Middlesex, CT Homes

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  $569,900

  • 5 Beds
  • 2.5 Baths
  • 2,379 Sq Ft

  41 S Main St, Westbrook, CT 06498

  Charming Single-Family with views of the marsh ready for new owners who appreciate the ambiance of Shoreline living. This property is in a desirable location South of Rt 1 near the Center of Westbrook, a short walk to Middle Beach, marinas, playground, bank, busline, restaurants, and shopping. This is currently being used as a legal two-family with short-term tenants in place for investors or

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 891-2925

  41 S Main St, Westbrook, CT 06498
• 

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  Worthington Manor

  1 Bed

  34 Worthington Dr, Westbrook, CT 06498

  34 Worthington Dr, Westbrook, CT 06498
• 

  $652,000 Sold Aug 01, 2025

  • 1,916 Sq Ft
  • $340/SF
  • 88 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1961

  510 McVeagh Rd, Westbrook, CT 06498

  Extraordinary home! Beautiful Colonial home with all new update's that include: brand new driveway, new vinyl siding, new roof, brand new septic tank, newer windows. new boiler and a new kitchen with stainless steel appliances, quartz countertops and a pot filler. Hardwood flooring has been refinished including the upper level. The second floor consists of 4 bedrooms and 2 full baths. For your

  Fred Romano Flat Fee Realty LLC

  510 McVeagh Rd, Westbrook, CT 06498
• 

  Est $700,075 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,014 Sq Ft

  71 Fiske Ln, Westbrook, CT 06498

  71 Fiske Ln, Westbrook, CT 06498
• 

  

  

  /40

  $979,000 Under Contract

  • 6 Beds
  • 5.5 Baths
  • 4,940 Sq Ft

  94 Waldron Dr, Westbrook, CT 06498

  Coastal Duplex in Chapman Beach Association. Set on nearly half an acre in the desirable Chapman Beach Association, this unique and spacious duplex blends coastal charm with modern comfort. Each unit offers 3 bedrooms, 3 baths, an attached garage, and an expansive deck for relaxing or entertaining. The main level includes a bedroom, full bath, and a kitchen with stainless steel appliances that

  

  Cathy Lynch

  Coldwell Banker Realty

  (860) 852-6114

  94 Waldron Dr, Westbrook, CT 06498
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  /7

  $3,500 per month

  • 5 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • House for Rent

  19 Underway Dr, Westbrook, CT 06498

  Stunning waterfront home available from 9/15/25 - 5/15/26. Fully furnished and beautifully decorated. Central air. Front patio overlooking the water. 2 BRs on the first floor with Full Bath and 1 BR upstairs with Full Bath. Owner retaining two bedroom for storage. No pets. No smokers. Owner/Agent.

  Mary Beth Murphy Shimkus, Murphy & Lemkuil

  19 Underway Dr, Westbrook, CT 06498
• 

  $1,835,000 Sold Jul 30, 2025

  • 2,499 Sq Ft
  • $734/SF
  • 242 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2006

  442 Seaside Ave, Westbrook, CT 06498

  Discover the ideal beachfront home or investment property with this exceptional turnkey waterfront residence. Already a successful summer rental this stunning property showcases breathtaking, unobstructed views of Long Island Sound from nearly every room, along with direct water access. The main floor features a spacious open layout, highlighted by a gourmet kitchen equipped with a Wolf range,

  Robin Linares William Pitt Sotheby's Int'l

  442 Seaside Ave, Westbrook, CT 06498
• 

  Est $878,391 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,540 Sq Ft

  2 Autumn Ridge, Westbrook, CT 06498

  2 Autumn Ridge, Westbrook, CT 06498
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  /40

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  448 Grove Beach Rd N, Westbrook, CT 06498

  Very special offering-3.39 acres with substantial frontage on the Menunketesuck River and direct access to Long Island Sound. Ideal for kayakers and small boat enthusiasts, boat launch right around the corner. This rare waterfront compound includes an antique Cape c.1745, featuring handhewn beams, wideboard chestnut floors, three fireplaces, and a beautifully remodeled farmhouse kitchen. A sunny

  

  Al Chiarito

  Chiarito Real Estate LLC

  (860) 792-5356

  448 Grove Beach Rd N, Westbrook, CT 06498
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  /3

  $1,800 per month

  • 3 Beds
  • 1.5 Baths
  • 1,441 Sq Ft
  • House for Rent

  89 Grove Beach Rd N, Westbrook, CT 06498

  Welcome to your future home in Westbrook, CT! This charming property is ideally situated, offering quick access to a variety of amenities, including a fantastic restaurant and several department stores. With LIVation just 11 minutes away, you'll enjoy a perfect balance of convenience and comfort.This property offers a spacious layout with multiple bedrooms and bathrooms, perfect for a

