Real Estate Investment Properties for Sale in Wakefield, MA

Looking for investment property in Wakefield, MA with high ROI ?

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
14 Plymouth Road Wakefield, MA Wow! Hereâs your chance to own & live in one of Wakefieldâs most sought-after location...	3 beds \| 3 baths \| 2,410 sq.ft.	$799,900	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.16% Airbnb Rental Income: $2687 Traditional Rental Income: $3910 Airbnb ROI: 0.66% Traditional ROI: 3.16%
47 Aborn Ave Wakefield, MA Just steps from Lake Quannapowitt and a short stroll to Wakefieldâs vibrant downtown, th...	3 beds \| 2 baths \| 1,386 sq.ft.	$859,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.81% Airbnb Rental Income: $2195 Traditional Rental Income: $3153 Airbnb ROI: -0.08% Traditional ROI: 1.81%
84 Redfield Rd Wakefield, MA * Offer Deadline is Wednesday 9/3 at noon! * Lovely Cape with fully remodeled mudroom ...	3 beds \| 2 baths \| 1,630 sq.ft.	$699,900	Airbnb cash on cash: 2.03% Traditional cash on cash: 2.8% Airbnb Rental Income: $3569 Traditional Rental Income: $3288 Airbnb ROI: 2.03% Traditional ROI: 2.8%
Investment Properties for Sale in Other Cities of Massachusetts
11 Robinwood Ave Boston , MA Right in the heart of Jamaica Plain, just steps from Jamaica Pond and the vibrant shops & ...	5 beds \| 4 baths \| 3,390 sq.ft.	$2,399,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 0.27% Airbnb Rental Income: $991 Traditional Rental Income: $4593 Airbnb ROI: -1.5% Traditional ROI: 0.27%
20 Hardings Beach Road Chatham , MA In a coveted Harding's Beach location, this fully renovated Chatham home offers sweeping v...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,995,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 1.38% Airbnb Rental Income: $5632 Traditional Rental Income: $4925 Airbnb ROI: 1.15% Traditional ROI: 1.38%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| 3 baths \| 1,662 sq.ft.	$2,195,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 0.17% Airbnb Rental Income: $5959 Traditional Rental Income: $3577 Airbnb ROI: 0.76% Traditional ROI: 0.17%
496 Shore Road unit: 21 #21 Truro , MA The Captains Quarters, is the most sought after '' YEAR ROUND'', rental and investment pro...	3 beds \| 2 baths \| 2,018 sq.ft.	$1,350,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.71% Airbnb Rental Income: $4038 Traditional Rental Income: $3609 Airbnb ROI: 0.36% Traditional ROI: 0.71%
496 Shore Road unit: 16 #16 Truro , MA This '' rare'' two bed'' , two full bath, ''YEAR ROUND'', second floor, direct ocean front...	2 beds \| 2 baths \| 607 sq.ft.	$720,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 1.08% Airbnb Rental Income: $2819 Traditional Rental Income: $2420 Airbnb ROI: 0.69% Traditional ROI: 1.08%
195 Ellis Landing Road Brewster , MA Just steps to beautiful Cape Cod Bay, sun and fun in the sand, breathtaking sunsets ... yo...	2 beds \| 1 baths \| 828 sq.ft.	$1,150,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.19% Airbnb Rental Income: $3072 Traditional Rental Income: $2064 Airbnb ROI: 0.48% Traditional ROI: 0.19%
73 Joshua Jethro Road Chatham , MA Located in Chatham's highly sought after Riverbay Estates community, this 3-bedroom, 2-bat...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,570,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.04% Airbnb Rental Income: $6412 Traditional Rental Income: $3418 Airbnb ROI: 2.24% Traditional ROI: 1.04%
5 Great Hills Road Truro , MA Discover a perfect seaside retreat in this light-filled contemporary home, water views gre...	5 beds \| 3 baths \| 2,456 sq.ft.	$1,850,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.82% Airbnb Rental Income: $4353 Traditional Rental Income: $4180 Airbnb ROI: 0.39% Traditional ROI: 0.82%
3 Seagull Lane Harwich , MA This home is full of possibility! It has lots of Old World charm but tastefully updated wi...	4 beds \| 2 baths \| 2,218 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $3102 Airbnb ROI: N/A Traditional ROI: 2.59%
53 Chilton Lane Brewster , MA Enjoy the scenic pond view from the living room and main bedroom of this condo! In fact, i...	2 beds \| 2 baths \| 935 sq.ft.	$389,500	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.64% Airbnb Rental Income: $3072 Traditional Rental Income: $2594 Airbnb ROI: 3.03% Traditional ROI: 3.64%
663 Crowells Bog Road Brewster , MA Expanded 4 bedroom Cape-style home ideally located between Sheep Pond and Long Pond in Bre...	4 beds \| 4 baths \| 3,738 sq.ft.	$1,589,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.01% Airbnb Rental Income: $6080 Traditional Rental Income: $5430 Airbnb ROI: 1.63% Traditional ROI: 2.01%
5 Glacier Drive Truro , MA Don't miss out on this beautifully renovated Cape Style home! This 3 bedroom home is move-...	3 beds \| 3 baths \| 1,734 sq.ft.	$989,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 1.93% Airbnb Rental Income: $4038 Traditional Rental Income: $3202 Airbnb ROI: 1.9% Traditional ROI: 1.93%
307 W Main Street unit: 7 #7 Hyannis , MA Colonial Court Condominiums-NOW Vacant, bright morning sun and affordable 2 bedroom, 1 bat...	2 beds \| 1 baths \| 824 sq.ft.	$275,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 4.41% Airbnb Rental Income: $2328 Traditional Rental Income: $2075 Airbnb ROI: 3.16% Traditional ROI: 4.41%
266 School Street Cotuit , MA This lovingly maintained cottage offers the perfect blend of Cape Cod charm and modern con...	2 beds \| 1 baths \| 1,000 sq.ft.	$625,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.8% Airbnb Rental Income: $2892 Traditional Rental Income: $2346 Airbnb ROI: 1.59% Traditional ROI: 1.8%
996 Main Street Cotuit , MA Relaxed coastal living meets glorious views at this harbor front retreat in the heart of C...	4 beds \| 2 baths \| 4,303 sq.ft.	$5,500,000	Airbnb cash on cash: -0.66% Traditional cash on cash: -0.68% Airbnb Rental Income: $5178 Traditional Rental Income: $4048 Airbnb ROI: -0.66% Traditional ROI: -0.68%

