3,896

Middlesex, CT Homes

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  • 76 Osprey Cir, Westbrook, CT 06498
    76 Osprey Cir, Westbrook, CT 06498
    76 Osprey Cir, Westbrook, CT 06498
    /24

    $749,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,981 Sq Ft

    76 Osprey Cir, Westbrook, CT 06498

    Welcome to exquisite living in Westbrook, Connecticut! Prime location in the desirable Osprey Circle subdivision, this extraordinary custom-built ranch is just 1/2 mile from Long Island Sound. Enjoy walking to area beaches, marinas, and restaurants or take a quick 3-minute drive to West Beach. This 2000-square-foot home features vaulted, custom wood-paneled ceilings, perfectly placed skylights,

    Gigi Giordano Taylor Compass Connecticut, LLC

    76 Osprey Cir, Westbrook, CT 06498
  • 42 Chapman Beach Rd, Westbrook, CT 06498
    42 Chapman Beach Rd, Westbrook, CT 06498
    42 Chapman Beach Rd, Westbrook, CT 06498
    /24

    $3,800 per month

    • 3 Beds
    • 1.5 Baths
    • 1,176 Sq Ft
    • House for Rent

    42 Chapman Beach Rd, Westbrook, CT 06498

    Academic rental. Fully furnished, renovated 1920 Dutch Colonial in private beach community, 3 Bedroom, 1 1/2 bath, new high efficiency heat and air conditioning, updated kitchen with stainless steel appliances with quartz counter top, hardwood floors throughout, new washer and dryer, open floor plan and 3 season front porch. Large open lot, private backyard, short walk to beach. Located in the

    Marta Elmasry Coldwell Banker Realty

    42 Chapman Beach Rd, Westbrook, CT 06498
  • 6 Green Acres Park Dr, Westbrook, CT 06498

    $65,000 Sold Jun 30, 2025

    • 657 Sq Ft
    • $99/SF
    • 11 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1968

    6 Green Acres Park Dr, Westbrook, CT 06498

    Escape to the tranquility of seaside living with this charming and move-in ready 2-bedroom, 1-bath mobile home nestled in the heart of our highly sought-after beach community. Possible 3rd bedroom or office. Unwind in the comfort of two generously sized bedrooms, each offering ample natural light and cozy spaces to relax or enjoy some down-time in the 3-season enclosed porch. Discover the

    Danielle Rownin Keller Williams Realty

    6 Green Acres Park Dr, Westbrook, CT 06498
  • 1110 Old Clinton Rd, Westbrook, CT 06498
    1110 Old Clinton Rd, Westbrook, CT 06498
    1110 Old Clinton Rd, Westbrook, CT 06498
    /40

    $725,000

    • 4 Beds
    • 4 Baths
    • 2,428 Sq Ft

    1110 Old Clinton Rd, Westbrook, CT 06498

    Great opportunity to own this duplex style 2 family home. The duplex has 2 side by side units each offering 2 bedrooms and 1.5 baths, hardwood floors throughout the first floors, each side has its own private driveway, nice level yard and each with their own private deck. The beautiful Westbrook beaches are within a one minute drive or a quick walk. The left side also has a finished basement with

    Jay Cusack Executive Real Estate Inc.

    1110 Old Clinton Rd, Westbrook, CT 06498
  • 173 Captains Dr, Westbrook, CT 06498
    173 Captains Dr, Westbrook, CT 06498
    173 Captains Dr, Westbrook, CT 06498
    /39

    $4,575 per month

    • 4 Beds
    • 3 Baths
    • 2,544 Sq Ft
    • House for Rent

    173 Captains Dr, Westbrook, CT 06498

    AVAILABLE 2 weeks in August, then September - May. OCEAN VIEWS from many Luxurious rooms, spacious 4 bedroom, 4 floor, rental in the beautiful PILOTS POINT section of Westbrook, a most desired location on the Ct. Shore. Year round contemporary home with stunning front OCEAN VIEWS of Long Island sound. PRIVATE BEACH access just steps away. Back of house has beautiful views of the MARINA. Gourmet

    Abby Goodman Keller Williams Realty-Longmdw

    173 Captains Dr, Westbrook, CT 06498
  • 24 Ripley Hill Rd, Westbrook, CT 06498

    $950,000 Sold Jun 30, 2025

    • 1,528 Sq Ft
    • $622/SF
    • 51 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1949

    24 Ripley Hill Rd, Westbrook, CT 06498

    Nestled in sought-after Stannard Beach w/DEEDED BEACH RIGHTS, this remodeled Nantucket-style cottage offers yr-rd comfort, rare privacy & one of the largest lots-just a short walk to the sand. Blending modern ease w/coastal charm, no expense spared in creating a stylish, functional space. Enjoy generous parking, no flood ins., & flexible layout incl. exercise rm & in-law/out-law/office potential.

