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$499,900
3 Beds 3 Baths 24192058 MLS
Hard-to-find 1960s ranch offering timeless craftsmanship, solid construction, and the convenience of true single-level living. Set along quiet Mountain Road in Seymour, the home sits beautifully on a level, tree-lined lot that provides privacy from neighboring properties. Inside, the comfortable floor plan features hardwood floors, oil-fired hot water heat with cast-iron radiators, and a charming stone-front exterior that reflects the quality of its era. The cozy living room includes a bay window and corner fireplace, while the dining room offers another bay window and views of the fireplace. A generously sized kitchen, three well-proportioned bedrooms, and a primary suite with a private full bath provide both comfort and functionality. Thoughtful updates include central air conditioning, a newer roof, replacement windows, and a repointed chimney. The partially finished lower level offers additional space for entertaining, recreation, or hobbies. Step outside to enjoy the peaceful setting, all while being conveniently located near shopping, dining, parks, and major commuter routes. Whether you're just starting, downsizing, or looking for easy everyday living, this delightful home is one you won't want to miss.

125 Mountain Rd, Seymour

$314,900
3 Beds 2 Baths 24190592 MLS
Move-in ready with more space than you would expect, this well-maintained home offers a flexible layout and convenient location. Inside, you'll find a large eat-in kitchen with access to the flat backyard and shed, giving you plenty of room for everyday living, entertaining, and extra storage. The main level features two well-sized bedrooms, a full bath, a spacious living room, and a formal dining room. A bright sunroom/breezeway at the front of the home adds even more usable space and is perfect for relaxing, a home office nook, or plant lovers. Upstairs offers an additional well-sized bedroom along with walk-in attic storage, providing extra flexibility and room to grow. The full basement adds even more value with additional storage space, a full bath, and a one-car garage bay. With public water, public sewer, and easy access to Route 8 and Route 67, this home offers a practical layout with the space and features to fit a variety of needs. HIGHEST AND BEST WEDNESDAY 7/22 12:00 PM

172 Cedar St, Seymour

$699,900
3 Beds 3 Baths 24191421 MLS
***Highest and Best due 7/21 at 5:00pm*** Enjoy scenic views, exceptional indoor-outdoor living, and a home designed for entertaining in this beautiful Seymour property. The heart of the home is a beautiful gourmet spacious kitchen featuring stainless steel appliances, and a unique gas-fired pizza oven, perfect for entertaining family and friends. The open-concept living and dining areas are filled with natural light and feature a stunning stone fireplace and large windows overlooking the surrounding landscape. The home offers comfortable living spaces, updated bathrooms, generous bedrooms, and flexible areas that can accommodate a home office, gym, or playroom. Step outside to an expansive deck overlooking the backyard, where you'll find an above-ground pool with pool house, beautifully maintained landscaping, and peaceful views that can be enjoyed year-round. Whether you're hosting gatherings, relaxing by the pool, or enjoying a quiet evening outdoors, this home offers the perfect setting. Owner is a licensed real estate agent.

70 N Benham Rd, Seymour

$360,000
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

$569,900
3 Beds 3 Baths 24191863 MLS
Welcome to your own private oasis, nestled on a lightly wooded lot at the end of a quiet cul de sac, this beautiful Colonial offers the perfect combination of privacy,space and convenience. Whether you are looking for a peaceful retreat or a home designed for entertaining, this property has it all. Ideally located just minutes from RT 8, you'll enjoy an easy commute both north and south while still feeling tucked away from the hustle and bustle.At the end of the street , Gary Park provides easy access to playgrounds, ball fields and outdoor recreation providing outdoor entertainment. Step inside to a warm and inviting floor plan designed for both every day living and many special occasions. The spacious kitchen opens seamlessly to the family room, creating the heart of the home. Large windows fill the space with natural light, while easy access s to the rear deck makes and indoor-outdoor entertaining effortless. Whether you are hosting summer cookouts, holiday gatherings or simply enjoying your morning coffee overlooking the private backyard, this home offers the perfect setting. For more formal occasions, the elegant living room and dining room low together beautifully, providing flexible space for entertaining guests or enjoying intimate dinners. Upstairs you'll find three generously sized bedrooms with beautiful hardwood flooring throughout,. The second and third bedrooms offer excellent closet space, the third bedroom featuring its own walk in closet.

32 Shari Dr, Seymour

$879,000
4 Beds 3 Baths 24189353 MLS
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

$580,000
3 Beds 3 Baths 24185980 MLS
Welcome to this custom-built contemporary home featuring quality 2x6 construction and beautiful hardwood flooring throughout. Nestled in a private, peaceful setting, the exterior features an impressive 60-foot back deck designed for entertaining, plus two sheds (one powered and ready for a pool setup!). Inside, the spacious kitchen is a chef's delight with endless Corian countertops and a second wall oven. Major updates provide peace of mind, including all-new windows and a basement slider (2023), plus a newer roof (2018). Stay cozy with a pellet stove in the living room and a propane fireplace in the lower-level family room. The unfinished basement area offers incredible workshop or storage potential. Settled in a great neighborhood! See attached for a complete list of highlights and upgrades.

