Seymour Real Estate

Welcome to Seymour, Connecticut – a charming town nestled in the heart of New Haven County. With its rich history, vibrant community, and picturesque landscapes, Seymour offers an ideal blend of small-town charm and modern conveniences, making it a perfect place to call home.

Founded in the early 19th century, Seymour boasts a rich historical heritage, evident in its well-preserved architecture and quaint downtown area. The town is known for its friendly atmosphere, where neighbors become friends, and community events bring everyone together. From seasonal festivals to farmers' markets, there’s always something happening in Seymour that celebrates the spirit of togetherness.

Nature enthusiasts will appreciate Seymour’s stunning outdoor spaces. The town is surrounded by beautiful parks, hiking trails, and the scenic Housatonic River, providing ample opportunities for outdoor recreation. Whether you enjoy fishing, hiking, or simply taking a leisurely stroll, Seymour’s natural beauty is sure to inspire.

Families will find Seymour to be an excellent place to raise children, with top-rated schools and a close-knit community that prioritizes education and growth. The town's commitment to maintaining a safe and nurturing environment makes it a sought-after destination for families of all sizes.

Conveniently located just a short drive from larger cities like New Haven and Bridgeport, Seymour offers easy access to urban amenities while maintaining its serene, suburban feel. With its unique combination of history, community spirit, and natural beauty, Seymour is not just a place to live—it's a place to thrive. Come discover your new home in this delightful Connecticut town!

Newest Listings in Seymour

$499,900

3 Beds ⋅ 3 Baths ⋅ 24192058 MLS

Hard-to-find 1960s ranch offering timeless craftsmanship, solid construction, and the convenience of true single-level living. Set along quiet Mountain Road in Seymour, the home sits beautifully on a level, tree-lined lot that provides privacy from neighboring properties. Inside, the comfortable floor plan features hardwood floors, oil-fired hot water heat with cast-iron radiators, and a charming stone-front exterior that reflects the quality of its era. The cozy living room includes a bay window and corner fireplace, while the dining room offers another bay window and views of the fireplace. A generously sized kitchen, three well-proportioned bedrooms, and a primary suite with a private full bath provide both comfort and functionality. Thoughtful updates include central air conditioning, a newer roof, replacement windows, and a repointed chimney. The partially finished lower level offers additional space for entertaining, recreation, or hobbies. Step outside to enjoy the peaceful setting, all while being conveniently located near shopping, dining, parks, and major commuter routes. Whether you're just starting, downsizing, or looking for easy everyday living, this delightful home is one you won't want to miss.

125 Mountain Rd, Seymour

$319,900

4 Beds ⋅ 3 Baths ⋅ 24193191 MLS

Yesteryear and today all rolled into one! This older two-story home brings some charm, character and recent updates. (Furnace, oil tank 2023; hot water heater 2025; roof 2017) Second floor remodeled aprox. 12 yrs. ago, with 1/2 bath included! Full bath on first floor boasts striking stained glass window. House sold "as is" for informational purposes. Owner must find suitable housing. Another full bath located in walk-out unfinished basement ideal for possible in-law setup (or framed room first floor possible.) Framed room , with fireplace, (approx. 18x16) adjacent to kitchen ready for your imagination. Bring your plans and envision a bonus room (or in-law) on the main level! Some remodeling on first floor.

1 Second Ave, Seymour

$479,900

2 Beds ⋅ 3 Baths ⋅ 24192697 MLS ⋅ Ridge View Townhomes(Pending Verification) BLDG.

This impeccably built, soon-to-be-completed 2-bed /2.5-bath End Unit townhouse offers a rare combination of modern, customizable design, premium materials, and exceptional comfort. Located within a newly constructed, peaceful, and private community, this three-story residence is thoughtfully designed to deliver bright, spacious living areas, everyday functionality, and timeless elegance. A perfect balance of upscale living-at a remarkably attainable price point. The first floor features a beautifully designed open-concept layout, highlighted by a spacious kitchen with quartz countertops, stainless steel appliances, and abundant cabinetry. The adjacent dining area flows seamlessly into a bright, generously sized living room, enhanced by sliding glass doors that open to a 10' x 12' sun-filled balcony. The second floor features a spacious master bedroom, complete with a walk-in closet and a large primary bathroom. An additional generously proportioned bedrooms with a second full bath complete the floor. Ample closet spaces. The ground level offers exceptional versatility, featuring a spacious one-car garage and an oversized, fully finished family room with walk-out access to a stunning patio. Ideally situated near major highways, regional employment centers, retail, dining, and neighboring hubs including New Haven. Completion date: August 31st. A rare opportunity to own a home in a vibrant new community featuring two pickleball courts and a beautifully designed fire pit area.