    Linda O'Hara William Raveis Real Estate

    24 Ripley Hill Rd, Westbrook, CT 06498
  • 80 Fawn Hill Dr, Westbrook, CT 06498
    80 Fawn Hill Dr, Westbrook, CT 06498
    80 Fawn Hill Dr, Westbrook, CT 06498
    /39

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    80 Fawn Hill Dr, Westbrook, CT 06498

    Enjoy coastal living and walkability in the heart of Westbrook! Welcome to this charming 3-bedroom, 2.5-bath raised ranch offering 1,080 square feet of main-level living space, plus an additional 504 square feet in the finished lower level-ideal for a home office, rec room, or guest space. Built in 1971, this home features a classic layout with a bright, open living area that flows into an eat-in

    Allison Ciarcia William Raveis Real Estate

    80 Fawn Hill Dr, Westbrook, CT 06498
  • 154 Osprey Cir, Westbrook, CT 06498

    $540,000 Sold Jun 27, 2025

    • 2,041 Sq Ft
    • $265/SF
    • 10 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1998

    154 Osprey Cir, Westbrook, CT 06498

    This 4-bedroom Cape Cod located in scenic Westbrook could be just what you're looking for! Nestled in a desirable sidewalk-lined subdivision just a half mile from the Long Island Sound, you can enjoy walking to local beaches, marinas, restaurants, shopping, and more! Highest & Best Hold Period active - expires 04/09/2025 01:00 PM CST. All submissions must be in by then, no exceptions. This

    Ryan King Aspen Realty Group

    154 Osprey Cir, Westbrook, CT 06498
  • 44 Linden Ave N, Westbrook, CT 06498
    44 Linden Ave N, Westbrook, CT 06498
    44 Linden Ave N, Westbrook, CT 06498
    /14

    $99,900

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    44 Linden Ave N, Westbrook, CT 06498

    Perfect opportunity! Come check out this affordable Beachside Living - Under a Mile from the Shore, nestled in the desirable Grove Beach 55+ Private Community. This charming and budget-friendly home offers 2 bedrooms, 1 full bath, and a surprisingly spacious layout, including a bright living area, eat-in kitchen, and in-unit laundry. Whether you're looking for a year-round residence or the

    Eli Joseph eXp Realty

    44 Linden Ave N, Westbrook, CT 06498
  • 1414 Essex Rd, Westbrook, CT 06498

    $675,000 Sold Jun 24, 2025

    • 2,665 Sq Ft
    • $253/SF
    • 40 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2002

    1414 Essex Rd, Westbrook, CT 06498

    This custom designed cape features an open floor plan, hardwood floors flow through the main living area complementing living room, kitchen and dining room. The gourmet kitchen features granite countertops, expansive island perfect for entertaining, double dishwasher and a wine chiller, living room with cathedral ceiling and stone fireplace. The primary bedroom suite is on the main level complete

    Sharon Linder Berkshire Hathaway NE Prop.

    1414 Essex Rd, Westbrook, CT 06498
  • 87 McVeagh Rd, Westbrook, CT 06498
    87 McVeagh Rd, Westbrook, CT 06498
    87 McVeagh Rd, Westbrook, CT 06498
    /20

    $459,999

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    87 McVeagh Rd, Westbrook, CT 06498

    This is a great home with lots of potential. It has an oversized two car garage, with a walkout basement. Within walking distance of Westbrook High School. Bring all offers - buyer back out due to personal reasons - no inspections done.