  89 Grove Beach Rd N, Westbrook, CT 06498
• 

  $158,000 Sold Jul 29, 2025

  • 672 Sq Ft
  • $235/SF
  • 34 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2013

  52 Linden Ave N, Westbrook, CT 06498

  CHARMING AND AFFORDABLE! EASY LIVING IN THIS DESIRABLE 55+ COMMUNITY. THIS 2013 1 BR,1 BATH HOME HAS EVERYTHING YOU NEED AND NO WORK TO BOOT! JUST PACK YOUR BAGS AND ENJOY THE QUIET AND CONVENIENCE OF THIS SHORELINE LIFESTYLE. IF IT'S THE BEACH YOU LOVE YOU HAVE 2 BEACHES WITHIN A COUPLE OF MINUTES. FINE DINING, SO MANY CHOICES. SHOPPING? EVERYTHING IS CLOSE BY. MAYBE JUST A COOL DRINK ON YOUR

  Judith DuMouchel J.M. REALTY

  52 Linden Ave N, Westbrook, CT 06498
• 

  Est $550,326 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,764 Sq Ft

  164 Hammock Rd N Unit 23, Westbrook, CT 06498

  164 Hammock Rd N Unit 23, Westbrook, CT 06498
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  /11

  $650,000

  • 3 Beds
  • 2 Baths
  • 2,191 Sq Ft

  79 Pine Lake Rd, Westbrook, CT 06498

  Lovingly owned for 37 years, this farmhouse-style Cape offers charm, space, and peaceful country living. The main level features a nice custom foyer and mudroom. The exceptional post-and-beam great room has custom knotty pine cathedral ceilings, skylights, a floor-to-ceiling brick chimney fireplace, thick hearth, a dry bar, and sliders to a multi-level deck. There's also a cozy living room with

  

  Al Chiarito

  Chiarito Real Estate LLC

  (860) 499-3475

  79 Pine Lake Rd, Westbrook, CT 06498
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  /22

  $6,500 per month

  • 4 Beds
  • 3 Baths
  • 1,618 Sq Ft
  • House for Rent

  156 Old Kelsey Point Rd, Westbrook, CT 06498

  This exceptional waterfront home, available for academic rental October-April or annually, has been meticulously updated to offer the ultimate in seaside living. Boasting a spacious open floor plan, four generously-sized bedrooms, and a sprawling backyard with an in-ground pool that overlooks the serene ocean, this property is an idyllic retreat for those seeking a blend of relaxation and

  Salvatore Carabetta William Raveis Real Estate

  156 Old Kelsey Point Rd, Westbrook, CT 06498
• 

  $1,525,000 Sold Jul 25, 2025

  • 1,606 Sq Ft
  • $950/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1915

  226 Old Kelsey Point Rd, Westbrook, CT 06498

  Classic 1920s Waterfront Cottage on Long Island Sound Step back in time and right into the Sound with this direct waterfront beach cottage on Long Island Sound. Built in the 1920s, this three-bedroom, two-bath home is full of classic New England charm. It features a sunroom with sweeping water views, an open living and dining area with a beautiful original beach stone fireplace. The kitchen is

  Angela Ruel Berkshire Hathaway NE Prop.

  226 Old Kelsey Point Rd, Westbrook, CT 06498
• 

  Est $678,086 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft

  8 Osprey Cir, Westbrook, CT 06498

  8 Osprey Cir, Westbrook, CT 06498
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  /34

  $875,000

  • 3 Beds
  • 3 Baths
  • 3,081 Sq Ft

  49 Economy Dr, Westbrook, CT 06498

  Experience breathtaking views of Long Island Sound with this exceptional shoreline property, a perfect opportunity for those seeking a vacation home, investors looking for an Airbnb, or buyers interested in a primary residence with an Accessory Dwelling Unit (ADU). Nestled in the charming town of Westbrook, this home allows you to enjoy refreshing salt air and warm summer breezes from the

  

  Kelly Puorro

  Puorro Realty Group

  (860) 968-0162

  49 Economy Dr, Westbrook, CT 06498
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  /11

  $1,550 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  1856 Boston Post Rd Unit 1, Westbrook, CT 06498

  1856 Boston Post Rd Unit 1, Westbrook, CT 06498
• 

  $525,000 Sold Jul 23, 2025

  • 1,943 Sq Ft
  • $270/SF
  • 64 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 2017

