# 66 Rolling Hill Drive, Naples, ME 04055

> **TL;DR:** 4bd/3ba single family, $795,000 ($281/sqft), built 1990, 2,829 sqft.
> Fireplace, Waterfront, Hardwood. Est. $5,452/mo.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $795,000 |
| Price/sqft | $281 |
| Bedrooms | 4 |
| Bathrooms | 2 full, 1 half |
| Square Feet | 2,829 |
| Year Built | 1990 |
| Lot Size | 108,029 sqft (2.48 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 0 |

## Why This Home Stands Out

- **Waterfront** - Direct water access
- **Hardwood Floors** - Throughout the home

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $4,020 |
| Estimated Insurance | $232 |
| HOA | $1,200 |
| **Total** | **$5,452** |

## Key Amenities

- Fireplace
- Waterfront
- Hardwood

## Property Highlights

- Built in 1990
- 2.48 acre lot
- Fireplace
- Waterfront

## Description

### Agent Description
Welcome to 66 Rolling Hill Drive, a rare opportunity to own 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 the heart of Maine's picturesque Lakes Region, this exceptional property offers the perfect balance of tranquility, natural beauty, and an active four-season lifestyle. Meandering roads, mature trees, thoughtfully placed homes, and beautifully landscaped surroundings create an atmosphere of timeless elegance and peaceful retreat. Residents enjoy exclusive access to outstanding community amenities, including a deeded boat dock and slips, along with two private beaches. One is considered among the finest on Sebago Lake, while the second features a swim raft, picnic and grilling areas, and well-maintained restroom facilities--perfect for making the most of Maine summers. From the moment you arrive, the home's inviting charm is unmistakable. Classic stone walls, lush gardens, and a welcoming approach set the tone for what awaits inside. Warm post-and-beam ceilings, a stunning fieldstone fireplace, and sun-filled living spaces create a home that is both comfortable and memorable. Designed for everyday living and effortless entertaining, the recently renovated custom kitchen is the heart of the home, flowing seamlessly into the three-season sunroom where walls of windows invite the outdoors in and provide the perfect place to relax while surrounded by nature. Meticulously maintained inside and out, this move-in-ready home offers four spacious bedrooms and two-and-a-half baths, providing ample room for family and guests alike. Whether you're searching for a year-round residence or the ultimate vacation retreat, this home delivers. Beyond your doorstep, the Lakes Region offers endless recreation in every season. Enjoy boating on Sebago Lake, hiking scenic trails, championship golf, skiing, ice fishing, snowmobiling with access to an extensive trail system reaching Canada

## Location

- **Address:** 66 Rolling Hill Drive, Naples, ME 04055
- **County:** Cumberland
- **Coordinates:** 43.925656, -70.603037
- **Google Maps:** https://www.google.com/maps?q=43.925656,-70.603037

## Listing Agent

- **Name:** Lois O'Connor
- **Brokerage:** Sunset Lakes Real Estate
- **Phone:** 2078415602

## Primary Photo

![66 Rolling Hill Drive - Primary Photo](http://lh.rdcpix.com/cf23a934820b3ec8c5d5332cca14634bl-f1664507759r.jpg)

*89 total photos available on [listing page](https://www.propertysimple.ai/listing/66-rolling-hill-drive-naples-me-04055-1673291)*

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**MLS#:** 1673291 | **Updated:** 2026-08-01
**Source:** listhub

*Copyright © 2026 Maine Listings. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/66-rolling-hill-drive-naples-me-04055-1673291)

---

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