Westbrook Homes for Sale

The quaint shoreline town of Westbrook, located on Long Island Sound, offers residents upscale living in a well-established coastal community.

Boasting 21.4 square miles of area and home to about 7,000 residents, Westbrook is known for its scenic shoreline, upscale lifestyle and unspoiled beauty. With four miles of shorefront between the Menunketesuck and Patchogue rivers, the Middlesex County community offers lovely beaches and is home to the Stewart B. McKinney National Wildlife Refuge.


Westbrook is between Boston and New York and 45 miles from Hartford, with easy access to I-95 and Route 9. Private beach Associations in town include Chapman Beach, Coral Sands, Grove Beach Point, Grove Beach Terrace, Horse Hill, Island View, Kelsey Point, Little Stannard, Middle Beach, Pilot’s Point, Pointina, Quotonset Beach, Sagamore Terrace, Salt Works, Stannard Beach and West Beach.


If you get tired of the beach Westbrook offers relaxation from Water’s Edge Resort to quaint Bed and Breakfast spots. If you find shopping relaxing and prefer to shop till you drop then the Tanger Outlets is your destination! This town also offers many local restaurants from casual dining to upscale gourmet.

Westbrook Schools

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Elementary Schools

Daisy Ingraham School
105 Goodspeed Dr, Westbrook, CT 06498
PK-4 No

Middle Schools

Westbrook Middle School
156 McVeagh Rd, Westbrook, CT 06498
5-8 No

High Schools

Westbrook High School
156 McVeagh Rd, Westbrook, CT 06498
9-12 No
Oxford Academy
1393 Boston Post Road, Westbrook, CT 06498
8-12 Yes
GreatSchoolsDetailed school information provided by GreatSchools.org. Public and private school information is provided by sources including GreatSchools.org and various MLS services including the HGMLS, CMLS, CT-MLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

Captain Stannard House

A Bed and Breakfast Country Inn

Connecticut’s recent burst of arctic-cold weather presents the perfect opportunity for a cozy New England escape in the country.  Watching the snow fall outside of frosted window panes isn’t so bad while relaxing in the warm comfort of a timeless afternoon indoors. Experience the ultimate charming winter atmosphere, hot chocolate and all, at this recently listed restored, historic, Italianate and Federal-style home that is well-recognized for its established bed and breakfast inn business. Known as Captain Stannard House, the inn is located at 138 South Main Street in the coastal town of Westbrook, Conn. Madison agent Cindy Gilhuly and Guilford agent Carol Cusano have the listing, which is offered at $1,250,000.


The residence was constructed in 1872 by Elbert Stannard, a native son of Westbrook who went to sea at the age of 14, returning as Sea Captain.  The house depicts Stannard’s strong sea roots with its signature cupola architectural style, which reflects the dome-like structure of a lookout. In 2004, the inn was restored and reborn after being purchased by its current on-site owners and inn keepers, one of whom was a U.S. Navy sailor.  From an architectural standpoint, the home, which rests on .97 acres of land, is transitional in nature with elements of both the Italianate and the Federal style.



Much of the building’s original character is maintained with many architectural details including brackets and quoins, a fan light window over the original front door and, as mentioned prior, the cupola. Inside, the first floor contains a living room, dining room, bedroom, private bath and entry that are used as the innkeepers’ residence, which boasts a total of four rooms. An additional room, serving as a home office, can be found in this section of the house. The balance of the first floor consists of a large commercial kitchen with keeping room, a captain’s room, multiple entry areas, a large recreational great room and guest dining room, both with fireplaces, and two restrooms. The level additionally contains what is called the “Imagination Room,” a 12×12 area that offers potential opportunity for private meetings, yoga, dining and more. The second floor is accessed via two interior stairwells—one in the front and one in the rear of the inn. There is also a covered emergency egress that leads from the second floor to grade level. The second floor contains 10 guest rooms, eight of which have private baths. The remaining two rooms share one bathroom. Each guest room offers sitting areas, desks, individual climate control and wifi internet.




Throughout the years, the residence has served as home to various local businesses including inns, a tavern, restaurant and more.  Proud town members always held great respect for the building, and even took possession of it to avert demolition in 1971 after a damaging fire occurred.  The restored house was then tried again as an inn, and later an antique shop and rooming house before eventual abandonment.  It wasn’t until 1991 that the home re-opened as the now thriving, top-rated by Trip Advisor Conn. shoreline destination, Captain Stannard House Bed and Breakfast Country Inn.




“Everything about this property is truly remarkable,” said Gilhuly.  “From its lovely seaside location to its great history and natural, New England charm, both residents and visitors of this unique shoreline home experience an impeccably timeless lifestyle amid an undeniably beautiful atmosphere and rich history.  I am honored to be representing such an established landmark of Connecticut’s coast.”


“Both its prime location approximately halfway between Boston and New York City and riveting history make this residence a definite find,” said Cusano. “It’s amazing to see the ways in which the home’s past and close proximity to the sea have influenced its style, charm and overall offerings, and I am beyond proud to share its exceptional story with our clients.”



For more information on the property, located at 138 South Main Street, visit our website here.

Posted by Megan Montemarano, William Pitt Sotheby’s

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