  931 Old Clinton Rd Unit 6, Westbrook, CT 06498

  Looking for perfection? Come see this stunning 2/3 bedrooms (tax record lists 3 bedrooms), 3 Bath townhouse in Redwood Common. The open floor plan is filled with natural light and features today's modern color palette. The chef's kitchen is a dream featuring white shaker cabinets, granite counters, Stainless Steel appliances, center island and a beverage center with built-in wine chiller and

  Janet Mashia William Pitt Sotheby's Int'l

  931 Old Clinton Rd Unit 6, Westbrook, CT 06498
• 

  Est $1,969,279 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,534 Sq Ft

  60 Captains Dr, Westbrook, CT 06498

  60 Captains Dr, Westbrook, CT 06498
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  /36

  $849,900

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  6 Indian Trail, Westbrook, CT 06498

  Enjoy beautiful sunrises overlooking the water with your morning coffee from the sunroom of this sweet two bedroom, two bath ranch home. A light-filled kitchen and second bedroom also offer water views and glimpses of local wildlife. A spacious living room features a fieldstone fireplace, and leads to the primary bedroom complete with a cathedral ceiling, a finished storage loft with skylights,

  Susan Malan William Pitt Sotheby's Int'l

  6 Indian Trail, Westbrook, CT 06498
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  /32

  $2,100 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • House for Rent

  14 Leeway Dr, Westbrook, CT 06498

  Immaculate 3 bedroom ranch at Pilot's Point, Totally painted from ceilings to floor, hardwood in main areas, rugs in 2 main bedrooms, Water, views of Long Island Sound, Minutes to walk to private beach and to Marina, deck off dining area, fenced in back yard with outside shower!! Come see for yourself!!

  Salome Kirkutis SKS Realty

  14 Leeway Dr, Westbrook, CT 06498
• 

  $880,000 Sold Jul 21, 2025

  • 4,066 Sq Ft
  • $216/SF
  • 59 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1990

  262 Fairview Rd, Westbrook, CT 06498

  Set on over 2 private, professionally landscaped acres in a sought-after, lamp post-lined neighborhood, this expansive one-owner Colonial offers timeless design, thoughtful updates, and a peaceful wooded backdrop. Built in 1990 and lovingly maintained, this 5-bedroom, 3 full and 2 half-bath home spans over 4,000 sq ft across three finished levels. A grand two-story foyer welcomes you into warm,

  Allison Ciarcia William Raveis Real Estate

  262 Fairview Rd, Westbrook, CT 06498
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  Est $771,838 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,759 Sq Ft

  101 Johnson Pond Ln, Westbrook, CT 06498

  101 Johnson Pond Ln, Westbrook, CT 06498
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  /39

  $860,000

  • 4 Beds
  • 2.5 Baths
  • 2,885 Sq Ft

  3 Autumn Ridge, Westbrook, CT 06498

  3 Autumn Ridge is an enclave of just eleven custom-built homes. This cul-de-sac neighborhood has sidewalks, streetlamps, and hiking trails. Upon entering, you're greeted by a cathedral foyer with batten board trim that leads to the open concept kitchen/living room. This home is bright and sunny throughout the day. You will enjoy the ease of entertaining, whether you choose to dine inside or

  Kimberly Maulucci William Raveis Real Estate

  3 Autumn Ridge, Westbrook, CT 06498
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  /15

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  109 Salt Island Rd, Westbrook, CT 06498

  Academic Rental | 109 Salt Island Rd, Westbrook, CT Available Sept 6 - May 15 | $1,800/month + utilities Minimum credit score: 700 | Dog or Cat considered | No Smoking Experience cozy coastal living in this adorable 2-bedroom, 1-bath retreat just a short stroll from the beach. Nestled in the heart of Westbrook, this charming and recently updated home is perfect for professionals, couples, or

  Ali White White-Ginnett Coldwell Banker Realty

  109 Salt Island Rd, Westbrook, CT 06498
• 

  $660,000 Sold Jul 16, 2025

  • 2,787 Sq Ft
  • $237/SF
  • 43 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  202 Horse Hill Rd, Westbrook, CT 06498

  Welcome to 202 Horse Hill Rd., Westbrook - Tucked away on a quiet cul-de-sac shared with just two other homes, this beautiful colonial offers privacy, comfort, and modern style just minutes from town, beaches, shopping, and major routes. A charming front porch welcomes you into a bright, open interior featuring gleaming hardwood floors, 9-ft. ceilings, and a spacious layout ideal for both

  Allison Ciarcia William Raveis Real Estate

  202 Horse Hill Rd, Westbrook, CT 06498
• 

  Est $458,415 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,672 Sq Ft

  523 Essex Rd, Westbrook, CT 06498

  523 Essex Rd, Westbrook, CT 06498
• 

  

