Real Estate Investment Properties for Sale in Wolfeboro, NH

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

Explore a variety of short-term homes & houses in Wolfeboro, NH. Invest wisely with VRBO & Wolfeboro, 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 Wolfeboro, NH

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
580 Pine Hill Road Wolfeboro, NH Come experience the remarkable 4,400 square foot historic Hersey Homestead! Circa 1810, wi...	4 beds \| 3 baths \| 4,446 sq.ft.	$2,195,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 0.6% Airbnb Rental Income: $3932 Traditional Rental Income: $4346 Airbnb ROI: -0.02% Traditional ROI: 0.6%
850 Center Street Wolfeboro, NH Welcome to 850 Center Street in Wolfeboro! This well-maintained 3-bedroom, 1-bath ranch ha...	3 beds \| 1 baths \| 1,348 sq.ft.	$419,000	Airbnb cash on cash: 2.65% Traditional cash on cash: 4.85% Airbnb Rental Income: $2419 Traditional Rental Income: $2690 Airbnb ROI: 2.65% Traditional ROI: 4.85%
369 Stoddard Road Wolfeboro, NH Stunning Post & Beam where distinctive architectural character meets thoughtfully curated ...	3 beds \| 4 baths \| 3,663 sq.ft.	$1,440,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.68% Airbnb Rental Income: $2419 Traditional Rental Income: $3266 Airbnb ROI: -0.4% Traditional ROI: 0.68%
68 Railroad Avenue #3 Wolfeboro, NH WATERFRONT CONDO equals Summer days on your private patio overlooking Lake Winnipesaukee's...	2 beds \| 2 baths \| 1,342 sq.ft.	$795,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.15% Airbnb Rental Income: $1852 Traditional Rental Income: $2658 Airbnb ROI: -0.61% Traditional ROI: 1.15%
108 Center Street Wolfeboro, NH NEW PRICE IMPROVEMENT! Imagine living within walking distance of the charming downtown Wol...	3 beds \| 3 baths \| 2,158 sq.ft.	$645,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.06% Airbnb Rental Income: $2419 Traditional Rental Income: $3640 Airbnb ROI: 1.05% Traditional ROI: 4.06%
449 N Wakefield Road Wolfeboro, NH Enjoy peace and quiet on over 5 acres with a warm and inviting home featuring wood accents...	3 beds \| 3 baths \| 3,740 sq.ft.	$630,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.98% Airbnb Rental Income: $2419 Traditional Rental Income: $3780 Airbnb ROI: 0.66% Traditional ROI: 3.98%
Winnipesaukee Drive Wolfeboro, NH Foundation and septic are in! Exceptional new construction ranch will have over 2,100 sq f...	3 beds \| 2 baths \| 2,117 sq.ft.	$899,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.28% Airbnb Rental Income: $2419 Traditional Rental Income: $3437 Airbnb ROI: 0.36% Traditional ROI: 2.28%
153 N Main Street Wolfeboro, NH Built in 1853 and known to generations of Wolfeboro residents as "The Varney House," this ...	5 beds \| 4 baths \| 4,716 sq.ft.	$1,685,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 2.08% Airbnb Rental Income: $2493 Traditional Rental Income: $6002 Airbnb ROI: -0.55% Traditional ROI: 2.08%
1 Harvey Brook Road Wolfeboro, NH Here's a great chance to own a 2 bedroom 2 bath home in the quiet neighborhood of The Birc...	2 beds \| 2 baths \| 1,248 sq.ft.	$305,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 5.84% Airbnb Rental Income: $1852 Traditional Rental Income: $2675 Airbnb ROI: 1.24% Traditional ROI: 5.84%
4 Farmhouse Lane Wolfeboro, NH Amazing Opportunity! End-Unit Condo Offering Privacy & Modern Luxury Near Downtown! Discov...	2 beds \| 3 baths \| 1,432 sq.ft.	$474,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.65% Airbnb Rental Income: $1852 Traditional Rental Income: $3125 Airbnb ROI: -0.34% Traditional ROI: 3.65%
16 Depot Street Wolfeboro, NH Opportunity knocks! Located at 16 Depot St in downtown Wolfeboro, this property is ready f...	3 beds \| 2 baths \| 2,656 sq.ft.	$645,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 3.59% Airbnb Rental Income: $2419 Traditional Rental Income: $3354 Airbnb ROI: 1.05% Traditional ROI: 3.59%
606 N Main Street Wolfeboro, NH A truly rare offering on the shores of Winter Harbor, this remarkable 20 acre property pre...	5 beds \| 1 baths \| 1,400 sq.ft.	$7,900,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.89% Airbnb Rental Income: $2493 Traditional Rental Income: $2923 Airbnb ROI: -1.03% Traditional ROI: -0.89%
606 and 607 N Main Street Wolfeboro, NH A truly rare offering on the shores of Winter Harbor, this remarkable 40+/- acre property ...	3 beds \| 1 baths \| 1,400 sq.ft.	$9,800,000	Airbnb cash on cash: -1.07% Traditional cash on cash: -0.97% Airbnb Rental Income: $2419 Traditional Rental Income: $2734 Airbnb ROI: -1.07% Traditional ROI: -0.97%
607 N Main Street Wolfeboro, NH 606 North Main Street, Wolfeboro, NH A rare opportunity to own one of Wolfeboro's hist...	3 beds \| 1 baths \| N/A	$1,900,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 0.29% Airbnb Rental Income: $2419 Traditional Rental Income: $2686 Airbnb ROI: -0.2% Traditional ROI: 0.29%
5 Robin Acres Drive Wolfeboro, NH This home features a to-the-studs renovation transforming a dated property into a brand-ne...	3 beds \| 2 baths \| 2,016 sq.ft.	$545,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 5.07% Airbnb Rental Income: $2419 Traditional Rental Income: $3354 Airbnb ROI: 2.07% Traditional ROI: 5.07%
