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: 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 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: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $1979 Airbnb ROI: N/A Traditional ROI: 3.72%
406 Back Ashuelot Road Winchester, NH Become a part of history! This amazing building was the center for education for generatio...	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%
82 Howard Street Winchester, NH Discover the potential in this 2-bedroom, 2-bath gem in Winchester, NH! Roll up your sleev...	2 beds \| 2 baths \| 1,060 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.48% Airbnb Rental Income: $null Traditional Rental Income: $2516 Airbnb ROI: N/A Traditional ROI: 10.48%
153 Back Ashuelot Road Winchester, NH **Back on the market due to Buyers Financing**Welcome Homeâan incredible opportunity...	3 beds \| 4 baths \| 2,688 sq.ft.	$355,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $2732 Airbnb ROI: N/A Traditional ROI: 4.86%
12 Miner Court Winchester, NH Welcome to 12 Miner Court - a delightful 3-bedroom, 1-bath home set on a .47-acre lot with...	3 beds \| 1 baths \| 1,416 sq.ft.	$269,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.89% Airbnb Rental Income: $null Traditional Rental Income: $2694 Airbnb ROI: N/A Traditional ROI: 7.89%
45 Forest Lake Circle Winchester, NH Forest Lake Access! This is a charming recently renovated Ranch house. Sprawling 3/4 Bedro...	4 beds \| 2 baths \| 1,500 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.77% Airbnb Rental Income: $null Traditional Rental Income: $3211 Airbnb ROI: N/A Traditional ROI: 6.77%
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%
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%

Real Estate investment in Winchester, NH

There are 12 properties for sale in the city of Winchester . The median list price in Winchester is $362,500 and the average price per square foot is $170. In December 2025, the average monthly cash on cash return in Winchester is 6.00%. The average monthly rental income in Winchester is $2,972.

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

There are 12 investment properties available for sale in Winchester.

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

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $N/A.

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: 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 Circle

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%

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%

82 Howard Street

Winchester, NH

2 beds | 2 baths | 1,060 sq.ft.

$199,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2516

Airbnb ROI: N/A

Traditional ROI: 10.48%

153 Back Ashuelot Road

Winchester, NH

3 beds | 4 baths | 2,688 sq.ft.

$355,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.86%

Airbnb Rental Income: $null

Traditional Rental Income: $2732

Airbnb ROI: N/A

Traditional ROI: 4.86%

12 Miner Court

Winchester, NH

3 beds | 1 baths | 1,416 sq.ft.

$269,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.89%

Airbnb Rental Income: $null

Traditional Rental Income: $2694

Airbnb ROI: N/A

Traditional ROI: 7.89%

45 Forest Lake Circle

Winchester, NH

4 beds | 2 baths | 1,500 sq.ft.

$370,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.77%

Airbnb Rental Income: $null

Traditional Rental Income: $3211

Airbnb ROI: N/A

Traditional ROI: 6.77%

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