Long Hill Real Estate

Welcome to Long Hill, a hidden gem nestled in the heart of Connecticut! This charming neighborhood offers a delightful blend of suburban tranquility and vibrant community spirit, making it an ideal place for families, young professionals, and retirees alike.

Long Hill is known for its picturesque landscapes, featuring tree-lined streets and well-maintained parks that invite residents to enjoy the great outdoors. The area boasts a variety of recreational facilities, including sports fields, walking trails, and playgrounds, ensuring that there's always something to do for everyone. The local community is tight-knit, hosting seasonal events and gatherings that foster a sense of belonging among neighbors.

One of the highlights of Long Hill is its accessibility. Conveniently located near major highways, commuting to nearby cities like Stamford and Bridgeport is a breeze. Residents appreciate the balance of suburban living with the convenience of urban amenities just a short drive away. The neighborhood is served by excellent schools, making it a top choice for families seeking quality education for their children.

Culinary enthusiasts will love the diverse dining options available, from cozy cafes to family-owned restaurants offering delicious local fare. Additionally, shopping enthusiasts can explore nearby boutiques and shopping centers, providing a variety of retail experiences right at their fingertips.

In Long Hill, you’ll find not just a place to live, but a vibrant community to call home. With its charming atmosphere, friendly neighbors, and convenient location, it’s no wonder that Long Hill is one of Connecticut’s most sought-after neighborhoods. Come and discover the warmth and charm of Long Hill today!

Newest Listings in Long Hill

$875,000

5 Beds ⋅ 4 Baths ⋅ 24205381 MLS

Perched above the street on a private, landscaped lot, this exceptional custom ranch offers an impressive blend of space, comfort, and resort-style living. Extensive improvements throughout include new hardwood floors, a redesigned kitchen, renovated bathrooms, new lighting, and fresh interior and exterior paint. With over 4,100 sq ft of living space plus a partially finished lower level, the semi open-concept floor plan seamlessly connects the living, dining, and kitchen areas. Vaulted ceilings and skylights fill the home with natural light, creating an inviting setting for both everyday living and entertaining. The showpiece is a private, heated indoor pool housed in an impressive two-story, approximately 900 sq ft cedar room with a diving board and direct access to the patio and backyard. Five spacious bedrooms and 3.5 baths include a private primary suite with an en-suite bath and jetted tub. Additional highlights include a dedicated home gym, 4-car underground garage, solar panels, manicured landscaping, and updated pool equipment. With the major work already completed, this is a rare opportunity to enjoy a turnkey home with exceptional amenities and space for the whole family.

223 Sterling Rd, Trumbull

$609,999

3 Beds ⋅ 2 Baths ⋅ 24205430 MLS

Nestled on a quiet corner lot, this adorable Cape has been lovingly cared for by the same family for nearly 36 years. Filled with charm and character, the light and bright interior features hardwood floors, built-ins, and a versatile layout with plenty of space for today's lifestyle. The main level boasts a spacious living room with a cozy wood-burning fireplace, open to a flexible room perfect for a playroom / home office. An additional room can serve as a den, family room, or potential 4th bedroom. The inviting dining room is ideal for hosting and offers a walkout to the back deck. The large eat-in kitchen is perfect for cooking and entertaining, featuring granite countertops, stainless steel appliances, and plenty of workspace. Upstairs are 3 generously sized bedrooms, while a partially finished "walk in" attic provides excellent storage and the potential for an additional office, playroom, or hobby space. The partially finished lower level offers even more flexibility along with additional storage. Enjoy your morning coffee on the back deck overlooking the beautiful professionally landscaped yard, filled with colorful annuals and established perennials. A detached one-car garage adds convenience and storage. Located in a desirable neighborhood close to stores, shops, Trumbull Center, parks, and major highways, this charming home offers a wonderful combination of character, space, privacy, and convenience. A special home for its next chapter! *See agent remarks*

32 Crown St, Trumbull

$499,900

3 Beds ⋅ 1 Baths ⋅ 24205095 MLS

Completely reimagined, this 1920 charmer pairs century-old character with a brand-new 2026 renovation. A welcoming covered front porch opens to a sun-drenched living space with wide-plank waterproof laminate wood flooring, recessed lighting, sleek black triple-pane windows, and a stone-accented fireplace. The showstopper kitchen features custom sage green cabinetry with brushed gold hardware and glass-front uppers, quartz counters, gas cooktop with stainless hood, wall oven, built-in microwave, dishwasher, and a Samsung smart refrigerator - plus an oversized picture window frame above the sink. The spa-inspired full bath is wrapped in marble tile with a frameless glass shower. Three bedrooms include a main-level primary and two upstairs with charming angled ceilings; upper-level laundry adds convenience. Outside, nearly half an acre of level lawn surrounds the home, with a long private driveway, two-car detached garage, and a private backyard. Basement offers abundant storage City water, city sewer, and new furnace! Minutes to the Merritt Parkway, Sacred Heart University, Westfield Trumbull, and award-winning Trumbull schools, with an easy commute to New Haven and NYC. Move-in ready! Welcome home.

