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 Rd Winchester, NH Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on Fo...	2 beds \| 1 baths \| 1,351 sq.ft.	$715,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 1.66% Airbnb Rental Income: $943 Traditional Rental Income: $2733 Airbnb ROI: -1.54% Traditional ROI: 1.66%
253 Back Ashuelot Rd Winchester, NH Not far from Rte. 91 and close to the Rail Trails is this yearround compound located on ...	1 beds \| 1 baths \| 1,290 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.82% Airbnb Rental Income: $null Traditional Rental Income: $1766 Airbnb ROI: N/A Traditional ROI: 1.82%
398 Scofield Mountain Rd Winchester, NH One of New England's most unique & premiere properties, a sprawling sanctuary set on over ...	4 beds \| 5 baths \| 5,120 sq.ft.	$4,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $8011 Airbnb ROI: N/A Traditional ROI: 0.93%
39 Headlands Rd Winchester, NH Step across the threshold and into a piece of history. A 1910 waterfront hidden treasure....	3 beds \| 2 baths \| 1,364 sq.ft.	$698,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.02% Airbnb Rental Income: $null Traditional Rental Income: $2928 Airbnb ROI: N/A Traditional ROI: 2.02%
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%
12 Wetherby Dr Winchester, NH 12 Wetherby Dr, Winchester, NH 03470 \| Manufactured Home	2 beds \| 2 baths \| 924 sq.ft.	$120,000	Airbnb cash on cash: -3.56% Traditional cash on cash: 10.88% Airbnb Rental Income: $943 Traditional Rental Income: $2269 Airbnb ROI: -3.56% Traditional ROI: 10.88%
00 Route 10 Winchester, NH 00 Route 10, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$2,100,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.59% Airbnb Rental Income: $null Traditional Rental Income: $1223 Airbnb ROI: N/A Traditional ROI: -2.59%
525 Richmond Rd Winchester, NH 525 Richmond Rd, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$115,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.05% Airbnb Rental Income: $null Traditional Rental Income: $1223 Airbnb ROI: N/A Traditional ROI: 7.05%
292 Richmond Rd Winchester, NH INVESTORS WANTED. This property is just a few minutes away from downtown Winchester. 3 uni...	N/A beds \| 4 baths \| 4,739 sq.ft.	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $2108 Airbnb ROI: N/A Traditional ROI: 4.42%
7 Purcell Road Winchester, NH Roomy, solidly built Post & Beam home awaits your tasteful touches and TLC! Enter this cen...	3 beds \| 2 baths \| 1,805 sq.ft.	$319,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.3% Airbnb Rental Income: $null Traditional Rental Income: $3156 Airbnb ROI: N/A Traditional ROI: 7.3%
19 Back Ashuelot Rd Winchester, NH Do you have a home business and are looking to relocate? This could be your opportunity to...	4 beds \| 2 baths \| 1,493 sq.ft.	$285,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.1% Airbnb Rental Income: $null Traditional Rental Income: $3329 Airbnb ROI: N/A Traditional ROI: 10.1%
369 Manning Hill Rd Winchester, NH Unique opportunity to get two for the price of one. Sale includes two (2) lots! House and ...	2 beds \| 1 baths \| 894 sq.ft.	$190,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 7.98% Airbnb Rental Income: $943 Traditional Rental Income: $2046 Airbnb ROI: -0.04% Traditional ROI: 7.98%
71 Headlands Rd Winchester, NH This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines...	3 beds \| 2 baths \| 1,066 sq.ft.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $2753 Airbnb ROI: N/A Traditional ROI: 3.72%
418 Forest Lake Rd Winchester, NH 418 Forest Lake Rd, Winchester, NH 03470 \| Single Family Residential	2 beds \| 1 baths \| 1,392 sq.ft.	$499,900	Airbnb cash on cash: -2.1% Traditional cash on cash: 1.31% Airbnb Rental Income: $943 Traditional Rental Income: $2192 Airbnb ROI: -2.1% Traditional ROI: 1.31%
65 Mechanic St Winchester, NH 65 Mechanic St, Winchester, NH 03470 \| Single Family Residential	3 beds \| 2 baths \| 2,128 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.9% Airbnb Rental Income: $null Traditional Rental Income: $3047 Airbnb ROI: N/A Traditional ROI: 8.9%
484 Scofield Mountain Rd Winchester, NH 484 Scofield Mountain Rd, Winchester, NH 03470 \| Single Family Residential	3 beds \| 2 baths \| 2,516 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.2% Airbnb Rental Income: $null Traditional Rental Income: $3093 Airbnb ROI: N/A Traditional ROI: 2.2%
166 Keene Rd Winchester, NH 166 Keene Rd, Winchester, NH 03470 \| Single Family Residential	3 beds \| 1 baths \| 1,808 sq.ft.	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $2358 Airbnb ROI: N/A Traditional ROI: 1.88%
295 Manning Hill Rd Winchester, NH 295 Manning Hill Rd, Winchester, NH 03470 \| Single Family Residential	3 beds \| 2 baths \| 2,671 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.77% Airbnb Rental Income: $null Traditional Rental Income: $3087 Airbnb ROI: N/A Traditional ROI: 1.77%
000 Burt Hill Rd Winchester, NH 000 Burt Hill Rd, Winchester, NH 03455 \| Other	N/A beds \| N/A baths \| N/A	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.12% Airbnb Rental Income: $null Traditional Rental Income: $1322 Airbnb ROI: N/A Traditional ROI: 0.12%
90 Old Swanzey Rd Winchester, NH 90 Old Swanzey Rd, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$90,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.96% Airbnb Rental Income: $null Traditional Rental Income: $1242 Airbnb ROI: N/A Traditional ROI: 9.96%
20 Lake Shore Dr Winchester, NH 20 Lake Shore Dr, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $1242 Airbnb ROI: N/A Traditional ROI: 5.74%
Map 6 Off Opportunity Dr Lot 15-5 Winchester, NH Map 6 Off Opportunity Dr Lot 15-5, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$109,500	Airbnb cash on cash: N/A Traditional cash on cash: 8.48% Airbnb Rental Income: $null Traditional Rental Income: $1322 Airbnb ROI: N/A Traditional ROI: 8.48%
Map 6 Off Opportunity Dr Lot 15-8 Winchester, NH Map 6 Off Opportunity Dr Lot 15-8, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$117,500	Airbnb cash on cash: N/A Traditional cash on cash: 7.72% Airbnb Rental Income: $null Traditional Rental Income: $1322 Airbnb ROI: N/A Traditional ROI: 7.72%
Map 6 Off Opportunity Dr Lot 15-0 Winchester, NH Map 6 Off Opportunity Dr Lot 15-0, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$118,200	Airbnb cash on cash: N/A Traditional cash on cash: 7.65% Airbnb Rental Income: $null Traditional Rental Income: $1322 Airbnb ROI: N/A Traditional ROI: 7.65%
Map 6 Opportunity Dr #15-7 Winchester, NH Map 6 Opportunity Dr #15-7, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$131,600	Airbnb cash on cash: N/A Traditional cash on cash: 5.96% Airbnb Rental Income: $null Traditional Rental Income: $1242 Airbnb ROI: N/A Traditional ROI: 5.96%
Map 6 Off Opportunity Dr Lot 15-1 Winchester, NH Map 6 Off Opportunity Dr Lot 15-1, Winchester, NH 03470 \| Other	N/A beds \| N/A baths \| N/A	$89,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.98% Airbnb Rental Income: $null Traditional Rental Income: $1242 Airbnb ROI: N/A Traditional ROI: 9.98%

