Islesboro, ME homes for sale & real estate

29 homes

Sort:

Recommended

ABOUT THIS HOME
Islesboro, ME Homes for Sale
Comfortable, cozy year-round home in a very convenient location. Large living room, open kitchen/dining area, great sun room. Simple, but lovely, landscaping Many extras such as whole-house generator, full basement, outbuilding suitable as guest bedroom or garden shed.

$595,000

2 beds1.5 baths1,463 sq ft

371 Pendleton Point Rd, Islesboro, ME 04848

Full basement • 1.01 acre lot • 2 garage spots

ABOUT THIS HOME
Islesboro, ME Homes for Sale
Discover a blend of history and modern comfort in this island farmhouse nestled on the picturesque island of Islesboro, Maine. Built in 1880, this home offers a unique opportunity to own a property steeped in local history with breathtaking views and modern comforts. Situated on 2.2 +/- acres, the property also includes a 2-car garage and multiple outbuildings, providing ample space for storage or creative endeavors. This home retains its original 1880s farmhouse charm, with stunning stained-glass windows, heart-pine flooring, and custom woodwork throughout. Surrounded by exquisite perennial gardens, the property offers a serene escape and overlooks the expansive fields of a saltwater farm

$630,000

3 beds2 baths1,614 sq ft

938 Main Rd, Islesboro, ME 04848

Perennial gardens • 2 car garage • Heart pine flooring

ABOUT THIS HOME
Islesboro, ME Homes for Sale
Quintessential coastal Maine island cottage with salt water views and beach access. Cozy year-round living with open concept kitchen and living room. Two bedrooms and 1½ baths. Many new improvements including new septic system, new south roof shingles, and exterior up-dates. Tax shown is for entire property. Tax for parcel to be conveyed will be far less, to be determined by assessor.

$499,000

2 beds1.5 baths825 sq ft

522 Ferry Rd, Islesboro, ME 04848

Open concept kitchen • Exterior up-dates • New septic system

ABOUT THIS HOME
Islesboro, ME Homes for Sale
Discover a unique opportunity in Mid-Island Islesboro, where history and potential converge in two remarkable buildings on one property. The Schoolhouse (300 Main Road): This was formerly the Pendleton School, Islesboro's main elementary school until the early 1950s. Currently operating as the Double Door Gallery during the summer, it features two large open rooms on the first floor with curved walls, bead board, wood paneling, and a half bath. The second floor offers a studio apartment with expansion potential, providing immediate income through gallery rentals and apartment leasing. This property is a piece of history with a bright future, ready for its next chapter as a vibrant art galle

$850,000

5 beds3 baths4,962 sq ft

292 & 300 Main Rd, Islesboro, ME 04848

Expansion potential • Wrap-around porch • Elegant staircase

VIDEO TOUR

ABOUT THIS HOME
Islesboro, ME Homes for Sale
Escape to an island, down a wooded road to this secluded seasonal cabin retreat, set on over 10 acres with sunset views. View our video for a more immersive experience!

