$447,820Average Value$276Average Price per Sq Ft20Homes For Sale
Tight-knit community in New Haven County
“Tight-knit” and “comfortably secluded” are words used to describe Seymour, a New Haven County town set around the Naugatuck River and full of dense, expansive wildlife areas. Established in 1850, this southwest Connecticut community retains much of that vintage charm, from its walkable downtown full of boutiques to its homes surrounded by trees. “Everyone's family, and everyone knows everyone," says Nickie O'Toole, a Realtor with O'Toole Realty LLC and Seymour resident. “Our downtown is an old, 1800s-type walking-around downtown with some great shops. We have a lot of parks and rec areas; there’s a really great natural scene here. Seymour’s a wonderful place to live.”
Enjoy a safe, family-oriented environment in the Seymour neighborhood.
The historic Seymour Post Office resides in Downtown Seymour.
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Vintage Victorians and custom contemporary homes
The homes in Seymour are found primarily in its expansive residential areas, in a range of architectural styles, including Minimal Traditional, ranch-style, and custom contemporary, and built anywhere between 1900 and 2022. Many of these homes sit on spacious lots, full of green grass and flanked by tall trees, with long driveways leading to two-car garages. Prices range from $225,000 for 800 square feet to $735,000 for 3,000 square feet. Those in the market for condos and townhouses can find them throughout the town, ranging from $136,000 for 600 square feet to $389,000 for 2,000 square feet. While the variety of homes in Seymour is wide, it can be challenging to purchase there. “If you find a home for sale that you like, move fast because inventory is often low,” says O’Toole.
Sit on your front porch and enjoy sunny days in Seymour.
Farmhouse-style homes are available in Seymour.
Raised Ranch-style homes are a common sight in the Seymour neighborhood.
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Area kids served by Seymour School District
Area kids usually start their education at Bungay Elementary School and then move on to Seymour Middle School and Seymour High, which are all part of the Seymour School District. Bungay Elementary and Seymour Middle have B-minus ratings on Niche, and Seymour High has a B rating. Seymour High serves about 600 students and has a student-teacher ratio of 12-to-1. It has a robust athletic department and is a part of the Naugatuck Valley League (NVL) and the Connecticut Interscholastic Athletic Conference (CIAC). Families considering private education for their kids have two faith-based schools in the area to choose from.
Seymour Middle School serves students grades 6 through 8
Bungay Elementary School serves students in Kindergarten through 5th grade in Seymour.
Seymour High School features multiple sports teams for students.
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Outdoor recreation at Chatfield Park
Among the many recreational opportunities in Seymour is Chatfield Park, which offers multiple amenities that get residents out in the fresh air. Two ball fields sit on either side of the park and buzz with excitement during the summer months. The basketball court is often busy with gameplay, too, and the small playground offers area kids slides and plenty of things to climb on. Anglers fish in the Naugatuck River, which runs through the town and has undergone a profound conservation effort over the years, from one of the most polluted bodies of water in the state to one consistently stocked with trout and salmon.
Seymour's Chatfield Park features a walking track for residents to enjoy.
The basketball court at Chatfield Park in Seymour is a local favorite.
Seymour's Chatfield Park features two baseball diamonds, a basketball court, and a playground.
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Shopping and dining in Downtown Seymour
Downtown Seymour is a small, walkable few blocks near the town’s center and is the go-to for boutique shopping and local restaurants. Residents pick up unique gifts at Tickled Pink and antiques at Charlie’s Treasures, then head to Tea with Tracy for a meal or an afternoon tea and pastry break. Or they head to Train Station Pizza, a neighborhood favorite for their signature Mashed Potato Pizza. They catch the latest blockbuster at Strand Theater or play virtual reality action-adventure games at The Vault. For weekend errands, Stop & Shop is conveniently located off Franklin Street and offers groceries, and Walgreens is nearby, offering home and medical essentials.
Explore the charm of Tea with Tracy in Seymour
Find a variety of food options at Seymour Train Station Pizza.
The unique space inside Vault Virtual Reality in Downtown Seymour.
Find your favorite grocery store chains in Seymour.
Check out the Glass Source in the heart of Seymour.
Explore the historic Haroula's Coffee Shop in Seymour.
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Easy access to Route 8 and I-84
To get to Waterbury and Interstate 84, residents take Route 8 north, about 13 miles. New Haven is about 12 miles southeast along Route 313, and Hartford is about 45 miles northeast. Those who want to reduce their time in the car can pick up the Amtrak train in New Haven and take it to New York, Boston, or just about anywhere else in the northeast United States they want to go.
Enjoy the convenience and accessibility and of living in Seymour.
Find easy access to i95 and route 8 from Seymour.
