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$330,000
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
$452,900
3 Beds ⋅ 2 Baths ⋅ 24175200 MLS
Charming Raised Ranch 7 rooms 3 bedroom 1-1/2 baths. This spacious home awaits a new owner! The Upper level has hardwood flooring throughout plus 2-stylights and Anderson Windows. Fully finished lower level with brick fireplace plus 1/2 bath & laundry. This can easily become extended family living space! Living room has a functional wood stove, Dining Room -slider opens to large trek deck with pergola, Kitchen fully applianced with oak cabinets, Granite counters and a skylight. Lower level Fmly Rm can be versatile, use for extended family- home office, gym, or playroom. Boiler is 8yrs old Close to everything -Schools, Shopping Churches ,Restaurants & Hospital. It's an easy commute by train or highway to all points. Relax and enjoy the private rear yard or towns parks great for hiking or mountain biking. This season be a participant or spectator at our local sporting events, Sold as is!

14 Poplar Dr, Seymour
$539,900
4 Beds ⋅ 2 Baths ⋅ 24162007 MLS
Tucked away on a quiet cul-de-sac and surrounded by the peaceful feel of nature, this spacious 4-bedroom, 2 full bath raised ranch offers the perfect balance of privacy and convenience. With generous living space throughout, the main level features a bright and welcoming flow between the living room, dining area, and kitchen-ideal for everyday living and gathering with ease. The finished lower level provides additional versatile space, perfect for a home office, rec room, or whatever suits your lifestyle. Step out from the dining area onto your deck overlooking a beautiful yard-an ideal setting to relax, entertain, or simply enjoy the outdoors. An oversized two-car garage adds even more functionality with plenty of room for storage, hobbies, or workspace. Thoughtfully maintained with a newer roof (2018), this home is move-in ready and offers peace of mind. Conveniently located just minutes from Route 8 and Route 67, you'll enjoy easy access to shopping, dining, and commuting while still coming home to a quiet, tucked-away neighborhood. A rare opportunity to own a home that truly offers space, setting, and location.

29 Evening Star Dr, Seymour
$145,000
24174675 MLS
Resting on a quiet dead-end street, 5 Bungay Terrace offers a rare opportunity to create something truly special in one of Seymour's established residential neighborhoods. Imagine mornings with coffee on your future front porch as deer wander nearby, all while being just minutes from downtown conveniences and major commuter routes. This cleared and gently sloping site blends peaceful suburban living with everyday practicality. Public water, sewer, electric, and cable are available at the street, making the path to building your dream home even more convenient. Sidewalk-lined main roads connect the neighborhood to nearby schools, parks, ball fields, and the Seymour train station with access to New York City. Whether you envision a cozy custom ranch or a modern farmhouse, this property provides the perfect canvas. Surrounded by a community investing in its future through infrastructure improvements and new school development, 5 Bungay Terrace is more than just land; it's a chance to put down roots in a town known for its charm, convenience, and sense of community. Rarely does the last available lot on a dead-end street become available. Here is your opportunity to build not just a house, but a lifestyle. Do not walk the property without a confirmed appointment. Seller does not have a survey. Sale to convey as-is. Buyer to perform due diligence.

5 Bungay Ter, Seymour
$585,000
2 Beds ⋅ 2 Baths ⋅ 24173848 MLS
Experience waterfront living at its finest in this exceptional DIRECT WATERFRONT home on the beautiful Housatonic River. Offering a rare combination of a private sandy beach, two floating docks with room for up to four boats, and breathtaking water views, this property is perfect for boating, kayaking, fishing, or simply relaxing by the river. The outdoor space is designed for entertaining with expansive Trex decking, floating walkways, a hot tub overlooking the water, gazebo, raised garden beds, and a beautifully landscaped yard. An oversized detached garage, additional one-car garage, lean-to, and pull-through driveway provide exceptional storage and parking for vehicles, boats, and recreational equipment. Inside, the bright and inviting 2-bedroom, 1.5-bath home features an open-concept layout filled with natural light, recessed lighting, tinted windows, and custom blinds. The kitchen flows seamlessly into the living area, creating an ideal space for everyday living and entertaining. Recent updates include a metal roof, siding and mini-split heating and cooling systems (2017), and a Blaze King wood stove (2023). The finished lower level offers additional living space with a propane stove, electric heat, and plenty of storage. Whether you're looking for a year-round residence or a weekend retreat, this one-of-a-kind waterfront property offers the perfect blend of comfort, recreation, and unforgettable riverfront views.

