Fairfield Open Houses Oct. 17-18: An 1817 Greenfield Hill Colonial And 7 More

FAIRFIELD, CT — Fairfield's open houses this weekend include a renovated 1817 Greenfield Hill Colonial with a barn, an accessory apartment and a gunite pool with a waterfall, a Winton Park house with soaring ceilings and walls of glass, and a center-hall Colonial at the end of an in-town cul-de-sac.

Eight Fairfield homes are holding open houses Saturday, Oct. 17, and Sunday, Oct. 18, with prices from $555,000 to $2,195,000, according to Zillow.com.

Saturday, Oct. 17

280 Brookbend Road, 11 a.m. to 1 p.m. (also Sunday, noon to 3 p.m.), $1,549,000. New to the market this week, this 1972 house in Winton Park has soaring ceilings, dramatic architectural details and expanses of glass that bring the outdoors in, according to the listing. The updated kitchen opens to a dining room with an exposed brick wall. It's a four-bedroom, 2.5-bath home with 2,706 square feet on 0.96 acres.

126 Dwight St., noon to 2 p.m. (also Sunday, noon to 2 p.m.), $1,225,000. At the end of a quiet cul-de-sac in the heart of Fairfield, this 1957 center-hall Colonial sits on an oversized 0.37-acre lot minutes from downtown, the beaches and the train, according to the listing. It has hardwood floors, a first-floor bedroom and full bath and formal living and dining rooms. It's a four-bedroom, three-bath home with 2,052 square feet.

2493 Redding Road, noon to 2 p.m. (also Sunday, 11 a.m. to 1 p.m.), $2,195,000. This renovated 1817 Greenfield Hill Colonial on 3.6 rolling acres has a private accessory apartment, a sunroom, a barn and a gunite pool with a waterfall, according to the listing. Inside are a two-story entry with a sweeping staircase, high ceilings, a chef's kitchen and fireplaces in the family room, dining room and den. It's a five-bedroom, five-bath home with 5,415 square feet. Its price was cut by $200,000 on Oct. 12.

1770 Stratfield Road, 1 to 2:30 p.m., $649,900. This refreshed 1938 house has an open first floor, fresh paint, an updated kitchen with all-new cabinets and appliances, and a living area with a fireplace and a wet bar, according to the listing. The backyard is level, fenced and freshly seeded. It's a three-bedroom, two-bath home with 1,800 square feet.

71 School St., 1:30 to 3:30 p.m., $599,900. This 1930 Cape has a remodeled eat-in kitchen, a living room with plantation shutters, a dining room that could be a third bedroom, a remodeled bath, hardwood floors, a newer roof and paid-off solar panels, according to the listing. Outside are a two-car attached garage and a level, fenced backyard with a fire pit. It's a two-bedroom, one-bath home with 941 square feet.

Sunday, Oct. 18

213 Knapps Highway, 1 to 3 p.m., $555,000. This 1943 Cape has hardwood floors, an updated eat-in kitchen with quartz and shaker cabinets that opens to the patio, two first-floor bedrooms and a renovated bath, with two more bedrooms upstairs, according to the listing. It's a four-bedroom, two-bath home with 1,075 square feet. Its price was cut by $14,000 on Oct. 14.

77 Round Hill Road, 1 to 3 p.m., $729,900. In the Fairfield Center neighborhood, moments from downtown, the Metro-North station and the beaches, this 1940 house has a finished lower level, according to the listing. It's a four-bedroom, 2.5-bath home with 1,990 square feet.

38 Milandale Road, 1 to 3 p.m., $865,000. On a level quarter acre within walking distance of the elementary school, this 1958 Colonial has fresh paint, refinished hardwood floors, a living room with a brick fireplace framed in mahogany and a sunlit family room with sliders to a wraparound deck, according to the listing. It's a four-bedroom, two-bath home with 2,292 square feet.

Also open Sunday: 280 Brookbend Road (noon to 3 p.m.), 126 Dwight St. (noon to 2 p.m.) and 2493 Redding Road (11 a.m. to 1 p.m.).

Make a weekend of it: Saturday, start in Winton Park at 11 a.m., catch Dwight Street and Greenfield Hill at noon, then Stratfield Road and School Street in the afternoon. Sunday, Greenfield Hill opens at 11 a.m., and Knapps Highway, Round Hill Road and Milandale Road all open at 1 p.m.

Listing details from Zillow.com as of Oct. 14, 2026. Open-house schedules can change; check each listing before you go.