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.
Active
$805,000
39 Shackleton's Way, Boothbay, ME 04537
5beds
3,300sqft
Single Family Residence
Built in 2008
1.2 Acres Lot
$-- Zestimate®
$244/sqft
$42/mo HOA
What's special
- 4 days |
- 499 |
- 31 |
Zillow last checked:
Listing updated:
Listed by:
Legacy Properties Sotheby's International Realty
Source: Maine Listings,MLS#: 1668144
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s), Above Garage, Built-in Features, Cathedral Ceiling(s), Full Bath
- Level: Second
Bedroom 2
- Features: Built-in Features, Cathedral Ceiling(s), Closet
- Level: Second
Bedroom 3
- Level: Basement
Bedroom 4
- Level: Basement
Bedroom 5
- Level: First
Dining room
- Features: Dining Area, Built-in Features
- Level: First
Family room
- Features: Built-in Features
- Level: Basement
Kitchen
- Features: Kitchen Island
- Level: First
Living room
- Features: Built-in Features
- Level: First
Loft
- Features: Built-in Features
- Level: Third
Mud room
- Level: First
Heating
- Heat Pump, Radiant
Cooling
- Heat Pump
Appliances
- Included: Dishwasher, Dryer, Gas Range, Refrigerator, Washer
Features
- In-Law Floorplan, Walk-In Closet(s)
- Flooring: Carpet, Tile, Wood
- Basement: Interior Entry,Walk-Out Access,Finished,Full
- Has fireplace: No
Interior area
- Total structure area: 3,300
- Total interior livable area: 3,300 sqft
- Finished area above ground: 3,300
- Finished area below ground: 0
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Gravel, 1 - 4 Spaces, On Site, Garage Door Opener
- Attached garage spaces: 2
Features
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 1.2 Acres
- Features: Near Country Club, Near Golf Course, Near Town, Neighborhood, Rolling Slope, Wooded
Details
- Parcel number: BOOTMR04B0002L04
- Zoning: Residential
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod,Contemporary
- Property subtype: Single Family Residence
Materials
- Wood Frame, Wood Siding
- Foundation: Poured Concrete
- Roof: Shingle
Condition
- Year built: 2008
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Private Sewer, Septic Tank
- Water: Private, Well
Community & HOA
Community
- Subdivision: Center Lookout Homeowners Association
HOA
- Has HOA: Yes
- HOA fee: $500 annually
Location
- Region: Boothbay
Financial & listing details
- Price per square foot: $244/sqft
- Tax assessed value: $270,278
- Annual tax amount: $3,270
- Date on market: 6/22/2026
- Road surface type: Gravel, Dirt
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 6/22/2026 | Listed for sale | $805,000+192.7%$244/sqft |
Source: | ||
| 3/24/2021 | Listing removed | -- |
Source: Owner Report a problem | ||
| 11/21/2015 | Listing removed | $275,000$83/sqft |
Source: Owner Report a problem | ||
| 8/23/2015 | Listed for sale | $275,000$83/sqft |
Source: Owner Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $3,068 +13% | $270,278 |
| 2023 | $2,716 +8% | $270,278 |
| 2022 | $2,514 -2.6% | $270,278 |
| 2021 | $2,581 | $270,278 |
| 2020 | $2,581 +1.1% | $270,278 |
| 2019 | $2,554 +1.6% | $270,278 |
| 2018 | $2,514 -2.2% | $270,278 -3.3% |
| 2017 | $2,570 +75.9% | $279,400 +68.3% |
| 2016 | $1,461 +0.6% | $166,000 |
| 2015 | $1,453 +3% | $166,000 |
| 2014 | $1,411 +1.2% | $166,000 |
| 2013 | $1,394 +18.9% | $166,000 |
| 2008 | $1,172 | $166,000 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 04537
Nearby schools
GreatSchools rating
- 6/10Boothbay Region Elementary SchoolGrades: PK-8Distance: 1 mi
- 4/10Boothbay Region High SchoolGrades: 9-12Distance: 1.1 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Maine
- Lincoln County
- Boothbay
- 04537
- 39 Shackleton's Way





