Real Estate Investment Properties for Sale in Winterport, ME

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
10 Lebanon Rd Winterport, ME This enchanting mid-coast Antique Cape has been beautifully restored by a skilled craftsma...	4 beds \| 2 baths \| 1,600 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.89% Airbnb Rental Income: $null Traditional Rental Income: $3463 Airbnb ROI: N/A Traditional ROI: 10.89%
567 Stream Road Winterport, ME This beautifully restored, spacious home will simply Wow you! From the welcoming front 3 s...	4 beds \| 3 baths \| 2,033 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $3030 Airbnb ROI: N/A Traditional ROI: 5.74%
4 Church Street Winterport, ME A delightful residence set in the picturesque riverside village of Winterport with stunnin...	3 beds \| 3 baths \| 1,982 sq.ft.	$384,500	Airbnb cash on cash: 1.67% Traditional cash on cash: 7.72% Airbnb Rental Income: $1952 Traditional Rental Income: $3621 Airbnb ROI: 1.67% Traditional ROI: 7.72%
110 Lebanon Rd Winterport, ME Charming 3-4 bedroom ranch in a convenient Winterport location! This well-maintained home ...	4 beds \| 1 baths \| 1,596 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.07% Airbnb Rental Income: $null Traditional Rental Income: $3066 Airbnb ROI: N/A Traditional ROI: 8.07%
177 Lebanon Rd Winterport, ME Looking for a property that can help pay for itself? This two-unit farmhouse in Winterport...	6 beds \| 2 baths \| 2,173 sq.ft.	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $2203 Airbnb ROI: N/A Traditional ROI: 4.46%
90 Whig St Winterport, ME Updated Ranch with Artistic Charm in Historic Winterport Set in the picturesque Rivertown ...	3 beds \| 1 baths \| 950 sq.ft.	$299,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 8.17% Airbnb Rental Income: $1952 Traditional Rental Income: $2782 Airbnb ROI: 3.39% Traditional ROI: 8.17%
1211 North Main Street Winterport, ME Welcome to 1211 N Main Street in Winterport, where classic New England charm meets thought...	3 beds \| 2 baths \| N/A	$259,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 4.97% Airbnb Rental Income: $1952 Traditional Rental Income: $1881 Airbnb ROI: 3.16% Traditional ROI: 4.97%
7 Moyse Road Winterport, ME Welcome to 7 Moyse Road in Winterport, where comfort, convenience, and Maine's coastal cha...	3 beds \| 3 baths \| 2,956 sq.ft.	$499,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.31% Airbnb Rental Income: $1952 Traditional Rental Income: $2993 Airbnb ROI: 0.98% Traditional ROI: 4.31%
437 Stream Rd Winterport, ME Nestled at the back of a beautifully landscaped 2 acre lot, this inviting 3 bedroom 1 bath...	3 beds \| 1 baths \| 1,104 sq.ft.	$327,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 6.9% Airbnb Rental Income: $1952 Traditional Rental Income: $2526 Airbnb ROI: 3.36% Traditional ROI: 6.9%
31 Dean St Winterport, ME Located in the heart of the Winterport Historic District, 31 Dean Street is a charming, ch...	3 beds \| 2 baths \| 1,796 sq.ft.	$269,900	Airbnb cash on cash: 2.94% Traditional cash on cash: 10.29% Airbnb Rental Income: $1952 Traditional Rental Income: $3308 Airbnb ROI: 2.94% Traditional ROI: 10.29%
55 Lower Oak Point Rd Winterport, ME 55 Lower Oak Point Rd, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.12% Airbnb Rental Income: $null Traditional Rental Income: $1477 Airbnb ROI: N/A Traditional ROI: 0.12%
12 Irish Lane Winterport, ME Nestled on a generous four-acre secluded property surrounded by woods, this well-maintaine...	2 beds \| 2 baths \| 2,200 sq.ft.	$355,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 4.31% Airbnb Rental Income: $1660 Traditional Rental Income: $2311 Airbnb ROI: 0.96% Traditional ROI: 4.31%
97 Cove Road Winterport, ME Nestled in a peaceful, wooded setting on 1.23 acres near the Winterport-Hampden line, this...	3 beds \| 2 baths \| 1,536 sq.ft.	$409,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 5.89% Airbnb Rental Income: $1952 Traditional Rental Income: $3252 Airbnb ROI: 1.16% Traditional ROI: 5.89%
11 Church St Winterport, ME This charming in-town home offers views of the Penobscot River in a convenient location! C...	3 beds \| 1 baths \| 1,400 sq.ft.	$299,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 9.49% Airbnb Rental Income: $1952 Traditional Rental Income: $3052 Airbnb ROI: 3.76% Traditional ROI: 9.49%
