Hilltop Real Estate

Welcome to Hilltop, a charming and vibrant neighborhood nestled in the heart of New Haven County, Connecticut. Known for its picturesque landscapes and a strong sense of community, Hilltop offers an ideal blend of suburban tranquility and urban convenience.

As you stroll through the tree-lined streets, you’ll discover a variety of beautifully maintained homes, each with its own unique character. The neighborhood is renowned for its friendly atmosphere, making it a perfect place for families, young professionals, and retirees alike. With a mix of historic architecture and modern residences, Hilltop caters to diverse tastes and lifestyles.

One of the standout features of Hilltop is its commitment to green spaces. Residents enjoy easy access to several parks, where children can play, and families can gather for picnics or leisurely walks. The nearby Hilltop Park is a local favorite, offering playgrounds, sports facilities, and scenic trails for outdoor enthusiasts.

Culinary delights await you just a stone’s throw away, with a variety of local eateries and cafes that showcase the rich flavors of the region. From cozy coffee shops to family-owned restaurants, Hilltop has something for every palate.

Conveniently located, Hilltop is just a short drive from downtown New Haven, where you can explore cultural attractions, shopping, and entertainment options. Excellent schools and a strong sense of community spirit make this neighborhood a wonderful place to call home.

Discover the charm and warmth of Hilltop, where community and comfort come together in perfect harmony. Whether you’re looking to buy or rent, you’ll find that Hilltop is not just a place to live, but a place to thrive.

Newest Listings in Hilltop

$535,000

4 Beds ⋅ 3 Baths ⋅ 24192653 MLS

Welcome to 1 Rev Taylor Drive, a beautifully maintained home nestled on a quiet cul de sac in Ansonia's desirable Hilltop neighborhood. This home offers the perfect combination of comfort, functionality, and outdoor living. Step outside to a level, fully fenced backyard designed for entertaining and everyday enjoyment. Relax on the spacious Trex deck while taking in the scenic views, stay cool under the electric awning on warm summer days. Electric installed for easy install of future pool and hot tub if desired. Inside, you'll find 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout. The updated kitchen features modern appliances (2024) and opens to the dining area, both accented by hardwood flooring, making it an ideal space for cooking and entertaining. The main level also includes a primary suite with a private full bath, two additional bedrooms, and another full bathroom. The lower level offers a warm and inviting family room with a fireplace, perfect for cozy winter evenings. You'll also find a half bath with a laundry area and a fourth bedroom that provides excellent flexibility as a guest room, home office, or workout space. Conveniently located near shopping, restaurants, parks, and major commuter routes, this move-in-ready home offers everything you need in one of Ansonia's most sought-after neighborhoods.

1 Rev Taylor Dr, Ansonia

$599,000

6 Beds ⋅ 2 Baths ⋅ 24192791 MLS

EXCELLENT HILLTOP LOCATION. BUILT IN 2010 TWO STORY WITH SAME UPSTAIRS/DOWNSTAIRS LAYOUT OF 3 BEDROOMS, FULL BATH & KITCHEN ON EACH FLOOR. NINE FOOT CEILINGS THROUGHOUT. HUGE BASEMENT. SHED IN BACK FOR TRACTORS, ETC. BEAUTIFUL PROPERTY IN A CONVENIENT LOCATION AVAILABLE IMMEDIATELY. EXECUTOR SALE-NO DISCLOSURES. POSSIBLE SIDE LAND PROPERTY PURCHASE.

