Seymour Real Estate

Welcome to Seymour, Connecticut – a charming town nestled in the heart of New Haven County. Known for its rich history and vibrant community spirit, Seymour offers a unique blend of suburban tranquility and easy access to urban amenities, making it an ideal place to call home.

Founded in the 1800s, Seymour boasts a quaint downtown area filled with local shops, delightful eateries, and a warm, welcoming atmosphere. The town's historic architecture tells the story of its past, while modern developments provide the conveniences of contemporary living. Residents enjoy a variety of recreational opportunities, with parks and outdoor spaces such as the scenic Housatonic River and the picturesque Great Hill Park, perfect for hiking, picnicking, and family outings.

Seymour is also known for its strong sense of community, hosting numerous events throughout the year, including the popular Seymour Pumpkin Festival, which brings together families and friends for a day of fun, food, and festivities. The local school system is highly regarded, making it an attractive option for families looking to settle down in a nurturing environment.

With easy access to major highways and public transportation, commuting to nearby cities like New Haven and Bridgeport is a breeze, allowing residents to enjoy the best of both worlds. Whether you’re seeking a cozy starter home, a spacious family residence, or a charming historic property, Seymour has a diverse range of real estate options to suit your needs.

Discover the warmth and charm of Seymour, where community, convenience, and character come together to create the perfect place to live. Come explore this hidden gem in Connecticut today!

Newest Listings in Seymour

$399,000

3 Beds ⋅ 1 Baths ⋅ 24203889 MLS

Welcome Home to This Adorable Completely Renovated Cape! Beautifully renovated in 2022, this charming 3-bedroom, 2 full bath Cape offers the perfect blend of modern updates, a comfortable living, and private outdoor space. The main level features beautiful hardwood floors throughout, an inviting open-concept large living room, and a nearly new eat-in kitchen complete with stainless steel appliances, granite countertops, tile backsplash, and an abundance of cabinet & counter space. The first floor also offers a cozy dining room, a renovated full bath, and a versatile bedroom currently being used as a playroom-perfect for guests, a home office, or additional living space. Upstairs, you'll find a nice size primary bedroom with a walk-in closet, a third generous bedroom both with hardwood floors and a second updated full bath. The full basement provides a dedicated laundry area & plenty of storage space. Recent improvements also include a 4 year old boiler and 40-gallon water heater. Step outside and discover a truly special .41-acre private property, featuring mature fruit trees and playscape. There is a patio and outdoor entertaining area, making this a wonderful setting for relaxing or hosting family and friends. A two-car detached garage and shed provide plenty of parking and storage. Move-in ready with thoughtful updates, wonderful indoor space, and a beautiful private lot-this charming Cape is a must-see to fully appreciate all it has to offer!

27 Rosko St, Seymour

$449,900

3 Beds ⋅ 2 Baths ⋅ 24204990 MLS

Welcome home to this beautifully updated 3-bedroom, 2-bath home, perfectly situated on a level .23-acre lot with a private, fully fenced backyard. Step inside to an expansive living room featuring hardwood floors and a beautiful fireplace. The main level offers an updated kitchen with granite countertops, a dining room, updated hall bath with marble tile, and three spacious bedrooms with hardwood floors. Just off the kitchen, a sunroom provides additional space to relax. The updated walk-out lower level adds approximately 1,000 square feet of additional living space and offers tremendous versatility. Highlights include a large kitchenette with white cabinetry and sleek black stone countertops, an expansive family room with vinyl flooring, home office, updated full bath with stall shower, and a dedicated laundry room. Natural light and direct access to the backyard make this space ideal for extended living, entertaining, or a potential future in-law setup. Outside, enjoy your own private retreat featuring a koi pond, pergola with Jacuzzi, charming farm-style red shed and an oversized carport. Major improvements include a new roof within the past year, newer heating system, updated electrical, and a newer pergola. Offering incredible value with pride of ownership evident throughout, this is a home you won't want to miss!