25 & 26 Rancourt Rd Winterport, ME For accurate info call Tyne or email - Visit for more details! Set on open, rolling fields...	4 beds \| 2 baths \| 1,850 sq.ft.	$494,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.43% Airbnb Rental Income: $null Traditional Rental Income: $3231 Airbnb ROI: N/A Traditional ROI: 4.43%
11 Baker Rd Winterport, ME This enchanting cottage-style 4BR, 2 Bath Farmhouse with Penobscot River views has just be...	4 beds \| 2 baths \| 2,325 sq.ft.	$598,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.21% Airbnb Rental Income: $null Traditional Rental Income: $3565 Airbnb ROI: N/A Traditional ROI: 5.21%
7 Upper Oak Point Rd Winterport, ME This charming saltbox-style home offers the perfect blend of privacy, tranquility, and con...	3 beds \| 2 baths \| 1,536 sq.ft.	$319,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 8.1% Airbnb Rental Income: $1952 Traditional Rental Income: $3226 Airbnb ROI: 2.14% Traditional ROI: 8.1%
28 Marine St Winterport, ME Located in the charming town of Winterport, this spacious Raised Ranch offers comfort, con...	3 beds \| 2 baths \| 1,612 sq.ft.	$349,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 8.67% Airbnb Rental Income: $1952 Traditional Rental Income: $3277 Airbnb ROI: 3.08% Traditional ROI: 8.67%
137 Main St Winterport, ME Some homes are simply lived in. Others are loved, preserved, and passed through generation...	4 beds \| 1 baths \| 2,268 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.7% Airbnb Rental Income: $null Traditional Rental Income: $3556 Airbnb ROI: N/A Traditional ROI: 8.7%
4 Whig Street Winterport, ME Situated within the Winterport Historical District, with scenic views of Penobscot River a...	N/A beds \| 4 baths \| 2,880 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.03% Airbnb Rental Income: $null Traditional Rental Income: $3874 Airbnb ROI: N/A Traditional ROI: 7.03%
642 Stream Rd Winterport, ME Cheaper than rent and packed with potential! If you've been waiting for an affordable oppo...	3 beds \| 1 baths \| 1,296 sq.ft.	$225,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 11.84% Airbnb Rental Income: $1952 Traditional Rental Income: $2833 Airbnb ROI: 5.29% Traditional ROI: 11.84%
MR09L093 Monroe Rd Winterport, ME MR09L093 Monroe Rd, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$232,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $1379 Airbnb ROI: N/A Traditional ROI: 3.52%
49 Lebanon Rd Winterport, ME 49 Lebanon Rd, Winterport, ME 04496 \| Single Family Residential	3 beds \| 2 baths \| 1,735 sq.ft.	$284,900	Airbnb cash on cash: 2.66% Traditional cash on cash: 3.93% Airbnb Rental Income: $1952 Traditional Rental Income: $1777 Airbnb ROI: 2.66% Traditional ROI: 3.93%
111 W Main St Winterport, ME 111 W Main St, Winterport, ME 04496 \| Single Family Residential	N/A beds \| N/A baths \| 800 sq.ft.	$105,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.62% Airbnb Rental Income: $null Traditional Rental Income: $1106 Airbnb ROI: N/A Traditional ROI: 7.62%
380 & 390 Stream Rd Winterport, ME 380 & 390 Stream Rd, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $1106 Airbnb ROI: N/A Traditional ROI: 0.73%
Lot #94 Harmony Ln Winterport, ME Lot #94 Harmony Ln, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$119,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.87% Airbnb Rental Income: $null Traditional Rental Income: $1379 Airbnb ROI: N/A Traditional ROI: 8.87%
Lot #96-2 Monroe Rd Winterport, ME Lot #96-2 Monroe Rd, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $1379 Airbnb ROI: N/A Traditional ROI: 2.9%
532 Lebanon Rd Winterport, ME 532 Lebanon Rd, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.08% Airbnb Rental Income: $null Traditional Rental Income: $1106 Airbnb ROI: N/A Traditional ROI: 6.08%
865 N Main St Winterport, ME 865 N Main St, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$229,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.31% Airbnb Rental Income: $null Traditional Rental Income: $1106 Airbnb ROI: N/A Traditional ROI: 2.31%
63 Lower Oak Point Rd Winterport, ME 63 Lower Oak Point Rd, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $1379 Airbnb ROI: N/A Traditional ROI: 3.1%
Map3 Lot38 Rabbit Hill Rd Winterport, ME Map3 Lot38 Rabbit Hill Rd, Winterport, ME 04474 \| Other	N/A beds \| N/A baths \| N/A	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $1377 Airbnb ROI: N/A Traditional ROI: 1.25%
39 Lower Oak Point Rd Winterport, ME 39 Lower Oak Point Rd, Winterport, ME 04496 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.73% Airbnb Rental Income: $null Traditional Rental Income: $1106 Airbnb ROI: N/A Traditional ROI: 0.73%

