41 Gildersleeve Road

Portland CT 06480

3355 sq. ft.

2.03 ac.

Single-Family

Last sold for $860,000

Deborah Walden, last sold this property on 16 October 2026 after 43 days on market.

Overview

Rarely available, this exceptional custom built home sits on 2.03 acres bordering the Portland Golf Course. Welcome to 41 Gildersleeve Road an oversized Cape, offering approximately 3,355 square feet of thoughtfully designed living space. The open-concept floor plan features spacious rooms, quality finishes, and an inviting layout designed for both everyday living and entertaining. Beautiful hardwood floors flow throughout the home, complemented by a gas fireplace framed by custom built-ins. On chilly evenings, gather around the fire and enjoy the warmth and comfort of this welcoming space. The thoughtfully designed floor plan creates an easy flow between the living, dining, and entertaining areas. Large windows fill the home with abundant natural light, enhancing the open and airy feel throughout. The home currently offers three bedrooms and three-and-a-half baths, with the flexibility of two potential primary bedroom suites-one on the first floor and another on the second floor. This versatile layout provides options to suit a variety of living arrangements. Convenience continues with laundry hookups on the first floor, as well as a dedicated laundry room in the basement. A spacious first-floor office provides an ideal work-from-home space and could also be used as a fourth bedroom. The home also offers a comfortable bonus room/family room, perfect for movie nights, game nights, or additional entertaining space. With its generous acreage, golf course setting, inground pool, flexible floor plan, and quality finishes this home is a sure winner for your next home. Step outside and enjoy your morning coffee on the private front porch or by the inground pool which provides a multitude of entertaining spaces whether it is seated on the deck, floating in the inground pool, at the table shaded by the umbrella or by the firepit. This home offers a wonderful balance of privacy, open space, and scenic surroundings. This home is located within minutes of 3 beautiful golf courses, driving range, large sports field and playground, seasonal splash pad and multiple marinas on the picturesque Connecticut River. SELLER IS REQUESTING HIGHEST AND BEST BY TUESDAY SEPT 8TH 12 NOON!! Thank you!

Features

3 bedrooms

4 bathrooms

2 carspaces

2 garage spaces

3355 sq. ft. floor area

2.03 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Portland over the last 12 months, the estimated median property value of 41 Gildersleeve Road is $420k.

Median value

$420k

Estimated value range

$215k - $860k

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Portland. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 41 Gildersleeve Road

2026

Sold

$860,000

16 Oct 2026 by Deborah Walden

Happy sellers in Portland

We have insufficient information to provide an overview of customer satisfaction for Portland. Viewing the agent profiles, reviews and sales for Portland can provide insights for this location.