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

$619,000

5 Beds ⋅ 4 Baths ⋅ 24204727 MLS

This beautiful home in the Hilltop section of Ansonia features a large In-law apartment setup that is very private from the main house. Main house consists of single story living. In-law apartment is completely separate from main house and above garages. Hardwood floors, Granite counter tops, Stainless steel appliances, Hot Tub, recently painted.

32 Benz St, Ansonia

$499,000

3 Beds ⋅ 2 Baths ⋅ 24203221 MLS

Welcome to 14 Farrel Dr Raised ranch in high desirable hilltop location. Featuring 7 rooms, 3/4 bedrooms, 2 full baths, 2 car garage, possible In-Law. Ideal for multigenerational living in a quiet residential neighborhood close to schools, restaurants, parks, shopping and major commuter routes.

14 Farrel Dr, Ansonia

$429,900

3 Beds ⋅ 2 Baths ⋅ 24193595 MLS

Not your average ranch! 12 Crestwood Road offers over 2,000 square feet of living space including a finished walk-out lower level all sited on a quiet street in desirable Hilltop. The bright main level features easy maintenance laminate flooring throughout the living room, large dining room, and eat in kitchen along with an expanded Primary bedroom with a private full bath. The finished lower level includes a large family room, laundry room with utility sink and a versatile bonus room ideal as a home office or guest room! Step outside to a backyard designed for entertaining or relaxing complete with a level deck, above-ground pool and a lower patio. Additional highlights include newer central air, gas heat, a 2 car garage and a 14 year old roof. A tremendous vale with space, comfort and flexibility~schedule your private showing today!

12 Crestwood Rd, Ansonia

$275,000

2 Beds ⋅ 2 Baths ⋅ 24203249 MLS ⋅ Applewood BLDG.

Welcome to 29 Winesap Court! This beautifully updated Ansonia townhouse offers an inviting open-concept kitchen, living area, perfect for everyday living and entertaining. The kitchen features stainless steel appliances while new flooring an an updated bathroom add to the home's move-in-ready appeal. A convenient half bath is located on the main level. Upstairs, you'll find two spacious bedrooms, including a primary bedroom with a walk-in closet and a second bedroom with an exceptionally large closet. The laundry is conveniently located on the bedroom level, and a pull-down attic provides additional storage. Assigned parking spaces are located directly outside the unit's front door for added convenience. With its open layout, thoughtful updates, abundant storage, and convenient features, 29 Winesap Court is ready to welcome you home!

29 Winesap Court, Unit 29, Ansonia

$374,900

3 Beds ⋅ 2 Baths ⋅ 24201780 MLS

Welcome to easy, comfortable living in Ansonia's desirable Hilltop neighborhood! This freshly painted bright and airy three-bedroom, two-bathroom ranch blends classic charm with the everyday features today's buyers are looking for. Beautiful hardwood floors, a spacious living room, and a convenient walk-in pantry create a warm, functional layout, while the sun porch adds a versatile space to enjoy your morning coffee, unwind, or take in the views of the backyard. Step outside and discover your own private retreat, complete with chain-link fencing, a shed, and mature garden spaces and areas ready for your green thumb. The one-car garage adds everyday convenience, while the expansive unfinished basement offers tons of potential for a home gym, office, recreation space or future finished living area. A full bathroom is already in place downstairs along with laundry and a workshop making this lower level even more versatile. Light, bright, and full of opportunity, this home is ready for its next owners to bring their vision and make it their own. A great combination of location, space, privacy, and potential-come see why this Hilltop ranch is one you won't want to miss! Close to shopping, parks, the Ansonia Nature Center and so much more.

34 Mountain View Rd, Ansonia

$385,000

3 Beds ⋅ 2 Baths ⋅ 24202132 MLS

Welcome to this spacious 3-bedroom, 1.5-bath raised ranch situated on a level corner lot in a desirable residential neighborhood. Offering a solid foundation for your vision, this home is ready for updates and improvements to make it truly your own. The main living area features beautiful hardwood floors and a comfortable layout filled with natural light. The eat-in kitchen overlooks the level backyard and is equipped with newer stainless steel appliances. Three bedrooms and a full bath complete the main level. The finished lower level provides valuable additional living space with a family room, plus a convenient half bath and plenty of storage. A spacious two-car garage adds even more storage. Enjoy the convenience of a residential setting close to shopping, dining, Routes 34 and the Merritt Parkway, while still offering a generous yard and room to enjoy the outdoors. With its desirable location, this home is an excellent opportunity to add your personal touches and create a home that fits your lifestyle. *City sewer possibly available. Contact the town of Derby for verification.