5167 Main St, Trumbull

$525,000

3 Beds ⋅ 2 Baths ⋅ 24203787 MLS

Welcome to "The Grid", a coveted section of Trumbull, close to everything - highways, shopping, schools and all amenities. Friendly, walkable neighborhood. Lovely Ranch style home with welcoming front deck. Offering 3 Bedrooms and 1 Full Bath. Primary Bedroom features two closets, including a large cedar closet. Lower Level laundry room. Hardwood Flooring throughout the main level. Wood burning fireplace in Living Room, with large picture window. Open floor plan between the Dining Room and Living Room, allowing for an easy flow throughout. Eat-in-Kitchen features granite counters and stainless steel appliances. Spacious with custom built cabinetry and ample kitchen storage. The "Bonus Room" or "Family Room" off of the Living Room, allows for additional living space, with a separate heat zone and custom built-ins. The finished Walk Out Lower Level is heated (radiator) offering an additional 1,000+ square feet. Oversized level lot with.35 acres. Central Air/Oil Heat. Two zones heat - one in main home and one in bonus room/family room. Bluestone patio overlooking large, level back yard.

86 Crown St, Trumbull

$689,000

4 Beds ⋅ 2 Baths ⋅ 24196779 MLS

Updated Ranch which features 5 bedrooms and 2 full bath. Legal 2 bedroom apartment in lower level with separate driveway and entrance. Updated kitchen and bathrooms. Heated sunroom was used as family room. Many updates include crown moldings, gazebo and recessed lights. Private fully fenced rear yard. Conveniently located.

4 Ascolese Rd, Trumbull

$639,000

4 Beds ⋅ 2 Baths ⋅ 24195939 MLS

Welcome Home to 16 Sunrise Ave! This beautifully maintained, 1,998 sf single-family home is perfectly situated in the desirable Long Hill neighborhood in Trumbull, CT. The inviting interior features four spacious bedrooms, two of the bedrooms are on the first floor with a full bath on each floor, an updated eat-in kitchen with Quartz countertops and sliding doors that open seamlessly to the deck, while a large formal living room features the first of two cozy fireplaces. The heart of the home is an expanded, light & bright family room, complete with a vaulted ceiling, additional sliding doors and a second coveted fireplace. Step outside to find a fantastic outdoor setup perfect for entertaining, featuring a patio and a deck equipped with a retractable awning overlooking the beautiful yard as well as a separate two car garage great for parking & extra storage making a total of three garages! Additional high-value amenities include newer windows that flood the home with natural light, a full home generator for absolute peace of mind. Enjoy all the amenities of Trumbull living and the award winning Trumbull School System! Move right in!

16 Sunrise Ave, Trumbull

$640,000

4 Beds ⋅ 3 Baths ⋅ 24198881 MLS

Welcome to the market 28 Brook Road! This charming Colonial-style home is located in the highly sought-after Long Hill district of town and within the Jane Ryan School District. Loved by the same owners for the past 43 years, this 4 Bedroom 3 Full-Bath home is sited on a beautiful .67 acre corner-lot on a small dead-end street offering you 2,205 sq. ft of sun-filled living space. Should you need an additional bedroom, the main level office can easily be used as a 5th Bedroom. Enjoy outdoor entertaining on the blue-stone patio while taking advantage of the spacious yard, which also includes a beautiful hand-built wood shed - perfect for storage or use as a workshop. Rows of beautiful green arborvitaes line the sides of the home providing you with a nice touch of privacy. Brook Rd places you less than 1.5 miles from the Merritt Parkway offering access to all the major commuting routes, including Metro-North Rail which will have you in New York City in under 1.5hrs! Fairfield County continues to offer a growing variety of arts & entertainment options to choose from. Come be part of a welcoming community and neighborhood known for its top-rated schools, beautiful parks, recreation areas, dining and shopping options. Don't miss your opportunity to own this cherished home in an unbeatable location!

