Westbrook Real Estate

Welcome to Westbrook, Connecticut, a hidden gem nestled in the heart of Middlesex County. This picturesque coastal town offers a perfect blend of serene landscapes, vibrant community life, and rich history, making it an ideal place for those seeking both tranquility and adventure.

Westbrook boasts a stunning shoreline along the Long Island Sound, where residents and visitors alike can enjoy sun-soaked beaches, scenic parks, and charming marinas. The town is renowned for its outdoor activities, from kayaking and fishing to hiking the lush trails of nearby natural reserves. For beach lovers, Westbrook’s sandy shores provide a perfect backdrop for family picnics, sunbathing, and enjoying breathtaking sunsets.

Culturally rich and community-focused, Westbrook hosts a variety of local events throughout the year, including farmers' markets, art festivals, and seasonal celebrations that bring neighbors together. The town is also home to an array of unique shops, delightful eateries, and quaint cafes, offering a taste of local flavor and charm.

Education is a priority in Westbrook, with well-regarded schools that provide a supportive environment for children to thrive. Families will appreciate the sense of security and community that Westbrook offers, making it a wonderful place to raise children.

With its perfect combination of natural beauty, community spirit, and convenient access to major highways, Westbrook is not just a place to live, but a place to call home. Whether you’re looking for a peaceful retreat or an active lifestyle, Westbrook welcomes you with open arms. Come explore all that this charming town has to offer!

Newest Listings in Westbrook

$1,440,000

24192570 MLS

Available for the first time in nearly 90 years, this exceptional 12 ACRES represents one of the very last large tracts of undeveloped land in the water community of Westbrook. The property features a striking combination of 8+ level acres of virgin open field--ideal for farming, equestrian use or building--framed beautifully by an elevated wooded backdrop. The flat acreage provide an unobstructed southern view of 9 acre Lake Louise & borders the protected land of both Essex & Westbrook Land Trusts. Location & accessibility are unmatched. With 379 feet of clear-line frontage on Route 153, the parcel is positioned perfectly midway between I-95 & Route 9, just minutes to the Old Saybrook/Westbrook Amtrak & Shoreline East train station for seamless travel from Boston, New York & beyond. A local civil engineer believes the site is primed for high-yield development. The property offers remarkable flexibility: a possible 3-4 substantial luxury residential lots or leveraging under CT Affordable Housing Law 8-30g to constructa high-density multi-unit complex ranging from 33 units to perhaps 100 units, mirroring successful transit-oriented development nearby. The land is also believed to have substantial on-site topsoil & gravel reserves for immediate asset value. NOTE This sale is contingent upon an adjoining actively listed for sale 20 acre parcel in Essex, owned by the same owners being sold individually, if not together. See related MLS numbers.

Essex Road, Westbrook

$750,000

3 Beds ⋅ 3 Baths ⋅ 24194893 MLS

Welcome to 2,736 sqft of comfortable living space set on a country lot that offers both tranquility and convenience. The main floor features a huge living room with propane fireplace, bright sunny windows, hardwood floors & recessed lights. The kitchen with tile floor & tile backsplash, quartz countertops & breakfast bar features all the amenities any cook could want. It's open to a generous sitting area with 3 pane sliding door and a cozy wood burning fireplace that could easily be addt'l casual eating space. However, the formal dining room off the cathedral ceiling foyer is the perfect spot to share a meal. Across from the DR is the cozy den & the 1st floor is complete with half bath, laundry closet, access to huge 2 car garage & access the back deck & lower patio (set up for a hot tub if you wish). The lower level is a large game room/home theater area plus cedar closet for long term clothes storage, a large utility room w/bulkhead access to the back yard and two utility closets. The uppermost level of the home features a master bedroom with private bath that has a clothes closet, linen closet and double vanities. Two additional bedrooms and a full bath plus a home office and spacious landing where you can access the attic from the pulldown stairs. Other things to note is the oil-fired hot water heat, central A/C and a new roof. This setting is conveniently located near Westbrook's beaches, shopping, schools, restaurants, other amenities and major commuter routes.

340 Toby Hill Rd, Westbrook

$749,000

3 Beds ⋅ 2 Baths ⋅ 24193856 MLS

Welcome to your private waterfront sanctuary retreat! This Contemporary Ranch is situated on Trout Brook and Johnson Pond, and is tucked away on a peaceful cul-de-sac. It's the perfect place for entertaining and rest & relaxation in & out. Step inside to a popular open-concept layout. The living, dining, and kitchen areas soar with cathedral ceilings and walls of windows framing breathtaking views of the beautiful 2 acres. A double-sided brick fireplace anchors the space, perfect for cozy gatherings or holiday feasts. The bright kitchen offers an abundance of natural light as well as recessed lighting. Large island and breakfast bar. The private bedroom wing features a primary suite with three closets and a spa-like bath with a walk-in shower. Two additional bedrooms and a full bath complete the while the first-floor laundry and an oversized two-car garage add effortless convenience. A generous sized basement offers room for storage, a workshop, or a home gym. Outside, the wrap-around deck invites summer barbecues; the fire pit with built-in seating promises cool evening s'mores and winter cuddles. Easy-care gardens and a level lawn - ideal for yard games and lively get-togethers - complete this mesmerizing retreat. A large, fenced flat area is just perfect for pets. This property checks off many boxes for everyone - with one-level living at its best on a gorgeous parcel filled with wildlife and amazing vistas. It makes every day feel like you are on vacation.

