Hillandale Real Estate

Welcome to Hillandale, a charming neighborhood nestled in the heart of Trumbull, Connecticut, within the picturesque Fairfield County. Known for its serene suburban atmosphere and close-knit community, Hillandale offers a perfect blend of comfort and convenience, making it an ideal place for families, young professionals, and retirees alike.

As you stroll through Hillandale, you'll be greeted by tree-lined streets and beautifully maintained homes, each exuding its own unique character. The neighborhood is renowned for its spacious yards and inviting outdoor spaces, perfect for weekend barbecues or leisurely evenings under the stars. With a variety of architectural styles, from classic colonials to contemporary designs, there's something for everyone to admire.

Hillandale is not just about beautiful homes; it’s also about community. Residents enjoy access to local parks, playgrounds, and recreational facilities that encourage an active lifestyle. The nearby Trumbull Center offers a range of shopping, dining, and entertainment options, ensuring that you have everything you need within reach. Families will appreciate the highly-rated schools in the area, providing quality education and a nurturing environment for children.

Conveniently located near major highways, Hillandale allows for easy commuting to nearby cities such as Bridgeport and Stamford, making it a prime location for those who work in the greater Connecticut area. Whether you’re looking for a peaceful retreat or a vibrant community, Hillandale is a hidden gem that promises to capture your heart. Come discover the warmth and charm of this delightful neighborhood!

Newest Listings in Hillandale

$789,900

4 Beds ⋅ 3 Baths ⋅ 24206168 MLS

Welcome to 31 Jackson Drive, a beautifully renovated, move-in-ready home in highly sought-after Trumbull! With limited inventory in town, opportunities like this don't come around often. This home has been thoughtfully updated from top to bottom, combining modern finishes with comfortable, functional living spaces. Step inside to a bright, inviting interior highlighted by a stunning high-end kitchen designed to be the heart of the home. Brand-new bathrooms feature fresh, modern finishes, while the spacious primary suite creates a private retreat you'll look forward to coming home to. Major improvements including a NEW roof and NEW windows provide additional peace of mind for years to come. The partially finished lower level offers plenty of flexibility for a home office, playroom, gym, media room, or additional recreational space. Outside, you'll find one of the property's standout features - a spacious and exceptionally private yard with room to entertain, relax, play, or simply enjoy your own outdoor escape. An oversized parking area provides plenty of room for multiple vehicles and even dedicated RV parking. Located in one of Fairfield County's most desirable towns, Trumbull is known for its highly rated schools, beautiful neighborhoods, and convenient location. Enjoy easy access to major highways, shopping, restaurants, parks, and everything the area has to offer. 31 Jackson Drive is truly move-in ready all that's left to do is unpack and make it yours!

31 Jackson Dr, Trumbull

$1,749,000

4 Beds ⋅ 6 Baths ⋅ 24202620 MLS

Magnificent 2026 New Construction in Private Porters Hill Enclave. Tucked within one of Trumbull's most desirable new subdivisions, this exquisite 5-bedroom, 5.5-bathroom residence offers the perfect combination of architectural drama and modern comfort. Spanning over 5,170 square feet of meticulously crafted living space, the home greets you with a grand covered front porch and a soaring two-story foyer that sets the tone for the impeccable finishes within. Wide-plank hardwood flooring flows seamlessly through the sun-drenched family room, formal dining area, and expansive eat-in kitchen. The chef's kitchen is a true centerpiece, anchored by an oversized quartz island, custom inset cabinetry, and a generous walk-in pantry. Large windows flood the main level with natural light, while a versatile first-floor office/guest suite, custom mudroom, and powder room add thoughtful functionality for a modern lifestyle. The Primary Bedroom Suite is a private sanctuary, featuring dual walk-in closets and a spa-like bath with a soaking tub, walk-in shower, and elegant dual vanities. Three additional generously sized bedrooms and a convenient laundry room complete the upper level. The walk-out lower level is a standout feature, fully finished with high ceilings, a full bathroom, and massive open space for a media room or home gym.

110 Porters Hill Rd, Trumbull

$859,900

4 Beds ⋅ 4 Baths ⋅ 24163140 MLS

Step into a piece of Trumbull's history with this enchanting, updated Craftsman Cape loc in the highly sought-after Daniels Farm section, close to top-rated schools, parks, shopping, restaurants, & major highways. Originally built by Col. William C. Weeks when Daniels Farm Rd was a rural farm district, this unique home, known as "Kobble Cot," blends historic charm w/ modern comfort & has long been a place where generations gathered & created lasting memories. From the moment you arrive, you'll feel the warmth-relax on the expansive stone front porch, perfect for morning coffee or evening gatherings, then enter through double doors into a grand Great Room featuring exposed beams & a striking stone FP. The formal DR w/ built-in glass shelving flows seamlessly into the living space & opens via French doors to a bright Sunroom overlooking the in-ground pool & patio. The updated Kitchen offers SS appliances, center island, & access to a spacious deck overlooking the landscaped yard. The main level includes a BR, Den, & full Bath, ideal for guests or home office. Upstairs features a Primary Suite w/remodeled bath, 2 add'l BRs, & updated bath w/wood slider door, along w/ charming cottage windows & cedar closet. The fin LL includes a game rm, laundry, 1/2 bath, & walk-out to pool area. The property, once filled w/apple trees where children played and made memories, now offers a spacious yard, in-ground pool, large patio, built-in BBQ, & 2 sheds. Circular drive provides ample parking.

1209 Daniels Farm Rd, Trumbull

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Hillandale Real Estate

Newest Listings in Hillandale

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