15 Briarwood Dr, Seymour

$475,000
5 Beds 2 Baths 24189350 MLS
Spacious 5-Bedroom Home on a Premium 2.25-Acre Lot! Offering incredible space and versatility, this unique property features 4 upper-level bedrooms and a 5th bedroom on the walk-out lower level-perfect for extended family or guests. Step inside to find classic hardwood floors throughout the living room and bedrooms, charming knotty pine accents, and a sealed fireplace waiting for your personal touch. The heart of the home features an extra-large addition dining room, ideal for hosting large gatherings. Recent updates include a fully renovated full bath (2023), ceiling lights in the rooms, a newer 10-yr +/- roof, and a brand-new water pump (2024). All appliances, including the basement washer and dryer, are included! Mechanically, the home is equipped with central air (older AC unit), oil hot water heat (dual furnaces/dual tanks; note: one tank needs replacement), and a solid main house block foundation. The property serviced by well and septic. Eco-conscious buyers will appreciate the solar panels (lease to be assumed). The exterior is an absolute standout for car enthusiasts, hobbyists, or homesteaders! It boasts an attached 2-car garage, an additional rear-entrance 1-car maintenance garage, and a chicken coop ready for use on the expansive 2.25-acre grounds. With a walk-out lower level and endless potential, this property is being sold as-is and is ready for your vision. Subject to seller finding and closing on home of choice.

67 Botsford Rd, Seymour

$279,900
3 Beds 1 Baths 24187711 MLS
24 HOUR NOTICE to see this Charming Ranch Home with Outdoor Living, Storage, and Commuter Convenience, Come see this inviting 918-square-foot ranch home offering comfortable one-level living and a practical layout with five rooms, including three bedrooms. A wonderful condominium alternative, this home provides the privacy, outdoor space, and flexibility of a single-family property without feeling overwhelming. Step outside to enjoy the deck, fenced yard ideal for pets, and a 16-foot above-ground vinyl pool-perfect for relaxing, entertaining, or making the most of warm-weather days. Located near the Housatonic River, the property offers a pleasant setting with convenient access to commuter routes, making daily travel easier while still enjoying the benefits of a neighborhood feel. Additional features include off-street parking, laundry, a pull-down attic for extra storage, and a basement with workshop and storage space. Whether you are downsizing, purchasing your first home, or seeking an affordable alternative to condominium living, this ranch offers a great combination of comfort, convenience, and usable space. NOTE: Refrigerator will be replaced.

117 Squantuck Rd, Seymour

$499,900
4 Beds 3 Baths 24155474 MLS
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 needs repair). 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.

30 Bunting Rd, Seymour

$449,900
4 Beds 3 Baths 24188026 MLS
Welcome to 123 Pearl Street - a breathtaking Victorian-style residence in the heart of Seymour, where timeless architectural charm meets modern luxury living. This magnificent home has been thoughtfully and completely updated / remodeled throughout, preserving its original character while offering every contemporary comfort today's owner expects. From the moment you arrive, the steeply pitched rooflines, ornate gingerbread trim, and inviting front porch announce the home's Victorian heritage. Step inside to discover soaring ceilings, rich millwork, beautiful turret and light-filled rooms that flow seamlessly for both everyday living and elegant entertaining. All the amenities of modern living with the charm of a classic Victorian. Bedrooms are all generous in size and the the home has a beautiful primary bedroom suite with an large bathroom and walk-in closet space. Potential: This home offers excellent two-family conversion potential - a rare opportunity for investors, multi-generational families, or buyers seeking rental income to offset their mortgage. Conveniently located with easy access to major commuter routes, train and downtown - this is the rare home that truly has it all. Seller is an agent

123 Pearl St, Seymour

$550,000
4 Beds 3 Baths 24187240 MLS
Wonderful opportunity at this 4 bedroom 3 full bathroom Cape located on the southern end of Seymour. From the foyer, the formal living and dining rooms are spacious and offer gleaming hardwood floors. The interior of the home has just been refreshed with new paint and carpets. The kitchen includes lots of cabinet and work space as well new quartz counter tops. The kitchen is open to the huge great room with vaulted ceilings wood burning fireplace and a slider to the deck. The main level also includes a full bath and the 4th bedroom/office. Upstairs is a primary bedroom suite with full bath that has a brand new vanity with stone top. Down the hall two more bedrooms and a third full bath. The basement is large and has high ceilings, offering additional finished space potential. All of this spread over 3100 sq/ft and a private backyard!

