Homes, values and local insight for Old Saybrook, Middlesex County, Connecticut. Typical home value $708,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
Live listings open in a new tab, highest price first. Or type exactly what you want in the search bar.
Old Saybrook sits where the Connecticut River meets Long Island Sound. It is known for its wide, walkable Main Street, its beach neighborhoods, and its link to Katharine Hepburn, who lived in the Borough of Fenwick. The town's Amtrak and Shore Line East station makes it a practical shoreline base.
English settlers arrived at Saybrook Point on November 24, 1635, and Lion Gardiner built Saybrook Fort there in 1636. The Collegiate School, later Yale University, was chartered here in 1701 and moved to New Haven in 1716. The town was incorporated as Old Saybrook on July 8, 1854. A small coastal town of about 10,500 people with year-round residents, weekenders and retirees. Days revolve around Main Street shops, the marinas and the beach associations.
An incorporated borough at the mouth of the Connecticut River with its own warden and local government. Katharine Hepburn lived here. ( source )
The original 1635 settlement at the river mouth, home to Fort Saybrook Monument Park, marinas and Saybrook Point Resort. Part of the Old Saybrook Center area. ( source )
The downtown core along a wide Main Street, lined with 18th century Colonial and 19th century Federal buildings, shops and restaurants. The town counts more than 100 homes of historic significance. ( source )
A shoreline neighborhood on Long Island Sound run through the Cornfield Point Association, which has its own tax collector. ( source )
A beach neighborhood with its own improvement association, next to the Chalker Beach and Cold Spring Brook marshes that the town is studying. ( source )
A census-designated beach community with its own association and tax collector. ( source )
A private beach association neighborhood with its own association and tax collector. ( source )
A beach improvement association neighborhood on the Sound with its own tax collector. ( source )
Seasonal menu built on local seafood and an award winning raw bar. Happy hour Tuesday to Friday. ( source )
Seafood shack · 26 Bridge Street, Harbor One MarinaCasual waterfront sister spot to Liv's Oyster Bar inside Harbor One Marina. ( source )
Seafood stand · 910 Boston Post RoadLong-running shoreline stop for fried seafood, clam chowder, lobster rolls and Hummel hot dogs. ( source )
Italian and New Haven style pizza · 1654 Boston Post RoadFamily owned spot with New Haven style pizza and hand-made pasta and bread made daily. ( source )
Japanese and sushi · 286 Main StreetSushi-focused fine dining with a 13 course omakase chef's tasting menu. ( source )
Ramen and noodles · 210 Main StreetFamily owned noodle shop known for ramen and other noodle bowls. ( source )
Breakfast, lunch and coffee · 210 Main StreetBreakfast, lunch and espresso with gluten friendly options. ( source )
Acai bowls and smoothies · 188 Main StreetLocal acai and smoothie shop with coffee and a small retail corner for local artisans. ( source )
Two-story English style pub on Main Street with pub fare, seafood specials, daily brunch specials and pet friendly outdoor seating in season. ( source )
Brewery and taproom at 39 Ragged Rock Road with its own beers and scheduled events. ( source )
Family friendly restaurant and bar at 256 Main Street known for burgers, wings, milkshakes and watching games. ( source )
Wine bar at 85 Main Street in the downtown strip. ( source )
Play cafe at 118 Main Street where kids play while parents get coffee and light bites. Reservations recommended. ( source )
New and used bookstore at 146 Main Street. ( source )
44,000 square foot home furnishings store at 2 Main Street with decor, rugs, lighting, gifts and apparel plus design services. ( source )
Backyard bird feeding shop at 434 Boston Post Road with seed, feeders and houses. ( source )
Running store at 238 Main Street with a fit process for runners and walkers. ( source )
Main Street shop at 168 Main Street that takes part in the chamber's summer sidewalk sale. ( source )
Outlet center at 314 Flat Rock Place in neighboring Westbrook with brand name stores and sales events. ( source )
Town beach on Plum Bank Road with white sand, lifeguards, a playground, concession stand and bath house. Open Memorial Day to Labor Day. ( source )
in townA 963-acre protected forest shared by Old Saybrook, Essex and Westbrook, conserved in 2015. It protects drinking water for two towns and has hiking trails. ( source )
in townTown conservation land. Great Cedars East is 110 acres and Great Cedars West is over 300 acres, with trails for hiking, on-leash dog walking and mountain biking. ( source )
