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35 Cogwheel Ln, Seymour
$1,200,000
24125956 MLS
Approved 51-unit apartment building site. See attached FLYER for details.

35 Cogwheel Ln, Seymour
130a Mountain Rd, Seymour
$750,000
4 Beds ⋅ 3 Baths ⋅ 24170964 MLS
Welcome to this stunning brand new construction home, thoughtfully designed for today's lifestyle and built to offer years of worry-free living. From the moment you enter, you're greeted by a bright, open-concept main level that effortlessly blends the living room, dining area, and kitchen into one expansive, airy space. With everything completely new-from systems to finishes-you can enjoy peace of mind knowing it's all built to last. The kitchen is the heart of the home, featuring brand new stainless steel appliances, an oversized center island, and abundant cabinetry-perfect for cooking, gathering, and entertaining. A built-in wine or coffee bar with its own refrigerator adds both charm and functionality. The main level also offers a dedicated home office, a convenient half bath, and easy access to a private deck, creating the perfect setup for indoor-outdoor living. A spacious two-car garage provides added convenience and storage. Downstairs, the fully finished lower level adds nearly 1,000 square feet of versatile living space-ideal for a extra room, playroom, or home theater. Upstairs, you'll find four spacious bedrooms, each complete with walk-in closets. The primary suite is a true retreat with a large walk-in closet and a private full bath. An additional full bathroom and a second-floor laundry room add everyday ease. Enjoy the benefits of brand new construction-modern design, energy efficiency, and minimal maintenance-making this home as practical as it is beautiful.

130a Mountain Rd, Seymour
51 Brookfield Rd, 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
22 Brookfield Rd, Seymour
$747,000
4 Beds ⋅ 3 Baths ⋅ 24137414 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial located in the highly desirable Brookfield Estates! Step into the impressive two-story foyer featuring an elegant chandelier with electric lift. The main level offers a spacious kitchen with an abundance of cabinetry, granite countertops, center island, and stainless steel appliances. The open-concept dining area flows seamlessly into the inviting family room with a cozy fireplace-perfect for relaxing on chilly evenings. Sliders lead to a large two-tier deck with a retractable awning and an above-ground pool, ideal for summer entertaining. The level yard includes a shed for additional outdoor storage.The first floor also features gleaming hardwood floors throughout, a formal dining room with tray ceiling, a private study/home office, and a convenient half bath. Upstairs, the massive primary suite impresses with a tray ceiling, luxurious full bath with Jacuzzi tub, separate shower, and a generous walk-in closet. Three additional spacious bedrooms, a full hall bath, and a separate laundry room complete the second level. The lower level includes a media room, fitness area, and ample storage space. Additional highlights include a two-car attached garage, central air, and meticulous upkeep inside and out. This wonderful home offers comfort, space, and style-an incredible opportunity to own in one of the area's most sought-after neighborhoods!

22 Brookfield Rd, Seymour
7 Old Town Rd, Seymour
$740,000
4 Beds ⋅ 3 Baths ⋅ 24160603 MLS
Entertainers Dream! Welcome to this gorgeous colonial on a beautiful level interior lot. Main level offers a nice layout with a two-story foyer and vaulted ceilings. Hardwood floors thru-out the house and freshly painted. Formal living room with a fireplace open to a huge kitchen with plenty of cabinet space and stainless-steel appliances Family room with vaulted ceiling. Office/den on main level with plenty of natural light. French doors leading to formal dining room. Laundry room and full bath complete first floor. Second floor we have four bedrooms two full baths. Lots of closet space thru the house. Theres also a fully finished basement with a full bath. Three car garage with lots of off-street parking. Back yard is ready to entertain family and friends with an above ground pool an outdoor kitchen a hot tub and a sauna. All of this on over three acres of level land on a cul-de-sac. Don't miss out on this beauty!