2 Melody Island Wolfeboro, NH Spanning the full width of Melody Island, 2 Melody Island is a truly remarkable and one-of...	3 beds \| 3 baths \| 1,935 sq.ft.	$3,999,000	Airbnb cash on cash: -0.81% Traditional cash on cash: -0.22% Airbnb Rental Income: $2419 Traditional Rental Income: $4012 Airbnb ROI: -0.81% Traditional ROI: -0.22%
61-2 Central Avenue #2 Wolfeboro, NH Make this immaculate, luxury condo in the heart of desirable Wolfeboro your new home! Eleg...	3 beds \| 3 baths \| 2,494 sq.ft.	$1,499,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 0.61% Airbnb Rental Income: $2419 Traditional Rental Income: $3919 Airbnb ROI: -0.89% Traditional ROI: 0.61%
6 Kehonka Hill Road Wolfeboro, NH $30,000 Price Reduction........Welcome to your peaceful retreat nestled within the quiet a...	1 beds \| 1 baths \| 648 sq.ft.	$329,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.61% Airbnb Rental Income: $1364 Traditional Rental Income: $1775 Airbnb ROI: 0.93% Traditional ROI: 3.61%
3 and 5 Ryefield Terrace Wolfeboro, NH NEW PRICE!! Wolfeboro Opportunity - Investment Property - Multi-Generation Living - Conver...	4 beds \| 4 baths \| 2,088 sq.ft.	$538,800	Airbnb cash on cash: 3.86% Traditional cash on cash: 6.65% Airbnb Rental Income: $3932 Traditional Rental Income: $4491 Airbnb ROI: 3.86% Traditional ROI: 6.65%
11 and 13 Ryefield Terrace Wolfeboro, NH A wonderful opportunity to own two townhouse-style condominium units at Mountain View Terr...	6 beds \| 4 baths \| 2,704 sq.ft.	$639,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 6.26% Airbnb Rental Income: $2493 Traditional Rental Income: $5002 Airbnb ROI: 1.04% Traditional ROI: 6.26%
29 Hemlock Drive Wolfeboro, NH Wake up on 5 private acres-then be downtown in minutes. This brand-new New England Colonia...	3 beds \| 3 baths \| 2,232 sq.ft.	$899,900	Airbnb cash on cash: -1.1% Traditional cash on cash: 1.29% Airbnb Rental Income: $2419 Traditional Rental Income: $3824 Airbnb ROI: -1.1% Traditional ROI: 1.29%
15 Abenaukee Drive Wolfeboro, NH Multi- level ranch home well sited on generous 1.45 acre lot abutting shared access to Lak...	3 beds \| 3 baths \| 2,472 sq.ft.	$895,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.89% Airbnb Rental Income: $2419 Traditional Rental Income: $3876 Airbnb ROI: 0.43% Traditional ROI: 2.89%
84 N Line Road Wolfeboro, NH Bring your ideas to this 1945 Cape set on over an acre in Wolfeboro, New Hampshire, known ...	1 beds \| 1 baths \| 976 sq.ft.	$299,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 5.03% Airbnb Rental Income: $1364 Traditional Rental Income: $2021 Airbnb ROI: 1.23% Traditional ROI: 5.03%
16 Canopache Road Wolfeboro, NH Single-floor living, a short walk from everything Wolfeboro has to offer. This 2-bedroom, ...	2 beds \| 2 baths \| 1,726 sq.ft.	$649,900	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.12% Airbnb Rental Income: $1852 Traditional Rental Income: $3019 Airbnb ROI: 0.37% Traditional ROI: 3.12%
10 Pine Hill Road Wolfeboro, NH Welcome to 10 Pine Hill Road in the lovely town of Wolfeboro, New Hampshire! This charming...	3 beds \| 1 baths \| 1,088 sq.ft.	$433,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 3.88% Airbnb Rental Income: $2419 Traditional Rental Income: $2395 Airbnb ROI: 2.48% Traditional ROI: 3.88%
4 Wolfeboro Common Wolfeboro, NH NEW, NEW, NEW! This stunning end unit at Wolfeboro Common I has just undergone a complete ...	3 beds \| 2 baths \| 1,400 sq.ft.	$495,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 4.61% Airbnb Rental Income: $2419 Traditional Rental Income: $2983 Airbnb ROI: 2.11% Traditional ROI: 4.61%
765 N Main Street Wolfeboro, NH Welcome to Libby Lodge, originally built in 1896 as a guest house for Dr. Libby of the Lib...	5 beds \| 6 baths \| 4,600 sq.ft.	$2,500,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.02% Airbnb Rental Income: $2493 Traditional Rental Income: $8245 Airbnb ROI: -0.72% Traditional ROI: 2.02%
4 Whispering Pines Way Wolfeboro, NH To-be-built new construction on a 2.05-acre lot on newly created Whispering Pines Way off ...	3 beds \| 2 baths \| 2,117 sq.ft.	$915,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 2.24% Airbnb Rental Income: $2419 Traditional Rental Income: $3449 Airbnb ROI: 0.33% Traditional ROI: 2.24%
325 Middleton Road Wolfeboro, NH Enjoy the privacy, space, and versatility of this 3-bedroom, 2-bath home offering 2,360 sq...	3 beds \| 2 baths \| 2,360 sq.ft.	$699,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 3.36% Airbnb Rental Income: $2419 Traditional Rental Income: $3350 Airbnb ROI: 1.03% Traditional ROI: 3.36%
165 Ambrose Way Wolfeboro, NH Set high on 3.62 quiet acres above Wolfeboro, this custom 2007 home looks across Lake Winn...	4 beds \| 5 baths \| 4,812 sq.ft.	$1,995,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.81% Airbnb Rental Income: $3932 Traditional Rental Income: $6504 Airbnb ROI: -0.03% Traditional ROI: 1.81%

