Seymour Homes under $400,000

Welcome to Seymour, Connecticut—a charming town nestled in the heart of New Haven County! Known for its picturesque landscapes and a strong sense of community, Seymour offers a unique blend of suburban tranquility and easy access to urban amenities. With a rich history dating back to the 1800s, this delightful town boasts beautiful parks, scenic trails, and a vibrant downtown area filled with quaint shops and restaurants.

For those looking to plant their roots in this welcoming community, Seymour offers a variety of homes priced under $400,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find an array of options that cater to diverse lifestyles and needs. From charming single-family homes with spacious yards to modern townhouses with community amenities, there’s something for everyone in this affordable price range.

Living in Seymour means enjoying a peaceful suburban lifestyle while being just a short drive away from the bustling cities of New Haven and Bridgeport. With excellent schools, friendly neighbors, and an array of recreational activities, it’s no wonder that so many are drawn to this hidden gem in Connecticut.

Explore the homes available under $400,000 in Seymour and discover the perfect place to call your own. Experience the warmth of this vibrant community and make your dream of homeownership a reality in this delightful corner of Connecticut!

Newest Seymour Homes under $400,000

$369,900

2 Beds ⋅ 2 Baths ⋅ 24211204 MLS

Welcome to this charming Cape Cod home on a picturesque level .60 acre with 2 car attached garage. Living room & dining room with hardwood flooring, eat in kitchen with wood cabinetry, family room plus office, first floor half bath & laundry. Oil tank in basement. Sump pump in basement (per owner basement gets damp in heavy rain).

22 Tomlinson Rd, Seymour

$209,000

2 Beds ⋅ 1 Baths ⋅ 24208488 MLS ⋅ Balance Rock BLDG.

Welcome to easy, convenient condo living at Balance Rock in the beautiful town of Seymour! This desirable main-level two-bedroom unit offers comfortable and functional living with a galley kitchen, dining area, and spacious living room featuring sliders leading to a private deck,perfect for relaxing or entertaining. The two generously sized bedrooms offer ample closet space, along with a full bathroom. Additional conveniences include a dedicated storage area and on-site laundry facilities located on the lower level. Heat and hot water are included in the HOA, providing added value and convenience. Enjoy an array of community amenities, including an in-ground pool, clubhouse, tennis court, basketball court, and tot/play area. Take a dip in the pool, enjoy the outdoor spaces, or reserve the clubhouse for gatherings with family and friends. The community is pet-friendly for owners. This condo also offers an excellent opportunity for an investor looking to add a rental property to their portfolio, or for a buyer looking to purchase now and potentially rent in the future, subject to HOA rules and regulations. Conveniently located near shopping, restaurants, medical facilities, and major roadways, with easy access to Routes 8 and 67. Whether you're looking for a comfortable home or an investment opportunity, this Balance Rock condo offers a great combination of comfort, amenities, and convenience.

79 Balance Rock Rd Unit 12, Seymour

$389,900

3 Beds ⋅ 1 Baths ⋅ 24207658 MLS

Your search for "one-level living" stops here!! This ranch-style has been remodeled within the last year! It boasts central air and new mechanicals, along with a 2-car detached garage. The walk-up attic is great for storage too! Deeded water/beach rights with dock and play area for tots on water side! The demand for ranch-style homes is greater than the supply and, with this home, just turn the key and move right in!! Nothing left to do but enjoy your new home!

2 Edgehill Ter, Seymour

$389,000

2 Beds ⋅ 2 Baths ⋅ 24207129 MLS ⋅ Valley View Townhomes BLDG.

You'll love this end unit with spectacular valley views. This move-in ready townhouse features an open floor plan, vaulted ceilings, hardwood flooring throughout, kitchen with center island, 2 full bathrooms, spacious loft area currently serving as a living room and home office area, 2-car garage with finished room ideal for a home gym or storage room. Gas heat and central air conditioning. Mudroom entry off garage. Unit owners association with low monthly common charges. Ideal commuter location! Less than 1 mile to train station and Routes 8, 67 and 33. Seymour is an easy commute to New Haven, Waterbury, Stratford. Don't miss this opportunity!

