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
69 Dawson Court Poughkeepsie, NY Welcome to 69 Dawson Court, a charming farmhouse-style colonial with a front porch, nestle...	4 beds \| 3 baths \| 3,148 sq.ft.	$772,000	Airbnb cash on cash: -2.3% Traditional cash on cash: 2.08% Airbnb Rental Income: $1575 Traditional Rental Income: $4272 Airbnb ROI: -2.3% Traditional ROI: 2.08%
28 Amber Court Poughkeepsie, NY Welcome to 28 Amber Court, a 2-bedroom, 1.5-bath townhouse with an attached garage, tucked...	2 beds \| 2 baths \| 1,455 sq.ft.	$279,000	Airbnb cash on cash: -2.82% Traditional cash on cash: 4.01% Airbnb Rental Income: $1211 Traditional Rental Income: $2618 Airbnb ROI: -2.82% Traditional ROI: 4.01%
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: 2.04% Traditional cash on cash: 4.91% Airbnb Rental Income: $2230 Traditional Rental Income: $2599 Airbnb ROI: 2.04% Traditional ROI: 4.91%
29 Kelsey Road Poughkeepsie, NY Classic Colonial Charm Near the Walkway Over the Hudson! This traditional Colonial blends ...	3 beds \| 2 baths \| 1,700 sq.ft.	$440,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.21% Airbnb Rental Income: $2230 Traditional Rental Income: $3078 Airbnb ROI: 0.79% Traditional ROI: 4.21%
2 Oriole Drive Poughkeepsie, NY Spacious and welcoming 4-bedroom, 2 full bath multi split level on a large corner lot all ...	4 beds \| 2 baths \| 1,998 sq.ft.	$465,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 2.55% Airbnb Rental Income: $1575 Traditional Rental Income: $2755 Airbnb ROI: -1.2% Traditional ROI: 2.55%
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: 1.12% Traditional cash on cash: 0.77% Airbnb Rental Income: $2581 Traditional Rental Income: $1811 Airbnb ROI: 1.12% Traditional ROI: 0.77%
45 Raker Road Poughkeepsie, NY Tastefully updated Bi-Level in the heart of Red Oaks Mill, Town of Poughkeepsie! Main leve...	3 beds \| 2 baths \| 1,684 sq.ft.	$450,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 3.64% Airbnb Rental Income: $2230 Traditional Rental Income: $2935 Airbnb ROI: 0.63% Traditional ROI: 3.64%
93 Delafield Street Poughkeepsie, NY Donât miss this excellent two-family investment property in the heart of Poughkeepsie. W...	4 beds \| 2 baths \| 2,750 sq.ft.	$370,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.88% Airbnb Rental Income: $2230 Traditional Rental Income: $2087 Airbnb ROI: 1.68% Traditional ROI: 2.88%
105 Cherry Hill Drive Poughkeepsie, NY Updated & Inviting Condo in Cherry Hill Welcome to your next chapter in the highly desi...	2 beds \| 2 baths \| 1,270 sq.ft.	$239,000	Airbnb cash on cash: -1.61% Traditional cash on cash: 5.35% Airbnb Rental Income: $1211 Traditional Rental Income: $2393 Airbnb ROI: -1.61% Traditional ROI: 5.35%
148 Bower Road Poughkeepsie, NY Welcome home to this beautifully updated 3-bedroom, 1-bath ranch offering modern comfort a...	3 beds \| 1 baths \| 1,200 sq.ft.	$399,900	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.29% Airbnb Rental Income: $2230 Traditional Rental Income: $2292 Airbnb ROI: 0.63% Traditional ROI: 2.29%
4008 Deer Path Poughkeepsie, NY Move-in ready condo with stylish updates and rare upgrades! Originally built as the show ...	2 beds \| 2 baths \| 1,040 sq.ft.	$299,900	Airbnb cash on cash: -1.58% Traditional cash on cash: 3.5% Airbnb Rental Income: $1211 Traditional Rental Income: $2255 Airbnb ROI: -1.58% Traditional ROI: 3.5%
27 Peckham Road Poughkeepsie, NY Cozy and welcoming 2-bedroom, 1-bath ranch offering convenient single-level living. Featur...	2 beds \| 1 baths \| 848 sq.ft.	$260,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 3.15% Airbnb Rental Income: $1211 Traditional Rental Income: $1895 Airbnb ROI: -1.23% Traditional ROI: 3.15%
156 Bart Drive Poughkeepsie, NY One level living at its finest! Immaculate 3-bedroom, 2 full bath Ranch style home, situat...	3 beds \| 2 baths \| 2,672 sq.ft.	$460,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 4.37% Airbnb Rental Income: $2230 Traditional Rental Income: $3279 Airbnb ROI: 0.63% Traditional ROI: 4.37%
