Real Estate Investment Properties for Sale in Poughkeepsie, NY

Looking for investment property in Poughkeepsie, NY with high ROI ?

Explore a variety of short-term homes & houses in Poughkeepsie, NY. Invest wisely with VRBO & Poughkeepsie, NY Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Poughkeepsie, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
51 Woodland Avenue Poughkeepsie, NY Welcome to 51 Woodland Avenue, a stunning stone-front Colonial located in the highly desir...	3 beds \| 2 baths \| 1,712 sq.ft.	$509,000	Airbnb cash on cash: 0% Traditional cash on cash: 3.29% Airbnb Rental Income: $1944 Traditional Rental Income: $2998 Airbnb ROI: 0% Traditional ROI: 3.29%
24 Greenhouse Lane Poughkeepsie, NY Super location for the end of cul de sac location duplex. There are no common charges for ...	3 beds \| 2 baths \| 1,206 sq.ft.	$345,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 4.91% Airbnb Rental Income: $1944 Traditional Rental Income: $2599 Airbnb ROI: 1.3% Traditional ROI: 4.91%
93 Delafield Street Poughkeepsie, NY Don't miss this excellent two-family investment property in the heart of Poughkeepsie. Whe...	4 beds \| 2 baths \| N/A	$370,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 6.16% Airbnb Rental Income: $1667 Traditional Rental Income: $3225 Airbnb ROI: 0.32% Traditional ROI: 6.16%
375 Salt Point Turnpike unit: 1G Poughkeepsie, NY Welcome to 375 Salt Point Turnpike - a beautifully maintained end-unit townhome offering 3...	3 beds \| 3 baths \| 1,418 sq.ft.	$299,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 5.68% Airbnb Rental Income: $1944 Traditional Rental Income: $3000 Airbnb ROI: 0.13% Traditional ROI: 5.68%
85 Sunset Avenue Poughkeepsie, NY This 4-bedroom, 1-bathroom property offers a layout ideal for renting, with close proximit...	4 beds \| 1 baths \| 1,144 sq.ft.	$365,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 2.45% Airbnb Rental Income: $1667 Traditional Rental Income: $2207 Airbnb ROI: -0.49% Traditional ROI: 2.45%
8 Van Wyck Drive Poughkeepsie, NY One level living at it's finest! With all the updates and maintenance items completed, all...	3 beds \| 1 baths \| 875 sq.ft.	$324,930	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.95% Airbnb Rental Income: $1944 Traditional Rental Income: $2035 Airbnb ROI: 0.97% Traditional ROI: 2.95%
18 Cardinal Drive Poughkeepsie, NY Charming ranch-style home offering comfortable one-level living in Poughkeepsie. This 3-be...	3 beds \| 2 baths \| 1,080 sq.ft.	$449,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.86% Airbnb Rental Income: $1944 Traditional Rental Income: $2547 Airbnb ROI: -0.79% Traditional ROI: 1.86%
11 Manitou Avenue Poughkeepsie, NY Welcome to this well-maintained two-family home located on a dead-end corner lot in Poughk...	5 beds \| 2 baths \| N/A	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.33% Airbnb Rental Income: $null Traditional Rental Income: $3394 Airbnb ROI: N/A Traditional ROI: 5.33%
77 Colburn Drive Poughkeepsie, NY Welcome to 77 Colburn Drive, located in the highly sought after Town of Poughkeepsie. This...	3 beds \| 2 baths \| 1,904 sq.ft.	$529,999	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.02% Airbnb Rental Income: $1944 Traditional Rental Income: $3065 Airbnb ROI: -0.28% Traditional ROI: 3.02%
104 SUTTON PARK Road Poughkeepsie, NY Renovated and move in ready. This spacious Raised Ranch has been refurbished with many new...	3 beds \| 2 baths \| 2,298 sq.ft.	$469,900	Airbnb cash on cash: 0.16% Traditional cash on cash: 1.76% Airbnb Rental Income: $1944 Traditional Rental Income: $2137 Airbnb ROI: 0.16% Traditional ROI: 1.76%
13 Hooker Avenue Poughkeepsie, NY Charming duplex located on Poughkeepsie's South Side, this home is just steps from parks, ...	2 beds \| 2 baths \| N/A	$309,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 4.9% Airbnb Rental Income: $1066 Traditional Rental Income: $2442 Airbnb ROI: -1.09% Traditional ROI: 4.9%
13 Timberline Drive Poughkeepsie, NY Pastoral park-like setting on a quiet street embraces this beautiful three bedroom, two an...	3 beds \| 3 baths \| 1,812 sq.ft.	$549,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 2.63% Airbnb Rental Income: $1944 Traditional Rental Income: $3329 Airbnb ROI: -1.07% Traditional ROI: 2.63%