28 Brook Rd, Trumbull

$699,900

5 Beds ⋅ 4 Baths ⋅ 24198021 MLS

Need space, flexibility, and a backyard built for summer? This one delivers. The main home offers 3 bedrooms, 2.5 baths, hardwood floors, a gas fireplace, an eat-in kitchen, first-floor laundry, and a spacious primary suite. A separate 2-bedroom in-law living area with its own full bath and plumbing already roughed in for a future kitchen creates incredible flexibility for extended family, guests, or multigenerational living. Outside, enjoy a propane-heated in-ground pool with solar cover, fully fenced yard, screened porch, and expansive deck made for entertaining. Major updates include a 3-year-old roof, a new oil tank, and a new hot water heater. Add in a garage, lower-level recreation space, and multiple living areas, and this is a home that truly offers more than meets the eye. Interior photos coming soon!

36 Clinton St, Trumbull

$649,999

3 Beds ⋅ 3 Baths ⋅ 24197181 MLS

Available for the first time in nearly 48 years, this lovingly maintained raised ranch has been thoughtfully cared for by the same family and is ready to welcome its next owners. Warm and inviting, the home features beautiful hardwood floors throughout most of the main level and a sun-filled layout designed for comfortable everyday living. The spacious eat-in kitchen, complete with a center island, flows seamlessly into the large family room, creating the perfect space to gather and entertain. Just off the kitchen, a bright sunroom with sliding glass doors overlooks the level, private backyard, offering a peaceful setting to enjoy your morning coffee. The main level includes 3 generously sized bedrooms. The primary BR features a private ensuite bath, direct access to the deck, and an adjoining room that offers endless possibilities as a 4th bedroom, home office, or nursery. The finished lower level provides additional living space with a cozy fireplace, ideal for a rec / media / playroom, along with a half bath, laundry area, and convenient walkout access to the backyard. Additional highlights include a two-car attached garage with abundant storage, an outdoor storage shed, vinyl siding, natural gas, and central air conditioning for year-round comfort and efficiency. Set in a desirable neighborhood close to shopping, dining, schools, and major highways, this home offers the perfect combination of convenience, privacy and timeless appeal. *See agent remarks*

95 Pemberton Dr, Trumbull

$495,000

3 Beds ⋅ 2 Baths ⋅ 24196862 MLS

Timeless charm exudes from this delightful vintage colonial bungalow in desirable, idyllic Long Hill neighborhood. Featuring sweet covered front porch, hardwood floors and solid craftsmanship. Welcoming entry sitting area and living room provides solid wood staircase and brick fireplace. Spacious formal dining room. Sun drenched eat-in kitchen features white painted cabinets, granite counters and a stylish backsplash. Convenient walk-in pantry and half bath. The kitchen steps out to lovely deck overlooking beautifully landscaped property boasting new patio. This wonderful outdoor retreat is a pleasure for entertaining or comfortable respite appointed with hammock and built-in TV! The upper-level features three light-filled bedrooms all provide large closets and share newly painted hall bathroom. The bonus continues to the lower-level providing a finished area for recreation or gym. Ample storage and laundry area. Detached 2 car garage with new garage doors. Recent updates include roof, furnace, washer dryer and patio. Classic architecture, functional living spaces, room to expand, and the opportunity to add your own personal choices in a quiet and quaint neighborhood. Exceptional value= Home Sweet Home in Trumbull!

48 John St, Trumbull

$689,000

4 Beds ⋅ 2 Baths ⋅ 24196739 MLS

4 Ascolese Rd, Trumbull

$324,900

3 Beds ⋅ 2 Baths ⋅ 24193921 MLS

Requesting Highest and best By Sunday @ 12pm.Welcome to 231 Long Hill Road, Waterbury, CT! This beautifully updated raised ranch offers approximately 2,256 square feet of comfortable living space, featuring 3 spacious bedrooms and 2 full bathrooms. The finished lower level provides additional versatile living space, perfect for a family room, home office, recreation area, or guest suite. Recent improvements include a new furnace, new flooring, fresh interior paint, a new driveway, a new garage door opener, and numerous additional updates throughout the home. The bright and functional floor plan is ideal for everyday living and entertaining, offering both comfort and flexibility. Conveniently located near shopping, restaurants, schools, parks, and major highways, this move-in-ready home is an excellent opportunity for buyers seeking a well-maintained property with modern updates. Schedule your private showing today!

231 Long Hill Rd, Waterbury

Start Your Search

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.