Seymour Real Estate

Welcome to Seymour, Connecticut – a charming town nestled in the heart of New Haven County. With its rich history, vibrant community, and picturesque landscapes, Seymour offers an ideal blend of small-town charm and modern conveniences, making it a perfect place to call home.

Founded in the early 19th century, Seymour boasts a rich historical heritage, evident in its well-preserved architecture and quaint downtown area. The town is known for its friendly atmosphere, where neighbors become friends, and community events bring everyone together. From seasonal festivals to farmers' markets, there’s always something happening in Seymour that celebrates the spirit of togetherness.

Nature enthusiasts will appreciate Seymour’s stunning outdoor spaces. The town is surrounded by beautiful parks, hiking trails, and the scenic Housatonic River, providing ample opportunities for outdoor recreation. Whether you enjoy fishing, hiking, or simply taking a leisurely stroll, Seymour’s natural beauty is sure to inspire.

Families will find Seymour to be an excellent place to raise children, with top-rated schools and a close-knit community that prioritizes education and growth. The town's commitment to maintaining a safe and nurturing environment makes it a sought-after destination for families of all sizes.

Conveniently located just a short drive from larger cities like New Haven and Bridgeport, Seymour offers easy access to urban amenities while maintaining its serene, suburban feel. With its unique combination of history, community spirit, and natural beauty, Seymour is not just a place to live—it's a place to thrive. Come discover your new home in this delightful Connecticut town!

Newest Listings in Seymour

$400,000

5 Beds ⋅ 3 Baths ⋅ 24218936 MLS

Located in Seymour's Bungay neighborhood, this 2-family home offers flexibility and income potential - the property is zoned for 3 units. The first unit features 3 bedrooms and 2 full bathrooms, while the second-floor unit offers 2 bedrooms and 1 bathroom, for a total of 5 bedrooms and 3 bathrooms across both units. Whether you're an investor looking for rental income with room to expand to a third unit, or an owner-occupant wanting to live in one unit while the other helps carry the mortgage, this property delivers options. Seymour itself is a classic Naugatuck Valley town with a walkable downtown full of local shops and restaurants - grab a bite at Train Station Pizza, browse antiques, or enjoy afternoon tea downtown. Outdoor lovers will appreciate Chatfield Park and French Memorial Park, plus the nearby Naugatuck River and miles of local trails. Commuting is easy with Route 8 close by and the Seymour train station on Metro-North's Waterbury Line, putting New Haven and the surrounding valley within reach. A great combination of investment potential and small-town New England living.

20 New St, Seymour

$389,900

3 Beds ⋅ 2 Baths ⋅ 24217727 MLS

Nestled on approximately 1.7 acres, this updated 3 bedroom 2 bathroom home offers the perfect combination of comfort and convenience. Inside you will find a flexible and functional layout highlighted by a new upper-level primary ensuite just finished in 2026. Seller has made many updates to the property including new roof (2023), new central air (2023), new siding (2026), new hot water heater (2026), new driveway (2026), upgraded 200amp electrical service (2026), and new ductless mini-split system in upper level. Kitchen and main floor bathroom received updates in 2023 as well as the living room to include a wood-burning fireplace insert w/ circulating blower. Nothing left to do but move in! Ring doorbell cameras on property.

214 Bungay Rd, Seymour

$249,900

3 Beds ⋅ 2 Baths ⋅ 24217225 MLS

ATTENTION INVESTORS & CONTRACTORS? Tremendous opportunity to restore this historic 1900 Victorian home set on a level, cleared 0.44-acre lot. Offering 2,214 sq. ft. of living space plus a massive 1,000 sq. ft. walk-up attic with a pre-existing finished room (not reflected on tax records), this property boasts endless upside. Zoned for multi-family use, the home features an existing 2nd-floor accessory apartment and 2 separate entrances on each floor, making it an ideal candidate for a multi-family conversion, income-generating investment, or expansive multi-generational estate. Easily reconfigured into a 4-to-5-bedroom home. Interior highlights include original coffered ceilings and gorgeous hardwood floors ready to be restored. Exterior features a detached 2-car garage with a spacious loft for additional storage or workshop space. NEEDS FULL REHAB. Strictly sold "AS-IS." Will NOT qualify for FHA or Conventional Financing-Cash, Hard Money, or Rehab loans only. Bring your crew and unlock this property's maximum value! Offers are due 12:00 pm on Friday 11/6.