63 Academy Hill Rd, Derby

$349,900

3 Beds ⋅ 1 Baths ⋅ 24192168 MLS

Welcome to 31 Webster Drive, a lovingly maintained home filled with decades of cherished memories and ready for its next chapter. Nestled in Ansonia's desirable Hilltop neighborhood, this beautifully remodeled 3-bedrooms, 1-bath Raised Ranch offers the perfect blend of comfort, style, and convenience. Step inside to discover a bright, sun-filled open-concept floor plan featuring gleaming hardwood floors throughout. The custom kitchen boasts newer cabinetry, granite countertops, and flows seamlessly into the dining area, where a slider leads to a deck overlooking the peaceful backyard, perfect for relaxing or entertaining. Down the hall, you'll find a refreshed tiled full bathroom, linen closet, and three generously sized bedrooms. The lower level features a finished room ideal for a home office, guest room, playroom, or potential fourth bedroom. The bright walk-out basement offers abundant storage and endless possibilities for future finished living space. Recent improvements include newer windows, central air conditioning, newer hot water heater, updated 5-panel interior doors and hardware, newer deck slider, and fresh interior paint. City water and sewer, this move-in-ready home is conveniently located near shopping, restaurants, and major commuting routes including Routes 8, 15, 34, and I-95, with easy access to Downtown New Haven. Don't miss your chance to make this home your own. Schedule a showing today! Estate Sale Proper

31 Webster Dr, Ansonia

$349,000

3 Beds ⋅ 1 Baths ⋅ 24191386 MLS

HIGHEST & BEST DUE 7/23, 3PM! Welcome to this well-maintained 3-bedroom ranch offering an efficient floor plan designed for comfortable living. The inviting living room features a bay window that fills the space with natural light and flows seamlessly into the dining area and kitchen, creating a functional layout for both daily life and entertaining. The kitchen is well-equipped with granite countertops, an abundance of cabinetry, a gas range, built-in microwave, and newer refrigerator. Just beyond the kitchen is a convenient mudroom with a utility closet, providing additional storage and easy access to the backyard. A 3-season sunroom extends the living space and features sliding doors leading to a generous patio overlooking the private backyard, an ideal setting for outdoor dining, grilling, or simply relaxing. The home offers 3 bedrooms, including a comfortable primary bedroom. The recently updated full bathroom features luxury vinyl plank flooring, a new vanity with a quartz countertop, and a new bathtub with a glass shower enclosure. An oversized one-car detached garage provides excellent storage and workspace options. Situated in Ansonia's desirable Hilltop neighborhood, this home offers convenient access to shopping, restaurants, parks, and recreation. Nearby Frank P. Witek Memorial Park and the Ansonia Nature & Recreation Center provide scenic walking trails around the Ansonia Reservoir, making it easy to enjoy the outdoors while remaining close to everyday convenie

3 Fairview St, Ansonia

$475,000

4 Beds ⋅ 3 Baths ⋅ 24189850 MLS

Located in the highly desirable Hilltop area of Ansonia, this spacious home offers the perfect combination of comfort, convenience, and versatility. Enjoy an unbeatable location just minutes from shopping, restaurants, schools, Griffin Hospital, major highways, and local parks. The sun-filled main level features a large living room and dining area with French doors that open to a deck overlooking a private, fully fenced backyard-ideal for entertaining or relaxing. The main floor also offers generously sized bedrooms, including a spacious primary suite with a full bath, along with a second full bathroom. The finished lower level provides exceptional additional living space, featuring a large family room, an additional bedroom, a third full bathroom, and a laundry area. With its flexible layout, this level offers excellent in-law potential or space for extended family, guests, a home office, or recreation. A wonderful opportunity to own a well-located home in one of Ansonia's most sought-after neighborhoods.

9 Benz St, Ansonia

$394,900

2 Beds ⋅ 1 Baths ⋅ 24188960 MLS

Welcome to 105 Sunset Drive! This lovely, updated ranch is set on a level, fully fenced lot-offering the perfect blend of privacy and outdoor relaxation. Inside, you'll find a versatile 2-to-3 bedroom layout, a welcoming living room, and a beautifully updated galley kitchen. Downstairs, the partially finished basement is bright, well-lit, and ready to become your ideal recreation room, home office, or gym. Come view 105 Sunset Drive today and see why this should be your next home!