Real Estate investment in Wolfeboro, NH

There are 41 properties for sale in the city of Wolfeboro . The median list price in Wolfeboro is $784,626 and the average price per square foot is $347. In November 2026, the average monthly cash on cash return in Wolfeboro is 2.00%. The average monthly rental income in Wolfeboro is $3,092.

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

There are 41 investment properties available for sale in Wolfeboro.

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

The ROI for Short-Term is higher than the Long-Term in Wolfeboro with average rental income of $2,419.

Your search for investment property begins and ends here

Investment Property for Sale in Wolfeboro, NH

580 Pine Hill Road

Wolfeboro, NH

4 beds | 3 baths | 4,446 sq.ft.

$2,195,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $3932

Traditional Rental Income: $4346

Airbnb ROI: -0.02%

Traditional ROI: 0.6%

850 Center Street

Wolfeboro, NH

3 beds | 1 baths | 1,348 sq.ft.

$419,000

Airbnb cash on cash: 2.65%

Traditional cash on cash: 4.85%

Airbnb Rental Income: $2419

Traditional Rental Income: $2690

Airbnb ROI: 2.65%

Traditional ROI: 4.85%

369 Stoddard Road

Wolfeboro, NH

3 beds | 4 baths | 3,663 sq.ft.

$1,440,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $2419

Traditional Rental Income: $3266

Airbnb ROI: -0.4%

Traditional ROI: 0.68%

68 Railroad Avenue #3

Wolfeboro, NH

2 beds | 2 baths | 1,342 sq.ft.

$795,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 1.15%

Airbnb Rental Income: $1852

Traditional Rental Income: $2658

Airbnb ROI: -0.61%

Traditional ROI: 1.15%

108 Center Street

Wolfeboro, NH

3 beds | 3 baths | 2,158 sq.ft.

$645,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $2419

Traditional Rental Income: $3640

Airbnb ROI: 1.05%

Traditional ROI: 4.06%

449 N Wakefield Road

Wolfeboro, NH

3 beds | 3 baths | 3,740 sq.ft.

$630,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $2419

Traditional Rental Income: $3780

Airbnb ROI: 0.66%

Traditional ROI: 3.98%

Winnipesaukee Drive

Wolfeboro, NH

3 beds | 2 baths | 2,117 sq.ft.

$899,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $2419

Traditional Rental Income: $3437

Airbnb ROI: 0.36%

Traditional ROI: 2.28%

153 N Main Street

Wolfeboro, NH

5 beds | 4 baths | 4,716 sq.ft.

$1,685,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 2.08%

Airbnb Rental Income: $2493

Traditional Rental Income: $6002

Airbnb ROI: -0.55%