Real Estate investment in Wakefield, MA

There are 3 properties for sale in the city of Wakefield . The median list price in Wakefield is $799,900 and the average price per square foot is $442. In September 2025, the average monthly cash on cash return in Wakefield is 3.00%. The average monthly rental income in Wakefield is $3,288.

Wakefield, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Wakefield.

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

The ROI for Long-Term is higher than the Short-Term in Wakefield with average rental income of $3,288.

Your search for investment property begins and ends here

Investment Property for Sale in Wakefield, MA

14 Plymouth Road

Wakefield, MA

3 beds | 3 baths | 2,410 sq.ft.

$799,900

Airbnb cash on cash: 0.66%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $2687

Traditional Rental Income: $3910

Airbnb ROI: 0.66%

Traditional ROI: 3.16%

47 Aborn Ave

Wakefield, MA

3 beds | 2 baths | 1,386 sq.ft.

$859,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $2195

Traditional Rental Income: $3153

Airbnb ROI: -0.08%

Traditional ROI: 1.81%

84 Redfield Rd

Wakefield, MA

3 beds | 2 baths | 1,630 sq.ft.

$699,900

Airbnb cash on cash: 2.03%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $3569

Traditional Rental Income: $3288

Airbnb ROI: 2.03%

Traditional ROI: 2.8%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

5 beds | 4 baths | 3,390 sq.ft.

$2,399,000

Airbnb cash on cash: -1.5%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $991

Traditional Rental Income: $4593

Airbnb ROI: -1.5%

Traditional ROI: 0.27%

Chatham , MA

4 beds | 4 baths | 2,770 sq.ft.

$1,995,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $5632

Traditional Rental Income: $4925

Airbnb ROI: 1.15%

Traditional ROI: 1.38%

Eastham , MA

3 beds | 3 baths | 1,662 sq.ft.

$2,195,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 0.17%

Airbnb Rental Income: $5959

Traditional Rental Income: $3577

Airbnb ROI: 0.76%

Traditional ROI: 0.17%

Truro , MA

3 beds | 2 baths | 2,018 sq.ft.

$1,350,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $4038

Traditional Rental Income: $3609

Airbnb ROI: 0.36%

Traditional ROI: 0.71%

Truro , MA

2 beds | 2 baths | 607 sq.ft.

$720,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $2819

Traditional Rental Income: $2420

Airbnb ROI: 0.69%

Traditional ROI: 1.08%

Brewster , MA

2 beds | 1 baths | 828 sq.ft.

$1,150,000