Hilltop Real Estate

Hilltop Real Estate

Welcome to Hilltop, a captivating neighborhood nestled in the heart of New Haven County, Connecticut. Known for its serene landscapes and vibrant community spirit, Hilltop offers a perfect blend of suburban tranquility and urban convenience.

As you stroll through the tree-lined streets, you’ll discover charming homes that reflect a variety of architectural styles, each exuding character and warmth. The neighborhood is characterized by its friendly atmosphere, where neighbors greet one another with smiles and children play freely in the parks. Hilltop is not just a place to live; it’s a community where lasting friendships are formed.

Nature enthusiasts will appreciate the lush green spaces and scenic parks that dot the area. With ample opportunities for outdoor activities, from hiking to picnicking, Hilltop is a haven for families and individuals who enjoy an active lifestyle. The nearby Hilltop Park features walking trails, playgrounds, and sports facilities, making it a perfect spot for weekend gatherings or leisurely afternoons.

Conveniently located, Hilltop provides easy access to major highways and public transportation, connecting residents to the vibrant culture and amenities of New Haven. Explore local shops, cozy cafes, and diverse dining options just a short drive away.

Education is a priority in Hilltop, with highly-rated schools that are dedicated to nurturing young minds and fostering a love for learning.

Whether you’re looking to buy your first home, raise a family, or enjoy your golden years, Hilltop offers a welcoming environment that truly feels like home. Discover the charm of Hilltop, where community and comfort come together seamlessly.

Newest Listings in Hilltop

65 Academy Hill Rd, Derby
$89,000
24215956 MLS
VERY CONVENIENT AREA. BEAUTIFUL VIEWS. CAN BE DIVIDED INTO 2 BUILDING LOTS.

65 Academy Hill Rd, Derby
17 General Wooster Rd, Derby
$598,000
4 Beds ⋅ 4 Baths ⋅ 24210788 MLS
Modern Colonial home located in the Hilltop area of Derby; tailor made for a family of any size. One of Derby's most sought-after locations, wake up each morning to a stunning view from your bedrooms, enjoy lazy afternoons on your deck overlooking the pool. Natural light fills each room during the day and quiet of evenings for a restful night. Hard wood floor throughout the main level, fireplace adorns the living/dining room, granite counter in kitchen with stainless steel appliances. Bonus room above the garage used for game and entertainment. Upstairs is carpeted, it has large master suite, walk-in closet, bathroom with jetted soaking tub to unwind from a long day, two additional bedrooms, and bathroom. Finished lower level with an ensuite for in laws, guest, or young adult children. or just additional finished space. Must see to appreciate.

17 General Wooster Rd, Derby
34 Elm St, Ansonia
$292,000
2 Beds ⋅ 1 Baths ⋅ 24214783 MLS
Make yourself at home in this two-bedroom ranch in Ansonia, offering single-level living, hardwood floors, and a fully fenced backyard on approximately 0.32 acre. The living room and both bedrooms feature hardwood flooring, while the kitchen includes an electric range and refrigerator. An attached one-car garage adds convenience, and the full unfinished basement provides storage and room for future possibilities. Solid house with furnace (2019) and roof (2016) The backyard offers space to garden, relax, or enjoy the outdoors, with a lightly wooded setting. Located across from the historic David Humphreys House, with convenient access to shopping, parks, Routes 8 and 34, and the Merritt Parkway. Bring your ideas and personal touches to make this home your own.

34 Elm St, Ansonia
23 Mountain View Rd, Ansonia
$434,900
4 Beds ⋅ 3 Baths ⋅ 24214939 MLS
Tucked away in a desirable hilltop area, 23 Mountain View Road offers a perfect blend of classic character and thoughtful modern updates. The heart of the home is the beautifully renovated kitchen, featuring granite countertops, newer appliances, and a stylish tiled backsplash. The interior has been freshly painted, and you'll find hardwood flooring running through most of the home. Designed for easy living, the main level includes a bedroom with a sliding glass door that leads directly out to an expansive Trex deck level, fenced yard. The upper level is spacious, featuring a primary bedroom with updated private bath, two additional bedrooms, and a fourth room that serves perfectly as a home office or an extra bedroom. You'll find great closet and storage space throughout every level of the home. Modern efficiency is a standout feature here. A solar panel system provides the benefit of low electric bills, while major upgrades like newer windows, updated electrical, central air and a natural gas heating and hot water system. The lower level provides even more versatile space with a partially finished area and a convenient half bath.The exterior is designed for low maintenance with vinyl siding and new oversized shed for all your storage needs. From the desirable hilltop location, refreshed interior to the functional outdoor spaces, this home is ready for its next chapter. View the floor plans and 3D virtual walkthrough to see everything this property has to offer.

