTORS ALIKE. EACH UNIT IS PRESENTLY UNDERGOING ITS INDIVIDUAL REFRESH AND UPDATES. ENJOY THE COMFORT OF HOME AND PRIVACY AS EACH UNIT IS OFFERING ITS OWN PRIVATE ENTRANCE, LIVING ROOM, DINING ROOM, KITCHEN, ENCLOSED PORCH FOR RELAXING ON THE FIRST FLOOR AND 3 BEDROOMS/FULL BATH ON THE SECOND FLOOR ACCESSIBLE TO A FULL SPACIOUS ATTIC. FOR ADDITIONAL STORAGE NEEDS THE FULL BASEMENT OFFERS AMPLE SPACE. THE RIGHT SIDE WILL BE DELIVERED WITH FULLY UPDATED WITH MODERN KITCHEN AND BATHROOM, LI

$469,000

6 beds2 baths2,708 sq ft

324-326 Church St, Poughkeepsie, NY 12601

4,792 sq ft lot • Very walkable

Listing by BHHS Hudson Valley Properties

ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, NY:
Investors Special! Looking to capitalize on a steal of a deal? Take a look at this Legal 4 family building in Poughkeepsie! (4) 1 bedroom apartments each with separate kitchen, and baths. High ARV approx. 600k! Priced to sell! Needs full rehab. All information deemed accurate but not guaranteed. Bidding will start at $275k and rise accordingly!

$275,000

4 beds4 baths2,719 sq ft

86 Montgomery St, Poughkeepsie, NY 12601

2,614 sq ft lot • Very walkable

Listing by Plush Properties Inc

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, NY:
Welcome to 34 Smith Street — Spacious & Move-In Ready with a Motivated Seller! Exceptionally Located in the heart of town, within a mile of historic district. This well-maintained 3-bedroom, 2-bathroom home offers over 2200 sq ft of above ground comfortable living space with a layout perfect for everyday living and entertaining. Step inside to find a traditional floorplan featuring a formal living room, formal dining room, full bathroom with window, and a bright, functional kitchen with stainless steel appliances, gas stove, washer and dryer conveniently situated. Beautiful hardwood, wood & wood laminate flooring run throughout the home. An abundance of closet space and ge

$365,000

3 beds2 baths2,200 sq ft

34 Smith St, Poughkeepsie, NY 12601

3,920 sq ft lot • Very walkable

Listing by eXp Realty

ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, NY:
Step into The Gilded Age! Come tour this treasure box in the registered National Historic District and count how many incredible original details you can find: crown molding, chandeliers and light fixtures, lead-glass windows, mahogany inlayed hardwood floors, built-ins, marble mantle, slate roof, cedar room, pocket doors, French doors and more! The craftsmanship is truly remarkable. With 4 bedrooms, two full baths and three half baths, this 3.354 square feet home also has a jaw-dropping dining room worthy of a Rockefeller, living room, updated eat-in- kitchen, office, mudroom, huge partially finished attic (with a cedar room!), large unfinished basement and detached garage. Live like a tyc

$474,999

4 beds3.5 baths3,354 sq ft

13 Garfield Pl, Poughkeepsie, NY 12601

7,405 sq ft lot • Garage • Very walkable

Listing by BHHS River Towns Real Estate

ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, NY:
Welcome to 21 Lent Street, a beautifully renovated two-family home in Poughkeepsie’s College Hill neighborhood offering turnkey living and excellent investment potential. Each spacious unit features two bedrooms and a full bath, brand-new kitchens, updated flooring, and modern finishes throughout. Recent upgrades include all-new siding, a new roof, updated plumbing and electric with separate meters plus a landlord meter, separate hot water systems, and pending separate heat and gas for maximum tenant independence. The home also offers a full basement for storage and off-street parking—rare in this area. With nothing left to do but move in or start renting, this property is perfe

