Hillandale Homes for Sale

Welcome to Hillandale, a picturesque neighborhood nestled in the heart of Trumbull, Connecticut, within the charming Fairfield County. Known for its serene ambiance and friendly community, Hillandale is an ideal place for families, young professionals, and retirees alike. The neighborhood boasts tree-lined streets, well-maintained parks, and a strong sense of community spirit, making it a perfect retreat from the hustle and bustle of city life.

Hillandale is conveniently located near shopping centers, top-rated schools, and recreational facilities, ensuring that residents have everything they need within easy reach. The area is well-connected to major highways and public transportation options, providing easy access to neighboring towns and cities, including Bridgeport and Stamford. Enjoy weekends exploring nearby nature trails, participating in community events, or simply relaxing in one of the local parks that dot the landscape.

For those considering a move to Hillandale, you'll find a diverse selection of homes for sale that cater to various tastes and budgets. From charming single-family homes with spacious yards to modern townhouses with contemporary finishes, there’s something for everyone. Many properties feature beautiful landscaping, ample living space, and proximity to local amenities, making them perfect for raising a family or enjoying a comfortable lifestyle.

Explore the vibrant community of Hillandale, where the warmth of small-town living meets the convenience of urban amenities. Discover your dream home in this inviting neighborhood today, and experience all that Hillandale has to offer!

Newest Hillandale Homes for Sale

$895,000

5 Beds ⋅ 4 Baths ⋅ 24193908 MLS

Located in the Hillandale area of Trumbull. This pristine and updated home sits perfectly on 1.14 acres of a gently rolling lot. With attention to details, every room is sure to put a smile on your face. Recent upgrades include: New on-demand hot water heater, primary bedroom bath and main bath, recently refinished hardwood floors throughout both levels, freshly painted exterior and interior, new kitchen with Quartz Counter tops, new oven and refrigerator. First floor in-law or au-pair apartment with no stairs with access to the main house. An additional bonus is a first floor office! Beautiful and inviting primary bedroom with a fully updated bath with a double vanity and large walk-in shower. Three additional bedrooms with ample closet space. Tastefully finished lower level with 2 additional. rooms. 3 car garage with plenty of storage cabinets and work bench areas. Enjoy the peaceful and tranquil setting in your back yard with a freshly stained deck, large gazebo, and patio overlooking park-like grounds. Public water, sewer and natural gas. See supplement with other notable features.

88 Scenic Hill Rd, Trumbull

$734,900

3 Beds ⋅ 2 Baths ⋅ 24185831 MLS

This immaculately maintained oversized ranch in prime Trumbull location and school district is a must see, whether downsizing to one level living or simply looking for a great open plan house for the growing family! The formal living and dining rooms are separate for privacy and intimate dinner parties. For more casual living you will find the oversized family room attached to the very tastefully remodeled kitchen with granite countertops, Carrara marble backsplash, large pantry and huge dining area. Large doors in the eat in area offer brightness to the home and lead to the enormous deck which spans the length of the house. Outdoor entertaining is made so easy here! The primary bedroom with updated full bath has a slider to the deck for you to enjoy your morning coffee! The other two bedrooms share a remodelled hall bath. The oversized two car garage is attached, with overhead storage, separate heat zone and hot water. There is also a garage door for access to backyard. Enter the home from garage through an oversized mud room with ample space for storage and outdoor wear. There is approx 840sq ft of living area in the basement which is accessed by the open stairway from the main level. It includes a den, laundry room and additional third full bathroom. and plenty of storage.Sliding doors lead to the backyard. There is great potential to update this level to a full time living area. The huge private and parklike backyard has room for a pool and plenty of space to play!

36 Bunker Hill Dr, Trumbull

$1,325,000

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

$850,000

4 Beds ⋅ 3 Baths ⋅ 24186190 MLS

Welcome to 56 Brookside Drive, a classic Colonial tucked away at the end of a cul-de-sac in Trumbull's highly sought after Daniels Farm neighborhood. This beautifully maintained 4-bedroom, 3- bath home offers the perfect blend of timeless charm and modern updates. The main level features a brand new eat in kitchen with a cozy breakfast nook, ideal for everyday living and entertaining. Enjoy a spacious family room and formal living room, each highlighted by a fireplace, along with a dedicated home office providing the perfect work from home space. Hardwood floors throughout have been recently refinished, and the home has been freshly painted inside and out. Upstairs, the large primary suite offers a walk in closet and private bath, while three additional generously sized bedrooms provide plenty of space for family and guests. Step outside to your own backyard retreat featuring a large level yard, in ground pool, and patio area designed for summer entertaining and relaxation. Additional updates include newer mechanicals and a new roof installed in 2025, offering peace of mind for years to come. Conveniently located near top rated schools, parks, shopping, and major commuting routes, this exceptional Daniels Farm Colonial is ready to welcome you home. ***HIGHEST AND BEST OFFERS DUE BY 8PM SUNDAY 6/28***

56 Brookside Dr, Trumbull

$978,000

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

$945,000

6 Beds ⋅ 3 Baths ⋅ 24174306 MLS

Spectacular Colonial for sale in the desirable Daniels Farms community. Featuring 6 bedrooms and 3 full bathrooms. This beautiful home offers spacious living areas, a perfect layout for entertaining, and easy access to major highways for commuters. Daniels Farm is known for its peaceful residential setting, large single- family homes, and excellent location in Fairfield County. Conveniently located near I-95, the Merritt Parkway, restaurants, shopping centers, parks and top-rated schools. Don't miss the opportunity to schedule a showing for this diamond home a perfect combination of space, location and comfort.

890 Daniels Farm Rd, 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

$1,790,000

4 Beds ⋅ 6 Baths ⋅ 24155322 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

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