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124 Chestnut Hill Rd, Trumbull
$649,999
5 Beds ⋅ 3 Baths ⋅ 24205007 MLS
NEW PRICE - REDUCED $50,000! 5BR/3BA Home in Trumbull Near the Merritt Parkway Now $649,999! Space, character, and opportunity at a newly reduced price. This spacious 5-bedroom, 3-full-bath home offers a flexible layout with two bedrooms on the main level and three upstairs. Hardwood floors, charming arched doorways, and two cozy fireplaces add warmth and character, while a bright sunroom overlooks a backyard with plenty of possibilities for gardens, flowers, and outdoor enjoyment. A partially finished basement offers flexible space for a home office, recreation room, or gym, while the two-car garage provides additional storage and convenience. The Merritt Parkway is just minutes away. Full of character and ready for your personal touch, this home offers the opportunity to update at your own pace and make it truly yours. Come see the possibilities! Schedule your showing today.

124 Chestnut Hill Rd, Trumbull

5 Asbury Rd, Trumbull
$649,900
3 Beds ⋅ 3 Baths ⋅ 24212399 MLS
Mornings here start w/ birdsong from the mature trees &, on a good day, a fox or a few deer crossing the yard. Set on a one-acre corner lot framed by professional landscaping, this home offers privacy & calm, w/ Tashua School's playground & fields a short walk away. The exterior was rebuilt to last: Maibec cedar shake siding, Azek trim, 4" stone veneer & Andersen windows & doors. A brick walkway leads to the bluestone front porch, an easy spot for morning coffee or a quiet evening. Inside, natural light moves across hardwood floors through most of the main level. The living room is anchored by a large picture window, & a separate family room gives everyone a place to settle in. The kitchen offers white cabinetry, granite counters, stainless appliances, & a dining area. The mudroom opens to a private bluestone patio made for summer evenings & time w/ friends. Three well-sized bedrooms sit at the end of the hall, including a primary suite w/ its own full bath. A full hall bath serves the other bedrooms & guests. The finished lower level adds porcelain-tiled living space, a half bath, laundry, & access to the large two-car garage. Electrical upgrades & a newer water heater add peace of mind. A detached outbuilding finished in cedar shake & stone veneer, w/ water & electric, is ready to become an office, gym, or studio. Quiet roads for bike rides & walks, among the first cleared after a storm, complete a ranch-built w/ intention, on land that feels like your own retreat.

5 Asbury Rd, Trumbull

16 Velvet St, Trumbull
$649,000
3 Beds ⋅ 2 Baths ⋅ 24198329 MLS
Nestled on a secluded setting surrounded by protected reservoir property, this one-of-a-kind ranch offers the privacy of a country retreat just minutes from everything Trumbull has to offer. Designed for comfortable living and effortless entertaining, the home features an expansive open-concept family room and dining room with soaring vaulted ceilings, gleaming hardwood floors, custom built-ins and a striking brick fireplace accented by a Harman pellet stove. The adjoining kitchen is the heart of the home, offering abundant cabinetry, generous counter space, stainless steel appliances, and an oversized breakfast bar with seating for family and guests. The spacious living room is equally inviting with hardwood floors, custom built-ins and a beautiful stone fireplace featuring a Vermont Castings Defiant wood stove, creating the perfect place to gather on cool New England evenings. A tiled three-season porch surrounded by walls of windows brings the outdoors in and overlooks the peaceful, private backyard. Step outside to the expansive deck where you'll enjoy dining, entertaining, or simply relaxing while surrounded by nature. There are three generously sized bedrooms and two full baths, while the unfinished lower level offers exceptional storage and future expansion potential. A rare bonus is the attached two-car garage plus an additional one-car garage-ideal for extra vehicles, hobbies, a workshop, or outdoor equipment.

16 Velvet St, Trumbull

280 Plattsville Rd, Trumbull
$619,000
3 Beds ⋅ 2 Baths ⋅ 24210345 MLS
Get ready for the turnkey, updated home you've been waiting for! A feel-good home from the moment you walk in. This 3 bedroom, 1.5 bath home is filled with natural light throughout the day and features a renovated kitchen, refinished hardwood floors, fresh interior and exterior paint, new front and back doors, new bluestone front steps, newer roof, updated light fixtures/ceiling fans, new heat and central air. The propane fueled Viessmann boiler/on-demand water heater combo provides efficient heat and endless hot water! The kitchen features white shaker cabinets, quartz counters, newer stainless appliances, and an island that makes entertaining easy, all open to the living and dining areas. Double glass doors flood the home with morning light and offer sweeping views of the back yard. The upper level offers 3 generously sized bedrooms and a spacious full bath. The lower level has a family room, half bath, and direct access to the garage and back yard. The partially finished basement includes laundry, extra storage and room for a home gym or office. The 2 car garage has been refinished with a moisture barrier and epoxy floor, providing clean, ample storage and parking. The back yard is a true highlight: half an acre with a covered patio for dining, an open patio for sun seekers, and a private, natural setting framed by stone walls and mature landscaping. Minutes to Sacred Heart University, the Merritt Parkway, the Westfield Trumbull mall, and local shopping and restaurants.