34 Micko Dr, Seymour

$314,900

3 Beds ⋅ 2 Baths ⋅ 24190592 MLS

Move-in ready with more space than you would expect, this well-maintained home offers a flexible layout and convenient location. Inside, you'll find a large eat-in kitchen with access to the flat backyard and shed, giving you plenty of room for everyday living, entertaining, and extra storage. The main level features two well-sized bedrooms, a full bath, a spacious living room, and a formal dining room. A bright sunroom/breezeway at the front of the home adds even more usable space and is perfect for relaxing, a home office nook, or plant lovers. Upstairs offers an additional well-sized bedroom along with walk-in attic storage, providing extra flexibility and room to grow. The full basement adds even more value with additional storage space, a full bath, and a one-car garage bay. With public water, public sewer, and easy access to Route 8 and Route 67, this home offers a practical layout with the space and features to fit a variety of needs. HIGHEST AND BEST WEDNESDAY 7/22 12:00 PM

172 Cedar St, Seymour

$699,900

3 Beds ⋅ 3 Baths ⋅ 24191421 MLS

***Highest and Best due 7/21 at 5:00pm*** Enjoy scenic views, exceptional indoor-outdoor living, and a home designed for entertaining in this beautiful Seymour property. The heart of the home is a beautiful gourmet spacious kitchen featuring stainless steel appliances, and a unique gas-fired pizza oven, perfect for entertaining family and friends. The open-concept living and dining areas are filled with natural light and feature a stunning stone fireplace and large windows overlooking the surrounding landscape. The home offers comfortable living spaces, updated bathrooms, generous bedrooms, and flexible areas that can accommodate a home office, gym, or playroom. Step outside to an expansive deck overlooking the backyard, where you'll find an above-ground pool with pool house, beautifully maintained landscaping, and peaceful views that can be enjoyed year-round. Whether you're hosting gatherings, relaxing by the pool, or enjoying a quiet evening outdoors, this home offers the perfect setting. Owner is a licensed real estate agent.

70 N Benham Rd, Seymour

$360,000

3 Beds ⋅ 2 Baths ⋅ 24191775 MLS

Welcome to 169 Derby Avenue, a renovated three-bedroom Colonial offering direct frontage and peaceful views of the Naugatuck River. The bright and inviting main level features a comfortable living room, dining area, updated kitchen and convenient half bathroom. An additional sitting room provides flexible space for a home office, library, playroom or quiet retreat. Upstairs, you'll find three comfortable bedrooms and a full bathroom. The finished basement offers additional space for recreation, storage and laundry. Outside, enjoy a spacious deck and backyard overlooking the river-an appealing setting for relaxing, entertaining and taking in the changing seasons. Additional highlights include central air, zoned cooling, public water, public sewer, vinyl siding, a security system and private off-street parking at the end of the shared driveway. Conveniently located near downtown Seymour, shopping, restaurants, Route 8 and the Metro-North train station. A distinctive opportunity combining historic Colonial character, modern updates and scenic riverfront living.

169 Derby Ave, Seymour

$569,900

3 Beds ⋅ 3 Baths ⋅ 24191863 MLS

Welcome to your own private oasis, nestled on a lightly wooded lot at the end of a quiet cul de sac, this beautiful Colonial offers the perfect combination of privacy,space and convenience. Whether you are looking for a peaceful retreat or a home designed for entertaining, this property has it all. Ideally located just minutes from RT 8, you'll enjoy an easy commute both north and south while still feeling tucked away from the hustle and bustle.At the end of the street , Gary Park provides easy access to playgrounds, ball fields and outdoor recreation providing outdoor entertainment. Step inside to a warm and inviting floor plan designed for both every day living and many special occasions. The spacious kitchen opens seamlessly to the family room, creating the heart of the home. Large windows fill the space with natural light, while easy access s to the rear deck makes and indoor-outdoor entertaining effortless. Whether you are hosting summer cookouts, holiday gatherings or simply enjoying your morning coffee overlooking the private backyard, this home offers the perfect setting. For more formal occasions, the elegant living room and dining room low together beautifully, providing flexible space for entertaining guests or enjoying intimate dinners. Upstairs you'll find three generously sized bedrooms with beautiful hardwood flooring throughout,. The second and third bedrooms offer excellent closet space, the third bedroom featuring its own walk in closet.

32 Shari Dr, Seymour

$379,900

3 Beds ⋅ 2 Baths ⋅ 24190315 MLS

Welcome home to this well-maintained property set on a level lot in a convenient Seymour location. Inside, you'll find a bright, functional layout with inviting living spaces and generously sized bedrooms. Step outside to a spacious backyard with plenty of room to relax, entertain, or enjoy outdoor activities. Ideally situated just minutes from shopping, restaurants, parks, schools, and Route 8, this home offers the perfect blend of everyday convenience and neighborhood charm.