65 Meadow St, Seymour

$420,000

4 Beds ⋅ 3 Baths ⋅ 24217960 MLS

Welcome to 80 Silvermine Road in Seymour! This spacious home offers a fantastic opportunity for buyers looking to add their personal touches and make it their own. Priced with future updates and improvements in mind, the property offers plenty of potential to build equity over time. Situated on a level lot in a quiet, established neighborhood, this home features 3 bedrooms, 3 full bathrooms, a 2-car garage, and propane cooking. The lower level offers additional flexible living space, complete with a wood-burning stove and an additional room that could serve as a home office, guest room, or potential fourth bedroom. With generous living space, a level yard, and a peaceful neighborhood setting, this property offers a great combination of space, potential, and opportunity. Whether you're looking to update the home over time or make improvements right away, 80 Silvermine Road provides an excellent opportunity to create a home that reflects your style and needs. Property is being sold as-is.

80 Silvermine Rd, Seymour

$315,000

3 Beds ⋅ 1 Baths ⋅ 24217916 MLS

This charming 3 bedroom, 1 bathroom ranch is nestled on a private secluded lot near the Housatonic River in Seymour. Enjoy the peaceful sounds of Spruce Brook that runs along the back of the property. The outdoor space features a beautiful stone patio and terrace along with a hot tub, perfect for relaxing, entertaining or just enjoying the natural surroundings. This home offers the comfort of one level living with a main level laundry room, 3 spacious bedrooms, including a primary with a fireplace, dining room, living room, and a bonus room. There is also a detached bonus space equipped with a mini-split heating and cooling system adding to the living space. Come see this unique property and all it has to offer!

115-A Squantuck Rd, Seymour

$599,000

3 Beds ⋅ 5 Baths ⋅ 24214960 MLS

Set on a private 0.83-acre lot in Seymour, this Colonial-style home delivers 2,161 sq ft of living space, 3 bedrooms, (main level in-law suite not included) and 4 full baths plus a half bath - rare flexibility for any household. The primary suite impresses with vaulted ceilings, a stained-glass accent window, and a spa-like en-suite featuring a marble double vanity, glass shower, and large soaking tub. Secondary bedrooms are bright and airy, one with a vaulted ceiling, and warm wood-toned furnishings that highlight the home's character. A second full bath offers a classic vanity and tub/shower combo. Step outside to a deck and open porch for easy indoor-outdoor living, with a basement-level garage adding everyday convenience. Built in 2001 and move-in ready, this home pairs comfortable living with a peaceful, tree-lined setting just minutes from downtown Seymour, multiple state parks, and the Housatonic River.

52 Buckingham Rd, Seymour

$379,900

3 Beds ⋅ 1 Baths ⋅ 24217227 MLS

Welcome to 4 Elaine Drive, Seymour. This 3-bedroom, 1-bath ranch sits on 0.28 acres on a quiet, established street and offers efficient one-level living. The home features hardwood floors throughout, an updated kitchen, and a 1-car garage. Recent updates have been completed for peace of mind, including a new kitchen, a new water heater, and a new well pump. Additional improvements in 2020 include a new oil tank, windows, siding, roof, and central AC. Solar panels are in place for energy efficiency - buyer to assume solar financing. Convenient location close to shopping, schools, and Route 8. Ideal for first-time buyers, downsizers, or anyone looking for a well-maintained, low-maintenance home that is ready to move in.

4 Elaine Dr, Seymour

$475,000

2 Beds ⋅ 2 Baths ⋅ 24217343 MLS

Welcome to 27 Bissell Place, a beautifully renovated ranch situated on 3 acres along a quiet dead-end street in Seymour! This charming home offers 2 bedrooms, 1 full and 1 half bathroom, and approximately 1,450 square feet of comfortable living space. Thoughtfully updated throughout, the home combines modern finishes with the convenience of single-level living. The inviting living room features a fireplace, while the spacious eat-in kitchen provides a welcoming setting for everyday living and entertaining. Additional highlights include a full walk-out basement, one-car under-house garage, and a lightly wooded 3-acre property offering exceptional privacy, outdoor enjoyment, and room to explore. Enjoy a peaceful setting while remaining conveniently located near downtown Seymour, shopping, dining, and major commuter routes. A wonderful opportunity to own a move-in-ready home with acreage in a desirable location!

