Seymour Real Estate

Seymour Real Estate

Welcome to Seymour, Connecticut – a charming town nestled in the heart of New Haven County. Known for its rich history and vibrant community spirit, Seymour offers a unique blend of suburban tranquility and easy access to urban amenities, making it an ideal place to call home.

Founded in the 1800s, Seymour boasts a quaint downtown area filled with local shops, delightful eateries, and a warm, welcoming atmosphere. The town's historic architecture tells the story of its past, while modern developments provide the conveniences of contemporary living. Residents enjoy a variety of recreational opportunities, with parks and outdoor spaces such as the scenic Housatonic River and the picturesque Great Hill Park, perfect for hiking, picnicking, and family outings.

Seymour is also known for its strong sense of community, hosting numerous events throughout the year, including the popular Seymour Pumpkin Festival, which brings together families and friends for a day of fun, food, and festivities. The local school system is highly regarded, making it an attractive option for families looking to settle down in a nurturing environment.

With easy access to major highways and public transportation, commuting to nearby cities like New Haven and Bridgeport is a breeze, allowing residents to enjoy the best of both worlds. Whether you’re seeking a cozy starter home, a spacious family residence, or a charming historic property, Seymour has a diverse range of real estate options to suit your needs.

Discover the warmth and charm of Seymour, where community, convenience, and character come together to create the perfect place to live. Come explore this hidden gem in Connecticut today!

Newest Listings in Seymour

30 Emma St, Seymour
$334,900
3 Beds ⋅ 1 Baths ⋅ 24219405 MLS
Welcome to 30 Emma Street! Tucked away on a quiet cul-de-sac, this charming ranch-style home offers comfortable one-level living with convenient commuting access. Featuring 3 bedrooms, 1 full bath, and an inviting open flow between the kitchen, dining area, and living room, this home offers a wonderful opportunity to make it your own. Proudly maintained by its original owner, the home features several important updates, including a new heat-pump hot-water-tank (2026), furnace and HVAC system (2024), newer windows (2017), a new front door and basement door (2019), and siding (2019). The oil tank was also replaced approximately 10 years ago. The full walk-out basement offers excellent potential for future expansion, additional living space, or whatever best suits your needs. With solid bones, valuable updates, and room to add your personal touch, all that's left is to bring your vision and make this home your own!

30 Emma St, Seymour
60 Birchwood Rd, Seymour
$429,900
3 Beds ⋅ 1 Baths ⋅ 24218542 MLS
Welcome to 60 Birchwood Road! This inviting three-bedroom home features hardwood flooring throughout and an open-concept kitchen and dining area that flows into the living room, creating a comfortable setting for everyday living and entertaining. The kitchen offers stainless steel appliances, an induction range, and a large center island with generous prep and gathering space. In the living room, a fireplace with a wood-burning insert adds warmth and character, while sliding glass doors lead to a patio overlooking the private backyard and established three-season garden-an inviting setting for outdoor dining or simply unwinding. The bathroom features a stone floor and tile detailing, and central air provides comfort during warmer months. The basement offers ample storage with shelving to keep everything organized. Located near Chatfield School and local parks, with convenient access to Routes 8 and 67, shopping, and everyday amenities. A welcoming place to make your own!

60 Birchwood Rd, Seymour
89 Balance Rock Rd Unit 1, Seymour
$215,000
2 Beds ⋅ 1 Baths ⋅ 24202636 MLS ⋅ Balance Rock BLDG.
2 bedroom unit clean and updated. Large living room, kitchen with dining area, and remodeled full bath. Electric range, refrigerator, dishwasher, and microwave. Sliders to private patio. One level living, heat and hot water are included in the condo fee. Each unit has their own storage area. Coin operated washer dryer units in the building. Offstreet parking. Inground swimming pool and clubhouse.

89 Balance Rock Rd Unit 1, Seymour
214 Bungay Rd, 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
65 Meadow St, 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
80 Silvermine Rd, 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
115-A Squantuck 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
52 Buckingham 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
4 Elaine Dr, 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
27 Bissell Pl, Seymour
$475,000
3 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
49 Micko Dr Unit 25, 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
150 Pearl St, 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
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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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