23 Mountain View Rd, Ansonia
7 Glenridge Dr, Ansonia
$435,000
3 Beds ⋅ 2 Baths ⋅ 24213280 MLS
Step inside this move-in-ready raised ranch near the Woodbridge-Ansonia line, where thoughtful updates, flexible living space, and exceptional energy savings come together (SOLAR PANEL LOAN WILL BE PAID OFF BY THE SELLER AT CLOSING), keeping your electricity bill minimal. The bright, open-concept main level welcomes you with a spacious living room and recessed lighting, an attractive beam that creates a natural transition to the sun-filled kitchen and dining area. Down the hall, you'll find a beautifully renovated full bathroom and three comfortable bedrooms, all complemented by stylish new plank flooring throughout the main floor. Sliding glass doors off the kitchen leads to a three-season sunroom, the perfect retreat for taking in the foliage, sipping morning coffee or evening wine, and simply unwinding. The finished, heated and cooled lower level offers additional living space with a walkout to the driveway creating an ideal layout for an in-law suite. The lower level includes a wood-burning fireplace with an electric insert, a dining area with ample cabinetry, a sink, space for your own appliances, a full bathroom, and a generous laundry, storage, and mechanical room. Outside, the fully fenced, level backyard provides both privacy and room to enjoy. With a three-year-old roof, well-maintained mechanicals, and a terrific neighborhood, this standout home offers comfort, flexibility, and peace of mind! Make your move!!

7 Glenridge Dr, Ansonia
26-R Hoinski Way, Ansonia
$499,900
3 Beds ⋅ 3 Baths ⋅ 24212394 MLS
Welcome to this spacious raised ranch located in Ansonia's desirable Hilltop area. Offering a comfortable and functional layout with plenty of space for everyday living and entertaining, this home is ready to welcome its next owners. The main level features soaring ceilings and an open-concept design that seamlessly connects the kitchen, dining area, and living room. Sliding doors open to the deck, creating an ideal spot for outdoor dining, relaxing, or entertaining. This level also offers three bedrooms, including a spacious primary suite with its own private full bathroom. A second full bathroom completes the main level. The lower level provides even more living space with a comfortable family room featuring a walkout to the backyard, along with a third full bathroom and convenient laundry area. The attached two-car garage offers plenty of room for parking and additional storage. With three bedrooms, three full bathrooms, soaring ceilings, and multiple living spaces, this home offers plenty of room to live, relax, and entertain.

26-R Hoinski Way, Ansonia
15 Belleview Ter, Ansonia
$317,700
3 Beds ⋅ 1 Baths ⋅ 24209259 MLS
Welcome home to 15 Belleview Terrace! Perched in a highly desirable hilltop neighborhood in Ansonia, this home has been cherished and meticulously cared for by the same owners for over 20 years. From the moment you arrive, you will feel the warmth and pride of ownership throughout. Step inside to discover beautifully maintained hardwood floors in great shape and an effortless single-level layout built on a solid slab foundation. The kitchen comes equipped with 5-year-old appliances, while major peace of mind comes built-in with a roof that is only 3 years old. The true centerpiece of the property awaits out back: step onto your private patio and take in breathtaking, panoramic views of the Naugatuck Valley. Whether you're sipping morning coffee or unwinding at sunset, this setting is simply unforgettable. Two outdoor storage sheds provide fantastic extra storage and organization. Whether you are looking for your very first home or searching for the perfect low-maintenance space to downsize, this turnkey hilltop treasure is ready to welcome its next chapter. Schedule your private tour today and fall in love with the view!