    Warner Hollister William Raveis Real Estate

    87 McVeagh Rd, Westbrook, CT 06498
  • 37 Menunketesuck Rd, Westbrook, CT 06498

    $585,000 Sold Jun 23, 2025

    • 960 Sq Ft
    • $609/SF
    • 33 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1930

    37 Menunketesuck Rd, Westbrook, CT 06498

    This cozy 2-bedroom/1-bath Ranch-style home is the ideal spot for beach lovers - located in a private association, with rights to Westbrook's sandy Grove Point Beach, just a short walk away. The airy, open floor plan, featuring vaulted ceilings throughout, flows nicely from the spacious living/dining area to the kitchen, with an island and stainless-steel appliances, and access to one of two

    Sue Woods William Pitt Sotheby's Int'l

    37 Menunketesuck Rd, Westbrook, CT 06498
  • 42 Bluff St, Westbrook, CT 06498
    42 Bluff St, Westbrook, CT 06498
    42 Bluff St, Westbrook, CT 06498
    /19

    $1,750,000

    • 4 Beds
    • 5 Baths
    • 4,236 Sq Ft

    42 Bluff St, Westbrook, CT 06498

    This beautiful seaside home has it all! Situated on a partially shaded bluff overlooking Long Island Sound, it has amazing views from almost every window. The 3 generously sized bedrooms, master bedroom suite, 3 full baths, and large dry basement fulfill all of your needs. The 2 car, attached garage will store not only your cars, but an abundance of beach and water toys. The carefully designed

    Jason Saphire www.HomeZu.com

    42 Bluff St, Westbrook, CT 06498
  • 1513 Essex Rd, Westbrook, CT 06498

    $620,000 Sold Jun 18, 2025

    • 1,967 Sq Ft
    • $315/SF
    • 38 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1720

    1513 Essex Rd, Westbrook, CT 06498

    Step into the timeless charm of this beautifully remodeled antique Cape, where classic character meets modern convenience. This inviting home features an open-concept kitchen with stunning soapstone countertops, custom cabinetry, farm sink and center island perfect for entertaining. The first floor boasts a spacious family room, dining area, a convenient laundry room, and a full bath, all

    Gigi Giordano Taylor Compass Connecticut, LLC

    1513 Essex Rd, Westbrook, CT 06498
  • 755 W Pond Meadow Rd, Westbrook, CT 06498
    755 W Pond Meadow Rd, Westbrook, CT 06498
    755 W Pond Meadow Rd, Westbrook, CT 06498
    /40

    $639,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 2,312 Sq Ft

    755 W Pond Meadow Rd, Westbrook, CT 06498

    Are you interested in the country charm of Westbrook? Close to schools, YMCA, town library, beaches, hiking trails, and Messerschmidt's Pond just over a mile away where you can canoe, kayak, fish or just relax nearby. A short drive to The Kate for a night at the theatre! Come join us for a walk through this beautifully spacious Colonial surrounded by plenty of open space outdoors with lovely

    Dianne Crawford Berkshire Hathaway NE Prop.

    755 W Pond Meadow Rd, Westbrook, CT 06498
  • 586 Essex Rd, Westbrook, CT 06498

    $615,000 Sold Jun 17, 2025

    • 1,569 Sq Ft
    • $392/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    586 Essex Rd, Westbrook, CT 06498

    This pristine 1569 sq. ft. colonial features 3-bedrooms and two full baths, with hardwood oak floors throughout. The eat-in kitchen is equipped with granite countertops and new stainless-steel appliances. Hot water is provided by natural gas from the street, and an on-demand Ranai hot water system. Adjacent to the kitchen is a formal dining room for convenient entertaining. The living room spans

    Pardi & Zucco Team William Pitt Sotheby's Int'l

    586 Essex Rd, Westbrook, CT 06498
  • 2 Lake Louise Dr, Westbrook, CT 06498
    2 Lake Louise Dr, Westbrook, CT 06498
    2 Lake Louise Dr, Westbrook, CT 06498
    /40

    $1,424,900

    • 4 Beds
    • 2.5 Baths
    • 3,381 Sq Ft

    2 Lake Louise Dr, Westbrook, CT 06498

    Stunning remodeled home in the Lake Louise community of fine homes! This home has been tastefully updated from top to bottom! Architectural details & mouldings throughout! A chef's gourmet kitchen with top of the line appliances: a sub-zero refrigerator, a European Gas range with double electric ovens, a commercial range hood, an oversized cast iron sink, custom cabinets, a 10 foot granite

    Laura Bitondo Berkshire Hathaway NE Prop.

