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$319,000

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!

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

$574,900

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*

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$624,500

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!

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$530,000

Welcome to 2 Westerman Avenue--- a two-family home for an investor or owner-occupants looking to offset their mortgage payments. This 4/4 two-family has the potential of an additional 900 s.f. of extra living space with the spacious walk-up attic. Both apartments offer washer-dryer set-ups in bright laundry areas. Relax on the deck/front porch and enjoy the seasons! Conveniently located on bus route with plenty of off-street parking. If you want to live in one unit while a tenant in the other unit helps pay the bills, this is a great opportunity! For the investor, these units are move-in ready to rent!

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24198367 MLS

Welcome to 2 Westerman Avenue--- a two-family home for an investor or owner-occupants looking to offset their mortgage payments. This 4/4 two-family has the potential of an additional 900 s.f. of extra living space with the spacious walk-up attic. Both apartments offer washer-dryer set-ups in bright laundry areas. Relax on the deck/front porch and enjoy the seasons! Conveniently located on bus route with plenty of off-street parking. If you want to live in one unit while a tenant in the other unit helps pay the bills, this is a great opportunity! For the investor, these units are move-in ready to rent!

2 Westerman Ave, Seymour

$349,900

***Highest and Best offers due 12:00 p on Tuesday 8/18. Welcome home to this charming 3-bedroom, 1.5-bath one-level Ranch offering easy, comfortable living in the desirable Great Hill area. This 1,150 sq. ft. home features hardwood floors throughout beneath the carpeting, central air, a newer roof, and a functional floor plan ready for your personal touches. Set on a .31-acre lot, the property boasts a gorgeous, private backyard surrounded by mature plantings, creating a peaceful outdoor retreat. A large deck provides the perfect setting for entertaining, outdoor dining, or simply relaxing and enjoying the beautiful surroundings. A two-car under-house garage offers plenty of parking and additional storage. Well-loved and full of character and potential, this home presents a wonderful opportunity for first-time buyers or anyone looking to make a home their own. Ready for its next chapter!

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24197853 MLS

***Highest and Best offers due 12:00 p on Tuesday 8/18. Welcome home to this charming 3-bedroom, 1.5-bath one-level Ranch offering easy, comfortable living in the desirable Great Hill area. This 1,150 sq. ft. home features hardwood floors throughout beneath the carpeting, central air, a newer roof, and a functional floor plan ready for your personal touches. Set on a .31-acre lot, the property boasts a gorgeous, private backyard surrounded by mature plantings, creating a peaceful outdoor retreat. A large deck provides the perfect setting for entertaining, outdoor dining, or simply relaxing and enjoying the beautiful surroundings. A two-car under-house garage offers plenty of parking and additional storage. Well-loved and full of character and potential, this home presents a wonderful opportunity for first-time buyers or anyone looking to make a home their own. Ready for its next chapter!

5 Oak Hill Rd, Seymour

$319,900

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.

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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

$320,000

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.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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