280 Plattsville Rd, Trumbull

63 Chatfield Dr, Trumbull
$599,000
3 Beds ⋅ 2 Baths ⋅ 24214733 MLS
Pristine and lovingly cared for, this bright, comfortable 1,960 square foot home is ready for you. A welcoming covered front porch leads to an open main level floor plan with dining room, living room, kitchen and three bedrooms. Gleaming hardwood floors flow throughout, while the kitchen features granite counters, custom craftsman cabinets, stainless appliances, and tiled flooring. The lower level offers a generous family room with a classic stone fireplace, plus an office with built-ins (ideal as a bedroom or game room), a full bath, and flexible multigenerational/in-law options. A 2-car attached garage is great for off street parking or extra storage. The professionally landscaped grounds include open space for vegetable and flower gardens and boasts beautiful views from the multi-tiered decks. Set in a quiet neighborhood perfect for walks, this Trumbull location is near highways, restaurants, and shopping, bordering Easton, Fairfield, and Bridgeport, and just minutes from Metro North making an easy commute to New York City. This is one you don't want to miss!

63 Chatfield Dr, Trumbull

4280 Madison Ave, Trumbull
$599,000
3 Beds ⋅ 2 Baths ⋅ 24205611 MLS
NEW PRICE! Exceptional value and an outstanding opportunity to own a spacious, move-in-ready home in Trumbull. Welcome to this well-maintained 3-bedroom, 2-bathroom split-level home situated on a large corner lot. An expansive kitchen offers generous cabinet and counter space, complemented by a spacious dining room that comfortably accommodates holiday celebrations, special occasions, and everyday gatherings. Together, these inviting spaces create a natural setting for bringing family and friends together. The flexible layout provides comfortable living and entertaining areas, along with three well-sized bedrooms, two full bathrooms, split-system A/C, a newer roof, and a 2-car attached garage. A wide long driveway provides ample parking for multiple vehicles, adding convenience for both daily living and visiting guests. The finished basement offers approximately 300 additional square feet of versatile living space not included in the reported total square footage-ideal for a recreation room, home office, gym, or additional gathering space. Outside, the fenced-in yard offers privacy and plenty of room for entertaining, pets, gardening, or relaxing. Conveniently located minutes from Sacred Heart University, Trumbull Mall, the Merritt Parkway, major highways, shopping, restaurants, and everyday essentials. A wonderful opportunity to enjoy generous space, comfort, and convenience in a desirable Trumbull neighborhood.

4280 Madison Ave, Trumbull

23 Great Neck Rd, Trumbull
$599,000
4 Beds ⋅ 2 Baths ⋅ 24177853 MLS
Nestled on a quiet cul-de-sac along a picturesque, tree-lined street, this charming ranch offers the perfect blend of comfort, convenience, and classic New England appeal. Ideally located just moments from Trumbull High School and Hillcrest Middle School, this home places you in one of Trumbull's most desirable neighborhoods. Step inside to find recently installed hardwood and vinyl flooring that add a fresh, modern touch throughout the home. Major mechanical updates provide peace of mind, including a newer furnace, oil tank, hot water heater, and central air unit. Enjoy summer in style with a private, tree-lined backyard perfect for entertaining, barbecues, or simply relaxing outdoors. The setting offers exceptional privacy while still being conveniently close to everything you need. Commuters will appreciate easy access to Route 25, the Merritt Parkway, and Route 8, while nearby shops, coffee spots, dining, and everyday conveniences are just around the corner. Discover everything Trumbull is known for, from its top-rated schools and beautiful parks to scenic walking trails, recreational amenities, and popular local dining. With a strong sense of community and conveniences nearby, this is a wonderful place to call home. *Note: There is an additional 600 square feet of space not included in the public record above the garage*