7 Old Town Rd, Seymour
28 Osprey Dr, Seymour
$735,000
4 Beds ⋅ 4 Baths ⋅ 24165206 MLS
Welcome to 28 Osprey Drive, a beautifully maintained colonial with a standout in-law suite, set in one of Seymour's most desirable neighborhoods, surrounded by newer homes and quiet, family-friendly streets. Situated on just under an acre of level land, this property offers the perfect balance of space, privacy, and neighborhood charm-complete with a lovely in-ground pool ideal for summer enjoyment and entertaining. Inside, you'll find almost 3,500 square feet of well-appointed living space, featuring a freshly painted interior and numerous updates throughout. The main home offers three generously sized bedrooms, including a modern and well-appointed primary suite. The inviting living room showcases a cozy fireplace, while the four-season sunroom provides a bright and versatile space to relax and enjoy the changing seasons year-round. A true highlight of this home is the exceptional in-law suite, thoughtfully designed with its own private entrance. Ideal for multi-generational living, it includes a spacious eat-in kitchen, a large primary bedroom, and the added convenience of a chairlift for accessibility. With its combination of size, flexibility, outdoor amenities, and prime location, this home presents an outstanding opportunity. Competitively priced and move-in ready, 28 Osprey Drive is expected to attract strong interest-schedule your showing today.

28 Osprey Dr, Seymour
4 Nickel Mine Dr, Seymour
$727,272
4 Beds ⋅ 4 Baths ⋅ 24119664 MLS
Exceptional custom-built Colonial Farmhouse offering timeless charm privately nestled on .95 acres backing up to the scenic Greenway & Nickelmine Brook. Built in 2006 & meticulously maintained, this spacious 4-BR, 3.5-BA home features over 3,600 sq ft of living space, including 700 sq ft of finished space in the lower level. A wrap-around front porch welcomes you into a bright, open layout w/ hardwood flooring, french doors to the porch, & a formal dining room w/ elegant wainscoting & tray ceiling-perfect for entertaining. The spacious family room boasts cathedral ceilings & a propane fireplace, creating a warm, airy atmosphere. The chef's kitchen is both functional & inviting with granite countertops, a large island, abundant cabinetry & premium appliances. A walk-in pantry sits just off the mudroom/laundry area with utility sink. Double sliders lead to a 12x30 back deck overlooking the professionally landscaped, private yard. Upstairs, the luxurious primary suite includes a walk-in closet & spa-like bath with soaking tub & separate shower. Finished walk-out lower level is ideal for guests or multigenerational living w/ a full bath, kitchenette, private entrance, storage & dedicated workshop. Add'l highlights: propane heat, new central A/C, solar panels, 20kW generator, tankless water heater, 500-gal buried propane tank, security system, invisible fence, auto irrigation, 3-car garage & 10x15 shed. This is a truly move-in ready home you won't want to miss!

4 Nickel Mine Dr, Seymour
70 N Benham Rd, Seymour
$725,000
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
387 S Main St, Seymour
$710,000
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
12 Forest Rd Extension, Seymour
$705,000
4 Beds ⋅ 3 Baths ⋅ 24194604 MLS
Tucked away on just over an acre of beautifully secluded property, this move-in ready home offers the perfect blend of privacy, space, and comfort. Enjoy your own backyard oasis featuring a heated in-ground pool with a NEW pool liner, a spacious patio surrounding the pool, and a deck that walks right out from the back of the home-creating the perfect setup for entertaining, relaxing, or making memories with family and friends all summer long. Inside, the open-concept layout seamlessly connects the kitchen, dining area, and living room, creating an inviting space for everyday living. A first-floor office with custom built-ins offers endless flexibility for working from home, a playroom, library, or hobby room. The oversized primary suite features ample closet space and a private full bath. Three additional generously sized bedrooms provide room for everyone, including an exceptionally large fourth bedroom with a spacious walk-in closet. With 2.5 bathrooms, a finished lower level, and tasteful finishes throughout, this home is clean, well maintained, and truly move-in ready. Recent updates include a NEW roof, NEW front porch, newer furnace and garage doors, a NEW pool liner and a pool patio. An oversized two-car garage and two storage sheds provide abundant room for vehicles, tools, toys, and extra storage. If you've been searching for privacy, modern updates, and the perfect outdoor retreat, this home checks every box. Just move in and start enjoying everything it has to offer

