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178 Maple St, Seymour
$554,900
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.

178 Maple St, Seymour

102 Colony Rd, Seymour
$419,000
3 Beds ⋅ 2 Baths ⋅ 24198641 MLS
A well-maintained 3-bedroom, 1.5-bath raised ranch tucked away on one of Seymour's most established residential streets - private, quiet, and completely secluded from the outside world. The layout delivers comfortable single-family living across two levels, with a 2-car attached garage adding everyday convenience. Radiant heat with individual thermostats in each room allows for customized temperature control, helping you heat only the spaces you need for added comfort and energy efficiency. The backyard is the standout - a spacious, versatile outdoor area currently set up for basketball and recreation, offering plenty of possibilities for active families, entertaining, or creating your own outdoor retreat. A home that checks every box for anyone who wants room, privacy, comfort, and a lifestyle the neighborhood fully supports.

102 Colony Rd, Seymour

32 Union St, 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

108 Buckingham Rd, Seymour
$789,900
4 Beds ⋅ 3 Baths ⋅ 24195157 MLS
To be built. Similar to image shown. Enjoy the benefits of watching your home be built from start to finish. Experience the perfect blend of quality craftsmanship and modern design in this exceptional new construction home by a well-known, respected builder. Thoughtfully designed with today's lifestyle in mind, this beautiful home will feature 4 spacious bedrooms, 2.5 baths, a 2-car garage, rear deck, front porch and upper level laundry room. The desirable main-level primary suite offers comfort and convenience, while the open-concept floor plan is ideal for both everyday living and entertaining. The kitchen and bathrooms will showcase elegant granite or quartz countertops, complemented by beautiful hardwood flooring throughout. Take in the great view of the Housatonic River from the wonderful front porch. 2x6 construction, built with attention to detail, quality finishes and optional Geothermal system. This is a rare opportunity to own a brand-new home at a great price.

108 Buckingham Rd, Seymour

169 Derby 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

4 Mead Farm Rd, Seymour
$889,000
4 Beds ⋅ 3 Baths ⋅ 24189353 MLS
Agent Owned. Classic 4 bedroom, 2 and a half bath home nearing completion. This home features a large eat-in country kitchen with granite countertops and a large center island, opening up to spacious family room with gas fireplace. French doors provide access to the deck over-looking the backyard and a private undeveloped area, in addition to the wrap-around front porch at overlooks the private front and side yard The connection to the dining room offers a small butler's pantry for ease and convenience for entertaining. Access into the home from the 2-car garage is through a large mud-room and an adjacent half bath. There is another deck off of the back of the mudroom. Upstairs there is a large MBR with a sitting area, generous master bath and 2 walk-in closets with a dressing room. The other 3 bedrooms all feature walk-in closets and share a hall bath with a double sink. The laundry is also located upstairs and features a large tub, as well as the washer and dryer. The pull-down stairs to the attic is also located in the laundry room The enormous (in excess of 1000 sf) walk-out lower level is finished and has sliders to a patio in the backyard.

4 Mead Farm Rd, Seymour

30 Bunting Rd, Seymour
$449,900
4 Beds ⋅ 3 Baths ⋅ 24155474 MLS
2 HOUSES IN ONE!! INLAW, IN LAW SUITE... Step inside this 11-room, 4-5 bedroom home with In-Law apartment on a prime corner lot!! Hardwood floors and cool breeze of central air conditioning. This house offers space for everyone, including a full in-law apartment perfect for extended family. Downstairs, you will find a spacious two-car garage. Lots of Storage!! Floored Walk-Up Attic. Great Workshop space for your next project, BRING YOUR TALENTS.. Private patio for relaxing barbecues (Roof has been repaired). The location is truly unbeatable steps away from the fun at Legion Pond Park, one block close to Chatfield-LoPresti Elementary School. Easy commuting, shopping, local restaurants, and major highways. Perfect blend of space, comfort, and convenience. Subject to Probate Approval. Photos digitally altered / staged to see the vision for this diamond to shine ! Bones are there, now make it yours !

30 Bunting Rd, Seymour

285 S Main St, Seymour
$329,988
5 Beds ⋅ 2 Baths ⋅ 24188227 MLS
Investors and owner-occupants welcome - motivated seller! Spacious Colonial on a level .36-acre lot in Seymour, now priced to sell. 2,310 sq ft above grade plus a full 1,260 sq ft basement and walk-up attic. Tax records reflect 4 legal bedrooms; home is currently used as 6 bedrooms. Possible in-law setup: main level has two bedrooms, a full bath, eat-in kitchen, formal living room, separate dining room, sun room, and a separate entry. Four more bedrooms and a second full bath upstairs. Paved driveway with parking for 6 cars plus a detached garage with workshop space - room for every vehicle, trailer, or weekend project. Paid-off solar panels (no lease, no payments) help keep electric costs down. Public water and sewer. Solid, livable home: move in or rent out now and update the kitchen, baths, and finishes on your own timeline. Conventional financing welcome, FHA possible, and renovation loans (203(k)/HomeStyle) are an option. Seller is motivated and ready to review all offers. Minutes to Route 8, downtown Seymour, and the Metro-North Waterbury line.

285 S Main St, Seymour

25 Beecher 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

74 Maple St, Seymour
$295,000
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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