Real Estate investment in Winterport, ME

There are 32 properties for sale in the city of Winterport . The median list price in Winterport is $402,259 and the average price per square foot is $222. In August 2026, the average monthly cash on cash return in Winterport is 8.00%. The average monthly rental income in Winterport is $1,881.

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

There are 32 investment properties available for sale in Winterport.

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

The ROI for Long-Term is higher than the Short-Term in Winterport with average rental income of $1,881.

Your search for investment property begins and ends here

Investment Property for Sale in Winterport, ME

10 Lebanon Rd

Winterport, ME

4 beds | 2 baths | 1,600 sq.ft.

$289,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.89%

Airbnb Rental Income: $null

Traditional Rental Income: $3463

Airbnb ROI: N/A

Traditional ROI: 10.89%

567 Stream Road

Winterport, ME

4 beds | 3 baths | 2,033 sq.ft.

$399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.74%

Airbnb Rental Income: $null

Traditional Rental Income: $3030

Airbnb ROI: N/A

Traditional ROI: 5.74%

4 Church Street

Winterport, ME

3 beds | 3 baths | 1,982 sq.ft.

$384,500

Airbnb cash on cash: 1.67%

Traditional cash on cash: 7.72%

Airbnb Rental Income: $1952

Traditional Rental Income: $3621

Airbnb ROI: 1.67%

Traditional ROI: 7.72%

110 Lebanon Rd

Winterport, ME

4 beds | 1 baths | 1,596 sq.ft.

$325,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.07%

Airbnb Rental Income: $null

Traditional Rental Income: $3066

Airbnb ROI: N/A

Traditional ROI: 8.07%

177 Lebanon Rd

Winterport, ME

6 beds | 2 baths | 2,173 sq.ft.

$349,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.46%

Airbnb Rental Income: $null

Traditional Rental Income: $2203

Airbnb ROI: N/A

Traditional ROI: 4.46%

90 Whig St

Winterport, ME

3 beds | 1 baths | 950 sq.ft.

$299,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 8.17%

Airbnb Rental Income: $1952

Traditional Rental Income: $2782

Airbnb ROI: 3.39%

Traditional ROI: 8.17%

1211 North Main Street

Winterport, ME

3 beds | 2 baths | N/A

$259,000

Airbnb cash on cash: 3.16%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $1952

Traditional Rental Income: $1881

Airbnb ROI: 3.16%

Traditional ROI: 4.97%

7 Moyse Road

Winterport, ME

3 beds | 3 baths | 2,956 sq.ft.

$499,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $1952

Traditional Rental Income: $2993

Airbnb ROI: 0.98%