$831,969Average Value$565Average 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
Joseph Moleano,
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 55 days. The median sale price for homes in Old Saybrook, CT over the last 12 months is $718,750, up 2% from the median home sale price over the previous 12 months.
KNOLLWOOD BEACH - Here is the opportunity! A Raised Ranch sitting on a wide .98-acre lot offering possibilities rarely found this close to the shoreline. 97 Feet of road frontage. Offered for the first time since it was built, enjoy it now, generate rental income or land bank this parcel while planning something much more commodious for tomorrow. Knollwood is renovation active, with 4+ projects
Your Year-Round Beach Home Awaits in Cornfield Point Welcome to your opportunity to own a year-round home in Cornfield Point, one of Connecticut's most desirable beach communities. Ideally located just steps from the beach. This move-in-ready home offers the perfect combination of comfort, coastal living, and breathtaking water views. The home features 3 bedrooms and 1 full bath, along with a
Experience refined coastal living in this stunning end-unit townhome, completed in 2021 and ideally located in the heart of downtown Old Saybrook. This exceptional residence offers convenient access to dining, shopping, the Katharine Hepburn Cultural Arts Center, Saybrook Point Marina, and local beaches. Bathed in natural light, the home features a spacious open floor plan with gleaming hardwood
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,
Coastal living is calling! This is a fully furnished shoreline retreat set within the sought-after Chalker Beach Association. Offered As-Is and thoughtfully updated, this inviting home is ideal as a year-round residence, weekend escape, or classic summer getaway. With marsh views, salt air, and a relaxed beach-community setting, this is a turnkey opportunity designed for immediate enjoyment
KNOLLWOOD BEACH - Here is the opportunity! A Raised Ranch sitting on a wide .98-acre lot offering possibilities rarely found this close to the shoreline. 97 Feet of road frontage. Offered for the first time since it was built, enjoy it now, generate rental income or land bank this parcel while planning something much more commodious for tomorrow. Knollwood is renovation active, with 4+ projects
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 1.16 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
A Rare Coastal Opportunity Awaits! Set in the highly sought-after North Cove Historic District of Old Saybrook, this grand colonial offers something truly special: a coveted prime coastal location, spectacular water views, and incredible potential to create the home you've always envisioned. Originally built in 1930 and expanded in 1987, this property has the character, scale, and bones of a
Introducing a rare opportunity to build your dream home in one of Connecticut's most desirable shoreline communities. Located at 81 Essex Road in Old Saybrook, this to-be-built home by Silvin Homes offers the flexibility to choose from multiple thoughtfully designed floor plans and finishes, allowing you to create a home that fits your lifestyle and budget. What truly sets this property apart is
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
Step back in time and discover the beauty of this extraordinary antique home, set on an acre of landscaped grounds, with an enchanting guest cottage. The Bushnell-Dickinson House is a Georgian colonial that retains its original features inside and out. including original wide-board pine flooring, paneled walls, four fireplaces, two staircases, dentil moldings, authentic hardware and classic
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
Welcome to your new home in the charming Saybrook Manor district of Old Saybrook, Connecticut! This inviting Academic rental property offers a perfect blend of comfort and convenience, making it an ideal choice for those seeking a vibrant community atmosphere.Key property features include spacious bedrooms and well-appointed bathrooms, offering ample space for relaxation and daily living.
Amazing views every day at 28 Beach Rd West, Old Saybrook! This beautiful Academic Rental beach home has 3 bedrooms and 2 baths and is available for your enjoyment ... across the street from Chalker Beach with spectacular and unobstructed views of Long Island Sound. The open kitchen, dining and living room with a gas fireplace are the focal point of the home. The kitchen has gorgeous granite
Welcome to your new home in Old Saybrook, CT! This charming Academic rental property is ideally located, providing easy access to a fantastic local restaurant and several department stores, ensuring you're never far from convenience and great dining experiences.This property offers the perfect balance of comfort and functionality, featuring both central heating and air conditioning,
Cornfield Point Beach area, Winter rental.Oct 1,2026- April 30, 2027 Furnished. Short term Rental.Conveniently located near town, restaurants and train station. You will fall in love with this Old Saybrook 3 bedroom, 2 full bathroom home. Newly renovated. Fully furnished, move in ready. Washer and dryer in basement. Open concept kitchen with stainless steel appliances, dishwasher,
CHALKER BEACH ACADEMIC RENTAL AVAILABLE 9/15/26 - 5/15/26. Adorable fully furnished 3 bedroom, 1.1 bathroom Cape featuring kitchen open to dining room, living room, 1 bedroom on the main level, 2 bedrooms on the 2nd floor, 3 season screened in porch, outdoor shower, off street parking for 4 cars. Tenants will be responsible for water, electric (lights, hot water, AC & Heat) and snow removal. The
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
Available Sept 4, 2026. One-year lease minimum; credit check; non-smoking; pet-flexible. Nicely updated 4 BR, 2.5 bath Colonial on a one-acre lot in Old Saybrook offers a formal living room, a beautifully renovated kitchen with granite counters, a breakfast bar, and an open family room with a fireplace and slider to the deck. The primary suite has a walk-in closet and full bath, three additional
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
ACADEMIC RENTAL until mid May 2027. Three BR Colonial with Sun Room located in the beautiful Indian Town Beach Association. Views of LIS and harbor. Bright and spacious rooms. This location is perfect for walking, biking or strolling along the beach. Conveniently located to I95, Train Station, Shopping and The Kate. Sorry NO pets or smoking allowed.
WINTER RENTAL available September 15, 2026 through May 31, 2027 for $4,500/month. Enjoy spectacular Long Island Sound views from this beautifully renovated 3-bedroom, 3-bath home in the desirable Knollwood Beach Association. Tucked away on a quiet street just off Maple Avenue and only one street from the beach, this exceptional home offers unobstructed water views and a peaceful shoreline
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