    2 Lake Louise Dr, Westbrook, CT 06498
  • 245 Toby Hill Rd, Westbrook, CT 06498

    $825,000 Sold Jun 12, 2025

    • 2,492 Sq Ft
    • $331/SF
    • 61 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2010

    245 Toby Hill Rd, Westbrook, CT 06498

    This custom-built home, completed in 2010, seamlessly blends contemporary design with classic colonial charm. Step inside to gleaming hardwood floors throughout the main open living area & a highly desirable first-floor primary suite with walk in closet and a beautiful custom bathroom. The spacious kitchen, equipped with modern amenities, granite counters, huge pantry & stainless appliances flow

    Gigi Giordano Taylor Compass Connecticut, LLC

    245 Toby Hill Rd, Westbrook, CT 06498
  • 166 Fiske Ln, Westbrook, CT 06498
    166 Fiske Ln, Westbrook, CT 06498
    166 Fiske Ln, Westbrook, CT 06498
    /40

    $3,575,000

    • 4 Beds
    • 5 Baths
    • 4,747 Sq Ft

    166 Fiske Ln, Westbrook, CT 06498

    This remarkable example of contemporary design with over 175' of LI Sound frontage and 25' ceilings makes you feel you are aboard ship from the moment you step inside. All white w/clean simple lines, a commanding 2 story wall of glass showcases this beautiful direct waterfront setting in a way not possible with most traditional coastline homes. Display substantial art & furnishings in a whole new

    Margaret Muir William Pitt Sotheby's Int'l

    166 Fiske Ln, Westbrook, CT 06498
  • 210 Duck Island Landing Unit 210, Westbrook, CT 06498

    $555,000 Sold Jun 02, 2025

    • 1,250 Sq Ft
    • $444/SF
    • 10 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2015

    210 Duck Island Landing Unit 210, Westbrook, CT 06498

    A lifestyle change is calling you to 210 Duck Island Landing, where wonderful water views and a prime location will astound you! This beautifully designed 2-bedroom end unit townhouse offers the perfect combination of elegance and comfort. Gleaming hardwood floors flow throughout the floor plan, with natural sunlight filling the kitchen, living room, and dining area. Step through the sliders to

    Alan Spotlow William Raveis Real Estate

    210 Duck Island Landing Unit 210, Westbrook, CT 06498
  • 0 Boston Post Rd Unit 24080344, Westbrook, CT 06498
    0 Boston Post Rd Unit 24080344, Westbrook, CT 06498
    /2

    $195,000

    • Land
    • 1.90 Acres
    • $102,632 per Acre

    0 Boston Post Rd Unit 24080344, Westbrook, CT 06498

    1.9 acres in NCD zone. Public Water in street Septic Required272 road frontage on route 1. Perc Tested for proposed Two Family, (6 BRs Max) or Mixed Use 1,500 SF Retail and 2 unit (4 BR Max) Multifamily. Full size A-2 Survey with Topo, boundary, wetlands available

    Ron Lyman Lyman Real Estate

    0 Boston Post Rd Unit 24080344, Westbrook, CT 06498
  • 164 Hammock Rd N Unit 8, Westbrook, CT 06498

    $579,000 Sold May 30, 2025

    • 1,767 Sq Ft
    • $328/SF
    • 17 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2000

    164 Hammock Rd N Unit 8, Westbrook, CT 06498

    **Direct Waterfront 55+ Community** Experience the beauty of direct waterfront living in this stunning end unit, designed for those aged 55 and older. This exceptional residence offers breathtaking water views from every room, allowing you to witness incredible sunrises and sunsets that will leave you in awe. With one-floor living, this home provides both comfort and convenience. The bright and

    Kelly Puorro Puorro Realty Group

    164 Hammock Rd N Unit 8, Westbrook, CT 06498
  • 201 Old Mail Trail, Westbrook, CT 06498
    201 Old Mail Trail, Westbrook, CT 06498
    201 Old Mail Trail, Westbrook, CT 06498
    /40