27 Bissell Pl, Seymour

$479,900

2 Beds ⋅ 3 Baths ⋅ 24217234 MLS ⋅ Ridge View Townhomes(Pending Verification) BLDG.

This impeccably built, soon-to-be-completed 2-bed, 2.5-bath FULLY CUSTOMIZABLE, end-unit townhouse offers a rare combination of modern design, premium finishes, 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 primary bedroom, complete with a walk-in closet and a stunning primary bathroom. An additional generously proportioned bedroom 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 large patio. Ideally situated near major highways, regional employment centers, retail, dining, and neighboring hubs including New Haven. Completion date: 01/30/27. A rare opportunity to own in a peaceful new community featuring pickleball courts and a beautifully designed fire pit, gazebo area.

49 Micko Dr Unit 25, Seymour

$419,000

3 Beds ⋅ 2 Baths ⋅ 24216722 MLS

Welcome to 150 Pearl Street! This charming two-story home offers nearly 2,000 square feet of living space, featuring 3 bedrooms, 1.5 bathrooms, and a wonderful blend of character, comfort, and functionality. Freshly painted throughout, the home features beautifully refinished hardwood floors, a fully renovated bathroom, refreshed landscaping, and additional updates waiting to be discovered! Inside, you'll find inviting living spaces, including a cozy living room with a wood-burning stove, perfect for relaxing evenings at home. Additional highlights include central air conditioning, updated electrical, and a flexible floor plan with plenty of room to make it your own. Step outside to enjoy the spacious, fully fenced backyard and concrete patio, ideal for entertaining, outdoor dining, or simply unwinding. The walk-out basement offers ample storage, a washer and dryer, and additional space ready for your personal touch. A walk-up attic provides even more possibilities for storage or future improvements, while ample off-street parking adds everyday convenience. Conveniently located in Seymour, just minutes from Route 8, the train station, downtown shops, restaurants, and local amenities, this home offers easy access to everything the area has to offer. With its generous living space, charming details, and recent improvements, 150 Pearl Street is a wonderful opportunity to create a home that feels uniquely yours. Schedule your showing today!

150 Pearl St, Seymour

$495,000

3 Beds ⋅ 2 Baths ⋅ 24216204 MLS

A must see! This completely renovated 2,210 total sqf- three bedroom, 1 1/2 bath ranch, nestled in the Garden City section of Seymour- on a cul-de-sac, just minutes to schools -will not disappoint. The main level features an open floor plan with recessed lighting throughout the home. The bright living area leads to the fully equipped kitchen with stainless steel appliances, butcher block countertops, and a eat-in breakfast bar. A cozy dining area complete with an open back yard view. The three spacious bedrooms feature extra closet space and meticulous attention to details. The lower level boasts a completely finished family room, barn doors leading to the uniquely designed 1/2 bath which is sure to impress. Then to the built-in bar and yes, an exercise room with sliding doors leading to the back deck. Laundry room complete with sink, and a home office. The outside is a perfect oasis, new Trex deck complete with breakfast bar and outside entertainment set up, fire pit, and above ground salt water, heated pool is virtually maintenance free. The home also has a complete workshop, solar panels, central air, a new roof, hybrid electric water heater with built in dehumidifier and generator interlock hardwired to house. This house has to many details to list and won't last!!!!!!

16 Paramount Dr, Seymour

$499,900

4 Beds ⋅ 4 Baths ⋅ 24216257 MLS

This Multi-Generational Home with NEW ROOF at a Fantastic Value in Desirable Great Hill! Welcome to this 4 bedroom 3 full and one half bath Colonial offering exceptional space, versatility, and a fantastic layout designed for today's lifestyle! This spacious home offers room for everyone with the added bonus of a possible in-law area! The inviting family room features a classic masonry fireplace, while the formal dining room flows seamlessly into the updated eat-in kitchen, complete with granite countertops, tile backsplash, stainless steel appliances, and sliders leading to a deck overlooking beautiful wooded grounds. A formal living room (virtually staged as office) provides additional space. The main-level possible inlaw area offers wonderful flexibility with its own separate entrance, bedroom, full bathroom, den/office, kitchenette, and access to the deck. A powder room completes the first floor. Upstairs, retreat to the spacious primary suite featuring TWO generous walk-in closets and an updated private bathroom with double sinks and granite vanity. Two additional bedrooms and a full hall bathroom complete the second level. Need even more space? The finished walkout lower level offers approximately 400 additional square feet, including a recreation room, office or exercise space, and plenty of storage! Addt'l highlights incl newer water heater, central air, two-car garage, carport, and shed. Move right in and make this exceptional property your own!

61 Davis Rd, Seymour

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Seymour Real Estate

Newest Listings in Seymour

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