Real Estate Investment Properties for Sale in Pleasant Valley, NY

Looking for investment property in Pleasant Valley, NY with high ROI ?

Explore a variety of short-term homes & houses in Pleasant Valley, NY. Invest wisely with VRBO & Pleasant Valley, 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 Pleasant Valley, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
58 Cole Road Pleasant Valley, NY Welcome to this beautifully updated Ranch in Pleasant Valley offering 3 bedrooms, 2 bathro...	3 beds \| 2 baths \| 1,250 sq.ft.	$499,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.28% Airbnb Rental Income: $2434 Traditional Rental Income: $2682 Airbnb ROI: -0.52% Traditional ROI: 1.28%
6 Swain Drive Pleasant Valley, NY Welcome to 6 Swain Drive, a charming Cape Cod-style home nestled in the heart of Pleasant ...	3 beds \| 2 baths \| 1,680 sq.ft.	$429,900	Airbnb cash on cash: 1.69% Traditional cash on cash: 4.7% Airbnb Rental Income: $2434 Traditional Rental Income: $3053 Airbnb ROI: 1.69% Traditional ROI: 4.7%
166 Creek Rd Pleasant Valley, NY 12569 Pleasant Valley, NY	4 beds \| 3 baths \| N/A	$625,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 4.22% Airbnb Rental Income: $2008 Traditional Rental Income: $4136 Airbnb ROI: -0.32% Traditional ROI: 4.22%
37 Patricia Drive Pleasant Valley, NY Welcome to this stunning contemporary masterpiece, featuring a resort-style indoor pool an...	4 beds \| 5 baths \| 6,085 sq.ft.	$1,099,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 1.2% Airbnb Rental Income: $2008 Traditional Rental Income: $4080 Airbnb ROI: -1.34% Traditional ROI: 1.2%
1675 Main Street Pleasant Valley, NY Discover this charming home with endless potential in the heart of Pleasant Valley, Dutche...	3 beds \| 2 baths \| 2,992 sq.ft.	$385,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 5.74% Airbnb Rental Income: $2434 Traditional Rental Income: $3487 Airbnb ROI: 1.18% Traditional ROI: 5.74%
89 Birch Drive Pleasant Valley, NY Accepted offer and showing for back up offers This spacious and impeccably maintained ...	4 beds \| 3 baths \| 2,600 sq.ft.	$584,500	Airbnb cash on cash: -0.44% Traditional cash on cash: 4.22% Airbnb Rental Income: $2008 Traditional Rental Income: $4029 Airbnb ROI: -0.44% Traditional ROI: 4.22%
12 Wolf Lane Pleasant Valley, NY Tucked away on over 14 acres of total privacy and tranquility, 12 Wolf Lane is a contempor...	4 beds \| 4 baths \| 4,024 sq.ft.	$949,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.46% Airbnb Rental Income: $2008 Traditional Rental Income: $5880 Airbnb ROI: -0.52% Traditional ROI: 4.46%
387 Freedom Road Pleasant Valley, NY Discover the potential at 387 Freedom Roadâa 3-bed, 1-bath in the highly sought after Ar...	3 beds \| 1 baths \| 920 sq.ft.	$349,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 2.45% Airbnb Rental Income: $2434 Traditional Rental Income: $2082 Airbnb ROI: 1.71% Traditional ROI: 2.45%
129 Barkit Kennel Road Pleasant Valley, NY Welcome to 129 Barkit Kennel Rd! As you pull into the driveway you are immediately taken b...	3 beds \| 4 baths \| 2,716 sq.ft.	$610,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 4.43% Airbnb Rental Income: $2434 Traditional Rental Income: $4542 Airbnb ROI: -0.31% Traditional ROI: 4.43%
15 Barbara Lane Pleasant Valley, NY A New Chapter Awaits in Pleasant Valley! Welcome to this charming 3-bedroom, 1-bathroom sp...	3 beds \| 1 baths \| 1,248 sq.ft.	$287,100	Airbnb cash on cash: 3.04% Traditional cash on cash: 4.98% Airbnb Rental Income: $2434 Traditional Rental Income: $2363 Airbnb ROI: 3.04% Traditional ROI: 4.98%
11 Demelis Drive Pleasant Valley, NY This charming Cape Cod style home features classic New England architecture with tradition...	3 beds \| 1 baths \| 1,520 sq.ft.	$195,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 8.02% Airbnb Rental Income: $2434 Traditional Rental Income: $2360 Airbnb ROI: 5.21% Traditional ROI: 8.02%
79 Frost Hill Road Pleasant Valley, NY TO BE BUILT Stunning Farmhouse Colonial with 4-bedrooms and 3.5 baths in the highly so...	4 beds \| 4 baths \| 3,008 sq.ft.	$995,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 4.53% Airbnb Rental Income: $2008 Traditional Rental Income: $5480 Airbnb ROI: 0.21% Traditional ROI: 4.53%
233 Rossway Road Pleasant Valley, NY Historic Charm Meets Cozy Cottage: A One-of-a-Kind Retreat. Step back in time and fall in ...	2 beds \| 1 baths \| 800 sq.ft.	$249,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 4.36% Airbnb Rental Income: $1617 Traditional Rental Income: $1840 Airbnb ROI: 1.47% Traditional ROI: 4.36%
661 Traver Road Pleasant Valley, NY If you're looking for one level living, don't miss out on this home. Enjoy this 3-bedroom,...	3 beds \| 2 baths \| 1,512 sq.ft.	$320,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 6.31% Airbnb Rental Income: $2434 Traditional Rental Income: $2928 Airbnb ROI: 2.69% Traditional ROI: 6.31%
198 Oswego Road Pleasant Valley, NY Welcome HOME to 198 Oswego Road - a beautifully maintained 3-bedroom, 2-bath One level Ran...	3 beds \| 2 baths \| 1,523 sq.ft.	$475,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 4.05% Airbnb Rental Income: $2434 Traditional Rental Income: $2979 Airbnb ROI: 1.49% Traditional ROI: 4.05%
453 Pine Hill Road Pleasant Valley, NY FULLY AVAILABLE ! Welcome to this cozy gem featuring 2 bedrooms and 1 full bathroom within...	2 beds \| 1 baths \| 846 sq.ft.	$239,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 5.18% Airbnb Rental Income: $1617 Traditional Rental Income: $1929 Airbnb ROI: 1.77% Traditional ROI: 5.18%
2042 Route 44 unit: 2038 #2038 Pleasant Valley, NY Investor Opportunity: Premium 24-Unit Asset in Heart of Dutchess County. A rare chance to ...	N/A beds \| N/A baths \| N/A	$4,500,000	Airbnb cash on cash: -1.83% Traditional cash on cash: -1.62% Airbnb Rental Income: $1109 Traditional Rental Income: $1617 Airbnb ROI: -1.83% Traditional ROI: -1.62%
686 Traver Road Pleasant Valley, NY Welcome to this beautifully maintained Cape Cod-style home, set on 7.79 picturesque acres ...	3 beds \| 3 baths \| 2,688 sq.ft.	$639,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.12% Airbnb Rental Income: $2434 Traditional Rental Income: $3734 Airbnb ROI: -0.06% Traditional ROI: 3.12%
90 Elm Lane Pleasant Valley, NY This spacious home features an open concept living room, dining area, and kitchen designed...	2 beds \| 2 baths \| 920 sq.ft.	$140,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 8.72% Airbnb Rental Income: $1617 Traditional Rental Income: $2173 Airbnb ROI: 1.16% Traditional ROI: 8.72%
9 Mcallister Drive Pleasant Valley, NY Mid-century design and creative use of space are perfectly expressed in this impeccably ma...	3 beds \| 2 baths \| 1,670 sq.ft.	$449,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.7% Airbnb Rental Income: $2434 Traditional Rental Income: $3027 Airbnb ROI: 0.88% Traditional ROI: 3.7%

