$795,000
PENDING

66 Rolling Hill Dr Naples, ME 04055

Naples Area

Estimated payment $4,887/month

Total Views 11,111
4 Beds
2.5 Baths
2,829 Sq Ft
$281 Price per Sq Ft

Highlights

  • Deeded Waterfront Access Rights
  • Docks
  • Scenic Views
  • 700 Feet of Waterfront
  • Boat Slip
  • 2.48 Acre Lot

About This Home

Welcome to 66 Rolling Hill Drive, a beautifully maintained home in one of Sebago Lake's most sought-after communities, Lake Sebago Estates. Set on a private 2.48-acre lot in Maine's scenic Lakes Region, this exceptional property offers the perfect blend of privacy, comfort, and year-round recreation. Residents enjoy exclusive access to a deeded boat dock and slips, along with two private beaches--one of the finest on Sebago Lake and another featuring a swim raft, picnic and grilling areas, and restroom facilities. From the moment you arrive, the home's stone walls, mature gardens, and welcoming entrance create an inviting first impression. Inside, warm post-and-beam ceilings, a stunning fieldstone fireplace, and abundant natural light make every space feel both comfortable and timeless. The recently updated custom kitchen and bright three-season sunroom are perfect for entertaining or simply enjoying the peaceful natural surroundings. Meticulously maintained, this move-in-ready home offers four bedrooms and two-and-a-half baths with plenty of room for family and guests. Whether you're boating, hiking, golfing, skiing, snowmobiling, or enjoying tennis and pickleball, the Lakes Region offers endless opportunities to experience the very best of Maine in every season. Don't miss this opportunity to own an exceptional home in a truly special Sebago Lake community where privacy, natural beauty, and an unmatched lifestyle come together.
All offers due Tuesday Aug 4 by 1pm

Listing Agent

Lois O'Connor

Sunset Lakes Real Estate Listed on: 07/31/2026

Sunset Lakes Real Estate

Co-Listing Agent

Jennifer O'Connor

Sunset Lakes Real Estate

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $5,017

Year Built

  • Built in 1990

Lot Details

  • 2.48 Acre Lot
  • 700 Feet of Waterfront
  • Lake Front
  • Property fronts a private road
  • Landscaped
  • Interior Lot
  • Lot Has A Rolling Slope
  • Wooded Lot

HOA Fees

  • $100 Monthly HOA Fees

Parking

  • 2 Car Direct Access Garage
  • Off-Street Parking

Property Views

  • Scenic Vista
  • Woods

Home Design

  • Cape Cod Architecture
  • Contemporary Architecture
  • Post and Beam
  • Poured Concrete
  • Wood Frame Construction
  • Shingle Roof
  • Metal Roof
  • Wood Siding
  • Radon Mitigation System
  • Clapboard

Interior Spaces

  • 2,829 Sq Ft Home
  • Multi-Level Property
  • Ceiling Fan
  • 1 Fireplace
  • Attic

Kitchen

  • Electric Range
  • Dishwasher

Flooring

  • Wood
  • Carpet
  • Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Primary bedroom located on second floor
  • En-Suite Primary Bedroom
  • Bathtub
  • Shower

Laundry

  • Laundry on main level
  • Dryer
  • Washer

Unfinished Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Interior Basement Entry

Outdoor Features

  • Pool Heated With Propane
  • Deeded Waterfront Access Rights
  • Property is near a beach
  • Boat Slip
  • Docks
  • Deck
  • Patio
  • Enclosed Glass Porch

Location

  • Near Waterfront

Utilities

  • Dehumidifier
  • Baseboard Heating
  • Hot Water Heating System
  • Power Generator
  • Private Water Source
  • Well
  • Tankless Water Heater
  • Septic Tank
  • Septic Design Available
  • Internet Available

Listing and Financial Details

  • Tax Lot 10

Home Details

Home Type

Single Family

Est. Annual Taxes

$5,017

Year Built

Built in 1990

Lot Details

2.48 Acres

HOA Fees

$100 per month

Parking

2

Listing Details

  • Property Sub Type: Single Family Residence
  • Prop. Type: Residential
  • Lot Size Acres: 2.48
  • Road Frontage Type: Private Road
  • Road Surface Type: Paved
  • Water Body Name: Sebago
  • MLS Status: Pending
  • Above Grade Finished Sq Ft: 2829.00
  • Architectural Style: Cape Cod, Contemporary
  • Garage Yn: Yes
  • Unit Levels: Multi-Level
  • Efficiency: Ceiling Fans, Dehumidifier
  • Structure Type: Post & Beam
  • Year Built: 1990
  • Property Information:Seasonal: No
  • Water Info:Water View2: No
  • Dining Room:Dining Room: Dining Room
  • Living Room:Living Room: Living Room
  • Sunroom:Sunroom: Sunroom
  • Water Info:Waterfront Amount -: 700.00
  • Water Info:Water Frontage Shared -: 700.00
  • Laundry Room:Laundry Room: Laundry
  • Den:Den: Den
  • Special Features: VirtualTour