Real Estate investment in Winchester, NH

There are 30 properties for sale in the city of Winchester . The median list price in Winchester is $274,336 and the average price per square foot is $123. In August 2026, the average monthly cash on cash return in Winchester is 6.00%. The average monthly rental income in Winchester is $2,192.

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

There are 30 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 $2,192.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, NH

27 Headlands Rd

Winchester, NH

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

$715,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: 1.66%

Airbnb Rental Income: $943

Traditional Rental Income: $2733

Airbnb ROI: -1.54%

Traditional ROI: 1.66%

253 Back Ashuelot Rd

Winchester, NH

1 beds | 1 baths | 1,290 sq.ft.

$425,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.82%

Airbnb Rental Income: $null

Traditional Rental Income: $1766

Airbnb ROI: N/A

Traditional ROI: 1.82%

398 Scofield Mountain Rd

Winchester, NH

4 beds | 5 baths | 5,120 sq.ft.

$4,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.93%

Airbnb Rental Income: $null

Traditional Rental Income: $8011

Airbnb ROI: N/A

Traditional ROI: 0.93%

39 Headlands Rd

Winchester, NH

3 beds | 2 baths | 1,364 sq.ft.

$698,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.02%

Airbnb Rental Income: $null

Traditional Rental Income: $2928

Airbnb ROI: N/A

Traditional ROI: 2.02%

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

Traditional ROI: 5.3%

12 Wetherby Dr

Winchester, NH

2 beds | 2 baths | 924 sq.ft.

$120,000

Airbnb cash on cash: -3.56%

Traditional cash on cash: 10.88%

Airbnb Rental Income: $943

Traditional Rental Income: $2269

Airbnb ROI: -3.56%