within 15 miles710-acre state park with a soft sand beach, trails and salt marsh viewing platforms. ( source )
about 15 milesConnecticut's largest shoreline park with a two-mile beach, a campground, a nature preserve and a three-mile bike trail. ( source )
within 15 milesWilliam Gillette's stone castle above the Connecticut River with castle tours, trails and river views. ( source )
next town westCoastal refuge first established in 1972 as Salt Meadow National Wildlife Refuge. The Salt Meadow Unit in Westbrook is an Important Bird Area. ( source )
The Kate is a 285-seat theater and Hepburn museum in the historic town hall theater on Main Street, reopened in 2009. ( source )
17-acre park at Saybrook Point with storyboards on the 1635 Saybrook Colony, a boardwalk and river mouth views. Free, dawn to dusk. ( source )
Runs the Hart House museum, gardens and Frank Stevenson Archives at 350 Main Street, plus tours and a house tour. ( source )
Valley Railroad steam train and riverboat rides through the lower Connecticut River Valley, running since 1971. ( source )
Art, history and nature museum across the river, open Tuesday through Sunday. ( source )
Chefs compete along Main Street and ballot holders sample and vote. Proceeds fund a chamber scholarship. ( source )
Late JuneMain Street closes for live music, food, craft beer tents, vendors and a drone show. ( source )
Early OctoberLong-running juried show with over 150 artists and crafters. ( source )
OctoberFamilies, schools and businesses build scarecrows and the public votes. ( source )
Early DecemberHoliday kickoff with afternoon festivities, part of a week of events like Ladies Night and the Stocking Walk. ( source )
Kathleen E. Goodwin School (PreK to grade 4)
MiddleOld Saybrook Middle School (grades 5 to 8)
HighOld Saybrook Senior High School (grades 9 to 12)
PrivateSt. John's Catholic School (PreK to grade 8), The Children's Tree Montessori School (ages 1 to 12)
Listed for reference, not ranked. Confirm school zoning for any address with the district. ( source )
I-95 (Exits 66 to 68), Route 9 (Exit 2), U.S. Route 1 (Boston Post Road), Route 154
AirportsTweed-New Haven Airport about 40 minutes; Bradley International about 1 hour; T.F. Green (Providence) about 1 hour 15 minutes. Amtrak and Shore Line East stop at the Old Saybrook station on North Main Street.
New Haven: about 35 min Hartford (40 miles): about 45 min Providence: about 1 hr 15 min New York City (100 miles): about 2 hr Boston (105 miles): about 2 hrRyan and Megan Winslow, broker owners of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Call 386-690-5858 Email Ryan and Megan Get pre-approvedResearched and verified 2026-09-28. Businesses change; call ahead.
The typical home in Old Saybrook is worth $708,000, 52% above the Middlesex County typical value of $465,000 and 57% above the Connecticut typical value of $451,000.
Zillow Home Value Index for Old Saybrook, August 2026. The middle of the market for single family homes and condos.
Home values in Old Saybrook moved +50.8% over five years and +98.5% over ten.
Median gross rent in Old Saybrook. Useful for investors running rental numbers.
Share of occupied homes in Old Saybrook lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Old Saybrook.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Old Saybrook home of $708,000:
Ryan and Megan price Old Saybrook homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $641,000 · 6,847 residents
Area guide →Typical value $688,000 · 7,721 residents
Area guide →Typical value $591,000 · 6,918 residents
Area guide →Typical value $444,000 · 4,483 residents
Area guide →Typical value $472,000 · 13,467 residents
Area guide →Typical value $808,000 · 2,421 residents
Area guide →See the full Middlesex County real estate guide or the Connecticut real estate guide.
The Zillow Home Value Index for Old Saybrook was $708,000 in August 2026, +5.0% over the past year.
Old Saybrook is in Middlesex County, Connecticut.
About 10,689 people as of the 2024 Census Bureau estimate, up from 10,486 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
85% of occupied homes in Old Saybrook are owner occupied, based on the 2019 to 2023 American Community Survey.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
No in-person meeting or phone call needed for most addresses. See your estimated value, price range and value trend in seconds.
Get coming-soon homes, pocket listings and price drops in Old Saybrook, CT before they hit the big home search sites.
The typical home in Old Saybrook is worth $707,840 as of August 2026 in ZIP code 06475. Values moved +5.0% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 06475 | $707,840 | +5.0% | +51.0% | $742,500 | 33 |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
