$774,261Average Value$508Average Price per Sq Ft32Homes 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 59 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 $722,500, up 5% from the median home sale price over the previous 12 months.
Framed by professional landscape and stunning hardscape, this expansive shingle-style home is located equidistant to Essex and Old Saybrook Main Streets, five Connecticut River marinas and Saybrook Station. Incredible updates include the creation of a main level laundry/mudroom update, the addition of central air and more. Well designed and appointed spaces include a stunning open kitchen with
76-1 River Street West! This is an incredible opportunity, less than a quarter mile to Old Saybrook Main Street and Amtrak train station. A cozy kitchen, dining and living open to an expansive great room with vaulted, beamed ceiling. There is a generous first-floor bedroom and an adjacent full bath. Upstairs find two larger bedrooms and a second full bath. The basement has an elevated ceiling,
Welcome to a home where quality meets comfort, starting with a charming brick walkway and vibrant perennials that lead to an inviting front entrance with a character-filled full dining area. This seamless one-floor layout continues into the eat-in kitchen, which boasts a spacious countertop, and a convenient first-floor laundry room complete with a half bath. Relax in the living room, featuring a
Welcome to your waterfront hidden gem! A once in a lifetime opportunity on the Connecticut River featuring 381 feet of direct waterfront, private two boat dock, private horseshoe bay and panoramic north facing views up the river. This modern Contemporary private estate features 5,600+ square feet of living space! Open floor plan, stunning water views from every room! The living room features cozy
Framed by professional landscape and stunning hardscape, this expansive shingle-style home is located equidistant to Essex and Old Saybrook Main Streets, five Connecticut River marinas and Saybrook Station. Incredible updates include the creation of a main level laundry/mudroom update, the addition of central air and more. Well designed and appointed spaces include a stunning open kitchen with
Considering a new build now or in the future? Can't find, "just the right property?" It's time to secure this very special location. Welcome to 124 Old Boston Post Road, an incredible .31 acre building lot in the heart of downtown Old Saybrook. Walk to the Acton Library, Trask Park tennis/pickleball and splash pad and a half mile to Main Street restaurants, shops, town offices and schools. Enjoy
76-1 River Street West! This is an incredible opportunity, less than a quarter mile to Old Saybrook Main Street and Amtrak train station. A cozy kitchen, dining and living open to an expansive great room with vaulted, beamed ceiling. There is a generous first-floor bedroom and an adjacent full bath. Upstairs find two larger bedrooms and a second full bath. The basement has an elevated ceiling,
Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 5,739 square feet, this residence combines timeless architectural sophistication with the serene beauty of nature. Leave the world behind as you travel
Welcome to a home where quality meets comfort, starting with a charming brick walkway and vibrant perennials that lead to an inviting front entrance with a character-filled full dining area. This seamless one-floor layout continues into the eat-in kitchen, which boasts a spacious countertop, and a convenient first-floor laundry room complete with a half bath. Relax in the living room, featuring a
Direct waterfront with phenomenal views! Perched on a bluff with 62 feet of shoreline frontage, this Nantucket-inspired residence provides an unparalleled, panoramic vantage point of Long Island Sound and the coastline. Perfectly positioned to capture the essence of being on the water, this home maximizes water views from every room and boasts magnificent sunrises and sunsets. Tucked away on a
A lovely renovated ranch in the heart of "Meadowood", a desirable family friendly community in the charming town of Old Saybrook. The home features hardwood floors throughout, and a comfortable open layout with a large living room, stylish dining room, and a beautiful kitchen designed by local Hanford Kitchens. Three ample bedrooms await just around the hall. The yard is nicely landscaped and
Cornfield Point, Old Saybrook - Coastal Living at Its Best! Steps to the beach with sparkling water views and stunning sunsets, this beautifully updated home blends timeless charm with modern upgrades. Originally built in 1926, it features an open layout perfect for entertaining. Imagine hearing the waves crash while dining on your brand new deck! The living room boasts the original Cornfield