47 Timberline Drive Poughkeepsie, NY Set in a beautiful neighborhood of mature trees and well kept homes, this four-bedroom, th...	4 beds \| 3 baths \| 2,280 sq.ft.	$499,900	Airbnb cash on cash: -1.62% Traditional cash on cash: 4.17% Airbnb Rental Income: $1667 Traditional Rental Income: $3906 Airbnb ROI: -1.62% Traditional ROI: 4.17%
17 Tamarack Hill Drive Poughkeepsie, NY Welcome to this move-in ready home offering comfort, style, and convenience. Enjoy a spaci...	3 beds \| 2 baths \| 2,072 sq.ft.	$489,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.86% Airbnb Rental Income: $1944 Traditional Rental Income: $3039 Airbnb ROI: -0.66% Traditional ROI: 2.86%
25 Woodcliff Avenue Poughkeepsie, NY Opportunity knocks at 25 Woodcliff Ave! This 3-bedroom, 1.5-bath home offers strong upside...	3 beds \| 2 baths \| 1,531 sq.ft.	$199,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 5.71% Airbnb Rental Income: $1832 Traditional Rental Income: $2087 Airbnb ROI: 1.74% Traditional ROI: 5.71%
30 Garfield Place Poughkeepsie, NY Opportunity awaits with this spacious 4 bedroom, 3 bath Southside Poughkeepsie home in a s...	4 beds \| 3 baths \| 2,952 sq.ft.	$350,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 7.61% Airbnb Rental Income: $1667 Traditional Rental Income: $3801 Airbnb ROI: -0.3% Traditional ROI: 7.61%
159 Rombout Road Poughkeepsie, NY Experience refined living in this stunning Great Hall Colonial, offering 3,225 sq ft of th...	4 beds \| 4 baths \| 4,657 sq.ft.	$850,000	Airbnb cash on cash: -1.42% Traditional cash on cash: 3.01% Airbnb Rental Income: $1667 Traditional Rental Income: $4706 Airbnb ROI: -1.42% Traditional ROI: 3.01%
48 Columbia Street Poughkeepsie, NY Turnkey investment opportunity delivering an 8.7% cap rate in Poughkeepsie's Campus Develo...	N/A beds \| N/A baths \| N/A	$899,000	Airbnb cash on cash: -2.79% Traditional cash on cash: -0.97% Airbnb Rental Income: $605 Traditional Rental Income: $1838 Airbnb ROI: -2.79% Traditional ROI: -0.97%
42 Beechwood Park Poughkeepsie, NY Welcome to 42 Beechwood Park, a well-maintained and inviting home nestled on a quiet, tree...	4 beds \| 3 baths \| 2,993 sq.ft.	$529,990	Airbnb cash on cash: -1.86% Traditional cash on cash: 4.1% Airbnb Rental Income: $1667 Traditional Rental Income: $4156 Airbnb ROI: -1.86% Traditional ROI: 4.1%
18 Dorland Ave Poughkeepsie, NY 18 Dorland Ave, Poughkeepsie, NY 12603 Arlington School District â¢ 1.65 Acres â¢ RM Zo...	3 beds \| 2 baths \| N/A	$699,975	Airbnb cash on cash: 0.21% Traditional cash on cash: 2.02% Airbnb Rental Income: $1944 Traditional Rental Income: $2616 Airbnb ROI: 0.21% Traditional ROI: 2.02%
113 Hooker Avenue Poughkeepsie, NY Discover the timeless charm of this 1915 Grand Colonial Estate on Poughkeepsie's desirable...	5 beds \| 6 baths \| 4,800 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.43% Airbnb Rental Income: $null Traditional Rental Income: $7851 Airbnb ROI: N/A Traditional ROI: 11.43%
320 Mansion Street Poughkeepsie, NY Excellent investment opportunity in the City of Poughkeepsie! This legal 2-family offers a...	5 beds \| 2 baths \| N/A	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.25% Airbnb Rental Income: $null Traditional Rental Income: $3179 Airbnb ROI: N/A Traditional ROI: 7.25%
10 Lori Street Poughkeepsie, NY 3 Level 4 Bedroom 1.5 bath Split Level home on .32 acre lot in Town of Poughkeepsie! Huge ...	4 beds \| 2 baths \| 1,525 sq.ft.	$380,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 5.3% Airbnb Rental Income: $1667 Traditional Rental Income: $3254 Airbnb ROI: -0.46% Traditional ROI: 5.3%
45 Delafield Street Poughkeepsie, NY Two family duplex located in the City of Poughkeepsie, separate utilities. This brick stru...	2 beds \| 2 baths \| N/A	$399,000	Airbnb cash on cash: -2.6% Traditional cash on cash: 2.75% Airbnb Rental Income: $1066 Traditional Rental Income: $2699 Airbnb ROI: -2.6% Traditional ROI: 2.75%
115 Innis Avenue Poughkeepsie, NY Rare 2-Family Opportunity in the Town of Poughkeepsie - Arlington Schools! Whether you're ...	4 beds \| 2 baths \| N/A	$385,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 5.38% Airbnb Rental Income: $1667 Traditional Rental Income: $3299 Airbnb ROI: -0.43% Traditional ROI: 5.38%
22 Old Mill Road Poughkeepsie, NY A Rare Find! 24 hour notice, tenants, need confirmation. This large brick home needs work ...	4 beds \| 3 baths \| 3,156 sq.ft.	$449,900	Airbnb cash on cash: -2.7% Traditional cash on cash: 4.19% Airbnb Rental Income: $1667 Traditional Rental Income: $4102 Airbnb ROI: -2.7% Traditional ROI: 4.19%
