49
$375,000
4 bd · 2 ba · 1,516 sqft
34 Chapel Street, Boothbay, ME
Jonathan Tindal · Tindal & Callahan Real Estate
School ratings (A+ to F) from HJN community data.
Boothbay Region Elementary School
PK-8 · Regular · Boothbay-Boothbay Harbor Community School District
307 students · 8.9:1 student–teacher
Boothbay Region High School
9-12 · Regular · Boothbay-Boothbay Harbor Community School District
172 students · 8.4:1 student–teacher
Southport Central School
KG-6 · Regular · Southport
16 students · 3.6:1 student–teacher
South Bristol Elementary School
PK-8 · Regular · South Bristol
63 students · 7.2:1 student–teacher
Within 2 miles of this home: 39+ restaurants and cafés, 3 grocery stores, 27 parks and green spaces, and 13 transit stops.
Place data from OpenStreetMap.
Bet's Fish Fry
Common Drive
Subway
Wiscasset Road
Paul's Steakhouse
Sugar Maple Lane
Grille 19
Sugar Maple Lane
Over The Ledge
Sugar Maple Lane
Kitchen Garden Cafe
The Market
Seahawk Snack Shack
Boothbay Farmers' Market
Common Drive
Pinkham's Gourmet Market
Townsend Avenue
Hannaford
Townsend Avenue
Clifford Park
Back River Road
Harold B. Clifford Playground
Boothbay Memorial Park
Boothbay Common
Common Drive
Coastal Maine Botanical Gardens
Knickerbocker Lake
Slater Forest Pond
Knickercane Island Park
Barters Island Road
Sherman Field
Flagship Inn
Meadow Mall
Brady's & Ports Pizzeria
Mid-Town Motel
The Hutch
Sherman's Bookstore & Janson's Clothing
Mama D's Cafe
Maine ListingsThis content last refreshed on 2026-11-05 09:14:38 UTC. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
49
$375,000
4 bd · 2 ba · 1,516 sqft
34 Chapel Street, Boothbay, ME
Jonathan Tindal · Tindal & Callahan Real Estate
Price Reduced58$795,000
3 bd · 2 ba · 2,427 sqft
29 Wiscasset Road, Boothbay, ME
Karen Perkins · Tindal & Callahan Real Estate
8$2,995,000
2 bd · 3 ba · 2,248 sqft
Lot 10 Whispering Pines Drive, Boothbay, ME
Jonathan Tindal · Tindal & Callahan Real Estate
11$3,995,000
3 bd · 4 ba · 3,672 sqft
Lot 7 Whispering Pines Drive, Boothbay, ME
Jonathan Tindal · Tindal & Callahan Real Estate
Price Reduced51$435,000
3 bd · 3 ba · 1,858 sqft
934 Wiscasset Road, Boothbay, ME
Jonathan Tindal · Tindal & Callahan Real Estate
Price Reduced71$865,000
7 bd · 6 ba · 3,722 sqft
8 Country Club Road, Boothbay, ME
Jonathan Tindal · Tindal & Callahan Real Estate





Est. $4,935/mo$227/sqft · 136 days on Realty
5
Beds
4
Baths
3,300
Sqft
2008
Built
Welcome to 39 Shackleton's Way in Boothbay, an extensively renovated 3,300 square foot residence offering an exceptional blend of modern craftsmanship, thoughtful design, and everyday comfort. Set on 1.2 private acres and reimagined down to the studs since 2022, the home has undergone a complete renovation with extensive updates throughout. The spacious floor plan features five bedrooms, one of which is currently used as a home office, three full bathrooms, one half bath, and an attached two-car garage. At the heart of the home is a beautifully appointed kitchen with commercial-grade appliances and an oversized island designed for gathering and entertaining. Hardwood floors, custom built-ins, and carefully curated finishes create a warm yet sophisticated atmosphere throughout. The primary suite serves as a private retreat, featuring cathedral ceilings and a luxurious spa-inspired bathroom. Additional living spaces include a dedicated office with built-in cabinetry, a beautifully finished wet bar, and a well-designed in-law apartment complete with its own living space, offering exceptional flexibility for guests, extended family, or multigenerational living. Recent improvements include new heat pumps, radiant heat flooring, new decks, and extensive interior and exterior enhancements completed as part of the home's comprehensive renovation. Thoughtful details throughout, including designer wallpaper accents and custom millwork, contribute to the home's distinctive character and quality. Surrounded by mature trees and offering a peaceful, private setting, the property is ideally located just 3 minutes from Boothbay Harbor Country Club and only 7 minutes from downtown Boothbay Harbor's restaurants, shops, marinas, and waterfront attractions. Offering the space, quality, and flexibility rarely found in today's market, 39 Shackleton's Way presents a unique opportunity to enjoy coastal Maine living in one of the region's most desirable locations.
Listing agent
Colin Harvey
Courtesy of Legacy Properties Sotheby's International Realty
(207) 615-4991
Maine Listings · Listing 1668144
$150,000
Estimated monthly payment
$4,935/mo
Loan amount $600,000. Estimate only — your actual rate and payment depend on credit, location, and lender.