DylanArmstrong

292 Main Road, Islesboro, ME 04848

$499,000
  • 292 Main Road, Islesboro, ME 04848 Main Photo

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Active Under Contract
BEDS5 BATHS1 full 1 partial SQUARE FEET2,409 MLS#1642544
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family

Property Description

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, 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 steward?someone who will appreciate its beautiful history, embrace its unique character, and continue to care for and enjoy this magnificent piece of Islesboro heritage.

292 Main Road | MLS# 1642544

This single family home located at 292 Main Road, Islesboro, ME 04848 is currently listed for sale with an asking price of $499,000. This property was built in 1887 and has 5 bedrooms and 1 full and 1 partial baths with 2409 sq. ft. Search Islesboro real estate on darmstrong.spragueandcurtis.com today.

Property Features

Property Type: Residential - Single Family
Basement: Bulkhead, Exterior Entry
Heating: Baseboard
Home Style: Federal
Lot Size: 2.00 Acres
Roof Type: Composition
Taxes: $4,640
Year Built: 1887

Feature Descriptions

Electric: Circuit Breakers
Flooring: Carpet, Laminate, Wood
Sewer: Private Sewer, Septic Design Available, Septic Tank
Special View Info: Scenic, Trees/Woods
SQ FT Above Grade: 2409
SQ FT Below Grade: 0
Total Rooms: 9
Water: Private, Well

Room Sizes

Kitchen: Level - First
Dining Room: Level - First
Den: Level - First
Living Room: Level - First
Bedroom 1: Level - Second
Bedroom 2: Level - Second
Bedroom 3: Level - Second
Bedroom 4: Level - Second
Bedroom 5: Level - Second

Listed By / Shown By

Listed By

Agency Name: Cates Real Estate
Agency Contact: info@catesre.com

Shown By

Agent Name: Dylan Armstrong
Agent Phone: (207) 441-6095
Agency Title: Sprague and Curtis Real Estate

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Estimated Payment

$ 1,642.77 per month $1,110.56 Principal & Interest $386.67 Property Tax $145.54 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/04/2026. The listing information on this page last changed on 03/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/04/2026 12:19:08 AM EST) or MREIS (last updated Wed 03/04/2026 12:15:16 AM EST). Real estate listings held by brokerage firms other than Sprague and Curtis Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.



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