    $1,899,000

    • 4 Beds
    • 3.5 Baths
    • 1,824 Sq Ft

    201 Old Mail Trail, Westbrook, CT 06498

    Surrounded by stunning water views, Long Island Sound on one side and Menunketesuck River inlet for Safe Harbor Pilots Point Marina on the other. Enjoy your days in the sun on the large deck and the sandy beach and dip your toes in the water. Picnic on the deck or relax in the hot tub. Fully renovated home. Large dining/living room with cobble stone fireplace, slider to the deck and full front

    Brenda Davenport Pearce Real Estate

    201 Old Mail Trail, Westbrook, CT 06498
  • 144 Old Horse Hill Rd, Westbrook, CT 06498

    $1,100,000 Sold May 30, 2025

    • 3,804 Sq Ft
    • $289/SF
    • 19 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1988

    144 Old Horse Hill Rd, Westbrook, CT 06498

    Extraordinary home! This unique Colonial, cherished by a single family, is exceptional. You'll find beautiful built-ins, intricate moldings, and gorgeous wide plank pine flooring throughout.The kitchen is a chef's dream, featuring top-of-the-line appliances, including a Sub-Zero fridge, a Wolf double oven, and a wine refrigerator. The stunning quartzite countertop boasts a breakfast bar,

    Robin Linares William Pitt Sotheby's Int'l

    144 Old Horse Hill Rd, Westbrook, CT 06498
  • 140 Salt Island Rd, Westbrook, CT 06498
    140 Salt Island Rd, Westbrook, CT 06498
    140 Salt Island Rd, Westbrook, CT 06498
    /39

    $599,900 Open Sun 11:30AM - 12:30PM

    • 3 Beds
    • 1 Bath
    • 1,170 Sq Ft

    140 Salt Island Rd, Westbrook, CT 06498

    Enjoying the best of all seasons by the beach is truly living the dream! Living in a beach community in this well cared for, lovely 3 bedroom, 1 bath ranch-style home with plenty of parking is peaceful and relaxing with the convenience of being just a short walk away from the beach. The year-round aspect is a huge feature, whether it's a summer day with endless sun or a cozy winter evening

    Jaime Serapilia Dasilva William Raveis Real Estate

    140 Salt Island Rd, Westbrook, CT 06498
  • 204 Old Kelsey Point Rd, Westbrook, CT 06498

    $1,685,000 Sold May 29, 2025

    • 1,742 Sq Ft
    • $967/SF
    • 9 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1920

    204 Old Kelsey Point Rd, Westbrook, CT 06498

    As perfect as it gets! Beautiful, year-round, waterfront home completely redone 15 years ago. This impeccable home sets the standard for tasteful renovation while still keeping its cottage charm. There are water views from almost every window in the house. The private association beach with limited membership provides for uncrowded beach relaxation and enjoyment. 3 bed, 3 bath, plus a couple of

    Libby Waldron Coldwell Banker Realty

    204 Old Kelsey Point Rd, Westbrook, CT 06498
  • 89 Norris Ave, Westbrook, CT 06498
    89 Norris Ave, Westbrook, CT 06498
    89 Norris Ave, Westbrook, CT 06498
    /30

    $450,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    89 Norris Ave, Westbrook, CT 06498

    Welcome to 89 Norris Avenue! Location, comfort and opportunity come together on 0.73 acres in the heart of Westbrook. This beautiful, modern ranch offers the perfect blend of tranquility and convenience - just minutes from the beach, downtown Westbrook, top-rated schools, shopping, dining and less than 30 minutes to Yale University & Hospital. Step inside to the bright, open-concept living area

    Samantha Rosano Marella Realty

    89 Norris Ave, Westbrook, CT 06498
  • 67 Captains Dr, Westbrook, CT 06498

    $1,200,000 Sold May 28, 2025

    • 2,448 Sq Ft
    • $490/SF
    • 4 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1969

    67 Captains Dr, Westbrook, CT 06498

    Nestled in the coveted Pilots Point community, this stunning home, with 2,508 sq. ft. of total living space, offers breathtaking ocean views and private beach access just a short walk away. Thoughtfully designed with high-end finishes and quality craftsmanship, it blends elegance and functionality. With two distinct levels and seamless indoor/outdoor areas, it's perfect for hosting guests or

    Doreen Amata Coldwell Banker Realty

    67 Captains Dr, Westbrook, CT 06498

Showing Results 41 - 80, Page 2 of 18

Connecticut Middlesex County Westbrook

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