23 Great Neck Rd, Trumbull

93 Woolsley Ave, Trumbull
$585,000
3 Beds ⋅ 2 Baths ⋅ 24206749 MLS
OPEN HOUSE CANCELLED SUNDAY DUE TO FALLEN BRANCHES. Welcome to 93 Woolsley Avenue nestled in a beautiful Trumbull neighborhood that offers just what you envision when searching for a place to call home! Featuring 3 bedrooms and 2 full baths, this home combines classic character with a warm and welcoming interior. The updated kitchen includes white cabinetry, sleek stainless steel appliances and opens to a family room highlighted by a vaulted ceiling, sliders leading to the exterior and access to a 2 car attached garage. From the kitchen, easily transition into the formal dining room, while the living room offers a fireplace and classic picture window, creating an inviting gathering space. A first-floor primary bedroom and full bath provide the convenience of main-level living. Upstairs, you'll find two generously sized bedrooms along with a second full bathroom. Outside, a deck overlooks the private, level, fully fenced backyard, with plenty of room for outdoor entertaining, gardening, play time, or simply relaxing. This home provides plenty of potential to update and personalize to suit your style. Approximately 50 miles from New York City, and just .5 mile from the fabulous Pequonnock River biking/walking trail. Conveniently located near, playgrounds, popular restaurants, shopping areas and highways. As a Trumbull resident, you have access to 2 community pools, a golf course and top-rated schools. Truly, an incredible opportunity to make this home your own!

93 Woolsley Ave, Trumbull

133 Governor Trumbull Way Unit 133, Trumbull
$548,000
2 Beds ⋅ 3 Baths ⋅ 24200216 MLS ⋅ Governor's Ridge BLDG.
Welcome to 133 Governor Trumbull Way! This beautifully maintained, three-level townhouse in Governor's Ridge offers privacy, comfort, and a bright, light-filled layout. Gorgeous hardwood floors flow throughout the main living spaces. The elegant living room features a charming bay window and wood-burning fireplace, creating a warm and inviting atmosphere. The space flows seamlessly into the crisp white kitchen, complete with stainless steel appliances, and an adjacent dining area with easy access to the private wood deck-perfect for outdoor dining and entertaining. Upstairs, the spacious primary suite offers a walk-in closet, ceiling fan, and a splendid, newly renovated full bath. The generously sized second bedroom features a beautiful bay window that fills the room with natural light. The finished lower level provides valuable additional living space and offers endless possibilities for a home office, playroom, family room, or other flexible-use space. There is two car attached garage with epoxy floor and charging station for EV. This complex offers salt-water, in-ground pool, clubhouse, beautiful grounds, two scenic ponds that create a serene landscape for walking, jogging or biking. Pet friendly community. Additional guest parking. With its thoughtful layout, abundant natural light, beautiful finishes, and desirable private setting, 133 Governor Trumbull Way is a wonderful place to call home!

133 Governor Trumbull Way Unit 133, Trumbull

464 Church Hill Rd, Trumbull
$530,000
2 Beds ⋅ 2 Baths ⋅ 24206471 MLS
Welcome to this beautifully maintained classic 1938 Ranch located in the heart of the Center District. This home offers single level living space with hardwood floors throughout. The inviting living room is highlighted with a beautiful stone fireplace, custom built-ins and a soaring ceiling. The kitchen boasts granite countertops, tile flooring, gas for cooking, plenty of cabinetry and a bright skylight that fills the space with natural light. A mud room is conveniently located off the kitchen. Both bedrooms are on the main level, including a huge primary bedroom, with an oversized double closet and a private en suite bath. The second bedroom has custom built-ins with plenty of storage along with a walk-in closet. This property sits on a spacious, level, park-like lot bordered by a classic stone wall. You will also find a massive stone patio, perfect for outdoor dining or entertaining. Other conveniences include central air conditioning, public sewer and water, and an attached 2 car garage. There is a massive walk-up attic for future use to create additional living space. You'll also find a cedar closet and plenty of additional storage. Don't miss this opportunity for a great house, with a massive lot, with plenty of room to expand, and plenty of room for a swimming pool. This home is in the perfect location for commuting, whether you need to catch the train, get to the Merritt Parkway, Route 8, or I95,

