Is a car needed in Naples, ME?

As of early 2026, 100% of users say car is needed

Are yards well-kept in Naples, ME?

As of early 2026, 100% of users say yards are well-kept

Is parking easy in Naples, ME?

As of early 2026, 93% of users say parking is easy

Does Naples, ME show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Is there wildlife in Naples, ME?

As of early 2026, 73% of users say there's wildlife

Do residents of Naples, ME plan to stay at least 5 years?

As of early 2026, 63% of users say they plan to stay for at least 5 years

As of early 2026, 60% of users say it's quiet

Are neighbors friendly in Naples, ME?

As of early 2026, 55% of users say neighbors are friendly

Is Naples, ME dog-friendly?

As of early 2026, 55% of users say it's dog friendly

Is Naples, ME walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Do kids play outside in Naples, ME?

As of early 2026, 47% of users say kids play outside

Would people walk alone at night in Naples, ME?

As of early 2026, 45% of users say people would walk alone at night

Are there community events in Naples, ME?

As of early 2026, 40% of users say there are community events

Is Naples, ME walkable to grocery stores?

As of early 2026, 29% of users say it's walkable to grocery stores

Are the streets well-lit in Naples, ME?

As of early 2026, 27% of users say streets are well-lit

NEW

COMING SOON

2.48 ACRES

66 Rolling Hill Drive
Naples, ME 04055

4 Beds
2.5 Baths
2,829 sqft (on 2.48 acres)

$795,000

Est. Mortgage $4,886/mo*

Get Pre-Qualified

$795,000

Est. Mortgage $4,886/mo*

Get Pre-Qualified

4 Beds

2.5 Baths

2,829 sqft

(on 2.48 acres)

Home Highlights

Parking

2 Car Garage

Outdoor

Porch, Patio, Deck

Climate Control

Heating only

HOA

$100/Monthly

Price/Sqft

$281

Listed

1 day ago

Local Information

Map ViewExplore the area around 66 Rolling Hill Drive.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Last check for updates: about 7 hours ago

Listing courtesy of Sunset Lakes Real Estate

Source: Maine Listings, MLS#1673291

Also Listed on Maine Listings.

About this House

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.

Home Details for 66 Rolling Hill Drive

Active Status
MLS Status: Coming Soon / No Show

Interior Features
Interior Details Basement: Interior Entry,Walk-Out Access,Full,UnfinishedNumber of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Den, Dining Room, Kitchen, Laundry, Living Room, Sunroom
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 2829 Square Feet
Appliances & Utilities Appliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Tankless Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling Heating: Baseboard,Hot WaterNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace
Gas & Electric Electric: Circuit Breakers
Windows, Doors, Floors & Walls Flooring: Carpet, Tile, Hardwood
Levels, Entrance, & Accessibility Levels: Multi/SplitFloors: Carpet, Tile, Hardwood
View Has a ViewView: Scenic, Trees/Woods
Security Security: Air Radon Mitigation System

Exterior Features
Exterior Home Features Roof: Metal ShinglePatio / Porch: Deck, Glassed-in Porch, PatioFoundation: Poured ConcreteNo Private Pool
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Paved,1 - 4 Spaces,Off Street
Frontage WaterfrontRoad Frontage: Private RoadRoad Surface Type: PavedOn Waterfront
Water & Sewer Sewer: Septic Design Available, Septic TankWater Body: Sebago
Farm & Range Frontage Length: Waterfrontage: 700, Waterfrontage Shared: 700
Finished Area Finished Area (above surface): 2829 Square Feet

Days on Market
Days on Market: 1

Property Information
Year Built Year Built: 1990
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: Post & BeamArchitecture: Cape Cod,Contemporary
Building Construction Materials: Wood Frame, Clapboard, Wood Siding

