Real Estate Investment Properties for Sale in Dover Plains, NY

Looking for investment property in Dover Plains, NY with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
Route 22 Dover Plains, NY LOT 27. Twenty five individual 1 - 4 acre available lots for sale in Sherman Hills Estates...	N/A beds \| N/A baths \| N/A	$190,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 10.26% Airbnb Rental Income: $903 Traditional Rental Income: $2215 Airbnb ROI: 1.12% Traditional ROI: 10.26%
56 Northrup Rd Dover Plains, NY Classic Country Home with Pond and Views - Charming 3 bedroom-2 full bath farmhouse in Dov...	4 beds \| 4 baths \| 2,412 sq.ft.	$2,475,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 0.37% Airbnb Rental Income: $7266 Traditional Rental Income: $4328 Airbnb ROI: 1.04% Traditional ROI: 0.37%
256 Hammond Hill Rd Dover Plains, NY Looking for a serene, quiet home to call your own? This property is just that! Located at ...	3 beds \| 2 baths \| 1,900 sq.ft.	$499,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 6.96% Airbnb Rental Income: $2585 Traditional Rental Income: $4317 Airbnb ROI: 1.92% Traditional ROI: 6.96%
105 Sand Hill Rd Dover Plains, NY 105 Sand Hill Rd, Dover Plains, NY 12522 \| Single Family Residential	1 beds \| 1 baths \| 805 sq.ft.	$450,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 2.69% Airbnb Rental Income: $922 Traditional Rental Income: $1814 Airbnb ROI: -0.24% Traditional ROI: 2.69%
1297 Route 343 Dover Plains, NY 1297 Route 343, Dover Plains, NY 12522 \| Other	N/A beds \| N/A baths \| N/A	$5,000,000	Airbnb cash on cash: -2.61% Traditional cash on cash: -2.51% Airbnb Rental Income: $903 Traditional Rental Income: $1043 Airbnb ROI: -2.61% Traditional ROI: -2.51%
9 Ter Bar Ct Dover Plains, NY 9 Ter Bar Ct, Dover Plains, NY 12522 \| Other	N/A beds \| N/A baths \| N/A	$100,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 7.27% Airbnb Rental Income: $903 Traditional Rental Income: $1059 Airbnb ROI: 2.18% Traditional ROI: 7.27%
163 Old State Route 22 Dover Plains, NY Discover the perfect blend of potential and land with this quaint cottage in Dover Plains....	2 beds \| 2 baths \| 1,440 sq.ft.	$249,999	Airbnb cash on cash: 7.36% Traditional cash on cash: 6.87% Airbnb Rental Income: $3519 Traditional Rental Income: $2628 Airbnb ROI: 7.36% Traditional ROI: 6.87%
37 Glen Ave Dover Plains, NY 2 homes for the price of 1. This is a multi-family property on multiple structures. Two se...	5 beds \| 3 baths \| 3,318 sq.ft.	$375,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 9.65% Airbnb Rental Income: $3519 Traditional Rental Income: $4335 Airbnb ROI: 5.12% Traditional ROI: 9.65%
21-23 Tinker Town Rd Dover Plains, NY A few minutes east of Route 22 on the Dover/Millbrook border in the municipality of Washin...	3 beds \| 1 baths \| 1,482 sq.ft.	$1,950,000	Airbnb cash on cash: -1.94% Traditional cash on cash: -1.79% Airbnb Rental Income: $2585 Traditional Rental Income: $2241 Airbnb ROI: -1.94% Traditional ROI: -1.79%
226 Cart Rd #C Dover Plains, NY This beautifully maintained 3-bedroom, 2.5-bath Colonial is being offered for sale for the...	3 beds \| 2 baths \| 2,188 sq.ft.	$575,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 3.89% Airbnb Rental Income: $2585 Traditional Rental Income: $3641 Airbnb ROI: 0.77% Traditional ROI: 3.89%
30 Tally-ho Dr Dover Plains, NY Welcome to this beautifully maintained 2-bedroom, 2-bath mobile home in a 55+ community in...	2 beds \| 2 baths \| 1,000 sq.ft.	$130,000	Airbnb cash on cash: 6.64% Traditional cash on cash: 2.03% Airbnb Rental Income: $3519 Traditional Rental Income: $2167 Airbnb ROI: 6.64% Traditional ROI: 2.03%
20 Craig Ln Dover Plains, NY A European Inspired Oasis in Dover Plains! This meticulously cared for custom built home i...	3 beds \| 2 baths \| 2,409 sq.ft.	$595,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 4.46% Airbnb Rental Income: $2585 Traditional Rental Income: $3877 Airbnb ROI: 1.02% Traditional ROI: 4.46%
365 Tower Hill Rd Dover Plains, NY 365 Tower Hill Rd, Dover Plains, NY 12592 \| Single Family Residential	4 beds \| 5 baths \| 7,500 sq.ft.	$16,500,000	Airbnb cash on cash: -2.34% Traditional cash on cash: -2.29% Airbnb Rental Income: $7223 Traditional Rental Income: $6572 Airbnb ROI: -2.34% Traditional ROI: -2.29%
110 Gina Dr Dover Plains, NY 110 Gina Dr, Dover Plains, NY 12522 \| Manufactured Home	2 beds \| 2 baths \| 1,056 sq.ft.	$175,000	Airbnb cash on cash: 7.73% Traditional cash on cash: 5.56% Airbnb Rental Income: $3519 Traditional Rental Income: $2383 Airbnb ROI: 7.73% Traditional ROI: 5.56%
151 Benson Hill Rd Dover Plains, NY 151 Benson Hill Rd, Dover Plains, NY 12522 \| Single Family Residential	7 beds \| 5 baths \| 6,138 sq.ft.	$3,750,000	Airbnb cash on cash: -2.74% Traditional cash on cash: -0.89% Airbnb Rental Income: $225 Traditional Rental Income: $6449 Airbnb ROI: -2.74% Traditional ROI: -0.89%
766 Route 343 Dover Plains, NY 766 Route 343, Dover Plains, NY 12522 \| Single Family Residential	3 beds \| 2 baths \| 1,824 sq.ft.	$549,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 2.49% Airbnb Rental Income: $2585 Traditional Rental Income: $2758 Airbnb ROI: 0.94% Traditional ROI: 2.49%
810 Route 343 Dover Plains, NY 810 Route 343, Dover Plains, NY 12522 \| Single Family Residential	4 beds \| 2 baths \| 2,148 sq.ft.	$599,408	Airbnb cash on cash: 7.61% Traditional cash on cash: 2.76% Airbnb Rental Income: $7266 Traditional Rental Income: $3152 Airbnb ROI: 7.61% Traditional ROI: 2.76%
7 Brookview Rd Dover Plains, NY 7 Brookview Rd, Dover Plains, NY 12522 \| Other	N/A beds \| N/A baths \| N/A	$110,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 7.59% Airbnb Rental Income: $903 Traditional Rental Income: $1186 Airbnb ROI: 1.74% Traditional ROI: 7.59%