15 Belleview Ter, Ansonia
23 Alan Dr, Ansonia
$365,000
3 Beds ⋅ 1 Baths ⋅ 24212598 MLS
Welcome to 23 Alan Drive, a move-in-ready ranch set on a quiet hilltop street in Ansonia. Well maintained and thoughtfully cared for, this home offers comfortable one-level living with three bedrooms conveniently located on the main floor. The freshly painted interior features new flooring, vinyl replacement windows, and an inviting open-concept kitchen and living area. The eat-in kitchen is appointed with granite countertops and newer appliances, creating a bright and functional space for everyday living. A window-filled three-season porch provides additional living and entertaining space while overlooking the generously sized backyard. Outside, you'll also find a rear porch, carport, and exterior ramp access. The lower level is accessible by both stairs and an existing chairlift and offers even more versatility, including a finished den with a separate walkout entrance. A large unfinished storage and mechanical area provides abundant storage along with potential for additional finished space in the future. Central air adds to the home's year-round comfort. With its convenient single-level layout, flexible lower-level space, numerous updates, and peaceful neighborhood setting, 23 Alan Drive is ready for its next owner to move right in and make it home.

23 Alan Dr, Ansonia
3 E Court, Unit 3, Derby
$337,000
3 Beds ⋅ 2 Baths ⋅ 24210763 MLS ⋅ Brookside Commons BLDG.
Welcome to this spacious and well appointed two bedroom, two bathroom townhouse featuring a versatile loft that can easily serve as an additional bedroom, home office, or guest space. The home offers a bright and functional layout with generously sized bedrooms and comfortable living spaces throughout. The dining area provides direct access to a walk-out porch, creating a seamless extension of the living space and the perfect spot to relax or enjoy the outdoors. Additional highlights include central air conditioning, two bathrooms, and the added flexibility of the loft. Combining comfort, functionality, and plenty of usable space, this townhome is a wonderful opportunity for anyone looking for a home that can adapt to their lifestyle.

3 E Court, Unit 3, Derby
47 Rockwood Ave, Ansonia
$379,917
3 Beds ⋅ 2 Baths ⋅ 24209648 MLS
This house has personality, privacy, and some surprisingly great features. With 3 bedrooms, 2 full baths, an updated upstairs bathroom, attached garage, plenty of parking, and a fully finished lower-level setup with separate entrance that offers some serious possibilities for the meddling mother-in-law. We're not saying it'll improve family relations...but it can't hurt. Let's just say what happens on the deck... stays on the deck. Your only audience back there is Mother Nature - and she's seen worse. Just enough yard to keep the lawn mower from developing abandonment issues, but not nearly enough to use yard work as your excuse to skip the next family gathering. Sorry! This gem also comes equipped with a laundry chute - because the fewer trips' downstairs to see your not so distant family member the better. We're kidding, of course. Mostly. Are the doors hollow? Yep. Have the windows seen a few decades? Also, yep. At this price, we're calling it character and moving right along. AGENT/OWNER

47 Rockwood Ave, Ansonia
21 7th St, Ansonia
$349,900
3 Beds ⋅ 2 Baths ⋅ 24208916 MLS
Ranch for sale, 3 bedroom 1.5 bath on corner lot. Hardwood floors throughout home with natural gas for heat and hot water, and public water and sewer. The primary bedroom has a half bath and a large double closet. Second bedroom has a cedar closet and additional closet. Basement has high ceilings and I-beam, great for finishing into living space. Come see this great opportunity! Sold AS-IS.

21 7th St, Ansonia
230 Shagbark Dr Unit 230, Derby
$314,900
3 Beds ⋅ 3 Baths ⋅ 24208832 MLS ⋅ Orangewood East Condo (#1-10) BLDG.
Orangewood East Essex style unit, the largest style in the complex, Three full sized bedrooms, the primary bedroom has a private bath and a private balcony to decompress on! This unit has many updates, flooring, windows, HVAC, baths and kitchen with additional cabinets. The living room/dining room combination is over 30 feet long, walk in the front door and follow it to the slider to the private, fenced deck. Construction was done to minimize any sound from side to side and the block walls run from basement to roof line, reducing insurance costs as well. This unit is located minutes from anything, you can even walk to stores, brewery and restaurants. Located close to the highways going North or South is just another convenience. The unit is priced to reflect new flooring need on the second level. Property taxes are in year one of a 5 year phase in.

230 Shagbark Dr Unit 230, Derby
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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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