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

What is 66 Rolling Hill Drive estimated to be worth?

Trulia's estimated value for 66 Rolling Hill Drive in Naples, ME is $803,700 .

What is the price history for 66 Rolling Hill Drive?

66 Rolling Hill Drive in Naples, ME last sold for $815,000 in September 2026.

Is Naples a buyer's or seller's market?

Naples is currently a seller's market, based on recent for-sale activity.

What do residents say about Naples?

Residents describe Naples, ME as well-kept, easy to park in, and established. Most residents say you need a car. See recently sold homes in Naples, ME .

Does 66 Rolling Hill Drive have laundry facilities?

Yes, 66 Rolling Hill Drive in Naples, ME has in-unit laundry.

How big is the lot at 66 Rolling Hill Drive?

The lot at 66 Rolling Hill Drive in Naples, ME is about 2.5 acres .

SOLD

SEP 25, 2026

$803,700

Trulia Estimate

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

66 Rolling Hill Drive, Naples, ME 04055

Est. Refi. Payment $4,944/mo*

Refinance Your Home

Currently Off Market - Sold Sep 25, 2026 for $815,000 (3% above list price)

Home Value

Trulia Estimate

$804K

Since last month

$1K (+0.2%)

Since last year

$1K (+0.2%)

Since last sale

$10K (-1.2%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +102% in the last 10 years

Month	Estimated value
2026
September 2026	$805K
August 2026	$804K
2020
September 2020	$399K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
90 Trickey Pond Road, Naples, ME	0.76	Single-Family Home	$835,000	08/13/26	4	3	2,300
510 Sebago Road, Naples, ME	0.91	Single-Family Home	$725,000	10/10/25	3	2	2,653
528 Sebago Road, Naples, ME	0.87	Single-Family Home	$429,900	08/24/26	3	2.5	1,728
878 Anderson Road, Sebago, ME	0.71	Single-Family Home	$570,000	06/24/26	3	2	1,673
827 Anderson Road, Sebago, ME	0.78	Single-Family Home	$901,000	07/20/26	3	2	1,943
131 Harbor Road, Naples, ME	0.70	Single-Family Home	$440,000	11/21/25	3	1	2,128
130 Whippoorwill Drive, Naples, ME	1.50	Single-Family Home	$1,741,500	07/10/26	4	3	4,005
95 Harbor Road, Naples, ME	1.07	Single-Family Home	$451,000	12/01/25	3	2	1,481
6-3 Boulder Beach Road, Naples, ME	1.28	Single-Family Home	$1,150,000	11/12/25	6	3.5	1,833

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
60 Rolling Hill Drive, Naples, ME 04055	0.03	$703,200	3	2.5	2,194	Off Market
78 Forest Ridge Drive, Naples, ME 04055	0.03	-	-	-	-	Off Market
44 Rolling Hill Drive, Naples, ME 04055	0.09	$687,900	-	-	-	Off Market
Lot 4 Rolling Hill Drive, Naples, ME 04055	0.13	$310,000	-	-	-	For Sale
3 Rocky Ridge Road, Naples, ME 04055	0.18	-	-	-	-	Off Market
8 Rocky Ridge Road, Naples, ME 04055	0.21	-	-	-	-	Off Market
Lot 5 Rocky Ridge Road, Naples, ME 04055	0.22	$145,000	-	-	-	Recently Sold
185 Rolling Hill Drive, Naples, ME 04055	0.22	$752,600	3	2.5	3,023	Off Market
7 Rocky Ridge Road, Naples, ME 04055	0.22	-	-	-	-	Off Market
32 Rocky Ridge Road, Naples, ME 04055	0.24	$546,100	4	3	1,550	Off Market
Lot 4 Rocky Ridge Road, Naples, ME 04055	0.25	-	-	-	-	Off Market

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

Home Highlights

Single-Family Home

Built in 1990

2.48 acre lot

2,829 sqft

$288/sqft

2 Car Garage

HOA $100/mo

Last check for updates: about 1 hour ago

Listed by Sunset Lakes Real Estate

Bought with: Sunset Lakes Real Estate

Source: Maine Listings, MLS#1673291

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.
All offers due Tuesday Aug 4 by 1pm

66 Rolling Hill Drive, Naples, ME 04055 is a 4 bedroom, 3 bathroom, 2,829 sqft single-family home built in 1990. It last sold for $815,000 on Sep 25, 2026 (3% above the $795,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $803,700, with a rent estimate of $3,804/month.