$1,200,000

0 beds1 bath360 sq ft

181 Oregon Rd, Islesboro, ME 04848

Over 10 acres • Sunset views • 10.7 acre lot

Property at 101 Derby Rd, Islesboro, ME 04848, 4 beds, 2.5 baths

$495,000

4 beds2.5 baths4,500 sq ft

101 Derby Rd, Islesboro, ME 04848

Property at 866 Pendleton Point Rd, Islesboro, ME 04848, 6 beds, 7.5 baths

$6,750,000

6 beds7.5 baths9,449 sq ft

866 Pendleton Point Rd, Islesboro, ME 04848

Property at 108 Derby Rd, Islesboro, ME 04848, 4 beds, 1.5 baths

$385,000

4 beds1.5 baths2,200 sq ft

108 Derby Rd, Islesboro, ME 04848

Property at 300 Main Rd, Islesboro, ME 04848, 1 bed, 1.5 baths

$425,000

1 bed1.5 baths2,553 sq ft

300 Main Rd, Islesboro, ME 04848

Property at 766 Billy Shore Dr, Islesboro, ME 04848, 3 beds, 1 bath

$685,000

3 beds1 bath864 sq ft

766 Billy Shore Dr, Islesboro, ME 04848

Property at 115 Babbidge Rd, Islesboro, ME 04848, 5 beds, 1.5 baths

$525,000

5 beds1.5 baths1,764 sq ft

115 Babbidge Rd, Islesboro, ME 04848

Property at 135 Rebel Hill Rd, Islesboro, ME 04848, 3 beds, 3 baths

$899,000

3 beds3 baths3,801 sq ft

135 Rebel Hill Rd, Islesboro, ME 04848

Property at 1446 Meadow Pond Rd, Islesboro, ME 04848, 2 beds, 1 bath

$700,000

2 beds1 bath500 sq ft

1446 Meadow Pond Rd, Islesboro, ME 04848

Property at 108 Colony Rd, Islesboro, ME 04848, 1 bed, 1 bath

$295,000

1 bed1 bath804 sq ft

108 Colony Rd, Islesboro, ME 04848

Property at 118 E East Shore Dr, Islesboro, ME 04848, 5 beds, 4 baths

$3,950,000

5 beds4 baths2,400 sq ft

118 E East Shore Dr, Islesboro, ME 04848

Property at 391 Main Rd, Islesboro, ME 04848, 2 beds, 2 baths

$795,000

2 beds2 baths2,154 sq ft

391 Main Rd, Islesboro, ME 04848

Property at 1317 Trim Ln, Islesboro, ME 04848, 1 bed, 1 bath

$2,000,000

1 bed1 bath936 sq ft

1317 Trim Ln, Islesboro, ME 04848

Property at 1027 Meadow Pond Rd, Islesboro, ME 04848, 1 bed

$185,000

1 bed— baths96 sq ft

1027 Meadow Pond Rd, Islesboro, ME 04848

Property at 399 Hermit's Point Rd, Islesboro, ME 04848, 8 beds, 10 baths

$6,500,000

8 beds10 baths9,025 sq ft

399 Hermit's Point Rd, Islesboro, ME 04848

Property at 1145 Moosewood Ln, Islesboro, ME 04848, 3 beds, 2 baths

$498,000

3 beds2 baths2,113 sq ft

1145 Moosewood Ln, Islesboro, ME 04848

Property at 228 Gooseberry Point Rd, Islesboro, ME 04848, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,670 sq ft

228 Gooseberry Point Rd, Islesboro, ME 04848

Property at 1159 Main Rd, Islesboro, ME 04848, 4 beds, 1 bath

$798,000

4 beds1 bath2,680 sq ft

1159 Main Rd, Islesboro, ME 04848

Property at 364 & 367 Main Rd, Islesboro, ME 04848, 4 beds, 2 baths

$599,000

4 beds2 baths4,470 sq ft

364 & 367 Main Rd, Islesboro, ME 04848

Property at Lot 23 Map 39 Babbidge Rd, Islesboro, ME 04848

$100,000

— beds— baths— sq ft

Lot 23 Map 39 Babbidge Rd, Islesboro, ME 04848

Property at Map 22 Lot 4B Big Tree Ln, Islesboro, ME 04848

$360,000

— beds— baths— sq ft

Map 22 Lot 4B Big Tree Ln, Islesboro, ME 04848

Property at 12D, 12I Mildred Grace Rd, Islesboro, ME 04848

$295,000

— beds— baths— sq ft

12D, 12I Mildred Grace Rd, Islesboro, ME 04848

Property at M15L20-TBD Golf Club Rd, Islesboro, ME 04848

$785,000

— beds— baths— sq ft

M15L20-TBD Golf Club Rd, Islesboro, ME 04848

Property at 1552 Turtle Head Rd, Islesboro, ME 04848

$325,000

— beds— baths— sq ft

1552 Turtle Head Rd, Islesboro, ME 04848

Property at 2Q Hermit's Point Rd, Islesboro, ME 04848

$280,000

— beds— baths— sq ft

2Q Hermit's Point Rd, Islesboro, ME 04848

Viewing page 1 of 1

Average home prices near Islesboro, ME

Cities

Zip Codes
Minor Civil Divisions

Islesboro, ME real estate trends

$835K

Sale price

-27.4%
since last year

$369

Sale $/sq ft

+28.1%
since last year

Under list price

6.7%

Days on market

156

Down payment

—

Total homes sold

See more Islesboro, ME market insights

More to explore in Islesboro, ME

How to buy a house in Islesboro, ME

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maine

Portland homes for sale
$677,499
Scarborough homes for sale
$622,500
South Portland homes for sale
$600,000
Falmouth homes for sale
$1,270,000
Cape Elizabeth homes for sale
$1,325,000
Bangor homes for sale
$298,500
Kittery homes for sale
$1,049,000
Kennebunk homes for sale
$537,450
Brunswick homes for sale
$384,000
Yarmouth homes for sale
$812,000
Saco homes for sale
$521,500
Kennebunkport homes for sale
$2,195,000
Camden homes for sale
$800,000
Freeport homes for sale
$549,000
Bar Harbor homes for sale
$692,000

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.