12 Forest Rd Extension, Seymour
22 Patrick Dr, Seymour
$691,000
4 Beds ⋅ 3 Baths ⋅ 24165355 MLS
Gorgeous Custom Colonial in the Desirable Great Hills area! This stunning 2,840 sq. ft. Colonial features 9-foot ceilings on the first floor and an inviting open layout, perfect for both everyday living and entertaining. The spacious Kitchen includes a center island, ample seating, and French door sliders that lead to beautiful Trex Decks, Ideal for hosting or relaxing outdoors. The formal Dining Room flows seamlessly into a bright and airy Great Room, complete with vaulted ceilings, a fireplace, and abundant natural light. This home offers 4 Bedrooms, all with hardwood floors. The Primary Suite features tray ceilings, a walk-in closet, and a private en suite bath. Additional highlights include a 3-car attached garage with capacity for up to 5 vehicles, plus a large paved driveway accommodating up to 8 more cars. Recent updates and features include: * Underground sprinkler system * Hardwood floors throughout * Fresh interior paint * Updated light fixtures and ceiling fans * Fenced-in backyard * Granite kitchen countertops and backsplash * Updated bathrooms * High-performance composite decking

22 Patrick Dr, Seymour
27 Partridge Dr, Seymour
$690,000
4 Beds ⋅ 3 Baths ⋅ 24164875 MLS
Beautifully renovated New England-style Colonial set at the end of a cul-de-sac on 1.21 private acres with direct access to Little Laurel Lime Ridge hiking trails. This 4-bedroom, 2.5-bath home offers the perfect blend of classic charm and modern updates.The updated kitchen features quartz countertops, a new island with built-in microwave, new refrigerator and dishwasher, and a dining area with sliders leading to a resort-style, fully fenced backyard complete with a new patio, deck, and professional landscaping-ideal for entertaining or relaxing. Interior highlights include a brand-new mudroom with custom built-ins, a cozy family room with fireplace, built-ins, and recessed lighting, and a spacious living room with French doors flowing into the formal dining room. Main-level laundry adds everyday convenience. Upstairs, the primary suite features barn doors, an updated full bath with glass-enclosed shower, and a walk-in closet with custom system. Three additional bedrooms and a full bath complete the upper level. Recent upgrades include new LVT flooring throughout, fresh interior paint, recessed lighting, new oil tank, newer furnace, central air, hot water heater, well bladder, updated electrical, and a basement water management system.2-car attached garage plus ample off-street parking. Move-in ready with exceptional updates throughout-don't miss this opportunity!

27 Partridge Dr, Seymour
9 Osprey Dr, Seymour
$685,000
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
29 Evergreen Ter, Seymour
$677,000
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
12 Red Oak Ln, Seymour
$660,000
4 Beds ⋅ 3 Baths ⋅ 24148964 MLS
Open, bright, and beautifully cared for-this Seymour colonial checks every box. This home has been impeccably maintained and is truly move-in ready. No shortcuts were taken with this home, beginning with the kitchen, which features GRANITE COUNTERTOPS, BUILDER UPGRADES, quality CABINETRY, and a layout designed for both FUNCTION AND FLOW. From here, the space opens seamlessly into the dining and living areas, creating an ideal setting for EVERYDAY LIVING AND ENTERTAINING. The inviting family room is highlighted by an electric stove, adding warmth and character to the main level. Upstairs, HARDWOOD FLOORS run throughout ALL bedrooms. Each bedroom is well-sized with AMPLE CLOSET SPACE, while the PRIMARY BEDROOM SUITE serves as a true retreat with a LARGE WALK-IN CLOSET and a private bath featuring DOUBLE SINKS, a SOAKING TUB, and a SEPARATE SHOWER STALL. The partially finished basement provides FLEXIBLE LIVING SPACE, along with AMPLE STORAGE and FUTURE FINISHING POTENTIAL. Step outside to enjoy the WELL-GROOMED YARD with an IN-GROUND SPRINKLER SYSTEM, VINYL FENCE a LARGE GARDEN, and MATURE FRUIT TREES-including pear, apple, prune, and peach-ready for harvest this year. The seller has thoughtfully planted flowers throughout the property, ensuring colorful blooms across multiple seasons and adding year-round curb appeal. Plenty of parking, a QUIET, WALKABLE NEIGHBORHOOD, and convenient access to ROUTES 67, 42, AND 8. Square footage includes 276 sq ft of finished basement space.