Home Details for 66 Rolling Hill Drive

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

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: $288/sqft
Status Change & Dates Off Market Date: Tue Aug 04 2026

Active Status
MLS Status: Closed

Media
See Virtual Tour

Location
Direction & Address City: Naples

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

Price and Tax history

Date	Event	Price
Sep 25, 2026 Source: Maine Listings #1673291	Sold	$815,000
Aug 5, 2026 Source: Maine Listings #1673291	Pending	$795,000
Jul 31, 2026 Source: Maine Listings #1673291	Listed For Sale	$795,000
Oct 26, 2008 Source: Agent Provided	ListingRemoved	$159,900
Sep 10, 2008 Source: Agent Provided	Listed For Sale	$159,900

Market trends in Naples

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

4MoM

Around this home

Songo Locks School
PK-2
Public
249 Students
Regional School Unit 61 Msad 61
NA
GreatSchools Rating
Parent Rating Average
Do not pick this school district if you have a special needs child. They do not work with you what so ever. They approach your child as a “bad kid” when they aren’t a “normal” child. I’ve had the principal call me asking why my child wasn’t acting like a normal first grader. The teacher are essentially forced to stay quiet during IEP meetings, leaving your child lacking the accommodations they need for a successful year. There are teachers that work there sending their elementary age kids to other charter schools around. I do not recommend.
Parent Review
11mo ago
7 Reviews

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

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

Frequently asked questions about 66 Rolling Hill Drive

What is 66 Rolling Hill Drive estimated to be worth?
Trulia's estimated value for 66 Rolling Hill Drive in Naples, ME is $803,700.
What is the price history for 66 Rolling Hill Drive?
66 Rolling Hill Drive in Naples, ME last sold for $815,000 in September 2026.
Is Naples a buyer's or seller's market?
Naples is currently a seller's market, based on recent for-sale activity.
What do residents say about Naples?
Residents describe Naples, ME as well-kept, easy to park in, and established. Most residents say you need a car. See recently sold homes in Naples, ME.
Does 66 Rolling Hill Drive have laundry facilities?
Yes, 66 Rolling Hill Drive in Naples, ME has in-unit laundry.
How big is the lot at 66 Rolling Hill Drive?
The lot at 66 Rolling Hill Drive in Naples, ME is about 2.5 acres.

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7 rentals with a washer/dryer in Naples, ME

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APPLY INSTANTLY
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12 Bay Village Rd,
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APPLY INSTANTLY
FURNISHED
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3 bd
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Naples, ME 04055
NEW - 1 DAY AGO
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Naples, ME 04055
FURNISHED
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Naples, ME 04055

Apartments for Rent

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Off Market Homes Near 66 Rolling Hill Drive

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SOLD
SEP 14, 2026
$735,000
4 bd
3 ba
3,355 sqft
69 Woodland Shore Drive,
Naples, ME 04055
Keller Williams Realty
SOLD
SEP 10, 2026
$635,000
2 bd
2.5 ba
1,880 sqft
23 Clifford Road #17,
Naples, ME 04055
Maine Real Estate Choice
SOLD
SEP 8, 2026
$599,900
3 bd
2 ba
2,044 sqft
36 Pine Rock Road,
Naples, ME 04055
Coldwell Banker Team Real Estate
SOLD
SEP 1, 2026
$820,000
2 bd
2.5 ba
2,080 sqft
15 Goodridge Drive #15,
Naples, ME 04055
Maine Real Estate Choice
SOLD
AUG 24, 2026
$650,000
3 bd
3 ba
2,582 sqft
79 Lukes Road,
Casco, ME 04015
Keller Williams Realty
SOLD
AUG 24, 2026
$429,900
3 bd
2.5 ba
1,728 sqft
528 Sebago Road,
Naples, ME 04055
Landing Real Estate
SOLD
AUG 21, 2026
$1,100,000
4 bd
2 ba
1,890 sqft
116 Salmon Point Road,
Sebago, ME 04029
Pine Tree Realty of Maine
SOLD
AUG 18, 2026
$810,000
890 sqft
4 Goodridge Dr,
Naples, ME 04055
SOLD
AUG 18, 2026
$775,000
4 bd
3.5 ba
3,536 sqft
37 Woodland Shore Drive,
Naples, ME 04055
Maine Real Estate Choice
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Homes for sale near 66 Rolling Hill Drive

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$899,000
3 bd
2.5 ba
1,225 sqft
805 Anderson Road,
Sebago, ME 04029
Meservier & Associates
0.28 ACRES
$485,000
3 bd
3 ba
2,468 sqft
101 Harbor Road,
Naples, ME 04055
Fontaine Family-The Real Estate Leader
0.55 ACRES
$315,000
2 bd
1 ba
1,056 sqft
128 Pleasant View Drive,
Naples, ME 04055
Maine Real Estate Co
1.39 ACRES
$674,900
4 bd
3 ba
2,588 sqft
255 Anderson Road,
Sebago, ME 04029
Pack Maynard and Associates
1.4 ACRES
$440,000
3 bd
2 ba
1,219 sqft
183 Dunton Road,
Naples, ME 04055
Hearth & Key Realty
1.64 ACRES
$370,000
3 bd
1 ba
1,142 sqft
9 Escott Way,
Naples, ME 04055
Dream Home Realty LLC
1.38 ACRES
$489,900
3 bd
2 ba
1,400 sqft
24 Mayberry Landing,
Naples, ME 04055
Maine Real Estate Choice
OPEN SAT, 11-1PM
NEW CONSTRUCTION
1.64 ACRES
$1,275,000
4 bd
3.5 ba
2,863 sqft
47 Fairway Drive,
Naples, ME 04055
Legacy Properties Sotheby's International Realty
0.59 ACRES
$749,900
3 bd
1.5 ba
1,696 sqft
31 Welch Drive,
Casco, ME 04015
Pine Tree Realty of Maine
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