Real Estate Investment Properties for Sale in Winchester, NH

Looking for investment property in Winchester, NH with high ROI ?

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

Single Family Homes for Sale in Winchester, NH

Search for Single Family Residential for Sale in Winchester, New Hampshire. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 12 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
27 Headlands Rd Winchester, NH Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on F...	2 beds \| 1 baths \| 1,351 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $2733 Airbnb ROI: N/A Traditional ROI: 1.63%
49 Forest Lake Cir Winchester, NH Kick back and relax at this stylish year-round lake area country cottage. Includes deed a...	2 beds \| 1 baths \| 937 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $1979 Airbnb ROI: N/A Traditional ROI: 3.72%
259 Bolton Rd Winchester, NH Stunning & modern unique True Timber Frame home has it all with incredible CT River views ...	3 beds \| 2 baths \| 3,472 sq.ft.	$849,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.52% Airbnb Rental Income: $null Traditional Rental Income: $2143 Airbnb ROI: N/A Traditional ROI: 0.52%
240 Forest Lake Rd Winchester, NH Real Country Living in an antique post & beam farmhouse on 11+ acres, COMPLETELY remod...	4 beds \| 2 baths \| 2,200 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $3883 Airbnb ROI: N/A Traditional ROI: 4.61%
130 Watson Road Winchester, NH This beautiful 3-bedroom home is set on 12 acres of designated wildlife habitat overlookin...	3 beds \| 2 baths \| 2,145 sq.ft.	$694,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.41% Airbnb Rental Income: $null Traditional Rental Income: $3247 Airbnb ROI: N/A Traditional ROI: 2.41%
159 Ashuelot Main St Winchester, NH MARKET ADJUSTMENT! Upgrade with this NEW, Classic and modern home close to all town servic...	4 beds \| 3 baths \| 2,832 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.16% Airbnb Rental Income: $null Traditional Rental Income: $3887 Airbnb ROI: N/A Traditional ROI: 6.16%
71 Parker Street Winchester, NH New Year, New Home! Come see this charming 3 bedroom, 1 bathroom home with a spacious yar...	3 beds \| 1 baths \| 1,372 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.63% Airbnb Rental Income: $null Traditional Rental Income: $2446 Airbnb ROI: N/A Traditional ROI: 7.63%
583 Burt Hill Rd Winchester, NH Welcome to your move-in-ready sanctuary! This beautifully updated home perfectly blends mo...	4 beds \| 3 baths \| 3,114 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $3994 Airbnb ROI: N/A Traditional ROI: 4.98%
20 Bilo Ave Winchester, NH Updated and ready to love, this bright and sunny 3-bedroom, 1-bath home offers 1,145 squar...	3 beds \| 1 baths \| 1,145 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.3% Airbnb Rental Income: $null Traditional Rental Income: $2328 Airbnb ROI: N/A Traditional ROI: 5.3%

Your search for investment property begins and ends here

Single Family Homes for Sale in Winchester, NH

27 Headlands Rd

Winchester, NH

2 beds | 1 baths | 1,351 sq.ft.

$725,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2733

Airbnb ROI: N/A

Traditional ROI: 1.63%

49 Forest Lake Cir

Winchester, NH

2 beds | 1 baths | 937 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.72%

Airbnb Rental Income: $null

Traditional Rental Income: $1979

Airbnb ROI: N/A

Traditional ROI: 3.72%

259 Bolton Rd

Winchester, NH

3 beds | 2 baths | 3,472 sq.ft.

$849,900

Airbnb cash on cash: N/A

Traditional cash on cash: 0.52%

Airbnb Rental Income: $null

Traditional Rental Income: $2143

Airbnb ROI: N/A

Traditional ROI: 0.52%

240 Forest Lake Rd

Winchester, NH

4 beds | 2 baths | 2,200 sq.ft.

$610,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.61%

Airbnb Rental Income: $null

Traditional Rental Income: $3883

Airbnb ROI: N/A

Traditional ROI: 4.61%

130 Watson Road

Winchester, NH

3 beds | 2 baths | 2,145 sq.ft.

$694,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.41%

Airbnb Rental Income: $null

Traditional Rental Income: $3247

Airbnb ROI: N/A

Traditional ROI: 2.41%

159 Ashuelot Main St

Winchester, NH

4 beds | 3 baths | 2,832 sq.ft.

$559,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3887

Airbnb ROI: N/A

Traditional ROI: 6.16%

71 Parker Street

Winchester, NH

3 beds | 1 baths | 1,372 sq.ft.

$239,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2446

Airbnb ROI: N/A

Traditional ROI: 7.63%

583 Burt Hill Rd

Winchester, NH

4 beds | 3 baths | 3,114 sq.ft.

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.98%

Airbnb Rental Income: $null

Traditional Rental Income: $3994

Airbnb ROI: N/A