Price & Status
Price List Price: $795,000Price Per Sqft: $281

Location
Direction & Address City: Naples

Agent Information
Listing Agent Listing ID: 1673291

Building
Building Area Building Area: 2829 Square Feet

HOA
Has an HOAHOA Fee: $1,200/Annually

Lot Information
Lot Area: 2.48 Acres

Energy
Energy Efficiency Features: Ceiling Fans, Dehumidifier

Miscellaneous
BasementMls Number: 1673291Above Grade Unfinished Area: 2829

Market trends in Naples

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Price History for 66 Rolling Hill Drive

Date	Price	Event	Source
10/26/2008	$159,900	ListingRemoved	Agent Provided

09/10/2008	$159,900	Listed For Sale	Agent Provided

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Comparable Sales for 66 Rolling Hill Drive

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
60 Rolling Hill Drive, Naples, ME	0.03	Single-Family Home	$685,000	08/26/25	3	2.5	2,194
185 Rolling Hill Drive, Naples, ME	0.22	Single-Family Home	$735,000	08/14/25	3	2.5	3,023
510 Sebago Road, Naples, ME	0.91	Single-Family Home	$725,000	10/10/25	3	2	2,653
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214 Gore Road, Naples, ME	1.09	Single-Family Home	$400,000	11/25/25	3	2	1,520

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OFF MARKET
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Skip to first item

Assigned Schools

These are the assigned schools for 66 Rolling Hill Drive.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Naples

At least 10 Trulia users voted on each feature.

100 % Say car is needed
100 % Say yards are well-kept
93 % Say parking is easy
75 % Say there's holiday spirit
73 % Say there's wildlife
63 % Say they plan to stay for at least 5 years
60 % Say it's quiet
55 % Say neighbors are friendly
55 % Say it's dog friendly
50 % Say it's walkable to restaurants
47 % Say kids play outside
45 % Say people would walk alone at night
40 % Say there are community events
29 % Say it's walkable to grocery stores
27 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Cjw.plymouth
Visitor
6y ago
"Not many sidewalks on roads outside of the main strip off long lake. Lots of the roads leading out of town are busy state roads that are also windy and for instance I noticed while driving that joggers can’t always been seen around corners."
8
Flag
Rrbygib
Resident
6y ago
"Naples has a lot to offer, from summer water sports, such as boating and swimming,to winter sports, skiing, snowshoeing, ice fishing, snowmobiling.....and the area is magical. "
2
Flag

LGBTQ Local Legal Protections

Sunset Lakes Real Estate

Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443

66 Rolling Hill Drive, Naples, ME 04055 is a 4 bedroom, 3 bathroom, 2,829 sqft single-family home built in 1990. This property is currently available for sale and was listed by Maine Listings on Jul 24, 2026. The MLS # for this home is MLS# 1673291.

66 Rolling Hill Drive
Naples, ME 04055

$795,000

$795,000

Home Highlights

Local Information

About this House

Home Details for 66 Rolling Hill Drive

Active Status

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Location

Agent Information

Building

HOA

Lot Information

Energy

Miscellaneous

Market trends in Naples

Price History for 66 Rolling Hill Drive

Similar Homes You May Like

New Listings near 66 Rolling Hill Drive

Comparable Sales for 66 Rolling Hill Drive

Nearby homes

Assigned Schools

What Locals Say about Naples

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

Nearby Real Estate

Nearby Zip Codes

Popular Cities in Maine

04055 Neighborhoods

04055 Property Types

Real Estate Guides

66 Rolling Hill Drive Naples, ME 04055

$795,000

$795,000

Home Highlights

Local Information

About this House

Home Details for 66 Rolling Hill Drive

Active Status

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Location

Agent Information

Building

HOA

Lot Information

Energy

Miscellaneous

Market trends in Naples

Price History for 66 Rolling Hill Drive

Similar Homes You May Like

New Listings near 66 Rolling Hill Drive

Comparable Sales for 66 Rolling Hill Drive

Nearby homes

Assigned Schools

What Locals Say about Naples

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

66 Rolling Hill Drive
Naples, ME 04055