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Written By
Conor Lobb
Video By
Tyler Cataldo
Interested in learning more about homes in this area?
Reach out to
Pamela Dostilio,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Seymour, CT sell after 55 days on the market compared to the national average of 55 days. The median sale price for homes in Seymour, CT over the last 12 months is $415,000, consistent with the median home sale price over the previous 12 months.
Great stand alone 3 bed, 2/1 Bath Laurel model which has been lovingly maintained by it's original owners. 2 decks, large unfinished walk-out lower level. Wooded setting behind house and situated on a lightly trafficked road in Oxford Greens. Kitchen with breakfast nook, granite and S'S appliances. 9' ceilings and hardwood floors (except primary bedroom, bath and laundry) on main level. Family
Better than new, this stunning Abbeyville model, completed December 2023, is ideally situated on a quiet cul-de-sac & shows like new! Offering the added peace of mind of transferable builder warranties, this home combines modern design w/ exceptional quality. The beautifully appointed kitchen features a large center island w/ quartz countertops, a tiled backsplash, pantry, & upgraded stainless
Welcome to 10 Anna Drive, a contemporary-style home situated at the end of a quiet cul-de-sac in Oxford's Quaker Farms area. Set on approximately 1.67 acres, the property offers 3 bedrooms, 2 full baths and approximately 2,289 square feet of living space. The main living area features a two-story living room with a floor-to-ceiling brick fireplace, large windows and an open balcony above. The
Welcome to the Pinehurst — 2,536 square feet of modern elegance and effortless comfort. The first-floor primary suite creates a private retreat with a spa-like ensuite and generous closet space. Throughout the main level, soaring ceilings, oversized windows, and hardwood floors set a bright, inviting tone. The kitchen features wood cabinetry, induction cooking, and stone countertops that open to
Step into the Bethpage — a beautifully designed 1,955-square-foot home that captures the ease and comfort of single-level living. Natural light fills the open floorplan, where vaulted ceilings and hardwood floors enhance the home’s spacious, airy feel. At the heart of it all is a kitchen with wood cabinetry, stone countertops, and a generous island — perfect for cooking, gathering, and creating
Welcome to 2 Great Oak Ridge Way, a beautifully updated, light-filled townhome in the sought-after Great Oak Ridge community. This move-in-ready home shows like new and offers the perfect blend of comfort, style, and peace of mind. Recent updates include a new roof (2024), HVAC system (2022), hot water heater (2025), driveway (2021), updated baths, lighting, window treatments, and an updated
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
The Sawgrass brings timeless style together with modern comfort across 2,455 square feet. The first-floor primary suite offers a peaceful retreat with an elegant ensuite and generous closet space. An open layout with hardwood floors connects bright, spacious living areas to a kitchen featuring wood cabinetry, stone countertops, and a large island — the perfect gathering spot for guests or family.
Welcome to an "Antique Gem" in Oxford, Connecticut. Step into a beautifully preserved piece of Connecticut history. Set on 1.6 private acres in Oxford, CT, this exceptional 1769 Vintage Home has remained in the same family for generations, and offers a rare combination of authentic period character, thoughtful restoration, and comfortable modern living. The current owner has invested more than
Incredible custom built home sited on a serene 1.61-acre lot with views of an adjacent pond. At over 6000 SQ FT this prestigious home with 4 bedrooms & 2.5 baths, this house checks all the boxes & more! A sundrenched great room has ~14 ft ceilings, wood molding & double arched door leading to a huge 1200 sq ft deck. Stunning open floor plan kitchen with granite counters, wood cabinets & built-ins
A six-year old, 10-unit condominium complex with spectacular valley views. This end unit features an open floor plan, vaulted ceilings, hardwood flooring throughout, kitchen with center island, 2 full bathrooms, spacious loft area currently serving as a living room and home office area, 2-car garage with finished room ideal for a home gym or storage room. Gas heat and central air conditioning.