12 Red Oak Ln, Seymour
17-23 Meadow St, Seymour
$660,000
9 Beds ⋅ 4 Baths ⋅ 24135234 MLS
Back on the market due to buyer default! Exceptional investment opportunity! 3 Income-Producing buildings all included in 1 purchase! This versatile property features a spacious side-by-side duplex, each unit offering 3 bedrooms, separate utilities, and strong rental potential. A large single-family home on the same parcel provides 3 additional bedrooms and was once used as a two-family home, offering the possibility to be divided again for added rental income (buyer to do their own due diligence). Completing the property is a 2-bay detached garage, perfect for tenant storage or additional revenue. Conveniently located near local amenities, this unique multi-building parcel offers endless potential for investors seeking strong cash flow and long-term value. French Park neighborhood, great walk-ability to local shops, restaurants, and more! Sold As Is. Some Photos have been decluttered for marketing purposes.

17-23 Meadow St, Seymour
9 Fox Run Ln, Seymour
$654,000
4 Beds ⋅ 4 Baths ⋅ 24166367 MLS
Welcome to your dream home! This beautiful 4-bed, 2full/2 half bath, colonial is located in a sought-after section of Seymour, CT. Nestled on a gorgeous .46 acre lot, the grounds are almost as impressive as the interior. Minutes away from RT8/RT15 and all the amenities Seymour has to offer, this home is perfect for the everyday or weekend traveler. Making your way into the home, you are greeted by dark hardwood floors that blanket the entire main level of the home. Continuing through, you will find a large dining room and office area. A tastefully done kitchen with granite countertops and stainless steel appliances is seen next, along with the open concept living room that houses a gas fireplace. Making your way to the upper level, you will see brand-new carpets, freshly painted rooms, and a desirable layout. The primary bedroom houses a full bath and an oversized closet. The remaining 3 bedrooms are all large with new carpets. The lower level of the home is partially finished and is ready to be customized to suit your needs. In the unfinished portion, there is ample storage, mechanicals, and room for further finishing. The exterior of the home has a custom aboveground pool and patio attachment. Off of the sliding door in the kitchen, you will see custom rock/masonry work that leads to the deck/pool area. This home is the one you have been waiting for!!

9 Fox Run Ln, Seymour
12 Great Meadow Rd, Seymour
$650,000
4 Beds ⋅ 3 Baths ⋅ 24143668 MLS
A modern Ranch all main floor living! 8rooms 4 bedrooms and 3 full baths. Several high end renovations. 3-Updated baths There is plenty of potential for extended family or In-law. A perfect space for every person or activity. The Kitchen has private pantry-laundry, Newer cabinetry, plenty of granite counters with an easy flow. Dining Room, Hardwood floors Shadow box built-ins surround the slider. The formal living room has Hardwood floors French doors, Wood fireplaces with wood burning insert. The Addition -Great Room (24x24) with exceptional German engineering Hurricane prof (Fox Block)10in thick construction, Energy Efficient 9 ft doors with triple pane glass also windows all have a shade channel system through out home for Energy Efficiency.Solar panels are owned by seller the attached Green House 18x9 with South East exposure adds to more energy efficiency (passive solar) and a slider to rear yard, fully venting with a power awning. A Bedroom & Bath at the rear of Great Room. There an unfinished upstairs too nearly 1500 sqft of potential living space.Lower Level has tiled 600 sqft area for exercise, wine cellar, play room and tons of room for storage. The home is located on level 1 acre private and tranquil lot.Previous owners passion was gardening several fruit trees, berry bushed & vegetable garden. Walk the 106 acre town park- trails for Hiking,Biking,Jogging or just exploring. Conveniently located close to everything mjr hwys, gym, restaurants, schools book a showing