21 Forbus Street Poughkeepsie, NY This tastefully updated 4-bedroom, 2-bath, Turn of the Century Cape-style home blends clas...	4 beds \| 2 baths \| 2,024 sq.ft.	$425,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.81% Airbnb Rental Income: $1575 Traditional Rental Income: $3286 Airbnb ROI: 0.38% Traditional ROI: 5.81%
34 Pine Echo Drive Poughkeepsie, NY Welcome to this stunning, fully renovated ranch-style home! This charming 3-bedroom, 2-bat...	3 beds \| 2 baths \| 1,032 sq.ft.	$379,500	Airbnb cash on cash: 0.38% Traditional cash on cash: 2.58% Airbnb Rental Income: $2230 Traditional Rental Income: $2451 Airbnb ROI: 0.38% Traditional ROI: 2.58%
190 Winnikee Avenue Poughkeepsie, NY Exceptional investment opportunity in the City of Poughkeepsie! Legal two-family property ...	N/A beds \| 2 baths \| N/A	$325,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.18% Airbnb Rental Income: $2230 Traditional Rental Income: $1945 Airbnb ROI: 2.28% Traditional ROI: 3.18%
115 Fulton Avenue Poughkeepsie, NY Charming Duplex Near Vassar â Great Investment Opportunity! Don't miss this fantastic o...	N/A beds \| 2 baths \| 2,250 sq.ft.	$450,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 0.89% Airbnb Rental Income: $2230 Traditional Rental Income: $2086 Airbnb ROI: -0.1% Traditional ROI: 0.89%
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: -0.68% Traditional cash on cash: 4.9% Airbnb Rental Income: $1211 Traditional Rental Income: $2442 Airbnb ROI: -0.68% Traditional ROI: 4.9%
51 Loockerman Avenue Poughkeepsie, NY POUGHKEEPSIE SCHOOLS!!! INGROUND POOL!!! Welcome to this beautifully updated 4 Bedroom, 2....	3 beds \| 3 baths \| 2,062 sq.ft.	$565,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 4.63% Airbnb Rental Income: $2230 Traditional Rental Income: $4051 Airbnb ROI: 0.12% Traditional ROI: 4.63%
5 Wood Street Poughkeepsie, NY BACK ON THE MARKET!! BUYERS FINANCING FELL THROUGHGH! Welcome to this beautifully maintain...	3 beds \| 3 baths \| 1,608 sq.ft.	$385,999	Airbnb cash on cash: 0.35% Traditional cash on cash: 4.3% Airbnb Rental Income: $2230 Traditional Rental Income: $3099 Airbnb ROI: 0.35% Traditional ROI: 4.3%
6 Glenwood Avenue Poughkeepsie, NY Built in 2023, this Southside Poughkeepsie home blends modern design with energy efficienc...	3 beds \| 3 baths \| 1,907 sq.ft.	$535,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.96% Airbnb Rental Income: $2230 Traditional Rental Income: $3524 Airbnb ROI: 1.25% Traditional ROI: 4.96%
2203 Mulberry Court Poughkeepsie, NY Welcome to Mulberry Ct, a sun-filled end unit townhome in the desirable Fox Hill community...	3 beds \| 2 baths \| 1,252 sq.ft.	$299,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 5.18% Airbnb Rental Income: $2230 Traditional Rental Income: $2549 Airbnb ROI: 2.05% Traditional ROI: 5.18%
31 Old Farms Road Poughkeepsie, NY PRICE REDUCED! Spackenkill Town of Poughkeepsie NY beautiful split-level home 4BR 3 Baths ...	4 beds \| 3 baths \| 2,067 sq.ft.	$499,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 6.02% Airbnb Rental Income: $1575 Traditional Rental Income: $4103 Airbnb ROI: -0.37% Traditional ROI: 6.02%
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.	$524,500	Airbnb cash on cash: -1.74% Traditional cash on cash: 3.93% Airbnb Rental Income: $1575 Traditional Rental Income: $3906 Airbnb ROI: -1.74% Traditional ROI: 3.93%
7 Phillips Road Poughkeepsie, NY Welcome to 7 Phillips Road â a beautifully updated Cape Cod-style home in the Town of Po...	3 beds \| 3 baths \| 1,880 sq.ft.	$450,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 5.08% Airbnb Rental Income: $2230 Traditional Rental Income: $3516 Airbnb ROI: 0.7% Traditional ROI: 5.08%
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: -0.14% Traditional cash on cash: 2.86% Airbnb Rental Income: $2230 Traditional Rental Income: $3039 Airbnb ROI: -0.14% Traditional ROI: 2.86%
202 Ridgeline Drive Poughkeepsie, NY Welcome to the Grove at Sleight Farm in the town of Lagrange. This beautiful, upgraded Dav...	4 beds \| 3 baths \| 2,108 sq.ft.	$635,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 2.07% Airbnb Rental Income: $1575 Traditional Rental Income: $3341 Airbnb ROI: -1.68% Traditional ROI: 2.07%