147 Johnson Pond Ln, Westbrook

$679,000

3 Beds ⋅ 3 Baths ⋅ 24191372 MLS

Nestled in Westbrook, Connecticut, 331 Dennison Road is a quintessential private retreat that seamlessly blends indoor comfort with outdoor splendor. This casual residence features a bright, open floor plan highlighted by a grand great room with a cozy fireplace, perfect for quiet evenings or lively gatherings. The kitchen opens directly onto a charming patio, ideal for alfresco dining overlooking the pool and woods. Outside, an inviting inground pool is encircled by a meticulously curated flower garden, while a dedicated, fenced-in vegetable garden with raised beds and a custom shed awaits the home gardener. With the convenience of a spacious first-floor primary suite, this home offers a thoughtful layout designed for modern living in a serene, park-like setting. Offering geothermal heating/cooling system and owner owned solar panels for a very efficient low cost utilities.

331 Dennison Rd, Westbrook

$539,900

3 Beds ⋅ 3 Baths ⋅ 24190053 MLS

Just the second owner of this lovingly maintained custom-built home set on a private, wooded lot with plenty of outdoor space to enjoy. Notable updates include refinished hardwood floors, an opened staircase, kitchen with newer refrigerator and dishwasher, and three beautifully renovated bathrooms. The primary suite features a walk-in closet and private bath, while the walkout lower level offers flexible space for a home office, recreation room, or hobbies. Additional improvements include upgraded exterior drainage, a radon mitigation system, cleared trees and yard, a newly paved lower driveway, and an upper driveway turnaround. Conveniently located just minutes from Westbrook's beaches, marinas, restaurants, shopping, with easy access to both I-95 and Route 9.

3 Docs Hill Rd, Westbrook

$150,000

2 Beds ⋅ 2 Baths ⋅ 24190452 MLS

Walk to the Beach and enjoy an over 55 community affordable shoreline living in this surprisingly spacious 2-bedroom, 1.5-bath home, ideally located in the heart of Westbrook. The bright eat-in kitchen offers ample space for everyday dining, with the privacy of split bedrooms, while the comfortable floor plan provides an open, inviting feel throughout. Step outside to your private patio-perfect for relaxing, entertaining, or enjoying warm summer evenings. This home includes two dedicated parking spaces, coveted Grove Beach rights along with a clubhouse for community functions that includes kitchen, cooking facilities, appliances and generator , giving you the opportunity to enjoy all the Connecticut shoreline has to offer. Leave the car behind and stroll to local favorites including Lenny & Joe's, nearby restaurants, shopping, and other conveniences. Whether you're looking for a year-round residence, weekend retreat, or an affordable way to enjoy the beach lifestyle, this is a wonderful opportunity to own a piece of the shoreline in a sought-after Westbrook location! 55+ community.

10 Chestnut Dr, Westbrook

$499,900

3 Beds ⋅ 4 Baths ⋅ 24184894 MLS

Tucked away on a cul-de-sac in the popular Cold Springs neighborhood, this 9 room, 3 bedroom, 3.5 bath, 2445 sf Raised Ranch sits on a level 1.05 acres and is less than 3 miles to the Town Beach! The main level went through a transformative gut renovation in 2022. From creating an open-concept layout, to all new sheetrock, electrical, plumbing, lighting, flooring, and design! The gorgeous kitchen offers high-end soft-close cabinets & drawers, granite countertops, large island w/ storage & breakfast bar, black stainless appliances and a gas stove! The primary suite has an integrated closet system, ceiling fan, sliders to a private deck, and beautiful spacious en-suite bath w/ large walk-in tile shower and rainfall shower heads! The lower level floor plan offers immense flexibility and was mostly updated with new sheetrock, flooring, and lighting in 2017! The left side has the 3rd bedroom, a spacious walk-out rec room, and a full bath. To the right is a large walk-out family room, a den, an office, and full bath! Perfect for a home office, primary suites, flex area, or multi-generational living! Additional updates include new vinyl siding (2026), Andersen replacement windows (2020), hot water heater (2017), and more! Centrally located .4 miles to the YMCA, 1 mile to 95, 1.5 miles to the Train Station and Town Center, while near equidistant to New Haven, New London, and Middletown! From L.I. Sound to inland waterways, come kayak, boat, fish, dine, and play your days away!