34 Belleview Dr, Derby

$289,900

2 Beds ⋅ 2 Baths ⋅ 24200870 MLS ⋅ Orangewood East Condo (#1-10) BLDG.

Welcome home to this turn-key, move-in ready 2-bedroom, 1.5-bath condo offering comfortable, low-maintenance living. As a prime end unit, this home is flooded with abundant natural light from extra windows, creating a warm and welcoming atmosphere from the moment you step inside. Featuring a spacious, well-thought-out layout, updated finishes, and generous living space, there is nothing left to do but unpack! Enjoy quiet outdoor relaxation on the private porch, beautifully screened by mature greenery, or grilling on the patio, all located off of the kitchen area.

138 Shagbark Dr Unit 138, Derby

$349,000

3 Beds ⋅ 1 Baths ⋅ 24197952 MLS

Welcome to 18 Harris Road, a charming ranch nestled in the highly desirable Hilltop area.This well-maintained home offers the ease of one-level living with 3 comfortable bedrooms and 1 full bathroom. Step inside to a bright, open-concept layout featuring a spacious living room that flows seamlessly into the dining area and kitchen, creating the perfect space for everyday living and entertaining while the functional floor plan provides both comfort and convenience. Large basement area with plenty of storage and walk out to driveway. Outside, you'll find a great backyard offering endless possibilities for outdoor entertaining, gardening, play, or simply relaxing. Conveniently located close to shopping, restaurants, parks, schools, and major commuter routes, this home combines a sought-after neighborhood with everyday convenience. Highest & Best by Thursday Aug 20th @ 10:00am

18 Harris Rd, Ansonia

$589,900

3 Beds ⋅ 3 Baths ⋅ 24196764 MLS

Classic New England Colonial with exceptional space and functionality for growing and multigenerational families! Ideally situated in the desirable Hilltop neighborhood, this home offers comfort, versatility, and room to grow. Step inside the sunny formal foyer with 11+ foot ceilings and immediately appreciate the home's open and inviting layout. The main level features a spacious formal living room and formal dining room, providing ideal spaces for entertaining and hosting holiday gatherings. The comfortable family room with a fireplace serves as the heart of the home, perfect for relaxing with family and friends. The spacious eat-in kitchen offers plenty of room for everyday dining and cooking and features sliders leading to a large rear deck overlooking the level backyard. Off the kitchen, you'll find a convenient half bath, a laundry room, and access to a large bonus room above the garage, offering endless possibilities. Upstairs, you'll find three spacious bedrooms, including a private primary suite with vaulted ceilings, a walk-in closet, and a full bath with a tub. A second full bath with a tub serves the two additional bedrooms. The walk-out basement, complete with full-size windows, provides abundant storage and incredible potential for future finished living space. Conveniently located close to shopping, gyms, restaurants, and major interstates, this home offers plenty of room to grow and comfortable living in a highly desirable location.

29 Commodore Hull Dr, Derby

$300,000

3 Beds ⋅ 1 Baths ⋅ 24195469 MLS

H & B offers due now. Ask a broker re:updates, disclosures, solar info. As sweet as can be! Tidy, well-kept by 1 family! Cheerful spacious eat-in kit bathed in morning sun. Powerful fan on curry night! New appliances. Breezy ceiling fan. 1st flr W/D. Tall, dry LL: Big game TV night cheer zone, rainy day trike track, art studio, study nook, card & boarhobbies. Good hdwd floors. Patio views leafy, tranquil yard. Very well maintained. Many recent upgrades: furnace, water heater, appliances, windows, more. Lovely neighbors! Quiet low traffic lane. Visit Eastside Greenhouse. Smell the roses.Drop into town. Graze/sip your way around. Many great spots! Target for your Starbucks fix. Conv shopping. Hike. bike through the Naug State Forest. Drop a line at Quinnillan Reservoir. Explore intriguing Nature Center. Rover votes Chatfield State Park! He can really romp. Skate at Picketts Pond. Just over the way is Roselands world-class pizza. Summer days boating on the Housatonic. Savor vino in Euro-style tasting rooms at Savino Vneyard. Folks here have a great community spirit. Catch a train to NYC - connect to San Fran if u want. New Haven's embarrassment of cultural riches just down the hill: The Symphony, fine theaters, concerts, an eclectic live music scene, the whole world of international dining, intercollegiate sports, events. Crystal clearocean beach just 15 min. Harvest fairs right now, apple picking soon! Don't miss out! Don't miss out.

38 Elaine Dr, Ansonia

$525,000

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

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