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: 0.03% Traditional cash on cash: 3.29% Airbnb Rental Income: $1959 Traditional Rental Income: $2998 Airbnb ROI: 0.03% 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: 1.34% Traditional cash on cash: 4.91% Airbnb Rental Income: $1959 Traditional Rental Income: $2599 Airbnb ROI: 1.34% Traditional ROI: 4.91%
11 Squires Gate #B Poughkeepsie, NY Welcome to easy living at The Commons at Cedar! This well-maintained townhouse offers a pe...	2 beds \| 3 baths \| 1,972 sq.ft.	$330,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 6.46% Airbnb Rental Income: $1123 Traditional Rental Income: $3089 Airbnb ROI: -1.09% Traditional ROI: 6.46%
77 Carroll Street Poughkeepsie, NY Fully available.... Three family home located on a quiet street in the desirable South Sid...	10 beds \| 3 baths \| N/A	$460,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.77% Airbnb Rental Income: $null Traditional Rental Income: $1811 Airbnb ROI: N/A Traditional ROI: 0.77%
375 Salt Point Turnpike #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: 0.17% Traditional cash on cash: 5.68% Airbnb Rental Income: $1959 Traditional Rental Income: $3000 Airbnb ROI: 0.17% 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: 0.48% Traditional cash on cash: 2.45% Airbnb Rental Income: $2063 Traditional Rental Income: $2207 Airbnb ROI: 0.48% Traditional ROI: 2.45%
63 Thompson Street Poughkeepsie, NY .Beautiful 1940 Traditional 2 Family in Poughkeepsie. This is a great investment opportuni...	4 beds \| 2 baths \| N/A	$420,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 5.33% Airbnb Rental Income: $2063 Traditional Rental Income: $3345 Airbnb ROI: 0.71% Traditional ROI: 5.33%
2 Poplar Street Poughkeepsie, NY Positioned in a highly convenient and consistently desirable location, this well-maintaine...	4 beds \| 2 baths \| 1,512 sq.ft.	$349,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 6.02% Airbnb Rental Income: $2063 Traditional Rental Income: $3057 Airbnb ROI: 1.37% Traditional ROI: 6.02%
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: 1.01% Traditional cash on cash: 2.95% Airbnb Rental Income: $1959 Traditional Rental Income: $2035 Airbnb ROI: 1.01% 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: -0.76% Traditional cash on cash: 1.86% Airbnb Rental Income: $1959 Traditional Rental Income: $2547 Airbnb ROI: -0.76% 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%
12 W Dogwood Drive Poughkeepsie, NY Welcome to this fully renovated home ideally located near IBM Headquarters, Marist College...	3 beds \| 2 baths \| 1,652 sq.ft.	$425,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.26% Airbnb Rental Income: $2239 Traditional Rental Income: $3071 Airbnb ROI: -0.24% Traditional ROI: 3.26%
12 May Street Poughkeepsie, NY Located in the heart of Poughkeepsie's rental corridor, this fully occupied 3-bedroom, 1-b...	6 beds \| 2 baths \| N/A	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.81% Airbnb Rental Income: $null Traditional Rental Income: $3444 Airbnb ROI: N/A Traditional ROI: 5.81%
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: 0.19% Traditional cash on cash: 4.19% Airbnb Rental Income: $1959 Traditional Rental Income: $3203 Airbnb ROI: 0.19% Traditional ROI: 4.19%
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	$299,999	Airbnb cash on cash: -0.93% Traditional cash on cash: 5.08% Airbnb Rental Income: $1123 Traditional Rental Income: $2442 Airbnb ROI: -0.93% Traditional ROI: 5.08%
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.	$534,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 2.73% Airbnb Rental Income: $1959 Traditional Rental Income: $3329 Airbnb ROI: -1.05% Traditional ROI: 2.73%
163 N Hamilton Street Poughkeepsie, NY Welcome home to this absolutely stunning Colonial nestled in the city of Poughkeepsie, con...	3 beds \| 2 baths \| 1,491 sq.ft.	$355,460	Airbnb cash on cash: 1.05% Traditional cash on cash: 5.29% Airbnb Rental Income: $1959 Traditional Rental Income: $2861 Airbnb ROI: 1.05% Traditional ROI: 5.29%
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: 3.54% Traditional cash on cash: 5.71% Airbnb Rental Income: $2239 Traditional Rental Income: $2087 Airbnb ROI: 3.54% 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: 0.7% Traditional cash on cash: 7.61% Airbnb Rental Income: $2063 Traditional Rental Income: $3801 Airbnb ROI: 0.7% Traditional ROI: 7.61%
50 Academy Street Poughkeepsie, NY Academy Street Development Opportunity Multi-Family + 2 Vacant Parcels \| Value-Add + Redev...	9 beds \| 3 baths \| N/A	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.01% Airbnb Rental Income: $null Traditional Rental Income: $1793 Airbnb ROI: N/A Traditional ROI: 1.01%
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: -1.01% Traditional cash on cash: 3.01% Airbnb Rental Income: $2063 Traditional Rental Income: $4706 Airbnb ROI: -1.01% 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: -2.77% Traditional cash on cash: -0.97% Airbnb Rental Income: $617 Traditional Rental Income: $1838 Airbnb ROI: -2.77% 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: -1.2% Traditional cash on cash: 4.1% Airbnb Rental Income: $2063 Traditional Rental Income: $4156 Airbnb ROI: -1.2% 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: 0.23% Traditional cash on cash: 2.02% Airbnb Rental Income: $1959 Traditional Rental Income: $2616 Airbnb ROI: 0.23% 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.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.65% Airbnb Rental Income: $null Traditional Rental Income: $7851 Airbnb ROI: N/A Traditional ROI: 11.65%
2740 South Road #G11 Poughkeepsie, NY This beautifully renovated 2-bedroom condo, located in the desirable Greenbriar community ...	2 beds \| 2 baths \| 1,000 sq.ft.	$250,000	Airbnb cash on cash: -2.35% Traditional cash on cash: 3.77% Airbnb Rental Income: $1123 Traditional Rental Income: $2192 Airbnb ROI: -2.35% Traditional ROI: 3.77%
34 Woodland Avenue Poughkeepsie, NY Price Improvement - Your Dream Home Just Got Closer! A Deal is to be made and back on the ...	3 beds \| 3 baths \| 1,850 sq.ft.	$389,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 6.53% Airbnb Rental Income: $1959 Traditional Rental Income: $3563 Airbnb ROI: 0.74% Traditional ROI: 6.53%
35 Fallkill Avenue Poughkeepsie, NY Welcome to 35 Fallkill Ave, a beautifully reimagined Colonial that blends timeless charm w...	2 beds \| 1 baths \| 1,025 sq.ft.	$240,000	Airbnb cash on cash: -1.96% Traditional cash on cash: 3.41% Airbnb Rental Income: $1123 Traditional Rental Income: $1965 Airbnb ROI: -1.96% Traditional ROI: 3.41%
150 Rinaldi Boulevard #1C Poughkeepsie, NY Bright and inviting 1 bed, 1 bath co-op located in a well-maintained community. Enjoy acce...	1 beds \| 1 baths \| 850 sq.ft.	$189,999	Airbnb cash on cash: 0.23% Traditional cash on cash: 6.7% Airbnb Rental Income: $970 Traditional Rental Income: $1788 Airbnb ROI: 0.23% Traditional ROI: 6.7%
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.	$370,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 5.47% Airbnb Rental Income: $2063 Traditional Rental Income: $3254 Airbnb ROI: 0.51% Traditional ROI: 5.47%
6 Zimmer Avenue Poughkeepsie, NY Fully occupied and income producing two-family home in a convenient Poughkeepsie location,...	4 beds \| 2 baths \| N/A	$310,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 7.04% Airbnb Rental Income: $2063 Traditional Rental Income: $3004 Airbnb ROI: 1.99% Traditional ROI: 7.04%
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: -2.47% Traditional cash on cash: 2.75% Airbnb Rental Income: $1123 Traditional Rental Income: $2699 Airbnb ROI: -2.47% 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: 0.48% Traditional cash on cash: 5.38% Airbnb Rental Income: $2063 Traditional Rental Income: $3299 Airbnb ROI: 0.48% 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: -1.91% Traditional cash on cash: 4.19% Airbnb Rental Income: $2063 Traditional Rental Income: $4102 Airbnb ROI: -1.91% Traditional ROI: 4.19%
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%
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: -0.37% Traditional cash on cash: 2.37% Airbnb Rental Income: $2063 Traditional Rental Income: $5588 Airbnb ROI: -0.37% 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%
14 W Dogwood Drive Poughkeepsie, NY In Poughkeepsie, this home presents an exceptional opportunity with 3 bedrooms, 1 full bat...	3 beds \| 1 baths \| 1,144 sq.ft.	$430,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 2.28% Airbnb Rental Income: $1959 Traditional Rental Income: $2376 Airbnb ROI: -0.03% Traditional ROI: 2.28%

