Hilltop Real Estate

Welcome to Hilltop, a hidden gem nestled in the heart of New Haven County, Connecticut. This charming neighborhood is renowned for its picturesque landscapes, friendly community vibe, and an array of amenities that cater to residents of all ages.

Hilltop is characterized by its rolling hills, lush greenery, and beautifully maintained parks, making it an ideal setting for outdoor enthusiasts. Whether you enjoy hiking, picnicking, or simply taking leisurely strolls, the scenic views and tranquil atmosphere will captivate your heart. Families will appreciate the proximity to top-rated schools, ensuring that children receive an excellent education in a nurturing environment.

The neighborhood boasts a vibrant local culture, with a delightful mix of quaint shops, cozy cafes, and family-owned restaurants that serve up delicious cuisine. Hilltop’s community events, such as farmers' markets and seasonal festivals, foster a strong sense of belonging among residents, creating opportunities to connect with neighbors and make lasting friendships.

Conveniently located, Hilltop offers easy access to major highways and public transportation, making it a breeze to commute to nearby cities for work or leisure. Additionally, the neighborhood is just a short drive away from the bustling downtown area of New Haven, where you can explore a rich tapestry of art, history, and entertainment.

In Hilltop, you’ll find not just a place to live, but a vibrant community that embraces the essence of Connecticut living. Come discover your dream home in this enchanting neighborhood, where every day feels like a retreat!

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

$269,000

2 Beds ⋅ 2 Baths ⋅ 24175480 MLS ⋅ Applewood BLDG.

Welcome to Applewood, a peaceful townhouse community tucked away in the desirable Hilltop area of Ansonia. This well-maintained 2-bedroom, 1.5-bath townhouse offers comfortable living with thoughtful updates and an inviting layout filled with natural light. The main living areas feature newer luxury vinyl plank flooring that adds both style and durability. The eat-in kitchen is designed for everyday convenience with granite countertops, stainless steel appliances including an electric range, hood vent, refrigerator, and dishwasher, plus tile flooring and an opening overlooking the living room for a connected feel. The unit's back door off the kitchen leads to a private patio, perfect for grilling, relaxing, and enjoying the surrounding green space. A convenient half bath completes the main level. Upstairs, the luxury vinyl plank flooring continues to the spacious primary bedroom and to the second bedroom, both with good closet space. The full bathroom features a tub with shower, granite counter vanity and tile floor. There is a convenient laundry closet in the hallway with full-size washer and dryer. Additional storage is available with pull-down attic access. Enjoy assigned parking along with plenty of visitor parking. Applewood is a quiet 32-unit complex known for its peaceful setting and pride of ownership, offering a wonderful place to call home.

24 Winesap Court, Unit 24, 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

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