5 Scott Ave, Seymour

$319,000

3 Beds ⋅ 1 Baths ⋅ 24205554 MLS

Living is easy in this one level updated 3 bedroom Ranch. Renovated in 2018 and truly move-in ready, this home is a smart alternative to a condominium: no association fees, your own yard, and everything on one floor. The open plan includes a stylish kitchen with granite counters and stainless appliances, while beautiful engineered wood floors run throughout, giving this home a clean, current feel from the moment you walk in. Perfect for anyone looking to downsize, as well as a family just getting started - just add your personal touch to make this house your home. Living here is a lifestyle, as the home is set across from the Housatonic River and waterfront community which features boat rentals, riverside restaurants, and nearby parks for walking, paddling, and spending weekend time exploring the outdoors. Next door, a future winery is taking shape adding to the ambiance of the neighborhood. Conveniently located, commuters will love the easy access to Route 8 and Route 84, making getting around a breeze. Don't miss this opportunity!

146 Roosevelt Dr, Seymour

$450,000

4 Beds ⋅ 3 Baths ⋅ 24205563 MLS

Beautifully updated 4 Br, 3 full Bath raised range perfectly located on lightly wooded private 0.5 acres lot. This perfect home offers legal in law apartment with separate entrance, large rear deck for summer gatherings. Truly nothing to doo, just move in.

47 Moss Ave, Seymour

$574,900

5 Beds ⋅ 4 Baths ⋅ 24204272 MLS

Exceptional space, flexibility and privacy await in this charming Colonial, set on 1.3 lightly wooded acres near the Woodbridge line. A true main-level in-law apartment with a private entrance is the standout feature, offering its own kitchen, living and dining areas, bedroom, full bath, and laundry with access to deck for extended family, guests or multigenerational living. In the main home, the eat in kitchen features granite counters, stainless steel appliances, hardwood flooring, generous cabinetry and a sunny breakfast nook. The inviting living room offers a masonry fireplace, abundant natural light and access to the expansive rear deck. Upstairs are four bedrooms, including a spacious primary suite with a private balcony, peaceful views, dressing room, office, walk-in closet, laundry area and full bath with separate glass-enclosed shower. In addition an office, craft room, and a finished walkup attic provides flexible space for a playroom, extra office or bedroom, or storage. Enjoy three decks, an awning and above-ground pool, creating the perfect setting for gatherings and enjoyment. Additional highlights include newer HVAC, unfinished dry lower level for storage, a circular driveway, ample parking and an attached two-car garage. Convenient to commuter routes, shopping, schools, parks, hiking and Seymour's historic district, this distinctive property offers room for everyone and possibilities for every stage of life. *Contingent Upon Seller Finding Suitable Housing*

178 Maple St, Seymour

$579,000

2 Beds ⋅ 2 Baths ⋅ 24203247 MLS

Direct Housatonic River waterfront living! This beautifully updated home is officially recorded as a 2-bedroom, 2-full-bath residence offering 2,104 total sq. ft. of heated living space, including 1,530 sq. ft. above grade plus 574 heated sq. ft. in the partially finished walk-out lower level. Hardwood floors, a renovated kitchen and bright living spaces welcome you inside. Downstairs, one finished room is currently utilized as additional sleeping space, conveniently located beside a full bath and walk-out, while an adjoining room serves as a podcast/media studio. Officially listed as a 2-bedroom, the flexible lower level offers endless possibilities for guests, office, gym, studio or playroom. Outside, over $100,000 in recent deck, patio and river-facing improvements have transformed the waterfront into an incredible extension of the home. Entertain overlooking the river, enjoy quiet mornings by the water or head down to two private docks for direct Housatonic access. A detached 1-car garage, central air, tankless propane hot water and fully owned, paid-off solar panels with no lease or loan to assume add even more value. Extensively improved inside and out, with two private docks and an impressive 120' of direct Housatonic River frontage, this property makes the most of its exceptional waterfront setting.

5 Roosevelt Dr, Seymour

$624,500

2 Beds ⋅ 3 Baths ⋅ 24202554 MLS ⋅ Meadow Brook BLDG.

Welcome to 188 Eastwood Drive, a beautifully updated and impeccably maintained home offering a bright, open floor plan with hardwood flooring throughout both levels. The fully renovated kitchen features extended white cabinetry, quartz countertops, stainless steel appliances, a deep sink, herringbone tile backsplash, under-cabinet lighting and abundant storage. The kitchen opens to the living room with a soaring vaulted ceiling, skylights with automatic shades and a gas-log fireplace framed by custom built-in cabinetry. French doors lead to the four-season sunroom with walls of windows and access to the back deck. A formal dining room provides additional entertaining space. The main-level primary suite includes a walk-in closet and private bath with dual sinks, a tile shower and jetted tub. Upstairs, a versatile loft offers space for a family room and office, along with a spacious second bedroom and full bath. The pristine walk-out lower level provides excellent storage. Extensive updates include new hardwood flooring upstairs, refinished main-level floors, fresh interior paint, updated lighting and hardware, separate second-zone heating and cooling, a high-efficiency gas furnace, upgraded central air and a 16 kW Generac automatic whole-house generator. Move-in ready and truly a must-see!