Real Estate investment in Poughkeepsie, NY

There are 109 properties for sale in the city of Poughkeepsie . The median list price in Poughkeepsie is $425,000 and the average price per square foot is $118. In May 2026, the average monthly cash on cash return in Poughkeepsie is 4.00%. The average monthly rental income in Poughkeepsie is $3,004.

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

There are 109 investment properties available for sale in Poughkeepsie.

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

The ROI for Short-Term is higher than the Long-Term in Poughkeepsie with average rental income of $1,959.

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: 0.03%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1959

Traditional Rental Income: $2998

Airbnb ROI: 0.03%

Traditional ROI: 3.29%

24 Greenhouse Lane

Poughkeepsie, NY

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

$345,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 4.91%

Airbnb Rental Income: $1959

Traditional Rental Income: $2599

Airbnb ROI: 1.34%

Traditional ROI: 4.91%

11 Squires Gate #B

Poughkeepsie, NY

2 beds | 3 baths | 1,972 sq.ft.

$330,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 6.46%

Airbnb Rental Income: $1123

Traditional Rental Income: $3089

Airbnb ROI: -1.09%

Traditional ROI: 6.46%

77 Carroll Street

Poughkeepsie, NY

10 beds | 3 baths | N/A

$460,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.77%

Airbnb Rental Income: $null

Traditional Rental Income: $1811

Airbnb ROI: N/A

Traditional ROI: 0.77%

375 Salt Point Turnpike #1G

Poughkeepsie, NY

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

$299,900

Airbnb cash on cash: 0.17%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $1959

Traditional Rental Income: $3000

Airbnb ROI: 0.17%

Traditional ROI: 5.68%

85 Sunset Avenue

Poughkeepsie, NY

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

$365,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $2063

Traditional Rental Income: $2207

Airbnb ROI: 0.48%

Traditional ROI: 2.45%

63 Thompson Street

Poughkeepsie, NY

4 beds | 2 baths | N/A

$420,000

Airbnb cash on cash: 0.71%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $2063

Traditional Rental Income: $3345

Airbnb ROI: 0.71%

Traditional ROI: 5.33%

2 Poplar Street

Poughkeepsie, NY

4 beds | 2 baths | 1,512 sq.ft.

$349,000

Airbnb cash on cash: 1.37%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $2063

Traditional Rental Income: $3057

Airbnb ROI: 1.37%