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.

Investment Property for Sale in Winchester, NH

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
27 Headlands Road Winchester, NH Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on F...	2 beds \| 2 baths \| 1,351 sq.ft.	$725,000	Airbnb cash on cash: -1.84% Traditional cash on cash: 1.63% Airbnb Rental Income: $694 Traditional Rental Income: $2733 Airbnb ROI: -1.84% Traditional ROI: 1.63%
49 Forest Lake Circle 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: -1.11% Traditional cash on cash: 3.72% Airbnb Rental Income: $694 Traditional Rental Income: $1979 Airbnb ROI: -1.11% Traditional ROI: 3.72%
886 Keene Rd Winchester, NH Welcome to 886 Keene Rd, a lovingly maintained home where timeless 1875 charm meets though...	2 beds \| 1 baths \| 1,424 sq.ft.	$259,900	Airbnb cash on cash: -1.04% Traditional cash on cash: 6.33% Airbnb Rental Income: $694 Traditional Rental Income: $2197 Airbnb ROI: -1.04% Traditional ROI: 6.33%
406 Back Ashuelot Road Winchester, NH VALUE! HISTORIC! CHARM! This property is now listed over $100,000 under the assessed va...	7 beds \| 5 baths \| 5,607 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.65% Airbnb Rental Income: $null Traditional Rental Income: $6809 Airbnb ROI: N/A Traditional ROI: 9.65%
259 Bolton Road 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: 0.61% Airbnb Rental Income: $null Traditional Rental Income: $2143 Airbnb ROI: N/A Traditional ROI: 0.61%
240 Forest Lake Road Winchester, NH Real Country Living in an antique post & beam farmhouse on 11+ acres, COMPLETELY remod...	4 beds \| 3 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%
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%
20 Bilo Avenue 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%

Real Estate investment in Winchester, NH

There are 11 properties for sale in the city of Winchester . The median list price in Winchester is $440,000 and the average price per square foot is $194. In March 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $2,358.

Winchester, NH Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 11 investment properties available for sale in Winchester.

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

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $2,358.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, NH

27 Headlands Road

Winchester, NH

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

$725,000

Airbnb cash on cash: -1.84%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $694

Traditional Rental Income: $2733

Airbnb ROI: -1.84%

Traditional ROI: 1.63%

49 Forest Lake Circle

Winchester, NH

2 beds | 1 baths | 937 sq.ft.

$350,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $694

Traditional Rental Income: $1979

Airbnb ROI: -1.11%

Traditional ROI: 3.72%

886 Keene Rd

Winchester, NH

2 beds | 1 baths | 1,424 sq.ft.

$259,900

Airbnb cash on cash: -1.04%

Traditional cash on cash: 6.33%

Airbnb Rental Income: $694

Traditional Rental Income: $2197

Airbnb ROI: -1.04%

Traditional ROI: 6.33%

406 Back Ashuelot Road

Winchester, NH

7 beds | 5 baths | 5,607 sq.ft.

$600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.65%

Airbnb Rental Income: $null

Traditional Rental Income: $6809

Airbnb ROI: N/A

Traditional ROI: 9.65%

259 Bolton Road

Winchester, NH

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

$849,900

Airbnb cash on cash: N/A

Traditional cash on cash: 0.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2143

Airbnb ROI: N/A

Traditional ROI: 0.61%

240 Forest Lake Road

Winchester, NH

4 beds | 3 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%

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%

20 Bilo Avenue

Winchester, NH

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