105 Walnut St, Seymour

$150,000

1 Beds ⋅ 1 Baths ⋅ 24190576 MLS ⋅ Balance Rock BLDG.

Main level one bedroom unit, no stairs into unit. Large living room with slider to patio, kitchen, dining area, full bathroom and large bedroom with spacious closet. Community washer and dryer located in the basement area along with extra storage space. Heat & hot water included in the HOA. Complex amenities include tot/play area, basketball, in ground pool & clubhouse. Great location close to shopping, library, restaurants, train station, Rt. 8, 67, & 34. Being sold as is. Subject to probate court approval

114 Balance Rock Rd Unit 10, Seymour

$475,000

2 Beds ⋅ 3 Baths ⋅ 24189232 MLS ⋅ Great Oak Ridge BLDG.

Built in 2024, this beautifully designed end unit townhouse offers an exceptional blend of modern style, energy efficiency, and everyday comfort. Nestled within a tranquil and private community, this three level story residence showcases quality craftmanship, functional living spaces, and timeless appeal. The main living level has an open concept floor plan highlighted by a kitchen with an added center island featuring stainless steel appliances, quartz countertops and an added bay window bench. The adjacent dining area flows seamlessly into a bright and inviting living room, complete with sliders leading to a deck, perfect for relaxing or entertaining. The upper level offers a primary bedroom featuring double closets with California closet organizers and a private en-suite bathroom. A generously sized second bedroom and an additional full bathroom to complete this floor. The hallway also provides convenient access to a laundry closet and two linen closets. The entry level has a brand-new epoxied floor, one car garage and fully finished playroom/office. Ideally located near major highways, shopping, dining, and local boutiques. This gorgeous end unit townhouse combines modern living, thoughtful design, and a highly convenient location.

11 Summer Brook Way Unit 11, Seymour

$410,000

2 Baths ⋅ 24190887 MLS

Historic Whittemore Tavern originally constructed in 1720 and expanded/updated in 2001, currently home to 2 thriving businesses. Town of Seymour Zoning confirms that residential occupancy is also permitted here (C2 Zoning). Total parcel size is .94 acre, including the adjacent lot with a small structure at 126-130 S. Main, which will convey with this sale. The 3,017 square-foot building is home to a well-known and successful ice cream retailer on the main level, and a popular dance studio upstairs (20 years here as a tenant). Excellent, clean and bright interior condition throughout both businesses, with some exterior cosmetic maintenance needed at this turn-key operation. Beautiful wraparound porch and mature trees contribute to the curb appeal enjoyed by locals at this well-recognized location. Public water and sewer, updated electrical and plumbing, with oil and propane heating plus Central A/C on the main level. Basement is spacious and easily accessed for storage. Heating, A/C and hot water are solid, while oil tank is brand new. Prime Valley location just a minute off Route 8 and plenty of easy parking have made this a convenient and popular ice cream and dance studio destination for decades! The lot is perfectly level and wide open, with the easy possibility of a second business being added. A great opportunity to take advantage of!

114 S Main St, Seymour

$474,900

2 Beds ⋅ 3 Baths ⋅ 24190758 MLS ⋅ Ridge View Townhomes(Pending Verification) BLDG.

This impeccably built, soon-to-be-completed 2 bed /2.5 bath townhouse offers a rare combination of modern, customizable design, premium materials, and exceptional comfort. Located within a newly constructed, peaceful, and private community, this three-story residence is thoughtfully designed to deliver bright, spacious living areas, everyday functionality, and timeless elegance. A perfect balance of upscale living-at a remarkably attainable price point. The first floor features a beautifully designed open-concept layout, highlighted by a spacious kitchen with quartz countertops, stainless steel appliances, and abundant cabinetry. The adjacent dining area flows seamlessly into a bright, generously sized living room, enhanced by sliding glass doors that open to a 10' x 12' sun-filled balcony. The second floor features a spacious master bedroom, complete with a walk-in closet and a large primary bathroom. An additional generously proportioned bedrooms with a second full bath complete the floor. Ample closet spaces. The ground level offers exceptional versatility, featuring a spacious one-car garage and an oversized, fully finished family room with walk-out access to a stunning patio. Ideally situated near major highways, regional employment centers, retail, dining, and neighboring hubs including New Haven. Completion date: August 15th. A rare opportunity to own a home in a vibrant new community featuring two pickleball courts and a beautifully designed fire pit area.

38 Micko Dr, Seymour

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