12 Great Meadow Rd, Seymour
5 Forest Hollow Rd, Seymour
$650,000
4 Beds ⋅ 3 Baths ⋅ 24114980 MLS
Step into timeless elegance with this beautifully crafted Colonial boasting 2828 sq ft, of luxurious living space, 4 Beds, 2.5 Full Baths all meticulously maintained since its construction in 2011 for a truly turnkey experience. Inside highlights a Grand foyer 2 Stories high, Eat in Kitchen complete with Granite countertops, (2024) Appliances shares open floor plan with a cozy Family room with a gas fireplace, and Hardwood floors installed (2024). , a Formal Dining room and Living room, a cozy Family room Gleaming hardwood floors, 9+ Ceilings, and Vaulted Ceilings throughout the Main Floor to elevate the ambiance. Over $50K in improvements, Spacious Upper-level primary suite with his/her walk-in closets, relaxing soaking tub with double sink vanity, three additional generous-sized bedrooms provide space for family/guests. Step outside from the Family Room to a private fenced-in backyard, patio, and new pool installed (2024) in your fully fenced-in private backyard, 2-car attached garage, and oversized shed that houses 1 car. (2024) Condenser for Central Air. Solar Panels reduce utility bills. Located in a picturesque neighborhood development known for its beauty and tranquility, this is more than just a home; it's a place to truly feel at home. Schedule your private tour today and experience the charm of Rolling Hills Estates Living!

5 Forest Hollow Rd, Seymour
40 Church St, Seymour
$640,000
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
115 Roosevelt Dr, Seymour
$635,000
5 Beds ⋅ 2 Baths ⋅ 24164993 MLS
Just in time for summer. Direct waterfront on the Housatonic river. Dual Ranch-Style homes with Incredible Flexibility and Scenic Views. Discover a truly unique property on the river. This rare offering features two separate ranch-style homes on one spacious, waterfront lot-perfect for those seeking a family compound, live-in and rent, or a smart investment opportunity. The main house boasts bright, open living space with serene water views, 1504 square feet with 3 comfortable bedrooms ideal for everyday living. Step outside to enjoy the views from the porch of the generous backyard that gently slopes toward the water, providing private access for boating, kayaking, or simply relaxing by the shore. The second dwelling offers its own full kitchen, living area, 2 bedrooms and private entrance, making it perfect for extended family, guests, or as a high-demand rental unit. Each home enjoys access to the lush outdoor space and direct water frontage, maximizing enjoyment and privacy. Additional amenities include direct boat launch, ample parking for residents and visitors, well-maintained grounds, and easy access to local shops, dining, and commuter routes. Whether you envision gathering with loved ones, generating rental income, or simply enjoying a peaceful waterfront lifestyle, this property delivers unmatched versatility and appeal. Don't miss your chance to own a one-of-a-kind dual dwelling on the water-schedule your private showing at 115 Roosevelt Drive today

115 Roosevelt Dr, Seymour
17 Tibbets Rd, Seymour
$600,000
4 Beds ⋅ 3 Baths ⋅ 24145243 MLS
A contemporary colonial nestled on 2.99 private acres featuring 3-5 bedrooms & 3 full baths with a welcoming double-door entry into an open foyer. The living room, recently divided into two spaces, features dual sliders leading to a new 21x10 composite deck overlooking a fenced yard. Descend to the family room, highlighted by hardwood floors, a beautiful picture window, and a cozy fireplace. The dining room provides access to a covered deck and a remodeled kitchen equipped with quartz counters, farmhouse sink, glass tile/quartz backsplash, and high-end stainless steel appliances, including an 8-burner gas double oven. Recent updates include fresh interior paint, new flooring, remodeled main level bath, new trim/lighting, new garage door/opener, new composite deck & balcony, partially finished basement w/dehumidifier system, radon system, driveway lighting, and new gutters/fascia. Conveniently located on the main floor are an office or 4th bedroom and laundry room. The second floor unveils a primary suite with walk-in closet, bathroom with oversized tile shower, second closet, and sliders leading to a balcony, plus two additional bedrooms and a full bath. The massive lower level walkout with expansion possibilities, with potential for an in-law suite complete with a private entry and workshop. Additional features: 2 car garage + additional parking, 4-zone heating & updated well system. Great Hill Area-a must see! SOLD AS IS; CA needs new condenser.

