Real Estate Investment Properties for Sale in Waldoboro, ME

Looking for investment property in Waldoboro, ME with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
350 Winslows Mills Road Waldoboro, ME Sitting privately on 1.80 acres surrounded by woods, this quaint home offers the feel of p...	3 beds \| 2 baths \| 1,443 sq.ft.	$365,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 7.63% Airbnb Rental Income: $1564 Traditional Rental Income: $3255 Airbnb ROI: 1.39% Traditional ROI: 7.63%
942 Winslows Mills Road Waldoboro, ME Welcome to this charming 3-bedroom, 2-bath Cape nestled on 1.29 acres in Waldoboro, provid...	3 beds \| 2 baths \| 1,404 sq.ft.	$299,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 9.76% Airbnb Rental Income: $1564 Traditional Rental Income: $3292 Airbnb ROI: 2.02% Traditional ROI: 9.76%
353 Controversy Lane Waldoboro, ME Move-in ready and refreshed throughout, this 3-bedroom, 2-bath double-wide offers comforta...	3 beds \| 2 baths \| 1,344 sq.ft.	$249,000	Airbnb cash on cash: 2% Traditional cash on cash: 8.52% Airbnb Rental Income: $1564 Traditional Rental Income: $2648 Airbnb ROI: 2% Traditional ROI: 8.52%
24 Old Route 1 Waldoboro, ME Bring your vision and restore this spacious 6-bedroom, 1-bath home to its full potential. ...	5 beds \| 1 baths \| 1,890 sq.ft.	$250,000	Airbnb cash on cash: 8.3% Traditional cash on cash: 9.58% Airbnb Rental Income: $3354 Traditional Rental Income: $2909 Airbnb ROI: 8.3% Traditional ROI: 9.58%
56 Gross Neck Road Waldoboro, ME Welcome to 56 Gross Neck Road in Waldoboro, where comfort, privacy, and rural Maine charm ...	3 beds \| 2 baths \| 1,404 sq.ft.	$349,900	Airbnb cash on cash: 2.09% Traditional cash on cash: 8.07% Airbnb Rental Income: $1564 Traditional Rental Income: $3080 Airbnb ROI: 2.09% Traditional ROI: 8.07%
398 Washington Road Waldoboro, ME Easy one floor living in this immaculate 2 bed/1 bath manufactured home in the country! Hu...	2 beds \| 1 baths \| 924 sq.ft.	$259,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 6.7% Airbnb Rental Income: $834 Traditional Rental Income: $1980 Airbnb ROI: 0.67% Traditional ROI: 6.7%
755 Winslows Mills Road N Waldoboro, ME Tiny Home on a large lot (2.6 acres) with 290 feet of waterfront on the Madomak. Home is f...	1 beds \| 1 baths \| 560 sq.ft.	$167,500	Airbnb cash on cash: -1.2% Traditional cash on cash: 10.91% Airbnb Rental Income: $556 Traditional Rental Income: $2209 Airbnb ROI: -1.2% Traditional ROI: 10.91%
935 Dutch Neck Waldoboro, ME MID-COASTAL SALTWATER FARM, pampered and updated circa 1814 center chimney cape retaining ...	3 beds \| 2 baths \| 2,000 sq.ft.	$950,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 2.28% Airbnb Rental Income: $1564 Traditional Rental Income: $2996 Airbnb ROI: 0.15% Traditional ROI: 2.28%
101 Butter Point Waldoboro, ME Tucked into idyllic Butter Point in Waldoboro, this waterfront retreat feels like a secret...	4 beds \| 4 baths \| 2,600 sq.ft.	$1,250,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.64% Airbnb Rental Income: $2471 Traditional Rental Income: $3576 Airbnb ROI: -0.82% Traditional ROI: 0.64%
1364 Winslows Mills Road Waldoboro, ME Welcome home this Christmas to a brand new, never lived in, 4bdrm, 2 full bath home. This...	4 beds \| 2 baths \| 1,568 sq.ft.	$325,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 7.45% Airbnb Rental Income: $2471 Traditional Rental Income: $3086 Airbnb ROI: 3.47% Traditional ROI: 7.45%
766 Atlantic Highway Waldoboro, ME Tucked at the end of a private dirt road, this 2022-built, nearly complete property offers...	2 beds \| 3 baths \| 2,880 sq.ft.	$485,995	Airbnb cash on cash: -1.44% Traditional cash on cash: 5.46% Airbnb Rental Income: $834 Traditional Rental Income: $3642 Airbnb ROI: -1.44% Traditional ROI: 5.46%
1455 Washington Road Waldoboro, ME Charming 3BR/1BA farmhouse in Waldoboro set on 5.5 scenic acres with established perennial...	3 beds \| 1 baths \| 1,285 sq.ft.	$319,900	Airbnb cash on cash: 2.38% Traditional cash on cash: 7.02% Airbnb Rental Income: $1564 Traditional Rental Income: $2510 Airbnb ROI: 2.38% Traditional ROI: 7.02%
175 Quarry Road Waldoboro, ME Welcome to Quarryside, a home built by Christopher Feyler in the late 1700s, as one of the...	4 beds \| 3 baths \| 2,995 sq.ft.	$549,900	Airbnb cash on cash: 2.45% Traditional cash on cash: 7.07% Airbnb Rental Income: $2471 Traditional Rental Income: $4244 Airbnb ROI: 2.45% Traditional ROI: 7.07%
13 Friendship Road Waldoboro, ME A classic brick building offering 4 floors of versatile living, working, and income-produc...	3 beds \| 4 baths \| 6,780 sq.ft.	$1,200,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 3.23% Airbnb Rental Income: $1564 Traditional Rental Income: $4819 Airbnb ROI: -0.09% Traditional ROI: 3.23%
275 Harriman Road Waldoboro, ME Set between the timeless coastal communities of Waldoboro and Bremen, this remarkable 167-...	3 beds \| 3 baths \| 1,610 sq.ft.	$2,450,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 0.57% Airbnb Rental Income: $1564 Traditional Rental Income: $3661 Airbnb ROI: -0.55% Traditional ROI: 0.57%
31 Dewdrop Lane Waldoboro, ME LOCATED ON A QUIET COUNTRY LANE, THIS MID-COASTAL HOME OFFERS PRIVACY in a very convenient...	2 beds \| 1 baths \| 1,064 sq.ft.	$335,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 6.15% Airbnb Rental Income: $834 Traditional Rental Income: $2350 Airbnb ROI: 0.3% Traditional ROI: 6.15%
439 Castner Road Waldoboro, ME Well-maintained manufactured home on private 2 acre lot in Waldoboro. 1999 76x14, Astro Ci...	2 beds \| 1 baths \| 1,008 sq.ft.	$210,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 9.57% Airbnb Rental Income: $834 Traditional Rental Income: $2203 Airbnb ROI: 1.05% Traditional ROI: 9.57%
67 Ralph Wink Road Waldoboro, ME Looking for a project with land, privacy, and real upside? 567 Ralph Wink Road offers an 1...	3 beds \| 2 baths \| 806 sq.ft.	$230,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 10.81% Airbnb Rental Income: $1564 Traditional Rental Income: $2669 Airbnb ROI: 3.67% Traditional ROI: 10.81%

