Gildersleeve Homes for Sale

Welcome to Gildersleeve, a charming neighborhood nestled in the heart of Portland, Connecticut, within the picturesque Middlesex County. This hidden gem boasts a unique blend of natural beauty, community spirit, and convenient living, making it an ideal place to call home.

Gildersleeve is characterized by its serene streets lined with mature trees and well-kept homes that reflect a variety of architectural styles. The neighborhood is perfect for families, professionals, and retirees alike, offering a peaceful atmosphere while being just minutes away from the vibrant downtown area of Portland. Residents enjoy easy access to local parks, recreational activities, and the stunning Connecticut River, which provides ample opportunities for outdoor adventures like kayaking, fishing, and hiking.

The community's strong sense of camaraderie is evident in its local events and gatherings, fostering connections among neighbors. With top-rated schools, friendly shops, and delightful eateries nearby, Gildersleeve ensures that all your daily needs are met within a short drive or a pleasant stroll.

Currently, there are several homes for sale in Gildersleeve, each offering its own unique charm and character. From cozy single-family houses to spacious family residences, you’ll find options that cater to a variety of lifestyles and budgets. Whether you're looking for a starter home or a place to settle down for years to come, Gildersleeve has something for everyone.

Discover the warmth and welcoming ambiance of Gildersleeve, where your dream home awaits in this delightful neighborhood. Come explore the possibilities and see why so many have chosen to call Gildersleeve their home sweet home!

Newest Gildersleeve Homes for Sale

$500,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191576 MLS

Location, Location, Location! Welcome to the sought-after 55+ community of Bartlett Hill! This move-in ready Berkshire style home offers 1,503 sq. ft. of comfortable living on a quiet cul-de-sac, backing to peaceful woods for exceptional privacy. An inviting front porch, beautifully landscaped gardens, and charming curb appeal welcome you home. Inside, the open floor plan is perfect for everyday living and entertaining. The first-floor primary suite features a walk-in closet and full bath with shower stall, providing the ease of one-level living. The kitchen flows into the dining area and cozy sunroom. The living room offers a direct-vent gas fireplace and convenient half bath. Hardwood floors enhance the entryway and kitchen.Enjoy your private rear deck overlooking the woods, perfect for relaxing and enjoying nature. Upstairs, you'll find a guest suite(perfect for live-in caregiver) with a full bath, generous closet space, and a versatile loft ideal for a home office, reading nook, or exercise area. The unfinished lower level provides abundant storage and future expansion potential, while the attached two-car garage adds convenience. Bartlett Hill offers beautifully maintained grounds, a welcoming atmosphere, clubs, social activities, pool exercise, scenic walking streets, strong association finances, and a low HOA fee. Conveniently located near golf, shopping, and dining, this home offers the perfect blend of privacy, low-maintenance living, and community. Schedule a tour

19 Plumrose Court Unit 19, Portland

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.