53 Holbrook Rd, Seymour

$650,000
5 Beds 5 Baths 24185373 MLS
Opportunity knocks! Been looking for a terrific house with an ideal in-law setup? This one checks all the boxes! Fabulous neighborhood, and huge, gorgeous 2.53 acre yard that extends far beyond the stone wall onto the woods for endless exploration and adventures! Plenty of space for everyone here, too. Choice of two home offices, one on the main level and another in the walk out lower level. Open concept living and dining area with double bay windows and gas fireplace in the living room. Walk in pantry in the eat in kitchen.Head on upstairs to your spacious primary bedroom with walk in closet and gorgeous remodeled full bath. Three more bedrooms up here share the full bath for a total of 4 bedrooms in the main house. Separate laundry room on 2nd floor keeps that chore simple! Head downstairs to the enormous walk out lower level where you will find a front to back family room with that second office. Sliders lead to your gorgeous yard complete with double patios and a wonderful above ground pool for loads of summer fun! Two story inlaw apartment with beautiful remodeled kitchen, also open floor plan with combination living room/dining area. Full bath with full size washer and dryer complete the main level. Head downstairs to your super sized bedroom with half bath and triple closets for plenty of storage. Walk out to your own patio. Two car attached garage plus huge 3 car detached garage for all your cars and toys! Solar on home and garage save you money on your electric bill!

29 Evergreen Ter, Seymour

$699,900
3 Beds 3 Baths 24184605 MLS
Welcome home to this beautifully maintained younger Colonial perfectly situated in a sought-after neighborhood. Offering 4 spacious bedrooms and a versatile recreation room. This home provides plenty of space for today's lifestyle, whether you need a home office, playroom, media room or a guest space. The thoughtfully designed floor plan features generous living areas, abundant natural light, and comfortable spaces for both everyday living and entertaining. The sun-drenched eat-in kitchen opens to inviting gathering areas, creating the perfect setting for family and friends. Upstairs, you'll find four generously sized bedrooms, including a spacious primary suite, along with the flexible recreation/bonus room that adds valuable extra living space. Pride of ownership is evident throughout, making this home truly move-in ready. Outside, enjoy the beautifully maintained grounds and the benefits of living in a welcoming neighborhood close to schools, shopping, dining, parks and commuter routes. A rare opportunity to own a meticulously cared-for Colonial that combines space, comfort, and an exceptional location. Don't miss it!

9 Osprey Dr, Seymour

$324,500
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

$649,900
4 Beds 3 Baths 24175013 MLS
Bring the whole family-and the extended family too! This completely remodeled grand Colonial sits on sprawling, park-like grounds and offers the perfect blend of charm and modern new conveniences. The property features a detached three-car plus garage with storage room and work area, a large in-ground pool surrounded by a new paver patio, expansive lawn space for recreation, and a covered outdoor entertaining area with a cozy exterior fireplace. Renovated from top to bottom, the home boasts all new mechanicals, a new driveway, and new garage doors. Inside, spacious rooms abound, beginning with a stunning chef's kitchen featuring new cabinetry, quartz countertops, tiled backsplash, updated lighting, and new appliances. The classic dining room with a bay window flows seamlessly into the oversized living room highlighted by abundant windows and recessed lighting. A bright study overlooking the pool provides an ideal home office or reading retreat. Upstairs, you'll find three generously sized guest bedrooms along with an enormous primary suite complete with a fireplace, walk-in closet, and private full bath. All three full bathrooms have been beautifully remodeled. Gorgeous views from a wrap around second level porch accent the architecture. Please see Agent-to-Agent remarks prior to submitting an offer.

40 Church St, Seymour

$399,999
3 Beds 2 Baths 24179444 MLS
Versatile 3-bedroom, 1.5-bath home currently configured as a single-family residence while offering multifamily zoning potential. This character-filled home features a cozy living room with a wood-burning stove, updated electrical, central air, and a flexible layout offering potential for in-home daycare use with ample off-street parking. Enjoy the fenced-in backyard complete with a concrete patio and outdoor fire pit, creating the perfect space for relaxing, entertaining, or enjoying outdoor gatherings. The basement includes a laundry setup adjacent to a large workshop space featuring direct exterior access, ideal for contractors, hobbyists, or storage, while the framed-out attic provides additional storage or future finishing possibilities. Conveniently located minutes to Route 8, the Seymour train station, downtown shopping and dining, local restaurants, the neighborhood deli, and a nearby ice cream shop, this property combines convenience with the charm of small-town Seymour living. A unique opportunity offering flexibility, functionality, and potential all in one. Don't miss out!

150 Pearl St, Seymour

$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

$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

$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

$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

$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

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