3 Roosevelt Dr, Seymour
$334,900
3 Beds ⋅ 2 Baths ⋅ 24173618 MLS
Beautifully maintained and full of charm, 3-bedroom, 1.5-bath Cape-style single-family home with garage in Seymour offers comfort, functionality, and timeless appeal. Featuring gleaming hardwood floors throughout much of the home and newer windows that provide abundant natural light and improved energy efficiency, this inviting property is ready for its next owner. A spacious layout offers comfortable living areas perfect for everyday living and entertaining alike. Step outside to enjoy the deck, ideal for relaxing evenings, outdoor dining, or hosting guests. A mostly finished basement provides valuable extra living space with endless possibilities for a family room, home office, gym, or recreation area, while the separate private laundry area adds practicality and organization. Conveniently located near local shopping, restaurants, parks, and commuter routes, this charming home combines classic New England character with modern updates in a desirable location. Don't miss the opportunity to make this wonderful property your next home!

205 S Main St, Seymour
$474,900
2 Beds ⋅ 3 Baths ⋅ 24173449 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: June 30. A rare opportunity to own a home in a vibrant new community featuring two pickleball courts and a beautifully designed fire pit area.

44 Micko Dr, Seymour
$477,000
2 Beds ⋅ 3 Baths ⋅ 24172754 MLS ⋅ Ridge View Townhomes(Pending Verification) BLDG.
This impeccably built, recently completed 2 bed/2.5 bath townhouse offers a unique combination of modern, customizable design, premium upgrades, quality 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: July 22. A rare opportunity to own a home in a vibrant new community featuring two pickleball courts and a beautifully designed fire pit area.

46 Micko Dr, Seymour
$749,900
4 Beds ⋅ 3 Baths ⋅ 24172332 MLS
BROOKFIELD ESTATES, Beautifully maintained and updated for 2026, this move-in-ready 4 bedroom 2.5 bath home sits on 1.08 acres and features 3142 s.f. of living space offering exceptional layout on generous scale. A bright, spacious foyer welcomes you with 9-foot ceilings throughout the main level. The heart of the home features a gourmet kitchen complete with granite countertops and brand-new appliances, flowing effortlessly into dining and living spaces. Unwind in the spacious family room, anchored by a dramatic 15-foot ceiling and a pristine, never-been-used fireplace. Upstairs, the spacious primary suite serves as a private sanctuary with 12-foot ceilings, a walk-in closet, and a spa-like bath. Three additional well-sized bedrooms offer total flexibility for family, guests, or a home office. No detail was spared in the recent top-to-bottom refresh, including fresh paint, brand-new doors and hardware, and modern cabinet fixtures throughout. The walk-out basement has painted floors and new French doors leading to your private oasis. Outside, the professionally designed and maintained landscaping backs up to serene, protected open space for privacy. Equipped with a pre-installed sprinkler system and security cameras, this property offers ultimate peace of mind. Located just minutes from downtown Seymour shopping, dining and all major highways. City water and sewers will keep your life flowing smoothly!

51 Brookfield Rd, Seymour
$39,592,000
317 Baths ⋅ 24166209 MLS
214-unit apartment portfolio with 5 Commercial units operating at approximately 97% occupancy, delivering immediate, durable cash flow from day one with virtually no lease-up risk. The assets are fully stabilized, professionally operated, and performing at the top of the market-providing a secure in-place income stream.

39 New Haven Rd Unit 8, Seymour
$499,900
3 Beds ⋅ 3 Baths ⋅ 24165961 MLS ⋅ Ridge View Townhomes(Pending Verification) BLDG.
This impeccably built, soon-to-be-completed 3 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. Two 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 7th. A rare opportunity to own in a vibrant new community featuring pickleball courts and a beautifully designed fire pit area.

