Hillandale Homes for Sale

Hillandale Homes for Sale

Welcome to Hillandale, a delightful neighborhood nestled in the heart of Trumbull, Connecticut, within the picturesque Fairfield County. This charming community is known for its serene environment and family-friendly atmosphere, making it an ideal place to call home. With tree-lined streets, well-maintained parks, and a strong sense of community, Hillandale offers residents a perfect blend of suburban tranquility and convenient access to urban amenities.

One of the highlights of living in Hillandale is its proximity to excellent schools, shopping centers, and recreational facilities. Families will appreciate the top-rated Trumbull school district, which provides quality education and a variety of extracurricular activities for children of all ages. For those who enjoy outdoor activities, the nearby parks and trails offer ample opportunities for hiking, biking, and picnicking, ensuring that residents can enjoy the natural beauty of Connecticut year-round.

As for homes for sale in Hillandale, you’ll find a diverse array of charming properties that cater to different lifestyles and budgets. From cozy single-family homes with spacious yards to modern townhouses with contemporary finishes, there’s something for everyone in this inviting neighborhood. Many homes boast updated kitchens, open floor plans, and beautiful outdoor spaces perfect for entertaining or relaxing.

Whether you’re a first-time homebuyer, looking to upgrade, or seeking a peaceful retirement haven, Hillandale presents an appealing option. Explore the homes for sale in this wonderful neighborhood and discover the perfect place to start your next chapter!

Newest Hillandale Homes for Sale

31 Jackson Dr, Trumbull
$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
110 Porters Hill Rd, 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
1209 Daniels Farm 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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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.

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