Homes, values and local insight for Madison, New Haven County, Connecticut. Typical home value $725,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Madison is a Long Island Sound shoreline town best known for Hammonasset Beach State Park, the state's largest shoreline park with a two-mile sandy beach and a campground. Its walkable downtown along the Boston Post Road holds RJ Julia Booksellers, an independent cinema and a historic town green with two local historic districts nearby.
The area was first settled about 1650 as East Guilford, a parish of Guilford, on land bought from the Nehantic and Mohegan people in 1641. The Town of Madison was incorporated in 1826 and named for President James Madison at the suggestion of Captain Frederick Lee. Once a center for fishing, shipbuilding, farming and charcoal making, the town celebrates its bicentennial in 2026. Madison grew from a summer resort for cottagers into a mostly residential shoreline town, and beach life still shapes the calendar. Days revolve around the town beaches, the Friday farmers' market on the green and the shops and cafes along Route 1.
The historic heart of town around the Madison Green and Meetinghouse Lane. It sits in a local historic district of private homes, churches and civic buildings, next to the downtown shops on the Boston Post Road. ( source )
A residential street protected as a local historic district in 2014. Exterior changes to homes here go through the Historic District Commission. ( source )
A stretch of the western Boston Post Road that the town is studying as a third local historic district. Buyers here should track the district process and its timeline. ( source )
The shoreline area off Middle Beach Road and West Wharf Road, home to the Madison Beach Hotel, the Madison Country Club and the Surf Club. Early 1900s developers carved this coast into neighborhoods such as Seaview for summer residents. ( source )
The western shoreline near the Guilford line, where the Shore Line Electric trolley once stopped around 1900. Circle Beach drew summer visitors as early as a 1908 postcard shows. ( source )
The rural, wooded north end of town along Route 79 toward the Durham line, first organized as its own parish in 1753. It is home to Rockland Preserve's cliffs, ledges and old roads. ( source )
A Madison seafood stand for more than 60 years that bills itself as home of the world's largest seafood rolls. ( source )
French bistro · 8 Scotland Avenue, downtownA Lyon-style bouchon serving traditional French comfort food, with a covered, heated patio. Reservations are recommended. ( source )
Italian Mediterranean · 725 Boston Post Road, downtownDinner spot run by Chef Ilario, whose family restaurant roots trace to Del Monaco's on Wooster Street in New Haven in 1972. ( source )
Pizza and pasta takeout · 391 Durham RoadPizzas often sell out on Friday and Saturday nights, so locals pre-order online to lock in a pickup time. ( source )
Bagels and breakfast · 1347 Boston Post RoadA Madison bagelry since June 2003, making bagels fresh daily. ( source )
Sandwiches, pizza and prepared foods · 96 Wall StreetCasual local shop for handcrafted sandwiches, stone-baked pizza and prepared meals to take home. ( source )
Ice cream · 724 Boston Post RoadShoreline ice cream maker with a Madison scoop shop, also selling ice cream cakes and pies. ( source )
Pizza, breakfast and grill · 1278 Durham RoadNorth Madison stop for breakfast sandwiches, grill items and pizza, open from 8 a.m. daily. ( source )
Independently owned downtown movie theater with luxury rockers, hot food, beer and Sunday Morning Classics screenings. 761 Boston Post Road. ( source )
Weekly market on the Madison Town Green at 26 Meeting House Lane, every Friday from 3:00 to 6:00, May to Thanksgiving. ( source )
The town's 45-acre beach park with grills, bocce, volleyball, horseshoes and a seasonal concession stand. The picnic grove is open until 9 p.m. ( source )
Madison's community library and gathering place since 1900, with programs for all ages. ( source )
Youth arts nonprofit running musicals, plays and creative programs for local kids and families. ( source )
Nationally known independent bookstore at 768 Boston Post Road, open seven days a week. ( source )
Gallery at 679 Boston Post Road representing about 50 artists. Susan Powell started the business in 1981. ( source )
Gift and home goods shop at 698 Boston Post Road that employs people with disabilities. ( source )
All-volunteer thrift shop at 170 Boston Post Road. Net proceeds have supported youth causes since 2004. ( source )
Small family farm at 353 Boston Post Road growing cut flowers and making jams. ( source )
Oyster farm working the waters off Madison and Clinton, with online ordering and pickup of Long Island Sound oysters. ( source )
Connecticut's largest shoreline park, with a two-mile sandy beach, boardwalk, campground and nature preserve at Meigs Point. 1288 Boston Post Road. ( source )