Real Estate investment in Waldoboro, ME

There are 18 properties for sale in the city of Waldoboro . The median list price in Waldoboro is $279,855 and the average price per square foot is $148. In June 2026, the average monthly cash on cash return in Waldoboro is 8.00%. The average monthly rental income in Waldoboro is $3,083.

Waldoboro, ME Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 18 investment properties available for sale in Waldoboro.

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

The ROI for Long-Term is higher than the Short-Term in Waldoboro with average rental income of $3,083.

Your search for investment property begins and ends here

Investment Property for Sale in Waldoboro, ME

350 Winslows Mills Road

Waldoboro, ME

3 beds | 2 baths | 1,443 sq.ft.

$365,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 7.63%

Airbnb Rental Income: $1564

Traditional Rental Income: $3255

Airbnb ROI: 1.39%

Traditional ROI: 7.63%

942 Winslows Mills Road

Waldoboro, ME

3 beds | 2 baths | 1,404 sq.ft.

$299,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 9.76%

Airbnb Rental Income: $1564

Traditional Rental Income: $3292

Airbnb ROI: 2.02%

Traditional ROI: 9.76%

353 Controversy Lane

Waldoboro, ME

3 beds | 2 baths | 1,344 sq.ft.

$249,000

Airbnb cash on cash: 2%

Traditional cash on cash: 8.52%

Airbnb Rental Income: $1564

Traditional Rental Income: $2648

Airbnb ROI: 2%

Traditional ROI: 8.52%

24 Old Route 1

Waldoboro, ME

5 beds | 1 baths | 1,890 sq.ft.

$250,000

Airbnb cash on cash: 8.3%

Traditional cash on cash: 9.58%

Airbnb Rental Income: $3354

Traditional Rental Income: $2909

Airbnb ROI: 8.3%

Traditional ROI: 9.58%

56 Gross Neck Road

Waldoboro, ME

3 beds | 2 baths | 1,404 sq.ft.

$349,900

Airbnb cash on cash: 2.09%

Traditional cash on cash: 8.07%

Airbnb Rental Income: $1564

Traditional Rental Income: $3080

Airbnb ROI: 2.09%

Traditional ROI: 8.07%

398 Washington Road

Waldoboro, ME

2 beds | 1 baths | 924 sq.ft.

$259,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 6.7%

Airbnb Rental Income: $834

Traditional Rental Income: $1980

Airbnb ROI: 0.67%

Traditional ROI: 6.7%

755 Winslows Mills Road N

Waldoboro, ME

1 beds | 1 baths | 560 sq.ft.

$167,500

Airbnb cash on cash: -1.2%

Traditional cash on cash: 10.91%

Airbnb Rental Income: $556

Traditional Rental Income: $2209

Airbnb ROI: -1.2%

Traditional ROI: 10.91%

935 Dutch Neck

Waldoboro, ME

3 beds | 2 baths | 2,000 sq.ft.

$950,000

Airbnb cash on cash: 0.15%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $1564

Traditional Rental Income: $2996

Airbnb ROI: 0.15%