Interior Features

  • Furnished: Negotiable
  • Appliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Tankless Water Heater
  • Other Equipment: Air Radon Mitigation System, Generator, Internet Access Available
  • Has Basement: Interior Entry, Walk-Out Access, Full, Unfinished
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Total Bedrooms: 4
  • Fireplaces: 1
  • Fireplace: Yes
  • Flooring: Carpet, Tile, Hardwood
  • Interior Amenities: Attic, Bathtub, Shower, Primary Bedroom w/Bath
  • Bedroom 2 Level: Second
  • Bedroom 3 Level: Second
  • Bedroom 4 Bedroom 4 Level: Second
  • Dining Room Dining Room Level: First
  • Kitchen Kitchen Level: First
  • Living Room Living Room Level: First
  • Primary Bedroom Primary Bedroom Level: Second
  • Laundry Room Laundry Room Level: First

Exterior Features

  • Lot Features: Interior Lot, Near Public Beach, Near Town, Neighborhood, Subdivided, Rolling Slope, Landscaped, Wooded
  • View: Scenic, Trees/Woods
  • Waterfront Features: Beach Rights, Boat Slip, Deeded, Dock, Lake/Fresh Water, Nearby, ROW to Water, Waterfront Deep
  • Waterfront: Yes
  • Construction Type: Wood Frame, Clapboard, Wood Siding
  • Foundation Details: Poured Concrete
  • Patio And Porch Features: Deck, Glassed-in Porch, Patio
  • Roof: Metal, Shingle

Garage/Parking

  • Attached Garage: Yes
  • Garage Spaces: 2.00
  • Parking Features: Paved, 1 - 4 Spaces, Off Street, Inside Entrance

Utilities

  • Laundry Features: Main Level
  • Cooling: None
  • Cooling Y N: No
  • Heating: Propane, Baseboard, Hot Water
  • Heating Yn: Yes
  • Electric: Circuit Breakers
  • Sewer: Septic Design Available, Septic Tank
  • Water Source: Private, Well

Condo/Co-op/Association

  • Association Fee: 1200.00
  • Association Fee Frequency: Annually
  • Association: Yes

Lot Info

  • Land Lease: No
  • Lot Size Sq Ft: 108028.80
  • Zoning: Residential

Tax Info

  • Tax Annual Amount: 5017.31
  • Tax Lot: 10
  • Tax Year: 2025

3D Interior and Exterior Tours

Floorplans

Map

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $4,912 $528,138 $163,880 $364,258
2024 $4,912 $528,138 $163,880 $364,258
2023 $4,832 $528,138 $163,880 $364,258
2022 $4,357 $528,138 $163,880 $364,258
2021 $4,960 $371,512 $129,440 $242,072
2020 $4,960 $371,512 $129,440 $242,072
2019 $4,960 $371,512 $129,440 $242,072
2018 $4,960 $371,512 $129,440 $242,072
2017 $4,960 $371,512 $129,440 $242,072
2016 $4,904 $371,512 $129,440 $242,072
2015 -- $371,512 $129,440 $242,072
2014 -- $371,512 $129,440 $242,072
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
08/05/2026 08/05/26 Pending -- -- --
07/31/2026 07/31/26 For Sale $795,000 -- $281 / Sq Ft
Source: Maine Listings

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Type Sale Price Title Company
Warranty Deed $250,000 None Available
Warranty Deed -- --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Loan Amount Loan Type
Previous Owner $337,000 Purchase Money Mortgage
Source: Public Records

About the Listing Agent

Lois O'Connor

Sunset Lakes Real Estate

(877) 342-0740

Section Image

Sunset Lakes Real Estate – Your Premier Maine Lakefront Experts

At Sunset Lakes Real Estate, we don’t just sell homes—we create seamless experiences that turn dreams into reality. Led by industry expert Lois O'Connor, with 35+ years of unmatched expertise in Maine's real estate market, our team goes above and beyond to ensure every client finds their perfect home or sells with confidence.

What sets us apart? Personalized service, deep market knowledge, and proven results. Clients

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Source: Maine Listings

MLS Number: 1673291

Maine Listings

APN: NAPL-000006R-000010-000008

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