Real Estate investment in Pleasant-valley, NY

There are 20 properties for sale in the city of Pleasant Valley . The median list price in Pleasant Valley is $462,000 and the average price per square foot is $219. In December 2025, the average monthly cash on cash return in Pleasant Valley is 4.00%. The average monthly rental income in Pleasant Valley is $3,027.

Pleasant-valley, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 20 investment properties available for sale in Pleasant-valley.

In 2025, the best neighborhood to buy investment property is Pleasant Valley.

The ROI for Long-Term is higher than the Short-Term in Pleasant-valley with average rental income of $3,027.

Your search for investment property begins and ends here

Investment Property for Sale in Pleasant Valley, NY

58 Cole Road

Pleasant Valley, NY

3 beds | 2 baths | 1,250 sq.ft.

$499,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $2434

Traditional Rental Income: $2682

Airbnb ROI: -0.52%

Traditional ROI: 1.28%

6 Swain Drive

Pleasant Valley, NY

3 beds | 2 baths | 1,680 sq.ft.

$429,900

Airbnb cash on cash: 1.69%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $2434

Traditional Rental Income: $3053

Airbnb ROI: 1.69%

Traditional ROI: 4.7%

166 Creek Rd Pleasant Valley, NY 12569

Pleasant Valley, NY

4 beds | 3 baths | N/A

$625,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $2008

Traditional Rental Income: $4136

Airbnb ROI: -0.32%

Traditional ROI: 4.22%

37 Patricia Drive

Pleasant Valley, NY

4 beds | 5 baths | 6,085 sq.ft.

$1,099,000

Airbnb cash on cash: -1.34%

Traditional cash on cash: 1.2%

Airbnb Rental Income: $2008

Traditional Rental Income: $4080

Airbnb ROI: -1.34%

Traditional ROI: 1.2%

1675 Main Street

Pleasant Valley, NY

3 beds | 2 baths | 2,992 sq.ft.

$385,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $2434

Traditional Rental Income: $3487

Airbnb ROI: 1.18%

Traditional ROI: 5.74%

89 Birch Drive

Pleasant Valley, NY

4 beds | 3 baths | 2,600 sq.ft.

$584,500

Airbnb cash on cash: -0.44%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $2008

Traditional Rental Income: $4029

Airbnb ROI: -0.44%

Traditional ROI: 4.22%

12 Wolf Lane

Pleasant Valley, NY

4 beds | 4 baths | 4,024 sq.ft.

$949,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $2008

Traditional Rental Income: $5880

Airbnb ROI: -0.52%

Traditional ROI: 4.46%

387 Freedom Road

Pleasant Valley, NY

3 beds | 1 baths | 920 sq.ft.

$349,000

Airbnb cash on cash: 1.71%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $2434

Traditional Rental Income: $2082

Airbnb ROI: 1.71%