in town45 acres on Long Island Sound with 1,200 feet of sandy beach, athletic fields, playgrounds and a sailboat and kayak area. Seasonal fees apply. ( source )
in townBuilt on the former Griswold Airport site, with playing fields, a fenced dog park, a runway walking path, coastal forest trails and a kayak launch. 1362 Boston Post Road. ( source )
in townFormer Bauer family farm given to the town in 1990, now open space with trails, community gardens and a pond with a covered bridge. 257 Copse Road. ( source )
in town (North Madison)Rocky hills, cliffs and woods in North Madison with old roads for hiking, a natural playground and the Singletracks of Rockland bike park. ( source )
Killingworth, neighboring town18 miles of trails, a rock climbing crag, a covered bridge and a working water wheel in the neighboring town of Killingworth. ( source )
Westbrook, a short drive eastRefuge unit in Westbrook named an Important Bird Area by the National Audubon Society. The refuge spans 10 units along 70 miles of Connecticut coast. ( source )
Historic house museum of the Madison Historical Society at 853 Boston Post Road, bought by the society in 1920. Open the 1st and 3rd Saturday, 11 a.m. to 1 p.m. ( source )
Schoolhouse founded by Captain Frederick Lee in 1821 and moved to the town green in 1830. Now a history center at 14 Meetinghouse Lane. ( source )
Outdoor sculpture exhibit curated by the Hollycroft Foundation, with works by artists such as Roger Bowie and Anthony Padovano. ( source )
Professional non-Equity company presenting opera, musical theater and drama on the shoreline, including a summer festival. ( source )
Self-guided audio and video tour of homes, churches and civic buildings around the green, created by Daniel Hand High School students. ( source )
Parade west on the Boston Post Road from Samson Rock Drive, ending with a flyover and remembrance ceremony at the Town Green. ( source )
Early JulyMadison Cultural Arts concert on the Town Green. The 2026 show featured the Lancraft Fife & Drum Corps and the Wallingford Symphony Orchestra. ( source )
July 4Morning parade west on Route 1 from Samson Rock Drive to West Wharf Road, ending at the Surf Club. ( source )
OctoberFree old-fashioned country fair with hay and pony rides, apple tasting, a cider press, a hay maze and live music. ( source )
Fridays, May to ThanksgivingWeekly market on the Town Green from 3:00 to 6:00 with local vendors. ( source )
Brown Elementary School, Neck River Elementary School
MiddlePolson Middle School
HighDaniel Hand High School
Listed for reference, not ranked. Confirm school zoning for any address with the district. ( source )
Interstate 95 (Exits 60, 61 and 62), Boston Post Road (Route 1), Durham Road (Route 79) and the Hammonasset Connector (Route 450). Shore Line East trains stop at Madison station, 77 Bradley Road, with connections to Amtrak and Metro-North in New Haven.
AirportsTweed New Haven Airport is about 24 miles away and Bradley International Airport is about 52 miles away, per the Town of Madison.
New Haven: about 20 miles JFK International Airport: about 96 miles Boston Logan International Airport: about 135 milesRyan 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 Madison is worth $725,000, 77% above the New Haven County typical value of $409,000 and 61% above the Connecticut typical value of $451,000.
Zillow Home Value Index for Madison, August 2026. The middle of the market for single family homes and condos.
Home values in Madison moved +45.6% over five years and +87.2% over ten.
Median gross rent in Madison. Useful for investors running rental numbers.
Share of occupied homes in Madison lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Madison.
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 Madison home of $725,000:
Ryan and Megan price Madison homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $632,000 · 6,284 residents
Area guide →Typical value $641,000 · 22,264 residents
Area guide →Typical value $472,000 · 13,467 residents
Area guide →Typical value $444,000 · 4,483 residents
Area guide →Typical value $591,000 · 6,918 residents
Area guide →Typical value $482,000 · 13,551 residents
Area guide →See the full New Haven County real estate guide or the Connecticut real estate guide.
The Zillow Home Value Index for Madison was $725,000 in August 2026, +3.8% over the past year.
Madison is in New Haven County, Connecticut.
About 17,688 people as of the 2024 Census Bureau estimate, up from 17,686 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.
91% of occupied homes in Madison 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.
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The typical home in Madison is worth $725,705 as of August 2026 in ZIP code 06443. Values moved +3.8% 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 |
|---|---|---|---|---|---|
| 06443 | $725,705 | +3.8% | +45.7% | $725,000 | 50 |
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.