238 Innis Avenue Poughkeepsie, NY Like-new construction! This completely renovated home features 3 spacious bedrooms, 2.5 mo...	3 beds \| 3 baths \| 1,539 sq.ft.	$400,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.91% Airbnb Rental Income: $2230 Traditional Rental Income: $2986 Airbnb ROI: 1.4% Traditional ROI: 4.91%
59 Montgomery Street Poughkeepsie, NY Fantastic Opportunity for business and/or residential! Multiple possibilities abound with ...	3 beds \| 2 baths \| N/A	$375,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.42% Airbnb Rental Income: $2230 Traditional Rental Income: $3050 Airbnb ROI: -0.5% Traditional ROI: 3.42%
42 Clark Street Poughkeepsie, NY This beautifully maintained 3-bedroom, 2-bath Brick Ranch offers easy one-level living in ...	3 beds \| 2 baths \| 1,424 sq.ft.	$399,500	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.95% Airbnb Rental Income: $2230 Traditional Rental Income: $2809 Airbnb ROI: 0.91% Traditional ROI: 3.95%
264 Lauer Road Poughkeepsie, NY Video tour and floor plans available! Welcome home! Set back on almost 2 acres is this bea...	3 beds \| 3 baths \| 1,922 sq.ft.	$589,930	Airbnb cash on cash: -0.19% Traditional cash on cash: 3.1% Airbnb Rental Income: $2230 Traditional Rental Income: $3482 Airbnb ROI: -0.19% Traditional ROI: 3.1%
175 Washington Street Poughkeepsie, NY Deal fell through. Back on the market. Welcome to 175 Washington Street - A Prime Two-Fami...	8 beds \| 2 baths \| N/A	$450,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 1.73% Airbnb Rental Income: $2581 Traditional Rental Income: $1824 Airbnb ROI: 2.06% Traditional ROI: 1.73%
32 Lagrange Avenue Poughkeepsie, NY Income generating property with existing lease and cashflow with a reliable and meticulous...	4 beds \| 2 baths \| 2,025 sq.ft.	$417,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 4.29% Airbnb Rental Income: $1575 Traditional Rental Income: $3281 Airbnb ROI: -1.23% Traditional ROI: 4.29%
117 Talmadge Street Poughkeepsie, NY Duplex in the heart of Poughkeepsie on a quiet street. Unit 1 renovated in 2018 with stain...	7 beds \| 2 baths \| N/A	$375,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 5.39% Airbnb Rental Income: $2581 Traditional Rental Income: $3012 Airbnb ROI: 2.41% Traditional ROI: 5.39%
83 Montgomery Street Poughkeepsie, NY Charming 1880 Triplex with Endless Potential Welcome to this spacious multi-family ...	N/A beds \| N/A baths \| 2,536 sq.ft.	$359,900	Airbnb cash on cash: -2.11% Traditional cash on cash: 2.22% Airbnb Rental Income: $723 Traditional Rental Income: $1878 Airbnb ROI: -2.11% Traditional ROI: 2.22%
62 Hillcrest Drive Poughkeepsie, NY Welcome to this beautifully updated 3-bedroom, 2-full-bath Ranch-style home, perfectly sit...	3 beds \| 2 baths \| 1,344 sq.ft.	$439,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.6% Airbnb Rental Income: $2230 Traditional Rental Income: $2749 Airbnb ROI: 0.98% Traditional ROI: 3.6%
15 E Dogwood Drive Poughkeepsie, NY Donât miss your chance to own this charming home in the desirable Town of Poughkeepsie, ...	2 beds \| 2 baths \| 852 sq.ft.	$469,000	Airbnb cash on cash: -1.87% Traditional cash on cash: 2.73% Airbnb Rental Income: $1211 Traditional Rental Income: $2839 Airbnb ROI: -1.87% Traditional ROI: 2.73%
Lot 54 Edwin Road Poughkeepsie, NY TO BE BUILT! Adams model, a 4,317 SF contemporary Colonial-style home. Reputable, local b...	4 beds \| 4 baths \| 4,064 sq.ft.	$1,060,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.92% Airbnb Rental Income: $1575 Traditional Rental Income: $4371 Airbnb ROI: -0.37% Traditional ROI: 2.92%
Lot 19a Old Field Road Poughkeepsie, NY TO BE BUILT. Gorgeous 4 BR 2.5 bath Ellington model colonial with pretty covered porch, 2 ...	4 beds \| 3 baths \| 3,011 sq.ft.	$794,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 2.52% Airbnb Rental Income: $1575 Traditional Rental Income: $3960 Airbnb ROI: -1.32% Traditional ROI: 2.52%
16 Bushwick Road Poughkeepsie, NY Located in the Town of LaGrange and within the Arlington School Districtâjust minutes fr...	4 beds \| 2 baths \| 2,404 sq.ft.	$500,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 5.19% Airbnb Rental Income: $1575 Traditional Rental Income: $3799 Airbnb ROI: -0.54% Traditional ROI: 5.19%

