$807,369Average Value$568Average Price per Sq Ft44Homes 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
Matt Pangman
Interested in learning more about homes in this area?
Reach out to
Betsy Anderson,
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 62 days on the market compared to the national average of 57 days. The median sale price for homes in Old Saybrook, CT over the last 12 months is $735,000, up 7% from the median home sale price over the previous 12 months.
Welcome to the heart of Saybrook Manor! This beautifully maintained ranch-style home offers the perfect blend of shoreline charm and everyday convenience. Situated on a desirable corner lot, this one-level home features comfortable living spaces, thoughtful updates, and a relaxed coastal lifestyle. Enjoy easy access to the private Saybrook Manor beaches, Oyster River, nearby marinas, restaurants,
Life by the water starts here at 3 Anchorage Ln, a spacious Colonial in Old Saybrook set beside the marina with deeded 10-foot access for convenient boat loading and unloading. This 4-bedroom, 3 full bath home offers 2,496 sqft designed for everyday comfort and coastal living. The beautifully remodeled kitchen is the true anchor of the home, ideal for gatherings and seamlessly connected to the
Welcome to 28 Gates Road, a charming seasonal retreat in the heart of Cornfield Point Beach Association, one of Old Saybrook's most cherished beach communities. C/A and heating! With picturesque water views, beautifully manicured landscaping, and iconic green awnings, this classic cottage offers timeless shoreline charm and standout curb appeal. The spacious enclosed front porch is the heart of
Welcome to the heart of Saybrook Manor! This beautifully maintained ranch-style home offers the perfect blend of shoreline charm and everyday convenience. Situated on a desirable corner lot, this one-level home features comfortable living spaces, thoughtful updates, and a relaxed coastal lifestyle. Enjoy easy access to the private Saybrook Manor beaches, Oyster River, nearby marinas, restaurants,
Join us for our latest 'Sunset Roll Out' Party / Saturday 6.20.26 / 4-7 pm. Great Music, Light Fare & Drink. It is always a great time! Dynamic 5000 Sq/Ft Contemporary Colonial w/ a Fabulous 700 Sq/Ft In-Law Apartment (seperate entrance) built in 2021 in the coveted Indian Town Beach Association! Check out those Pics! 5 Brs , 4.5 Bths, Soaring Ceilings w/ Open Balconies, Two Story Linear
An exceptional opportunity - Nestled on 1.25 acres of vacant land with public water access, this prime property is located in the sought-after Gateway Business B-4 District In an area of national tenants, boasting a daily traffic count of 15,900. This versatile lot is zoned for a variety of uses such as retail stores, professional offices, medical clinics, theaters, and more. Its strategic
Ron LymanLyman Real Estate Brokerage & Development
Life by the water starts here at 3 Anchorage Ln, a spacious Colonial in Old Saybrook set beside the marina with deeded 10-foot access for convenient boat loading and unloading. This 4-bedroom, 3 full bath home offers 2,496 sqft designed for everyday comfort and coastal living. The beautifully remodeled kitchen is the true anchor of the home, ideal for gatherings and seamlessly connected to the
Bushnell Farm presents a rare opportunity to acquire one of the Connecticut shoreline's most unique and historically significant properties. Located on Boston Post Road in Old Saybrook, this 20.21-acre property offers an exceptional combination of history, character, visibility, and development potential. The property features open meadows, mature trees, historic New England stone walls, and the
Welcome to 28 Gates Road, a charming seasonal retreat in the heart of Cornfield Point Beach Association, one of Old Saybrook's most cherished beach communities. C/A and heating! With picturesque water views, beautifully manicured landscaping, and iconic green awnings, this classic cottage offers timeless shoreline charm and standout curb appeal. The spacious enclosed front porch is the heart of
Gracious 4 bedroom/ three full baths Cape Cod with an attached two-car garage. Set on a picturesque, one-acre lightly wooded, corner lot with beautiful stone walls, mature plantings, gardens, large patio and an oversized L-shaped in-ground pool which becomes the centerpiece for summer enjoyment complete with lots of privacy. With approximately 2500 square feet of thoughtfully designed living
Charming Coastal Ranch in an incredible Old Saybrook location! This well-maintained ranch offers the perfect blend of comfort, convenience, and shoreline lifestyle. An easy flow layout which includes 3 bedrooms, living room, dining room, kitchen, full bath and a full unfinished basement for additional storage or workshop. Step outside to a spacious backyard designed for entertaining, relaxing,
Rare opportunity to create your dream home in one of Old Saybrook's most sought-after beach communities! Located across from Cornfield Point Beach Association, with deeded beach rights, this .23-acre property includes access to the beautiful sandy beach a short walk away making daily walks to the shoreline effortless. Surrounded by attractive homes, the setting alone makes this a standout
Welcome to an exceptional year-round home located in one of Connecticut's most renowned beach communities, the Knollwood Beach Association. Just steps from a private beach, this property offers the perfect blend of coastal living and everyday comfort. This spacious home features a finished above-grade lower level. Please note: the official square footage does not include the fully furnished first