17 Tibbets Rd, Seymour
194 Eastwood Dr Unit 194, Seymour
$580,000
2 Beds ⋅ 3 Baths ⋅ 24165974 MLS ⋅ Meadow Brook Estates BLDG.
Beautiful detached condominium located in the highly desirable Meadow Brook Estates community, offering more space than most units in the complex. This home features an open floor plan filled with natural light, enhanced by skylights, cathedral ceilings, and elegant crown moldings throughout. Ideally situated on a quiet cul-de-sac within the complex, the property provides excellent privacy and utility. The spacious great room with fireplace offers comfortable everyday living, while the formal dining room is generously sized and perfect for entertaining. Additional highlights include a bright sunroom and private patio, ideal for outdoor relaxation. The home also offers newer mechanical systems, a full unfinished basement with abundant storage potential, a two-car garage, and ample closet space throughout. A truly well-rounded home offering space, comfort, and value-this is a must see!

194 Eastwood Dr Unit 194, Seymour
22 Greenwood Cir, Seymour
$580,000
4 Beds ⋅ 3 Baths ⋅ 24156943 MLS
Welcome to 22 Greenwood Circle, a beautiful home set on a quiet residential street in a highly convenient Seymour location. This inviting property offers the perfect blend of comfort, space, and everyday accessibility. Step inside to a stunning living room featuring soaring cathedral ceilings and abundant natural light, creating an open and airy space that serves as the true heart of the home. Perfect for both relaxing and entertaining, the layout offers a comfortable flow for modern living with versatile spaces to suit a variety of needs. With four well-proportioned bedrooms, 2 living rooms, and 2.5 bathrooms, there is ample room for comfortable living, guests, or a home office setup. Outside, enjoy a peaceful yard ideal for outdoor gatherings, gardening, or simply unwinding in a neighborhood setting. Location is a standout feature. Ideally situated close to Seymour's school system, including the elementary school less than a mile away, Bungay School just a short 3-4 minute drive, and Seymour High School approximately 5 minutes away, this home offers exceptional everyday convenience. You're also just minutes from local shopping, restaurants, grocery stores, and everyday essentials, with quick access to Route 8 for an easy commute. Don't miss this wonderful opportunity to own a spacious home in a desirable Seymour neighborhood that combines charm, convenience, and a prime location.

22 Greenwood Cir, Seymour
5 Roosevelt Dr, Seymour
$575,000
2 Beds ⋅ 2 Baths ⋅ 24203247 MLS
Direct Housatonic River waterfront living! This beautifully updated home is officially recorded as a 2-bedroom, 2-full-bath residence offering 2,104 total sq. ft. of heated living space, including 1,530 sq. ft. above grade plus 574 heated sq. ft. in the partially finished walk-out lower level. Hardwood floors, a renovated kitchen and bright living spaces welcome you inside. Downstairs, one finished room is currently utilized as additional sleeping space, conveniently located beside a full bath and walk-out, while an adjoining room serves as a podcast/media studio. Officially listed as a 2-bedroom, the flexible lower level offers endless possibilities for guests, office, gym, studio or playroom. Outside, over $100,000 in recent deck, patio and river-facing improvements have transformed the waterfront into an incredible extension of the home. Entertain overlooking the river, enjoy quiet mornings by the water or head down to two private docks for direct Housatonic access. A detached 1-car garage, central air, tankless propane hot water and fully owned, paid-off solar panels with no lease or loan to assume add even more value. Extensively improved inside and out, with two private docks and an impressive 120' of direct Housatonic River frontage, this property makes the most of its exceptional waterfront setting.