23 Robert Road Poughkeepsie, NY Stylish and unique ranch style home featuring the ultimate open-concept living experience....	3 beds \| 2 baths \| 2,228 sq.ft.	$495,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.35% Airbnb Rental Income: $1944 Traditional Rental Income: $3068 Airbnb ROI: -0.18% Traditional ROI: 3.35%
56 Daley Road Poughkeepsie, NY Hudson Valley Haven - 56 Daley Rd, Poughkeepsie, NY Step into your private retreat in the ...	5 beds \| 2 baths \| 2,823 sq.ft.	$570,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $3971 Airbnb ROI: N/A Traditional ROI: 4.63%
3 Hook Road unit: 32 Poughkeepsie, NY This spacious three level townhouse has full basement walk-out located at The Arbors condo...	3 beds \| 2 baths \| 1,729 sq.ft.	$289,888	Airbnb cash on cash: -1.69% Traditional cash on cash: 3.9% Airbnb Rental Income: $1944 Traditional Rental Income: $2957 Airbnb ROI: -1.69% Traditional ROI: 3.9%
3 Shelley Road Poughkeepsie, NY Step inside this beautiful raised ranch that offers 3 bedrooms and 1.5 bathrooms with a pr...	3 beds \| 2 baths \| 1,510 sq.ft.	$425,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 4.7% Airbnb Rental Income: $1944 Traditional Rental Income: $3077 Airbnb ROI: 0.57% Traditional ROI: 4.7%
16 Kingwood Lane Poughkeepsie, NY TO BE BUILT NEW CONSTRUCTION IN THE PRESTIGIOUS KINGWOOD PARK DEVELOPMENT WITHIN THE S...	4 beds \| 4 baths \| 3,867 sq.ft.	$1,595,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 2.37% Airbnb Rental Income: $1667 Traditional Rental Income: $5588 Airbnb ROI: -0.59% Traditional ROI: 2.37%
6 North Drive Poughkeepsie, NY Welcome to this beautiful home located in a quiet neighborhood. This home offers the perfe...	5 beds \| 3 baths \| 2,362 sq.ft.	$580,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $3931 Airbnb ROI: N/A Traditional ROI: 4.54%
24 Villa Lane Poughkeepsie, NY TO BE BUILT - MODERN FARMHOUSE ON 23 PRIVATE ACRES WITH STUNNING HUDSON VALLEY MOUNTAIN VI...	4 beds \| 5 baths \| 4,356 sq.ft.	$2,495,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.66% Airbnb Rental Income: $1667 Traditional Rental Income: $6884 Airbnb ROI: -0.79% Traditional ROI: 1.66%
15 Milano Drive Poughkeepsie, NY Motivated Seller. Welcome to 15 Milano Drive, an updated 3-bedroom house, 2 bath gem nestl...	3 beds \| 2 baths \| 2,700 sq.ft.	$459,900	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.7% Airbnb Rental Income: $1944 Traditional Rental Income: $3212 Airbnb ROI: -0.44% Traditional ROI: 3.7%
33 Virginia Avenue Poughkeepsie, NY Unlock the potential of steady income, long term income with this well maintained multi fa...	4 beds \| 4 baths \| N/A	$620,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 6.18% Airbnb Rental Income: $1667 Traditional Rental Income: $5352 Airbnb ROI: -0.99% Traditional ROI: 6.18%
14 Bellmore Drive Poughkeepsie, NY Attention INVESTORS & Home Flippers! Opportunity knocks at 14 Bellmore Dr in Poughkeepsie....	3 beds \| 2 baths \| 1,724 sq.ft.	$290,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 6.14% Airbnb Rental Income: $1944 Traditional Rental Income: $2970 Airbnb ROI: 0.5% Traditional ROI: 6.14%
45 Old Farms Rd Poughkeepsie, NY A beautifully updated and maintained large property with lots of possibilities. Five large...	5 beds \| 3 baths \| 2,406 sq.ft.	$710,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.89% Airbnb Rental Income: $null Traditional Rental Income: $4238 Airbnb ROI: N/A Traditional ROI: 2.89%
95 Sutton Park Road Poughkeepsie, NY Welcome to this spacious 5-bedroom home located on a quiet, walkable street in the Wapping...	5 beds \| 2 baths \| 2,386 sq.ft.	$479,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $3343 Airbnb ROI: N/A Traditional ROI: 3.44%
19 Maryland Avenue Poughkeepsie, NY Nestled in the charming Southside neighborhood of Poughkeepsie, this 4 bedroom 2 full bath...	4 beds \| 2 baths \| 1,776 sq.ft.	$379,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 5.74% Airbnb Rental Income: $1667 Traditional Rental Income: $3216 Airbnb ROI: 0.07% Traditional ROI: 5.74%
302-304 Main Street Poughkeepsie, NY Property Overview: Mixed-Use Building in Poughkeepsie Prime Location: Main Street, Heart o...	N/A beds \| N/A baths \| N/A	$1,290,000	Airbnb cash on cash: -3.26% Traditional cash on cash: -2.44% Airbnb Rental Income: $605 Traditional Rental Income: $1292 Airbnb ROI: -3.26% Traditional ROI: -2.44%