To be built. Similar to image shown. Enjoy the benefits of watching your home be built from start to finish. Experience the perfect blend of quality craftsmanship and modern design in this exceptional new construction home by a well-known, respected builder. Thoughtfully designed with today's lifestyle in mind, this beautiful home will feature 4 spacious bedrooms, 2.5 baths, a 2-car garage, rear
EG Home, a trusted multi-award-winning builder, introduces the Sawgrass home at Oxford Greens, Connecticut's premier active-adult community. This two-level plan offers 2,455 sq. ft. of low-maintenance living. The main floor features hardwood floors, a spacious primary suite, a vaulted Great Room, and a chef's kitchen-perfect for quiet mornings or entertaining friends. Upstairs, the loft adds
Experience the Bethpage at Oxford Greens, a premier active-adult community in Connecticut, crafted by the award-winning EG Home. This single-level townhome offers 1,955 sq. ft. of expertly designed living space, featuring 2 bedrooms, 2 bathrooms, and a Great Room with vaulted ceilings that opens effortlessly into a chef's kitchen, complete with hardwood floors, wood cabinetry, and upscale
Experience the Bethpage at Oxford Greens, a premier active-adult community in Connecticut, crafted by the award-winning EG Home. This single-level townhome offers 1,955 sq. ft. of expertly designed living space, featuring 2 bedrooms, 2 bathrooms, and a Great Room with vaulted ceilings that opens effortlessly into a chef's kitchen, complete with hardwood floors, wood cabinetry, and upscale
Current Concession - Apply within 72 Hrs. of your 1st tour and receive 1 month rent free on select lease terms. Enjoy newly-built luxurious 1 and 2 bedroom apartments located inside Quarry Walk, Connecticut’s best answer to “Live, Work, Play” living. Residents enjoy premium amenities at our environmentally friendly community in Oxford, Connecticut, located in Upper Fairfield County / Western New
Situated on the scenic Housatonic River, in Seymour Connecticut, the Residences at the Kestrel feature modern luxury amenities with a rustic feel. Brand new Building built in 2023All of our 1 and 2 bedroom apartments have private washer and dryers, granite and stainless kitchens and tiled baths, central air and heat and hard surface floors. There is onsite parking, electric vehicle
BRAND NEW FACTORY-BUILT RENTAL HOMES - ONE-FLOOR LIVING!To set up a live tour, please submit an Application for Rental on the GHMCO website. Once received, our friendly leasing staff will contact you to set up a live tour. A credit check fee of $13 will be collected electronically at the time of application. **Master Bedroom with Full Bath (walk-in shower)**Full Hall Bath
Property Id: 2813313 Welcome to 5 Rolling Hills Drive! This beautifully maintained home is located in a desirable Seymour neighborhood on a spacious 1/2-acre lot. The freshly painted interior features beautiful hardwood floors, an open-concept layout, and a spacious family room with soaring cathedral ceilings. Enjoy the added peace of mind of a brand-new roof installed in 2026. The private,
Welcome to your new home in beautiful Seymour, CT! This property offers a perfect blend of comfort and convenience, making it an ideal choice for those looking to settle in a vibrant community.Key features of this rental include spacious living areas and welcoming bedrooms that provide a serene retreat after a busy day. Enjoy the benefits of central heating and cooling, along with air
Welcome to your new home in beautiful Seymour, CT! This property offers a perfect blend of comfort and convenience, making it an ideal choice for those looking to settle in a vibrant community.Key features of this rental include spacious living areas and welcoming bedrooms that provide a serene retreat after a busy day. Enjoy the benefits of central heating and cooling, along with air
Welcome to your next home in the charming district of Seymour, CT! This inviting property is perfect for those seeking comfort and convenience in a friendly neighborhood. Enjoy easy access to several fantastic restaurants, department stores, and the nearby French Memorial Park, all within walking distance. Plus, Yale New Haven Health Urgent Care is just a quick 14-minute drive away for peace of
Property Id: 2713122 Welcome to your charming 3 bedroom, 1 bathroom single-family home in Oxford. Built in 1950, this cozy property features hardwood floors, a fireplace, and a spacious lawn. This listing does not have a stove or a refrigerator. Tenant is to supply their own stove and refrigerator. Washer/dryer hookups are available in the basement. Full kitchen, and dining room. Driveway,
Welcome to your next home in the charming district of Seymour, CT! This inviting property is perfect for those seeking comfort and convenience in a friendly neighborhood. Enjoy easy access to several fantastic restaurants, department stores, and the nearby French Memorial Park, all within walking distance. Plus, Yale New Haven Health Urgent Care is just a quick 14-minute drive away for peace of
Don't miss this charming half duplex with 2 bedroom 1 bath. With a total of 7 rooms, a 3rd floor bonus space leads to endless possibilities. Enjoy the convenience of an included washer and dryer, a brand-new front and side porch, and a large, level, fully fenced backyard. Conveniently located close to highway. Trash removal and water are included.
Discover this recently remodeled 3-bedroom, 1-bath apartment in Seymour, CT. The unit features brand new appliances and a reserved parking space for convenient parking. Fresh updates throughout provide a modern, comfortable living environment in a desirable location. Contact us to schedule a viewing and learn more about leasing details.
This ground floor, updated condo in the sought after complex of Balance Rock is the perfect option for someone downsizing or isn't quite ready to buy yet. The entire condo has been updated with new appliances, kitchen cabinets, floors, bathroom vanity & tub, paint, and a customized closet in one of the two large bedrooms. The complex offers a pool, tennis court, basket ball court, playground,
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