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Residential Land with Home for Sale in Islesboro, Maine

292 Main Rd, Islesboro, ME 04848

$499,000
2 acres
Active
Est $2,932/mo

Winfield Scott Pendleton House: A Historic Islesboro Gem. Step back in time and discover the rich history of this stately 1887 Federal-style home, once owned by Winfield Scott Pendleton, a prominent ship captain and influential figure in Islesboro. Built shortly after Pendleton acquired the property in 1876 from his parents, the house served as a summer retreat for the Pendleton family until 1959. This grand home with its distinctive cupola and expansive wrap-around porch is perfect for enjoying the summer breeze and watching island life unfold. French doors off the porch invite you into this elegant old home and once inside the architectural details speak to a bygone era of detailed craftsmanship. Discover an elegant staircase, bespoke built-in closets, a breakfront in the dining room, six-over-six windows, a stained-glass window, and a bespoke carved wooden mantle. Original interior trim throughout the house, along with a claw-foot tub and natural stone vanity, evoke a sense of timeless charm. While the kitchen has been thoughtfully modernized, the home retains its historical integrity. This 5-bedroom residence is prominently situated on Pendleton Point Road, offering a mid-island location close to the library, public park and playground, island market, and post office. Beyond the main house, you'll find recently built post and beam two-story outbuildings, offering versatile space for a workshop, storage, or other possibilities. This stately 1887 home is now seeking its next stewardaEUR"someone who will appreciate its beautiful history, embrace its unique character, and continue to care for and enjoy this magnificent piece of Islesboro heritage. Proudly presented by Cates Real Estate. FMI contact Virginia (Ginnie) Hess | Cates Real Estate | 401-222-9583 | ginnie@catesre.com | www.catesre.com

2,409
Sq feet
5
Beds
1
Full bath
1
1/2 bath
1887
Built

Location

Street address
292 Main Rd
Elevation
66 feet
Coordinates
44.3023, -68.9023

Property details

Acreage
2 acres
Zoning
Residential
MLS #
MREIS 1642544
Posted

Parcels

  • ISBR-000019-000000-000011

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Lot

Features
Level, Near Town, Rural

Exterior

Pool
Porch
Structures
Outbuilding

Structure

Style
Federal
Basement
Crawl Space, Partial, Unfinished
Water
Private, Well
Sewer
Private Sewer, Septic Tank
Heating
Baseboard
Materials
Clapboard, Wood Frame

Interior

Room Count
9
Rooms
Bathroom x 2, Bedroom x 5, Den, Dining Room
Flooring
Carpet, Laminate, Wood
Features
1 st Floor Bedroom, Bathtub

Listing history

DateEventPriceChangeSource
Nov 2, 2025New listing$499,000MREIS
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This 2-acre property is located at 292 Main Rd in Islesboro, ME 04848. The property is available for sale for $499,000. It has a 2,409 sq ft 5 bedroom, 1 bath house built in 1887.

Checked 1 hour ago — Updated

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