105 Sunset Dr, Derby

$549,900

4 Beds ⋅ 3 Baths ⋅ 24187897 MLS

Perched on Ansonia's quiet hilltop, this spacious colonial offers a rare combination of size, location, and property. The 1.18 acre setting alone sets it apart - complete with a level backyard, freshly painted deck, above-ground pool, and a shed. Inside, the home balances open flow with an intentional space for everything. The kitchen anchors the main level, with granite countertops, stainless appliances, plenty of cabinetry, and a connected dining area that easily fits everyone for gatherings. Just beyond, a vaulted living room and a light-filled sunroom with skylights (and a sunken hot tub!) create a year-round destination for entertaining. A laundry closet, powder room, formal dining space, and a flexible office or den conveniently round out the main level. Upstairs, a spacious primary en-suite is completed with a double sink vanity, walk-in closet, and second closet space. A second full bath serves the three spacious additional bedrooms. Notable upgrades include a hot water heater (2024) and roof (Dec 2025), offering value and peace of mind. Additional features include natural gas heat, central air, central vacuum, and energy-efficient solar panels. Set in a location that connects you to the best of the area, with easy access to Woodbridge's Massaro Community Farm, the Ansonia Nature Center, local vineyards, nearby golf, shopping, and commuter routes including Route 8 and the Merritt Parkway. Professional photos coming 7/2

91 Ford St, Ansonia

$325,000

3 Beds ⋅ 2 Baths ⋅ 24185810 MLS

61 Mount Pleasant Street, Derby, Connecticut 06418 - Rare opportunity to own a legal two-family home with incredible flexibility for homeowners and investors alike. The main unit spans two levels and offers 2 bedrooms and 1 full bath, while the lower-level unit features 1 bedroom, 1 full bath, and a full kitchen perfect for rental income, multi-generational living, or house hacking. Both units enjoy private decks overlooking the property, providing separate outdoor spaces to relax and unwind. Live in one unit and rent the other, accommodate extended family, or utilize the entire property as a single-family residence. With multiple living options and income-producing potential, this versatile property is a must-see.

61 Mount Pleasant St, Derby

$375,000

3 Beds ⋅ 2 Baths ⋅ 24179674 MLS

WOW PRICED REDUCED TO SALE! WELCOME TO 16 HOLBROOK COURT! 3 BEDROOM THAT CAN BE USED AS 4, OR 5 if family desires. Versatility for an office and/or dining room. Enjoy 1.5 BATHS, above ground pool, fenced back yard great for small ones or pets' safety! Offers 2 parking spaces at minimum, shed and privacy in small Cul De Sac. ONLY 3 HOMES ON THE BLOCK. HARDWOOD FLOORS, NEWER ROOF less than 7YRS OLD, and porch recently updated. Motivated seller, thank you for viewing!

16 Holbrook Ct, Ansonia

$369,900

3 Beds ⋅ 1 Baths ⋅ 24178462 MLS

Welcome to 242 Marshall Lane! This charming 3-bedroom, 1-bath home offers a spacious living room and great potential for additional finished space in the basement. Situated on a .24-acre lot, the property features a 1-car garage, a private rear deck, and the convenience of public water and public sewer. Additional highlights include a newer furnace and electric hot water heater. Located in a desirable hilltop area close to shopping, restaurants, parks, and major highways, this home is a wonderful opportunity with room to make it your own. Make your appointment today!

242 Marshall Ln, Derby

$629,900

4 Beds ⋅ 4 Baths ⋅ 24176048 MLS

Meticulously maintained and spacious Raised Ranch on a quiet cul de sac with a main level in-law featuring its own bedroom, living room, eat-in-kitchen and full bathroom-perfect for extended family, guests or multigenerational living offering access to a sunny deck. The main living area boasts a huge open-concept layout with an expansive kitchen flowing seamlessly into the dining room and living room, creating the ideal space for entertaining and everyday living. The primary bedroom suite features a full private bath and walk-in closet, offering comfort and convenience. Additional highlights include central air conditioning, a 2-car garage, enormous storage space, a shed and a fully fenced-in yard perfect for pets, play, and outdoor gatherings. Enjoy peaceful living in a prime cul-de-sac location while being close to shopping, dining, and commuter routes. Flagpole does not stay."subject to seller obtaining suitable housing. They already have an accepted offer in on a property that they love. "

2 Gracie Ln, Ansonia

$59,000

24172522 MLS

Excellent cafe business opportunity in Ansonia, CT, ideal for an owner-operator, entrepreneur, or family-run business looking to step into an existing food service concept. This cafe provides a welcoming local atmosphere with strong potential to grow through breakfast, lunch, specialty coffee, desserts, catering, delivery, online ordering, and community-focused events. Don't wait and make you showing request.

52 Platt St, Ansonia

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