Upcoming Open Houses In Chester, Essex & Deep River

ESSEX, CT — The lower Connecticut River Valley has a full weekend: two historic houses on River Road in Essex, open side by side Saturday morning, a 1923 cottage a few minutes' walk from Chester's galleries and theater, and a pair of Ivoryton homes near the Ivoryton Playhouse, including one whose listing pitches its spare rooms as an artist's studio.

Eight Chester, Essex and Deep River homes are holding open houses Saturday, Oct. 31, and Sunday, Nov. 1, with prices from $450,000 to $2,250,000, according to Zillow.com. Three are in Chester, four are in Essex, including two in Ivoryton, and one is in Deep River.

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Saturday, Oct. 31

25 River Road, Essex, 11 a.m. to 1 p.m., $2,250,000. This four-bedroom, 2.5-bath home was built in 1803, a short sidewalk walk from Essex Village, and comes with an adjacent 0.48-acre waterfront parcel looking across a meadow and stream toward the Falls River. It has four fireplaces, original beams, a wood-shingle roof and a kitchen with a Lacanche range, plus a detached 384-square-foot studio and a brick "pub room" with a woodstove in the walk-out lower level. Zillow lists 3,232 square feet on 1.38 acres.

28 River Road, Essex, 11 a.m. to 1 p.m., $1,595,000. This three-bedroom, 2.5-bath home is the Benjamin F. Post House, which the listing dates to about 1801. A fenced backyard holds a gunite pool, and inside are a chef's kitchen with a commercial-grade six-burner range, a library with floor-to-ceiling bookshelves and a four-season sunroom with a wet bar. It has 2,359 square feet on 0.48 acres, about a 20-minute walk from the village, according to the listing.

42 Straits Road, Chester, 11 a.m. to 1 p.m., $699,000. This three-bedroom, 2.5-bath home has been completely renovated, according to the listing, with refinished hardwood floors, 9-foot ceilings and a new kitchen with quartz counters and a wine cooler. A 17-by-13-foot room works as an office or guest room, and the finished lower level adds a family room. It has 2,882 square feet on 2.71 acres and a backup generator.

6 School Lane, Chester, 1:30 to 3:30 p.m. (also Sunday, 1 to 3 p.m.), $450,000. This three-bedroom, one-bath home is a 1923 home 0.2 miles from downtown Chester, with an enclosed front porch, original wood moldings and a built-in corner hutch in the dining room. The listing cites 2026 work including fresh interior paint, refinished floors and a professionally waterproofed basement. It has 1,179 square feet on just under half an acre.

Sunday, Nov. 1

13 High Field Lane, Chester, 11 a.m. to 2 p.m., $749,900. This four-bedroom, 2.5-bath home is a 1996 custom Colonial at the end of a cul-de-sac on more than two acres, with a covered front porch, a family room with a propane fireplace and a kitchen island. A bonus room over the two-car garage could be a den, office or playroom. It has 2,662 square feet on 2.24 acres.

73 Long Hill Road, Deep River, noon to 2 p.m., $625,000. This four-bedroom, 2.5-bath home is less than five minutes from the Essex and Chester town centers, according to the listing, which points to nearby walking and nature trails. It has 2,196 square feet on 1.5 acres and was built in 1986.

3 Rachel Lane, Ivoryton, noon to 2 p.m., $559,900. This three-bedroom, two-bath ranch sits on a corner lot in historic Ivoryton, with a front porch, freshly painted main level, a granite kitchen island and a fire pit out back. Lower-level bonus rooms add 638 square feet, on top of Zillow's 1,226. The listing says the appliances are sold as-is, though the dishwasher is new.

5 Northwinds Drive, Ivoryton, noon to 2 p.m., $599,000. This three-bedroom, 2.5-bath home is a one-owner custom home whose flexible rooms, the listing says, could serve as two offices, a craft room or an artist's studio. It has a first-floor primary suite, a sunroom with floor-to-ceiling windows and a wood-burning fireplace, and a screened porch. The listing notes the Ivoryton Playhouse and the Essex Steam Train nearby. It has 2,314 square feet on 1.13 acres.

Also open Sunday: 6 School Lane, 1 to 3 p.m. (see Saturday).

Saturday starts with the two River Road houses in Essex, both open from 11 a.m. to 1 p.m., and Straits Road in Chester at the same time, before School Lane opens at 1:30. On Sunday, High Field Lane opens at 11, and Deep River and both Ivoryton homes all open at noon.

Listing details from Zillow.com as of Oct. 29, 2026. Open-house schedules can change, so check each listing before you go.