Real Estate investment in Poughkeepsie, NY

There are 104 properties for sale in the city of Poughkeepsie . The median list price in Poughkeepsie is $417,500 and the average price per square foot is $121. In April 2026, the average monthly cash on cash return in Poughkeepsie is 4.00%. The average monthly rental income in Poughkeepsie is $2,754.

Poughkeepsie, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 104 investment properties available for sale in Poughkeepsie.

In 2026, the best neighborhood to buy investment property is Poughkeepsie.

The ROI for Long-Term is higher than the Short-Term in Poughkeepsie with average rental income of $2,754.

Your search for investment property begins and ends here

Investment Property for Sale in Poughkeepsie, NY

51 Woodland Avenue

Poughkeepsie, NY

3 beds | 2 baths | 1,712 sq.ft.

$509,000

Airbnb cash on cash: 0%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1944

Traditional Rental Income: $2998

Airbnb ROI: 0%

Traditional ROI: 3.29%

24 Greenhouse Lane

Poughkeepsie, NY

3 beds | 2 baths | 1,206 sq.ft.

$345,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 4.91%

Airbnb Rental Income: $1944

Traditional Rental Income: $2599

Airbnb ROI: 1.3%

Traditional ROI: 4.91%

93 Delafield Street

Poughkeepsie, NY

4 beds | 2 baths | N/A

$370,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 6.16%

Airbnb Rental Income: $1667

Traditional Rental Income: $3225

Airbnb ROI: 0.32%

Traditional ROI: 6.16%

375 Salt Point Turnpike unit: 1G

Poughkeepsie, NY

3 beds | 3 baths | 1,418 sq.ft.

$299,900

Airbnb cash on cash: 0.13%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $1944

Traditional Rental Income: $3000

Airbnb ROI: 0.13%

Traditional ROI: 5.68%

85 Sunset Avenue

Poughkeepsie, NY

4 beds | 1 baths | 1,144 sq.ft.

$365,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $1667

Traditional Rental Income: $2207

Airbnb ROI: -0.49%

Traditional ROI: 2.45%

8 Van Wyck Drive

Poughkeepsie, NY

3 beds | 1 baths | 875 sq.ft.

$324,930

Airbnb cash on cash: 0.97%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $1944

Traditional Rental Income: $2035

Airbnb ROI: 0.97%

Traditional ROI: 2.95%

18 Cardinal Drive

Poughkeepsie, NY

3 beds | 2 baths | 1,080 sq.ft.

$449,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 1.86%

Airbnb Rental Income: $1944

Traditional Rental Income: $2547

Airbnb ROI: -0.79%

Traditional ROI: 1.86%

11 Manitou Avenue

Poughkeepsie, NY

5 beds | 2 baths | N/A

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.33%

Airbnb Rental Income: $null

Traditional Rental Income: $3394

Airbnb ROI: N/A