Real Estate investment in Poughkeepsie, NY

There are 144 properties for sale in the city of Poughkeepsie . The median list price in Poughkeepsie is $424,965 and the average price per square foot is $212. In December 2025, the average monthly cash on cash return in Poughkeepsie is 4.00%. The average monthly rental income in Poughkeepsie is $3,023.

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

There are 144 investment properties available for sale in Poughkeepsie.

In 2025, 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 $2,230.

Your search for investment property begins and ends here

Investment Property for Sale in Poughkeepsie, NY

69 Dawson Court

Poughkeepsie, NY

4 beds | 3 baths | 3,148 sq.ft.

$772,000

Airbnb cash on cash: -2.3%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $1575

Traditional Rental Income: $4272

Airbnb ROI: -2.3%

Traditional ROI: 2.08%

28 Amber Court

Poughkeepsie, NY

2 beds | 2 baths | 1,455 sq.ft.

$279,000

Airbnb cash on cash: -2.82%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $1211

Traditional Rental Income: $2618

Airbnb ROI: -2.82%

Traditional ROI: 4.01%

24 Greenhouse Lane

Poughkeepsie, NY

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

$345,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 4.91%

Airbnb Rental Income: $2230

Traditional Rental Income: $2599

Airbnb ROI: 2.04%

Traditional ROI: 4.91%

29 Kelsey Road

Poughkeepsie, NY

3 beds | 2 baths | 1,700 sq.ft.

$440,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $2230

Traditional Rental Income: $3078

Airbnb ROI: 0.79%

Traditional ROI: 4.21%

2 Oriole Drive

Poughkeepsie, NY

4 beds | 2 baths | 1,998 sq.ft.

$465,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $1575

Traditional Rental Income: $2755

Airbnb ROI: -1.2%

Traditional ROI: 2.55%

77 Carroll Street

Poughkeepsie, NY

10 beds | 3 baths | N/A

$460,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $2581

Traditional Rental Income: $1811

Airbnb ROI: 1.12%

Traditional ROI: 0.77%

45 Raker Road

Poughkeepsie, NY

3 beds | 2 baths | 1,684 sq.ft.

$450,000

Airbnb cash on cash: 0.63%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $2230

Traditional Rental Income: $2935

Airbnb ROI: 0.63%

Traditional ROI: 3.64%

93 Delafield Street

Poughkeepsie, NY

4 beds | 2 baths | 2,750 sq.ft.

$370,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $2230

Traditional Rental Income: $2087

Airbnb ROI: 1.68%