$749,071Average Value$505Average Price per Sq Ft40Homes For Sale
Waterside living and a competitive housing market in Old Saybrook
The quiet town of Old Saybrook lies on the Long Island beach. It's a fantastic catch for buyers searching for a waterside house with many beach and water activities. "From that perspective, Old Saybrook offers a lot, whether you want to live by a river, a cove, or the Long Island Sound," states Linda O'Hara, who leads Linda's team at William Raveis Real Estate. But Lewis Jump III, a Realtor with Remax ONE, says housing stock in the area is sparse. “It’s a tough area to sell,” he says. “The homes are in demand and sell really quick.”
Town Hall in Old Saybrook is right at its center.
Old Saybrook is never far from the water.
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Waterfront access and homes with spacious lots
In Old Saybrook, single-family homes with 1,200 square feet, three bedrooms, and two bathrooms on a spacious 2.5 acres start at about $340,000. Housing styles consist of colonials, ranch-style and Cape Cods. Larger acreages of land are typically found further inland, where certain Old Saybrook neighborhoods are tucked away in The Preserve, a wildlife preserve. In Old Saybrook, prices peak near the water at about $4.2 million. These opulent seaside residences typically feature 2,700 square feet, four bedrooms, and three bathrooms with views of the Long Island Sound. Due to the proximity to the beach, Jump III warns that the neighborhood and the Main Street district have “a lot of foot traffic.” There are some HOAs in the area and Jump says they usually charge by the years and most are reasonably priced. The community comes together annually for holiday celebrations, a Fourth of July parade and an annual art festival.
You can find a range of architectural styles, from historic colonial homes to modern designs.
Brick Homes in Old Saybrook, CT.
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An array of extracurriculars at Old Saybrook High
Old Saybrook Public Schools, which are renowned for their academics, teachers, clubs, activities, and college preparation—all of which have earned an A-minus grade or higher on Niche—teach students in the community. Additionally, Niche ranks the district as the best in Middlesex County. The youngest students in Old Saybrook begin their education at Kathleen E. Goodwin Elementary School. This school is well-known for its academics, teachers, and 10 to 1 student-teacher ratio. It has a B-plus rating on Niche. Old Saybrook Middle School's academic performance and teacher quality both get A-minus ratings on Niche. Old Saybrook High School, ranked No. 1 in Middlesex County and with an A grade on Niche, is where students complete their secondary education. The school offers popular clubs, activities, and top-notch academics and teachers. Numerous extracurricular activities are available to students, including groups for sailing, skiing, and dungeons & dragons. At Old Saybrook High, family frequently attend games to cheer on their teams. Sports are quite popular there.
The Daisy Ingram School is a public elementary school
The Children's Tree Montessori School in Old Saybrook is a private school.
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Drive a golf cart to nearby recreation
Old Saybrook is renowned for its stunning beaches, each with its own village, ranging from Cove Beach to Great Hammock, Harvey's, and Chalker. "Everybody drives around in their golf carts in those communities," adds O'Hara. "The town is walkable as well. Everywhere you go, you may ride and walk." Another well-liked activity in Old Saybrook is golfing. A well-liked option is the Fenwick Golf Course near South Cove, so golfers can practice their swing while enjoying ocean views.
Old Saybrook's Parks and Recreation has a ball field and basketball court.
Clark Community Park in Old Saybrook has ball and soccer fields.
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Local eateries along Route 1
Most of Old Saybrook’s eateries are along Route 1, which passes through Old Saybrook's southern section along the shore. Meals fit for gods may be found at the Parthenon Diner, where residents especially enjoy the "really hungry man" breakfast platter, which lives up to its name with bacon, ham, sausage, two eggs, home fries and toast. Groceries are found at Walt’s Food Market and Sam’s Food Store.
Visit Turtle Cafe and enjoy a good breakfast and coffee in Westbrook, CT.
The Parthenon Diner in Old Saybrook is the place to get a bite
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Holiday celebrations in Old Saybrook
The community comes together annually for holiday celebrations, a Fourth of July parade and an annual art festival.
Access to I-95
Interstate 95 can be accessed via Main Street and Route 1 for those who must commute.
Photography Contributed By
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Video By
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Interested in learning more about homes in this area?
Reach out to
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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.
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On average, homes in Old Saybrook, CT sell after 51 days on the market compared to the national average of 52 days. The median sale price for homes in Old Saybrook, CT over the last 12 months is $703,000, up 9% from the median home sale price over the previous 12 months.
This FEMA compliant coastal residence in Old Saybrook offers panoramic views of South Cove at the mouth of the Connecticut River, where the river meets the sound. The property features a new deck, providing an ideal vantage point for observing the sunrise and local wildlife each morning, as well as evening views of Lynde Lighthouse and passing boats.The interior has been thoughtfully remodeled
No Flood Insurance with this rare opportunity to own a newly built luxury residence with unobstructed water views, high-end finishes, and an exceptional location. Homes of this caliber in Old Saybrook are limited-don't miss your chance to experience elevated shoreline living. 26 Meadowood Lane, is an unparalleled blend of upscale shoreline living and architectural excellence in a premier Old
Welcome to SummerWood on the Sound, a premier waterfront community in Old Saybrook offering resort-style living on the Long Island Sound. This beautifully maintained 2-story condo with a 3rd-floor sleeping loft is perfect for year-round living or a cozy coastal getaway. Features include 2 bedrooms, with a primary suite and en-suite full bath, an updated guest bath, and a half bath on the main
GET YOUR SPOT AT THE BEACH! The perfect getaway, just a short walk from the Chalker Beach Sandy Shoreline. Ready for love, sun, swim, and enjoying all the fun-with no traffic and plenty of relaxation right outside this home. A spacious deck overlooks a beautiful backyard, ideal for entertaining family and friends. Rinse off the day in the outdoor shower. Chalker Beach offers an abundance of
This property is located in the private Chalker Beach community. This 3 Bedroom / 1.5 Bathroom house is a short walk from the white sandy Beaches and all the fun that comes with this Beach Community. Imagine all the unforgettable moments you'll create in this incredibly desirable location! Property is being sold As Is.
18 King Street in Old Saybrook is a rare find that checks every box-space, flexibility, location, and income potential. This updated ranch-style home offers over 3 spacious bedrooms, 3.5 modern baths, and two fully renovated kitchens, creating the perfect setup for multigenerational living, private guest quarters, or short- and long-term rental income. Inside, the open-concept design flows easily
Fantastic opportunity to spend the "off season" at the beach. Come and see this completelyRenovated to the hilt beachhouse. High ceilings, the finest of everything! This is a Academic Rental available from 9/1/25-5/31/26. It is not available for yearly rental. NOT Annual Rental. But for 9 Months come and enjoy the vistas of the Long Island sound. Put your toes in the sand every morning. This home
Located in Old Saybrook, with easy access to Main Street and Boston Post Road, Saybrook Station Apartments are just a quick jaunt to the train station, a four-minute drive to the historic Town Green, and minutes away from 1000 acres of coastal forest at The Preserve. Not to mention, all of the shopping, dining, and entertainment that nearby New Haven has to offer. Picture coming home every day to
Lovely Ranch home that has been remodeled within the last few years. It features an eat-in kitchen with granite counters, newer appliances and plenty of cabinets. The living room has hard wood floors and a large picture window allowing tons of sunlight to stream in making this room light and bright. The large full bath on the main level is also newer and features heated tile floors, a vanity and
Brian JermainneTeam Jermainne Real Estate Services, LLC
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