43 George St Unit 1, 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

$399,900

4 Beds ⋅ 2 Baths ⋅ 24197488 MLS

Looking for more space and value? This 4-bedroom, 2-bath Victorian-style Colonial offers over 2,400 square feet, a finished third floor, detached 2-car garage and plenty of flexibility to make it your own. Step inside from the inviting covered front porch to hardwood floors, original moldings, high ceilings and abundant natural light. The spacious eat-in kitchen features newer stainless steel appliances and recessed lighting, while the farmhouse-style dining room and oversized living room provide plenty of room to gather and entertain. The finished third floor offers valuable bonus space for a home office, playroom, guest area or additional living space. Outside, enjoy a landscaped yard, newer paver patio and partially fenced backyard. Central air, public water and sewer, plus convenient second-floor laundry add everyday functionality. Convenient to Route 8, Route 67, shopping, dining and local amenities. A rare opportunity to get over 2,400 square feet, 4 bedrooms and a 2-car garage at an exceptional value in Seymour. Seller is open to reviewing creative financing proposals and flexible purchase structures. Contact listing agent for additional details.

32 Union St, Seymour

$299,900

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. 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

$370,000

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

$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

$374,988

5 Beds ⋅ 2 Baths ⋅ 24188227 MLS

Picture Sunday mornings in the family room, holiday dinners in a separate dining room, and a formal living room set aside for quiet moments or entertaining guests. This 2,310-square-foot Colonial in Seymour offers five bedrooms, with tax records reflecting four legal bedrooms, and two full bathrooms - one on each level - giving every part of the day its own space. Step outside to a large, level yard with room for gardening, play space, or simply open air to enjoy, and a detached garage with a separate work area ready for weekend projects or extra storage. The paid-off solar panels are a quiet, lasting benefit for whoever calls this home next. With space to grow into and make your own, 285 S Main Street is ready for its next chapter. FHA and conventional financing options may open the door for a range of qualified buyers. Come walk through and see how it feels. Please note: The kitchen and bathrooms are outdated, offering the next owner an opportunity to update these spaces over time and make them their own.

285 S Main St, Seymour

$315,000

3 Beds ⋅ 2 Baths ⋅ 24184443 MLS

Move right into this beautifully updated 3 bedroom, 2 bath Cape Cod located in a desirable Seymour neighborhood. Recent improvements include brand new hardwood flooring throughout the main level, new carpeting upstairs, fresh interior paint, updated ceiling fans, and a new oil tank and boiler, providing both style and peace of mind for years to come. The flexible floor plan offers comfortable living spaces filled with natural light and is ideal for owner occupants or investors seeking a turnkey opportunity. Enjoy scenic river views from the backyard, creating a peaceful setting while remaining conveniently close to shopping, dining, parks, and major commuter routes. Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in ready property offers exceptional value in a great Seymour location.

25 Beecher St, Seymour

$305,000

3 Beds ⋅ 2 Baths ⋅ 24172664 MLS

Welcome home to this charming Cape Cod, with a fabulous front porch to rock away your cares. Also, where timeless character meets thoughtful updates. Renovated over the years while preserving its classic appeal, this warm and inviting home truly "feels like home" from the moment you arrive. Start your mornings or unwind in the evenings on the spacious front porch, perfectly suited for rocking chairs and relaxed conversation. Inside, you'll find comfortable living spaces with a natural flow, ideal for everyday living and entertaining alike. The dining room slider opens to a covered patio, creating a seamless indoor-outdoor connection-perfect for summer gatherings or quiet evenings outside. Featuring low-maintenance vinyl siding and replacement windows, many of the important updates have already been taken care of, offering both efficiency and peace of mind. If you're looking for a home with character, comfort, and a welcoming feel, this Cape is not to be missed.

74 Maple St, Seymour

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