188 Eastwood Dr Unit 188, Seymour

$490,000

3 Beds ⋅ 2 Baths ⋅ 24203468 MLS

Lovely move-in ready and well-maintained Raised Ranch with 7 rooms 3 bedroom 1-1/2 baths. This clean and modern home awaits a new owner! Many updates have been lovingly done by the current owners including a whole house gutter system; the main level has recently refinished hard wood floors, included in all three spacious bedrooms. There is a fully finished basement and laundry room with vinyl floors, new Wi-Fi washer and dryer with direct access to the garage with electric door openers . The center wall of the living room has beautiful stone wood-burning fireplace with newly done chimney liner and flue as well as dimmable recessed lighting. New Thermopane windows and Thermopane Dining room slider that opens to a large newly painted deck that overlooks a private expansive level lawn with a recently installed firepit to enjoy with your family and friends. Newly remodeled kitchen with granite countertops, stainless steel appliances. Septic was as removed in 2022 and house is now on city water and sewer and a brand newly installed water heater. Hook-up also for fiber internet.

99 Botsford Rd, Seymour

$420,000

3 Beds ⋅ 3 Baths ⋅ 24203187 MLS

Welcome to 80 Silvermine Road in Seymour! This spacious home offers plenty of room and a great opportunity to make it your own. The home could benefit from some updating, and the asking price has been positioned with those improvements in mind, giving the next owner the opportunity to update and add value over time. Situated on a level lot in a quiet, established neighborhood, the property features 3 bedrooms, 3 full baths, a 2-car garage, and propane for cooking . The lower level offers an additional room that provides flexible living space and could be used as a home office, guest room, or potential 4th bedroom. With generous living space and plenty of potential, this home is ready for a buyer to bring their ideas and personal touches. A great opportunity for those looking for space, a level yard, a peaceful neighborhood setting, and the ability to make a home their own. The sale is as is.

80 Silvermine Rd, Seymour

$89,900

24201500 MLS

Great opportunity to build your dream home on this approved building lot situated on over half an acre! The lot is already cleared and ready for your builder to begin. Conveniently located to shopping and highways.

61 Bellevue Ter, Seymour

$130,000

24200063 MLS

Builders take note! Two lots one behind another situated on a private road. There is a standing foundation on one of them that is in poor condition. With a beautiful stream bisecting the two properties and woods that keep you especially hidden, its the perfect location for a secluded getaway right near the heart of Seymour.

72-B Walnut St, Seymour

$115,000

24200283 MLS

Turnkey food service opportunity in a highly visible Seymour location along the New Haven Road retail corridor. This approximately 1,500 SF commercial space is already configured for restaurant/deli use and offers a new operator the chance to step into a fully built-out operation without starting from scratch. The business includes a substantial equipment package featuring commercial refrigeration, deli case, grill and hood system, sandwich and hot-food stations, convection oven, dough machine, freezers, prep areas, slicer, panini presses, coffee station, shelving, seating, and additional kitchen equipment. Current hours of operation are 6:00 AM-3:00 PM, creating clear upside potential through expanded hours, delivery, online ordering, catering, specialty menu offerings, and evening service. Catering is not currently part of the existing sales model, providing an additional avenue for growth. Positioned along the New Haven Road retail corridor near the entrance to the Seymour Industrial Park, the location benefits from proximity to area businesses, employment centers, established residential neighborhoods, and daily commuter traffic. The property sits on approximately 0.35 acres in a C-2 commercial zone, supporting an established food-service use. Ideal for an owner-operator, chef, caterer, or entrepreneur looking for a ready-to-go location with existing infrastructure, equipment, and room to build additional revenue streams. Business opportunity only; real est

132 New Haven Rd, Seymour

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