Real Estate investment in Dover-plains, NY

There are 19 properties for sale in the city of Dover Plains . The median list price in Dover Plains is $370,000 and the average price per square foot is $154. In August 2026, the average monthly cash on cash return in Dover Plains is 5.00%. The average monthly rental income in Dover Plains is $2,288.

Dover-plains, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 19 investment properties available for sale in Dover-plains.

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

The ROI for Long-Term is higher than the Short-Term in Dover-plains with average rental income of $2,288.

Your search for investment property begins and ends here

Investment Property for Sale in Dover Plains, NY

Route 22

Dover Plains, NY

N/A beds | N/A baths | N/A

$190,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 10.26%

Airbnb Rental Income: $903

Traditional Rental Income: $2215

Airbnb ROI: 1.12%

Traditional ROI: 10.26%

56 Northrup Rd

Dover Plains, NY

4 beds | 4 baths | 2,412 sq.ft.

$2,475,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $7266

Traditional Rental Income: $4328

Airbnb ROI: 1.04%

Traditional ROI: 0.37%

256 Hammond Hill Rd

Dover Plains, NY

3 beds | 2 baths | 1,900 sq.ft.

$499,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 6.96%

Airbnb Rental Income: $2585

Traditional Rental Income: $4317

Airbnb ROI: 1.92%

Traditional ROI: 6.96%

105 Sand Hill Rd

Dover Plains, NY

1 beds | 1 baths | 805 sq.ft.

$450,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 2.69%

Airbnb Rental Income: $922

Traditional Rental Income: $1814

Airbnb ROI: -0.24%

Traditional ROI: 2.69%

1297 Route 343

Dover Plains, NY

N/A beds | N/A baths | N/A

$5,000,000

Airbnb cash on cash: -2.61%

Traditional cash on cash: -2.51%

Airbnb Rental Income: $903

Traditional Rental Income: $1043

Airbnb ROI: -2.61%

Traditional ROI: -2.51%

9 Ter Bar Ct

Dover Plains, NY

N/A beds | N/A baths | N/A

$100,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 7.27%

Airbnb Rental Income: $903

Traditional Rental Income: $1059

Airbnb ROI: 2.18%

Traditional ROI: 7.27%

163 Old State Route 22

Dover Plains, NY

2 beds | 2 baths | 1,440 sq.ft.

$249,999

Airbnb cash on cash: 7.36%

Traditional cash on cash: 6.87%

Airbnb Rental Income: $3519

Traditional Rental Income: $2628

Airbnb ROI: 7.36%

Traditional ROI: 6.87%

37 Glen Ave

Dover Plains, NY

5 beds | 3 baths | 3,318 sq.ft.

$375,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 9.65%

Airbnb Rental Income: $3519

Traditional Rental Income: $4335

Airbnb ROI: 5.12%