Gildersleeve Real Estate

Welcome to Gildersleeve, a hidden gem nestled in the charming town of Portland, Connecticut, within Middlesex County. This picturesque neighborhood offers a delightful blend of natural beauty, community spirit, and convenient access to modern amenities, making it an ideal place to call home.

Gildersleeve is characterized by its serene surroundings, with lush greenery and scenic views that invite outdoor enthusiasts to explore. The nearby Connecticut River provides ample opportunities for boating, fishing, and picnicking, while the surrounding parks and trails invite residents to enjoy leisurely strolls or invigorating hikes. This neighborhood truly embodies the essence of suburban tranquility, where the hustle and bustle of city life feels a world away.

Families will appreciate the strong sense of community in Gildersleeve, where friendly neighbors often gather for local events and activities. The area boasts excellent schools, ensuring that children receive a quality education while fostering lifelong friendships. Portland’s vibrant downtown area is just a short drive away, offering an array of shops, restaurants, and cultural attractions to explore.

For those who commute, Gildersleeve’s convenient location provides easy access to major highways and public transportation, making travel to nearby cities like Hartford and New Haven a breeze.

In Gildersleeve, you’ll find a perfect balance of peaceful living and accessibility to urban conveniences, making it a wonderful choice for families, professionals, and retirees alike. Discover the charm of Gildersleeve and experience the warmth of a community that truly feels like home.

Newest Listings in Gildersleeve

$500,000

2 Beds ⋅ 3 Baths ⋅ 24192478 MLS ⋅ Bartlett Hill BLDG.

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

$500,000

2 Beds ⋅ 3 Baths ⋅ 24191576 MLS

19 Plumrose Court Unit 19, Portland

$389,000

4 Beds ⋅ 2 Baths ⋅ 24189489 MLS

*** Highest and Best Tomorrow 7.15.26 by Noon*** Welcome to 564 Main St. Portland. This is the one you%27ve been waiting for! Brimming with Charm and Character, a spacious Eat In Kitchen and an Oversized Two Car Garage with electricity for Enthusiasts. This Well Built Quintessential Cape offers 4 bedrooms with a Main floor Primary loacated off the Living room for Privacy, or an In-Law situation, while the half bath is Conveniently located off the kitchen. A Full Dining room gives extra options for space, including a three season sunroom with a heater that stays. Hardwood Flooring throughout including under the brand new carpets. Upstairs you%27ll find three bedrooms and a full bathroom. Other Features include a Newer Furnace, Newer windows, Newer roof on home, Fridge approx. 2Y old, Dishwasher 6Y old, New Shed in 2020, and a clean unfinished basement with Tall ceilings giving an abundance of storage. Natural gas and public utilities complete your worry free living. Set on almost an acre, this Lush Private flat level yard is perfect for Sports, Entertaining Huge Outdoor bashes, or just relaxing in your private Oasis among tall trees including a historic Holly bush. Portland is home to many golf courses, The Ct River for Boating enthusiasts, and Minutes away from Downtown Middletown restaurants and shopping, yet quietly tucked away for the best of both worlds. Come see What this hometown has to offer!

564 Main St, Portland

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