65 Micko Dr, Seymour
$499,000
3 Beds ⋅ 2 Baths ⋅ 24164590 MLS
Welcome everyone to this 3 bedroom, 2.5 bath home located in the highly desirable Great Hill area of Seymour. This inviting property offers a wonderful blend of comfort, space, and convenience- perfect for today's lifestyle. Step inside to find a great layout featuring beautiful hardwood floors with a bright living room with a fireplace , dining room, spacious kitchen that seamlessly flows into a stunning sun room. Filled with natural light, the sun room leads out to an over sized deck and overlooks the beautiful, flat, and fully usable back yard-ideal for entertaining, gardening, or simply relaxing. You'll find a great finished lower level which provides additional living space with a full bath- perfect for a family room, home office or gym.This home has been lovingly cared for and offers both functionality and charm at every turn. Conveniently located close to schools, shopping, restaurants, train station and highways.This home is a commuters dream while still offering a peaceful neighborhood setting. Don't miss the opportunity a little TLC to make this wonderful home yours!!

9 Stanley Dr, Seymour
$579,000
6 Beds ⋅ 4 Baths ⋅ 24162082 MLS
Welcome to your dreaming and beautifully preserved single family Brick Colonial House, initially built in 1911 and remodeled in 2019, blending timeless charm with modern fashion. This home is bathed in natural light from oversized windows, complemented by soaring over 9 ft ceilings. The first floor showcases an open living room with exposed beams and a fireplace, an eat-in kitchen, a half bath, and a versatile dining area that could easily serve as a bedroom. Natural light enhances the warmth and appeal throughout. Upstairs, you'll see three spacious bedrooms and a full bath, all filled with abundant light. The master suite includes a generous layout with a walk-in closet, dressing area, and private full bath. The third floor introduces two newly finished bedrooms and an added full bath. The 2019 updates include a high-efficiency furnace, central air, new architectural roof, gutters, high-end stainless-steel appliances, hardwood floors, and fully renovated baths with designer finishes. Additional upgrades from the current owner feature a privacy fence with double gates leading to the 2-car garage, an above-ground pool, crown molding throughout, a new retaining wall, and a gutter downspout system. This home is ideal for large families or anyone looking for extra space to live, work, and relax. Enjoy outdoor gatherings, backyard fun, and the comfort of a solid, beautifully built home.

26 Union St, Seymour
$729,900
8 Beds ⋅ 4 Baths ⋅ 24148310 MLS
Excellent investment opportunity in a prime location! This well maintained 4 family property sits on a corner 1acre lot and offers a true turnkey experience for investors. Featuring city water and sewer, separate entrances and utilities, and off street parking, this asset is designed for easy management and long term stability. The building includes four basement storage units plus a walkup attic for additional storage, providing valuable extra space for tenants or owner use. Located on the bus line and just moments from the Sochrin Pond walking trail and dog park, the property offers convenience and lifestyle appeal. Current long term tenants are significantly under market rent, presenting immediate upside potential for the next owner. Initial showings will include Apartment 2 and the basement.

387 S Main St, Seymour
$99,000
24160206 MLS
Wonderful opportunity to purchase a turn key business! This Subway is situated right on Route 67, and is also conveniently located close to Route 8, maximizing exposure to a constant flow of traffic. Approximately 20,000 vehicles travel that stretch of Route 67 DAILY!! Rent is currently only $1,538/month with $400 additional for common charges. This location underwent an $86,000 renovation in recent years. Perfect space to open up your OWN small business or be a part of an established franchise. Great visibility and ample parking in the lot next to the building. Motivated seller!

78 Bank St, Seymour
$1,800,000
24093806 MLS
A preliminary design has been created for a 115 unit townhouse conceptual development, offering tremendous potential for a higher-density project. Approved 20-Lot Residential Subdivision. 20 Single-family lots with city water and sewer. Nestled in a wooded setting just minutes from Route 8, this location offers excellent schools and commuter convenience. Approximately 1,800 feet of road is already roughed in-averaging under 100 feet per lot-making the layout efficient and cost-effective. Engineering plans, reduced bonding details, and copies of approvals are available upon request. A shovel-ready opportunity with multiple paths forward!

50 Bissell Pl, Seymour
$159,900
24078049 MLS
Building lot located in the Mountain Rd and Bungay area on Frances Drive. Build your dream home here or save as a future investment. This lot has access to city sewer and water located on the street. Your new home will be located close to all conveniences such as shopping, banking, restaurants, medical facilities, schools, health clubs, bars, coffee shops and much more. Close to RT. 67 ,RT 8 and RT 15. Come make Seymour your future home!!!

22 Frances Dr, Seymour

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