67 Winterberry Cir, Westbrook

$250,000

2 Beds ⋅ 1 Baths ⋅ 24190472 MLS

Situated in a quaint, private 55-and-over community in the heart of Westbrook, Connecticut, this low-maintenance ranch offers the ultimate in stress-free Shoreline living. Completely updated with beautiful finishes and thoughtful customizations, this 2-bedroom, 1-bathroom home is entirely turn-key and ready for its next chapter. Inside, the seamless open-concept layout creates a bright and airy flow, perfect for both daily living and entertaining. Slide open the glass doors to find your private, covered back porch-an ideal spot for morning coffee or evening relaxation. The home sits on a peaceful and quiet corner lot, featuring manicured landscaping and a dedicated vegetable garden for the green thumb.The heart of the home is the updated kitchen, fully equipped with sleek stainless steel appliances. You will have total peace of mind knowing all major mechanical components have been updated in recent years, including: Roof: Replaced just 4 years ago Electrical: Upgraded to a 200-amp panel 2 years ago Climate Control: High-efficiency heating and cooling mini-split system Storage: A handsome, 1-year-old detached storage shed The low-stress lifestyle is further enhanced by a comprehensive HOA that covers trash collection, snow removal, road maintenance, property management and all septic maintenance and repairs. Located just minutes from pristine Westbrook beaches, the renowned Water's

18 Old Forge Rd, Westbrook

$189,000

2 Beds ⋅ 1 Baths ⋅ 24190741 MLS

Well cared for low maintenance Ranch close to town and shopping. Many updates. Property shows very nice. New siding w/insulation approximately 2 years old. New stove, new kitchen window. Newer slider to rear sun porch overlooking very private setting, perfect for your morning coffee. Excellent retirement location or part-time summer residence. Quiet community. Easy to show.

11 Old Forge Rd, Westbrook

$1,295,000

4 Beds ⋅ 5 Baths ⋅ 24190188 MLS

Discover your own private oasis, this expansive custom-built home built on over 8 acres offers the perfect blend of privacy, comfort, and modern amenities. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and an oversized 2-car garage. Situated on the end of a private cul-de-sac the home is surrounded by peaceful natural beauty and thoughtfully designed for both everyday living and entertaining. Outdoor living is truly unmatched, with stunning decks and exterior stairways crafted from premium IPE Brazilian hardwood overlooking a private 3-acre, 30-foot-deep lake. Complete with a dramatic center fountain, lighting, and an aeration system, this remarkable setting creates a one-of-a-kind backdrop for relaxing, entertaining, or simply enjoying the serenity of your surroundings. Located just minutes from award-winning restaurants, shopping, marinas, and Westbrook's three town beaches, this hidden gem offers the rare opportunity to enjoy the best of Connecticut shoreline living while retreating to your own private sanctuary.

53 Oakridge Dr, Westbrook

$1,565,000

3 Beds ⋅ 4 Baths ⋅ 24188767 MLS

A rare combination of privacy, functionality, and sweeping water views distinguishes this exceptional year-round shoreline estate, ideally situated in one of Westbrook's most desirable coastal enclaves. Positioned on the quiet, exclusive end of Seaside Avenue just steps from a pristine private beach, the residence is set upon a rare double lot that offers an uncommon sense of openness, tranquility, and room to grow. Thoughtfully designed for effortless coastal living and grand-scale entertaining, the home is bathed in natural light and frames spectacular vistas of Long Island Sound from multiple viewing decks. The heart of the home features a bright, open-concept main level that seamlessly connects the living, dining, and kitchen areas. This floor hosts two bedrooms, including a convenient additional ensuite-perfect for guests, an office, or multi-generational living. The primary suite privately perched on the third floor has it's own living area and a deck for morning coffee or sievening sunsets. The thoughtfully finished lower level serves as a seamless indoor-outdoor transition, complete with a kitchenette and full bath for effortless post-beach gatherings.

449 Seaside Ave, Westbrook

$675,000

3 Beds ⋅ 3 Baths ⋅ 24190134 MLS

Escape to your own private 3-acre compound offering endless possibilities! This charming 3-bedroom, 2-bath Cape Cod is nestled in a serene setting surrounded by nature. The bright, open floor plan features an updated kitchen with granite countertops, stainless steel appliances, and flows into a cozy dining area and den with heated hardwood floors. The main level also offers a spacious bedroom, flexible bonus room perfect for an office or guest space, and an updated full bath with a large tiled walk-in shower. Upstairs you'll find two generously sized bedrooms and a second full bath. The walkout lower level includes a home office, oversized laundry room, 1/2 bathroom, refrigerator and stove, ideal for future expansion or possible in-law. Relax on the expansive front and rear decks overlooking beautifully landscaped grounds, mature gardens, a saltwater in-ground pool, and gardening shed. A standout feature is the oversized barn with two large garage doors and an enormous unfinished second floor, ideal for hobbyists, car enthusiasts, workshop space, storage, or future possibilities. Whether you're looking for a peaceful retreat, room for your hobbies, or space to grow, this exceptional property offers privacy, versatility, and country living at its best while remaining conveniently located.

170 Dennison Rd, Westbrook

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