$459,000

4 beds2 baths— sq ft

21 Lent St, Poughkeepsie, NY 12601

3,049 sq ft lot • Very walkable

Listing by Clarke Realty & Associates LLC

ABOUT THIS HOME
Vintage Home for sale in Downtown Poughkeepsie, NY:
Two Family Home Consisting Of A Two And Four. .. Possible FIve Bedroom Apartments. This Could Be A Great Investment Property With Apt 1 Being A Bi-Level Rental Unit And Apt 2, A One Level Rental In This Solid Built Structure. Home Allows A Level Of Privacy As Residents Have Their Own Separate Entrances, Separate Utilities Plus Each Unit Has Newer Gas Furnaces And Hot Water Heaters. Updates Also Include A Newer Roof. Convenience Of A City Property Allows Many Amenities; Close To Train Station, On Bus Route, Close To Schools, Parks, Shopping, Restaurants And More. This One's Easy To Show And An As Is Sale. Agents, Please Read Other Remarks For More Information.

$429,000

7 beds3 baths2,936 sq ft

24 Smith St, Poughkeepsie, NY 12601

4,356 sq ft lot • Very walkable

Listing by Century 21 Hudson Valley Rlty.

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 88 S Hamilton St, Poughkeepsie, NY 12601, 3 beds, 1.5 baths

$320,000

3 beds1.5 baths1,476 sq ft

88 S Hamilton St, Poughkeepsie, NY 12601

Listing by Houlihan Lawrence Inc.

Property at 228 Mansion St, Poughkeepsie, NY 12601, 4 beds, 2 baths

$465,000

4 beds2 baths2,200 sq ft

228 Mansion St, Poughkeepsie, NY 12601

Listing by Four Seasons Sothebys Intl

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 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 77 Academy St, Poughkeepsie, NY 12601, 8 beds, 4 baths

$699,000

8 beds4 baths— sq ft

77 Academy St, Poughkeepsie, NY 12601

Listing by Clarke Realty & Associates LLC

Property at 57 Smith St, Poughkeepsie, NY 12601, 6 beds, 2 baths

$460,000

6 beds2 baths2,112 sq ft

57 Smith St, Poughkeepsie, NY 12601

Listing by Century 21 Hudson Valley Rlty.

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 Oxford Property Group USA

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 86 S Hamilton St, Poughkeepsie, NY 12601, 6 beds, 3 baths

$549,000

6 beds3 baths3,249 sq ft

86 S Hamilton St, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 4 Fairmont St, Poughkeepsie, NY 12601, 4 beds, 1.5 baths

$380,000

4 beds1.5 baths1,576 sq ft

4 Fairmont St, Poughkeepsie, NY 12601

Listing by RE/MAX Integrity Leaders

Property at 59 Montgomery St, Poughkeepsie, NY 12601, 3 beds, 2 baths

$375,000

3 beds2 baths3,976 sq ft

59 Montgomery St, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 94 Academy St, Poughkeepsie, NY 12601, 6 beds, 2 baths

$425,000

6 beds2 baths2,100 sq ft

94 Academy St, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Property at 55 Smith St, Poughkeepsie, NY 12601, 2 beds, 2 baths

$480,000

2 beds2 baths2,112 sq ft

55 Smith St, Poughkeepsie, NY 12601

Listing by BHHS Hudson Valley Properties

Based on information submitted to the MLS GRID as of Fri Oct 31 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 Downtown Poughkeepsie

There are currently 3 vintage homes for sale in Downtown Poughkeepsie at a median listing price of $465K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Downtown Poughkeepsie stay on the market for 180 days. Popular neighborhoods include Arlington District, Waterfront, Waterfront District, College Hill, and Downtown Modesto. This map is refreshed with the newest listings in Downtown Poughkeepsie every 15 minutes.

In the past month, 1 home has been sold in Downtown Poughkeepsie. In addition to houses in Downtown Poughkeepsie, there were also 0 condos, 0 townhouses, and 1 multi-family unit for sale in Downtown Poughkeepsie last month. Find your dream home in Downtown Poughkeepsie 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 Downtown Poughkeepsie are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Downtown Poughkeepsie. If you're looking to sell your home in the Downtown Poughkeepsie area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Downtown Poughkeepsie with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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