Hillandale Real Estate

Welcome to Hillandale, a hidden gem nestled in the charming town of Trumbull, Connecticut. This picturesque neighborhood, surrounded by lush greenery and serene landscapes, offers a perfect blend of suburban tranquility and modern convenience. Hillandale is known for its friendly community atmosphere, making it an ideal place for families, young professionals, and retirees alike.

One of the standout features of Hillandale is its beautiful tree-lined streets, where residents enjoy leisurely strolls and friendly chats with neighbors. The area is home to a variety of well-maintained parks, including the nearby Twin Brooks Park, which boasts walking trails, playgrounds, and picnic areas, perfect for weekend family outings or afternoon relaxation.

For those who appreciate a vibrant community spirit, Hillandale hosts various local events throughout the year, fostering connections among residents. The neighborhood is also conveniently located near top-rated schools, making it an attractive choice for families looking to provide their children with an excellent education.

Shopping and dining options are just a short drive away, with the Trumbull Mall and numerous local eateries offering a delightful array of choices. Commuters will appreciate Hillandale’s accessibility to major highways, providing a smooth commute to nearby cities and job hubs.

In Hillandale, you’ll find not just a home, but a community where you can create lasting memories. With its perfect blend of nature, convenience, and camaraderie, Hillandale is truly a wonderful place to call home in the heart of Fairfield County. Come and discover the charm of this delightful neighborhood today!

Newest Listings in Hillandale

$799,900

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

$649,900

2 Beds ⋅ 3 Baths ⋅ 24188589 MLS ⋅ Bridle Trail BLDG.

Welcome to this charming detached single-family home situated on a corner lot. This move-in-ready home features an updated kitchen with modern finishes and updated bathrooms, offering both style and functionality. The flexible floor plan offers two spacious bedrooms, with the potential for a third bedroom, home office, or guest room to suit your needs. The property offers comfort, inviting living spaces and easy access to schools, shopping and commuter routes. Whether you're a first-time home buyer, looking to downsize or seeking extra flexibility, this home is a wonderful opportunity you won't want to miss!

4 Bridle Trl Unit 4, Trumbull

$1,275,000

5 Beds ⋅ 5 Baths ⋅ 24178123 MLS

Welcome to 141 Putting Green Rd in the sought after Hillandale / Daniels Farm neighborhood. Steeped in local history and built directly on the rolling fairways of the historic former Hillandale Country Club, this striking, move-in-ready Georgian-inspired Colonial is the pinnacle of modern luxury. Boasting 2.22 Private acres, a freshly painted exterior, a brand-new driveway, and new garage doors, this estate commands an elite presence on a quiet cul-de-sac in Trumbull's premier Daniels Farm district, celebrated for its award-winning schools. Spanning four spectacular levels of pristine living space, the interior greets you with soaring 9+ ft. ceilings, sophisticated custom moldings, and a sun-drenched, airy layout. At the heart of the home is a magnificently renovated new kitchen, meticulously redesigned with a center island, an expansive peninsula for prep work and bar seating, a bright breakfast nook, and seamless access to your private outdoor oasis. The main level transitions into a generously sized great room anchored by a dramatic floor-to-ceiling stone fireplace, built-in bookshelves, a dedicated wet bar, and elegant French doors leading to a tranquil sunroom. Upstairs, the masterfully updated hall bathrooms and a luxurious Primary Bedroom Suite offer the ultimate escape. The Primary Suite features a cozy two-sided fireplace, an intimate sitting area, and a completely updated, spa-like primary bath with soaking tub. Four additional spacious bedrooms complete this level.

141 Putting Green Rd, Trumbull

$948,000

4 Beds ⋅ 4 Baths ⋅ 24175370 MLS

Situated on Cranbury Drive in the highly sought-after Hillandale area of Trumbull. This sprawling residence offers approximately 5,176 sq ft of living space on two main levels and rests on a peaceful and private 2.38-acre lot. Blending scale, flexibility, and opportunity, this home features 4+ over sized bedrooms including two primary suites each with its own private en-suite bath, providing ideal separation for multi-generational living or guest privacy. In total, the residence includes 4+ bathrooms. A standout feature is the lower-level accessory apartment with a walk-out and private entrance, ideal for an in-law suite, au pair quarters, or extended guest accommodations. The home offers generous room sizes and a versatile layout suited to a wide range of lifestyles. The expansive, level rear yard provides a rare opportunity for outdoor enjoyment, entertaining, recreation, barbecues, and gatherings in a serene and private natural setting surrounded by mature landscaping. Many new improvements that also include a brand new septic tank (May 2026). Come experience why Trumbull is celebrated for its award-winning school system and why Realtor.com recently highlighted Trumbull, CT, as a top-tier housing market, ranking it on their "Hottest ZIP Codes" list due to high demand, a "family-focused" appeal, and strong commuter access. *Home is being sold as-is.

89 Cranbury Dr, Trumbull

$995,000

5 Beds ⋅ 4 Baths ⋅ 24165397 MLS

Welcome to this multi-generational dream home featuring a private in-law suite with separate entrance, set on a peaceful 0.85-acre lot in one of Trumbull's most desirable neighborhoods. This exceptional ranch-style residence offers approximately 4,016 sq ft of versatile living space. The main level includes 4 bedrooms and 2 full bathrooms, a beautifully designed kitchen, and an inviting family room with brick fireplace and built-ins creating a warm gathering space. The walk-out lower-level in-law suite offers its own kitchen, 1 bedroom, 1 full and 1 half bathroom, private entrance, and patio overlooking the backyard-ideal for extended family or guests. Outdoor amenities create a true backyard retreat featuring lush landscaping, a tranquil koi pond, babbling brook, outdoor kitchen, stone fire pit, and an above-ground pool with surrounding deck. An outdoor theater setup provides entertainment day or night. Seasonal gardens showcase peonies, azaleas, tulips, daffodils, hydrangeas, lilacs, hyacinths, spiderwort, orange day lilies, Asian bleeding hearts, and a striking flaming pink Love Tree in the front yard. Energy-efficient upgrades include new solar panels, Tesla battery backup, and EV charger for off-grid capability. Designed for relaxation and entertaining, this unique property blends comfort, flexibility, and resort-style living. Seller relocating-priced to sell quickly.

57 Gray Rock 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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