464 Church Hill Rd, Trumbull

227 Mayfield Dr Unit 227, Trumbull
$529,900
2 Beds ⋅ 2 Baths ⋅ 24213949 MLS ⋅ Trumbull Town Commons BLDG.
Welcome to 227 Mayfield Drive, a beautifully appointed end unit in Trumbull Town Commons, nestled in a picturesque Long Hill neighborhood. Privately situated amid lush foliage and beautifully maintained grounds, this inviting home offers a peaceful retreat just a short walk from shopping and the town library. Inside, an open, flowing layout is enhanced by abundant natural light, custom built-ins, and charming architectural details. The well-appointed kitchen features engineered hardwood flooring, granite countertops, stainless steel appliances, generous cabinetry, open soffits, and flows seamlessly into the dining area, ideal for everyday living and entertaining. The spacious primary bedroom offers a walk-in closet and private full bath, while the second bedroom also features its own bathroom. A versatile den or home office off the kitchen provides additional flexible living space. Step onto the private deck and enjoy peaceful views of nature, perfect for morning coffee or unwinding at the day's end. Additional highlights include an intercom system, automatic door latch, ample closet space, custom window blinds, laundry area with utility sink, new hot water tank, two-car garage, and separate storage unit. Select furnishings available for purchase. Residents enjoy beautifully landscaped grounds and a heated community pool. A wonderful opportunity to enjoy privacy, comfort, and low-maintenance living in a convenient Trumbull location.

227 Mayfield Dr Unit 227, Trumbull

176 Stonehouse Rd, Trumbull
$525,000
4 Beds ⋅ 2 Baths ⋅ 24167415 MLS
Looking for a hidden gem in the heart of Tashua? Welcome to 176 Stonehouse Road. Set on .40 of an acre, follow the private driveway to discover this charming Contemporary Cape home. The professionally landscaped yard features stone walls, mature trees, and perennial gardens. This four-bedroom, two-full-bath home has been freshly painted and professionally cleaned, making it ready for its next chapter. The sun-filled living room offers beautiful natural light, creating the perfect start to the day before stepping outside to enjoy your morning coffee on the wraparound deck. A BRAND-NEW water heater has been installed, as well as a newer oil tank. All utilities & appliances have been well maintained throughout the years. Minutes away from dining, retail, & recreational amenities including Indian Ledge Park and Tashua Knolls Golf Course & Pool. Commuter friendly with easy access to Route 25 & Merritt Parkway. Don't miss out on privacy, convenience, and all that Trumbull has to offer!

176 Stonehouse Rd, Trumbull

10 Crown St, Trumbull
$519,900
3 Beds ⋅ 2 Baths ⋅ 24203074 MLS
Welcome to 10 Crown Street! A classic home steeped with New England charm while settling comfortably into the highly desirable Fairfield County. This very Charming Vintage Colonial has 3 bedrooms & 1.5 baths. It is situated on a perfectly level corner lot. Features include: An updated Kitchen with granite countertops. A separate Breakast Room. Living Room has a brick fireplace, built-ins, & 2 lovely stained glass decorative windows. Formal Dining Room. Family Room is carpeted & has a vaulted ceiling, skylight, built-ins, & ceiling fan. Hardwood Floors throughout. You will love the Sunroom with French doors & sliders to a wrap around deck. The upper level has 3 bedrooms & an updated tiled full bath. A partially finished lower level office/recreation room. Many recent brand new 2025-2026 updates include: New Central Air, New Furnace, New Hot Water Heater, New Roof, New Driveway, New Vinyl Replacement Windows, New Sliders, New Tiled Bathroom. Step outside & enjoy outdoor entertaining on a stone patio with fire pit. The home is vinyl sided & has an oversized two car garage with plenty of storage. This wonderful and very well maintained home is located in Trumbull, a town renowned for its excellent parks and Top-tier public school system. Crown Street offers a seamless access to Merritt Parkway, Route 8 & Highway Connector. Perfect commuter location. Close by to parks, schools & shopping. Ready to move in today!

10 Crown St, Trumbull

18 Southgate Rd, Trumbull
$500,000
3 Beds ⋅ 1 Baths ⋅ 24212788 MLS
Set just a few houses from Pinewood Lake in Trumbull's Nichols neighborhood, this 3 bedroom ranch offers one-level living with the opportunity to make it your own. Hardwood floors extend throughout the main level, which includes a living room, kitchen with quartz countertops and stainless steel appliances, three bedrooms, and an updated full bath. Sliding glass doors lead to a spacious deck and fenced backyard with room for outdoor dining, gardening, or relaxing. A detached 2 car garage and full unfinished basement offer additional storage and room for hobbies. Town water & sewer services. Pinewood Lake rights are available, with shopping, restaurants, town parks, and major commuter routes conveniently nearby!