5 Roosevelt Dr, Seymour
26 Greenwood Cir, Seymour
$575,000
3 Beds ⋅ 3 Baths ⋅ 24174821 MLS
** BEST AND FINAL BY THURSDAY 7/16 9AM PLEASE ** Welcome to 26 Greenwood Circle, an immaculate 3-bedroom, 2.5-bathroom Colonial that perfectly blends classic elegance with pride of ownership. Each bedroom comes complete with its own walk-in closet. The primary suite features an additional cedar closet and full bathroom. Lovingly cared for and meticulously maintained by the same family for over 20 years, this 2,256 sq. ft. home shines with an unmatched attention to detail from the moment you step through the door. The thoughtfully decorated interior offers a warm, inviting floor plan featuring spacious rooms, flawless finishes, and a cozy fireplace ideal for gathering. Every corner of this home has been kept in pristine condition, offering a true move-in-ready experience for its next chapter. Step off the back deck to discover a private, 0.59-acre backyard oasis. Years of craftsmanship has been poured into creating a custom garden sanctuary, complete with winding stone pathways, lush perennial landscaping, and peaceful spaces to unwind. This property is looking for its next dedicated caretaker to carry on the rich appreciation, love, and care that built it. (3) A/C units, (2) dehumidifiers, (2) space heaters for basement, and a basement refrigerator will stay with the property. Some furniture may also be available to purchase separately. Schedule your private tour today to experience this true real estate gem.

26 Greenwood Cir, Seymour
15 Briarwood Dr, Seymour
$570,000
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
18 Forest Rd Extension, Seymour
$570,000
3 Beds ⋅ 3 Baths ⋅ 24151203 MLS
WOW!! Perfect location for this one owner, lovingly cared for comfortable home! Get ready to add your personal touches to this spacious home offering newer high quality laminate floors through-out the main level. Large Livingroom with a gas fireplace and sliders to a deck overlooking your spacious and level back yard. Formal dining room, eat in kitchen with center island and breakfast nook with a bay window to bring nature in. First floor laundry with access to the 2 garage completes the 1st floor. Primary bedroom with full bath 2 closets, one a walk-in. 2 additional spacious bedrooms. As an additional feature, there is a sizable bonus room with a gas burning stove with access from the primary bedroom or a second staircase off the kitchen. Public water, sewer and natural gas heat makes this home a must see.

18 Forest Rd Extension, Seymour
4 Brook St, Seymour
$570,000
4 Beds ⋅ 2 Baths ⋅ 24122568 MLS
Welcome to this like-new ranch-style home offering the perfect blend of comfort, convenience, and space. With 2,000 sq. ft. of living area, this 4-bedroom, 2-bathroom home sits on over an acre of land in a highly desirable location right on the Seymour/Oxford line. Step inside to find a bright and open layout with generously sized rooms and modern finishes throughout. The spacious kitchen flows effortlessly into the dining and living areas, making it ideal for both everyday living and entertaining. The primary suite features a private bath, while three additional bedrooms offer flexibility for family, guests, or a home office. With C/A, Propane heat, hot water, cooking and fireplace, city sewer and oversized garage plus a huge basement for the possibility for additional finished space, this home has much to offer. Nothing to do but move right into this one.

4 Brook St, Seymour
17 Shari Dr, Seymour
$570,000
3 Beds ⋅ 3 Baths ⋅ 24127150 MLS
Set on a quiet cul-de-sac street in Seymour's desirable Great Hill neighborhood, this meticulously maintained custom-built Colonial stands out with exceptional curb appeal and quality craftsmanship. The property showcases a large, level front yard with impressive street frontage, a sidewalk-lined street, Belgium block-lined driveway, welcoming front porch, intricate roofline, and low-maintenance vinyl siding-all highlighted by a bluestone walkway and front step entry. Inside, thoughtful details shine through with solid-core six-panel doors, Anderson 8-over-8 wood-frame windows, and a decorative front door with sidelights. The family room features vaulted ceilings, a fireplace, and an Anderson slider leading to a composite deck overlooking the private, level backyard-ideal for everyday living and entertaining. The expansive eat-in kitchen offers plenty of cabinets, countertops, stainless steel appliances, and generous space for gathering. Additional highlights include main-level laundry, two convenient access points to the backyard, city water/sewer, central air powered by dual Carrier systems, and a generator hook-up. Upstairs, the primary suite includes a walk-in closet and private bath, complemented by two additional good-size bedrooms. Lots of storage and closet space throughout. A rare opportunity to own a home that blends curb appeal, functionality, and a premier neighborhood setting. Turn-key and ready for you to add your personal touches-Welcome Home!

17 Shari Dr, Seymour

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