True tranquility awaits at this waterfront oasis! Unparalleled water views from every vantage point! Privately set on a generous 0.37-acre lot, this 3-bedroom home provides direct water access- perfect for kayaking out to Long Island Sound right from your backyard. Inside, the home blends charm and character with thoughtful updates. Its architectural lines evoke a Normandy chalet vibe, while the
This well-maintained 2-bedroom, 1-bathroom ranch is the ultimate turnkey opportunity in one of Connecticut's most beloved shoreline communities. Offered fully furnished - just move right in! Enjoy easy single-level living with a comfortable layout, all within minutes of Old Saybrook's downtown, local beaches, the Connecticut River, marinas, and charming shops and restaurants. Don't miss your
Experience the best of Connecticut shoreline living this fall, winter, and spring in this stunning beachfront home on Long Island Sound. Completely renovated with exceptional attention to detail, this beautifully appointed residence features soaring ceilings, premium finishes, designer furnishings, and every modern comfort. This is an academic rental available September 1 through May 31 only
Where Old Meets New...... Old Saybrook is one of the most charming, historical, and sought-after towns in Connecticut. SAYBROOK STATION is one of the only modern luxury apartment communities in the area, built near Saybrook’s historic train station. This central location in the heart of everything is also only four minutes from the Old Saybrook Town Green – yes, we’ve made a place where old truly
Welcome to Hanford Commons – The Definition of LuxuryDiscover modern living at its finest with our brand-new apartments in the picturesque town of Old Saybrook. Hanford Commons perfectly blends style, convenience, and comfort, offering you a home that exceeds expectations. Each thoughtfully designed unit features stainless steel appliances, an in-unit washer and dryer, central heating and
DOWNTOWN location! Beautifully remodeled, 1 bedroom/1 bath apartment in the heart of Old Saybrook. Features hardwood floors, granite countertops, new appliances, bath and mechanicals. Vaulted ceilings throughout. Located on a quiet street just steps to restaurants, coffee shops and galleries. Lawn maintained by owner. Easy electric heat and ductless air conditioning. Off-Street parking. No pets,
This beautifully refreshed 2,520 square foot gambrel colonial is set on a private cul-de-sac in desirable Old Saybrook and comes fully furnished for effortless living. The home features four bedrooms and two and a half bathrooms, along with recent updates including fresh paint, updated bathrooms and new kitchen appliances. Both the sitting room and living room offer scenic views of tall grasses
Step into this delightful and charming fisherman's cottage in the heart of downtown Old Saybrook. Built in 1800, 43 Pennywise Lane blends warm and cozy character with surprising spaciousness. The owner has preserved this home's historical integrity while adding in modern comforts. The first floor features an oversized primary suite with full bath, office space and reading nook. The eat-in kitchen
This spectacular home with a fantastic location is an Academic Rental; from September 15, 2026 through May 15, 2027. Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with
Welcome to Old Saybrook. This beautifully updated 4-bedroom, 2-bath academic rental offers the perfect blend of comfort and coastal living, complete with deeded beach rights to Cornfield Point Beach for the 2026-2027 academic calendar. Tucked away at the end of a quiet cul-de-sac on a full acre, this fully furnished home is truly move-in ready. The thoughtfully designed layout includes a heated
Beautiful Knollwood Beach winter rental available 8/15/2026 through 5/31/27. Enjoy living one block from LIS with lovely walking path along the waterfront and association amenities like tennis, and a great park with playground and basketball court. Nicely decorated and never rented before. Lovely livingroom with fireplace , 3 bedrooms, one bathroom. Oversized one car garage ok for tenant storage
Turn-key Academic Shoreline Rental for today's modern-living and tastefully decorated in Old Saybrook, CT. Beautifully renovated home in South Cove neighborhood great for morning walks with coffee or evening strolls with a cocktail in hand. This lovely light filled home has an open floor plan, custom built kitchen with modern stainless steel appliances, new hardwood floors throughout, first floor
Academic rental available October 1, 2026 - May 28, 2027. This beautiful beach home is a direct waterfront, 4 bedroom, one-level home situated on a deep soft-sand beach in a private association. Wake up every morning to ocean waves, and watch the panoramic sunrises and sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The large patio on
Welcome to the popular Indian Town Beach Association in Old Saybrook. This is a fully furnished academic rental available from October 1st, 2026, to May 15, 2026. Bright and neat, this home has been well taken care of both inside and out. The home features central air, propane heat, 2 bedrooms, a living room, a generously sized eat-in kitchen, a full set of laundry on the main floor, and a full
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