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$795,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,829 Sq. Ft.
  • 2.48 Acres
  • 2 Car Garage
  • Updated 1 day ago
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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

Full Property Details for 66 Rolling Hill Dr

General

  • Price: $795,000
  • HOA FEE: $100/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,017 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MREIS
  • MLS ID: 1673291
  • Updated: 8/3/2026
  • Added to Site: 4 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: Attic, Bathtub, Shower, Primary Bedroom w/Bath
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Tankless Water Heater
  • Furnishings: Negotiable
  • Flooring: Carpet, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Main Level

Additional Information

  • Equipment: Air Radon Mitigation System, Generator, Internet Access Available

Exterior

  • Porch/Patio/Deck: Deck, Glassed-in Porch, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking Features: Paved, 1 - 4 Spaces, Off Street, Inside Entrance

Location

  • County: Cumberland

Community

  • Association: Yes

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Propane, Baseboard, Hot Water

Utilities

  • Sewer: Septic Design Available, Septic Tank
  • Water: Private, Well
  • Well: Yes

Structural Information

  • Architectural Style: Cape Cod, Contemporary
  • Structure Type: Post & Beam
  • Construction: Wood Frame, Clapboard, Wood Siding
  • Basement: Yes
  • Basement Desc.: Interior Entry, Walk-Out Access, Full, Unfinished
  • Roof: Metal, Shingle
  • Square Feet: 2,829
  • Sq. Ft. Source: Seller
  • Finished Total: 2,829 Sq. Ft.
  • Finished Above Grnd: 2,829 Sq. Ft.
  • Year Built: 1990

Lot Features

  • Property View: Scenic, Trees/Woods
  • Lot Size (Acres): 2.48
  • Lot Size (Sq. Ft.): 108,028.8
  • Street/Road Desc.: Private Road, Paved
  • Zoning: Residential
  • Lot Description: Interior Lot, Near Public Beach, Near Town, Neighborhood, Subdivided, Rolling Slope, Landscaped, Wooded

Water Features

  • Water Front: Yes
  • Water Front Name: Sebago

Green Features

  • Energy Efficient: Ceiling Fans, Dehumidifier

Financial Considerations

  • Association Fee: $1,200
  • Assoc Fee Freq.: Annually
  • Tax Amount: $5,017.31
  • Tax Year: 2025

Disclosures and Reports

  • Lot Number: 10

Listed by Sunset Lakes Real Estate (207) 655-2139

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Listing agents

— 66 Rolling Hill Dr —

  • Sunset Lakes Real Estate

    207-655-2139

  • Sunset Lakes Real Estate

    207-655-2139

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 66 Rolling Hill Dr

School District:School Administrative District 61
NameGradesDistance
Songo Locks School
25 Songo School Road, Naples, ME 04055
K-52.8 mi
Lake Region Middle School
204 Kansas Road, Naples, ME 04055
6-85.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 66 Rolling Hill Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/31/2026
Listed
$795,000
218%
MLS
12/09/2024
Sold
$250,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 66 Rolling Hill Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,912
2%
$528,138
—
2023
$4,832
11%
$528,138
—
2022
$4,357
-12%
$528,138
42%
2021
$4,960
—
$371,512
—
2020
$4,960
—
$371,512
—
2019
$4,960
—
$371,512
—
2018
$4,960
—
$371,512
—
2017
$4,960
1%
$371,512
—
2016
$4,904
100%
$371,512
—
2015
100%
$371,512
—
2014
-100%
$371,512
—
2013
$4,830
—
$371,512
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 66 Rolling Hill Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Sunset Lakes Real Estate (207) 655-2139

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66 Rolling Hill Drive, Naples, ME 04055 (MLS# 1673291) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 66 Rolling Hill Drive is currently listed for $795,000 and was received on July 31, 2026. Want to learn more about 66 Rolling Hill Drive? Do you have questions about finding other Single Family real estate for sale in Naples? You can browse all Naples real estate or contact a Coldwell Banker agent to request more information.

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