Saybrook Point! This fully renovated coastal retreat with partial water views offers an exceptional blend of privacy, charm and effortless lifestyle. Steps aways from desired Saybrook Point, marinas, mini golf, Fenwick Golf Course and a stroll to beaches, restaurants and Main Street - everything that defines the Old Saybrook lifestyle is just steps away. Set on a generous sized lot this home is
Direct waterfront living in Old Saybrook with deeded Cornfield Point beach rights and a private dock (dock in need of repair). Set on a private lot at 33 Briarwood Dr, this 3 bedroom, 2 bath residence captures expansive marsh and tidal channel views with stunning daily sunsets that define the coastal lifestyle. Out with the old and in with the new! Move-in ready with thoughtful updates including
Enjoy effortless shoreline living with sweeping views of North Cove from this beautifully renovated, move-in ready townhouse-style condo in the heart of Old Saybrook. Perfect as a second home or easy downsize, this light-filled residence offers an open layout designed to capture the water. A desirable end-unit, this spacious two-bedroom design includes a stunning primary suite with its own full
GREAT STUDIO APARTMENT. OPEN CONCEPT OF LIVING. NEXT TO ISLAND COVE MARINA. OVER SIZE BALCONY/DECK WITH AMAZING RIVER VIEWS. BEDROOM WITH THE BUILD INS , BRIGHT AND FRESHLY PAINTED. PLENTY OF STORAGE. KITCHEN WITH BREAKFAST NOOK .ONE CAR ASSIGNED PARKING. CREDIT CHECK , SECURITY DEPOSIT . CALL-SHOW-RENT :)
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
Great year round rental with 3 bedrooms 1.5 bathrooms, hardwood floors throughout with tiled bathrooms. A large deck with awning overlooking a private back yard. Excellent location, close to beaches, schools and Main Street. Long term tenant would be ideal.
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
Available immediatly, if your looking for a place in Old Saybrook to enjoy the summer while your shopping for your forever home great short term rental with water views and plenty of privacy. The best of one level living this adorable ranch has 3 bedrooms and 2 newly renovated bathrooms. Everything is immaculate. This is a great location uniquely situated off of RT one but at the end of a cul de
2026 Beach cottage -- April 15 to Oct 15 -- $3,500/month. One lucky renter will get to spend spring, summer, and fall in this charming Chalker Beach cottage! Located in a private association, this home is just a short walk to the large soft-sand beach. Walk for miles along adjoining beaches and neighborhoods during the day, and enjoy the magical pastel sunsets over the ocean at night. Inside,
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
Adorable 4-bedroom, 1-1/2 bath beachfront retreat available as an academic rental from early September through the end of May in the highly sought-after Chalker Beach neighborhood of Old Saybrook. Offered fully furnished with all utilities included, this charming coastal home that was completely rebuilt in 1986 is the perfect place to enjoy off-season shoreline living. Warm coastal wood paneling
Studio unit includes heat, hot water, electricity, cable, and internet. Recently remodeled. Clean and freshly painted. Private bath. Parking available. Conveniently located. Walking distance to beach.
Classic New England year round beach house across the street from the ocean in the private Knollwood beach area. This home has 4 bedrooms, 2 full baths and an outside shower ! Master bedroom has a king bed, 2nd bedroom has a full size bed, 3rd bedroom has a queen size bed and 4th bedroom has a full and twin bed. Stunning views on every side and amazing sunsets ! This is a great location the
Fantastic Opportunity to Rent in Fabulous Fenwick! This charming water-view traditional Fenwick Cottage is available from September, 2026, through June 20, 2027! Boasting 4 bedrooms and 4 baths plus a huge third-floor rec room/bunk room space, the home offers over 3,700 sq. ft. of comfortable beach living. Open floor plan living room with walls of windows and French door access to a spacious back
Summer 2026 -- Available: June 15-30 for $9,000 -- Rented: July/Aug/Sept. This beautiful property is a direct waterfront, 4 bedroom, one-level home situated on a sandy beach in a private association. Wake up every morning to ocean waves, and enjoy the panoramic sunrises/sunsets which are magical here. Upon pulling into the driveway, you'll be greeted by breathtaking water views. The expansive
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