18 Southgate Rd, Trumbull

4438 Madison Ave, Trumbull
$499,900
3 Beds ⋅ 3 Baths ⋅ 24205538 MLS
Set in a picturesque Trumbull setting just moments from Canoe Brook Lake, this 3-bedroom, 3-bath home offers a flexible layout, multiple living spaces, tremendous potential, and deeded lake rights to Canoe Brook Lake. The bright, updated kitchen features stainless-steel appliances, generous counter space, and an open pass-through connecting to the adjoining living area. Hardwood floors, oversized windows, and abundant natural light bring warmth and character throughout. The spacious lower level, highlighted by a stone fireplace, offers excellent flexibility with potential for an in-law setup, home office, recreation space, or additional living area. Outside, enjoy a private, peaceful setting surrounded by mature trees and landscaping, a deck for outdoor living, circular driveway, and detached two-car garage providing ample parking and storage. With deeded lake rights and Canoe Brook Lake just moments away, this property offers a rare combination of space, privacy, character, and convenience to Trumbull's schools, shopping, recreation, and commuter routes.

4438 Madison Ave, Trumbull

34 Lansing Ave, Trumbull
$499,000
3 Beds ⋅ 2 Baths ⋅ 24190923 MLS
Expected to turn heads and generate strong interest! Welcome to 34 Lansing Ave, where style, flexibility, and location come together in one incredible package. Beautifully maintained and move-in ready, this home offers bright, inviting living spaces designed for today's lifestyle. A true standout is the versatile garage, expertly converted into an impressive entertainment retreat while still functioning as a garage when needed. Whether you're envisioning the ultimate game room, home gym, media space, or the perfect spot to host family and friends, this unique feature sets the home apart from the competition. Comfortable bedrooms, a functional layout, and an inviting outdoor space provide the perfect setting for relaxing or entertaining year-round. Located in one of Trumbull's most sought-after neighborhoods, you'll enjoy top-rated schools, parks, shopping, restaurants, and convenient commuter access-all just minutes away. Homes offering this combination of condition, versatility, and location don't come along often. Be prepared-this is the type of home buyers have been waiting for, and multiple offers are anticipated. Schedule your private showing before someone else calls it home!

34 Lansing Ave, Trumbull

48 John St, 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

35 Columbine Dr, Trumbull
$489,900
3 Beds ⋅ 1 Baths ⋅ 24215442 MLS
A rare opportunity to own this beautifully renovated 3-4 bedroom home, ideally situated in the highly desirable Nichols section of Trumbull. Offered for the very 1st time, this charming home has been completely transformed from top to bottom w/ exceptional attention to detail, quality materials, & thoughtful craftsmanship throughout. Nearly every aspect of the home has been updated, including a new roof, new siding, new windows, new sewer connection, & beautifully finished interior spaces. All renovations were completed w/ permits & a Certificate of Occupancy issued by the Town of Trumbull, providing added peace of mind for the next owner. Offering approximately 1,180 sq ft of beautifully updated living space, the home features 4 bedrooms, office is the 4th bedroom, and a full bath. The unfinished lower level offers excellent storage & exciting possibilities for future expansion. An attached 2-car gar provides additional conv, while the spacious backyard offers plenty of room for outdoor entertaining, gardening, & relaxation. Ideally located in the sought-after Nichols neighborhood, this property enjoys close proximity to schools, parks, shopping, restaurants, & major commuter routes, including Route 8 & the Merritt Parkway. Combining the charm of an established neighborhood w/ the comfort & conv of extensive modern renovations, this exceptional, truly move-in-ready home is a rare find in today's market. Simply unpack and enjoy!

35 Columbine Dr, Trumbull

109 Woolsley Ave, Trumbull
$485,000
3 Beds ⋅ 1 Baths ⋅ 24210851 MLS
Welcome to 109 Woolsey Avenue, a well-maintained three-bedroom, one-and-a-half-bath brick ranch offering comfortable one-level living and plenty of potential! Step inside to a bright, open floor plan featuring hardwood floors, abundant natural light, and a beautiful centrally located fireplace that adds warmth and character to the kitchen, dining, and living areas. All three bedrooms feature hardwood flooring, while the spacious full bath is finished with tile. Downstairs, the expansive basement provides excellent storage and exciting possibilities for future finished living space. Outside, enjoy a cleared, open backyard along a quiet neighborhood road. Conveniently located near shopping, restaurants, parks, medical facilities, and major commuting routes including the Merritt Parkway and Route 8. The home has been well cared for and offers a wonderful opportunity to update and personalize over time. With its classic brick construction, desirable layout, convenient Trumbull location, and attractive price point, 109 Woolsey Avenue is ready for its next chapter. Schedule your showing today!

109 Woolsley Ave, Trumbull

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