  /40

  $1,125,000

  • 5 Beds
  • 6 Baths
  • 5,028 Sq Ft

  1 Lake Louise Dr, Westbrook, CT 06498

  Custom-Built Waterfront Home in Coveted Lake Louise Neighborhood Welcome to this stunning custom-built home located in the highly desirable Lake Louise community, offering beautiful water views and 1/3 ownership of the lake. Enjoy peaceful waterfront living with private access for kayaking, canoeing, and more. Step inside to find gleaming hardwood floors throughout the main level and an open

  David Hughes Century 21 AllPoints Realty

  1 Lake Louise Dr, Westbrook, CT 06498
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  /40

  $4,000 per month

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • House for Rent

  62 Brookside Ave E, Westbrook, CT 06498

  Welcome to this charming three-bedroom, two-full-bathroom Cape located in Westbrook, CT! As you enter, you'll be greeted by the inviting living room, filled with natural light. The main level features an open kitchen connected to the dining room. Additionally, there's a bedroom and a full bathroom with a washer/dryer conveniently located on this level. Heading upstairs, you'll find two bedrooms,

  Samantha Celentano Coldwell Banker Realty

  62 Brookside Ave E, Westbrook, CT 06498
• 

  $1,050,000 Sold Jul 14, 2025

  • 2,292 Sq Ft
  • $458/SF
  • 102 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1950

  12 Bellstone Ave, Westbrook, CT 06498

  Escape to West Beach with this stunning, fully renovated year-round beach home, just steps from the sand. Designed for easy coastal living, this home features a brand-new designer kitchen with white quartz countertops and a cozy natural gas wood stove. The first-floor bedroom and bath offer convenience, while the master suite provides a luxurious retreat. Everyone has room with 4 bedrooms and 4

  Joel Lucas Coldwell Banker Realty

  12 Bellstone Ave, Westbrook, CT 06498
• 

  Est $564,430 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,834 Sq Ft

  789 Toby Hill Rd, Westbrook, CT 06498

  789 Toby Hill Rd, Westbrook, CT 06498
• 

  

  /40

  $975,000

  • 3 Beds
  • 1.5 Baths
  • 1,318 Sq Ft

  92 Grove Beach Rd S, Westbrook, CT 06498

  ALSO AVAILABLE AS ACADEMIC RENTAL. Recently renovated this 3 bedroom, 1.5 bathroom, located in a shoreline community, with amazing ocean views is a fantastic opportunity if you missed it. Just a short walk to a private, beautiful beach that is shared by only 8 properties. Home has additional space in basement with a half bath. The yard has not 1 but 2 patios, an electric awning, outdoor kitchen

  Jay Cusack Executive Real Estate Inc.

  92 Grove Beach Rd S, Westbrook, CT 06498
• 

  

  /22

  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 968 Sq Ft
  • House for Rent

  96 Post Ave, Westbrook, CT 06498

  Academic Rental from 9/1/2025 thru 5/31/2026. Live near the water --- great views! 2 houses from beach! This home has been lovingly maintained by it's owners who are looking for folks to rent for the Academic year. No pets/No smoking. First floor consists of Living room, kitchen/dining, Sun room/porch, bedroom. Second floor has 2 bedrooms, 1 full bath. Credit, eviction, criminal check;

  Lisa Genovali Re/Max Valley Shore

  96 Post Ave, Westbrook, CT 06498
• 

  $665,000 Sold Jul 03, 2025

  • 2,220 Sq Ft
  • $300/SF
  • 39 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1985

  55 Fishing Brook Rd, Westbrook, CT 06498

  Welcome to this renovated Colonial nestled in Westbrook Connecticut. This picturesque neighborhood boasts sidewalks, providing a quaint and safe atmosphere. Enjoy the convenience of living close to beaches, marinas, restaurants and shopping, all just a short distance away. This spacious, updated layout includes four bedrooms, two-and-a-half baths, a family room, living room, formal dining room

  Bonnie Foster William Pitt Sotheby's Int'l

  55 Fishing Brook Rd, Westbrook, CT 06498
• 

  Est $910,709 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,642 Sq Ft

  1 Whittemore Place, Westbrook, CT 06498

  1 Whittemore Place, Westbrook, CT 06498
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  /37

  $749,900

  • 2 Beds
  • 2 Baths
  • 2,457 Sq Ft

  157 Pine Lake Rd, Westbrook, CT 06498

  Welcome to Your Year-Round Waterfront Retreat! Tucked away in a serene setting in the desirable shoreline town of Westbrook, this well-maintained ranch offers the perfect balance of privacy, comfort, and nature. Set on over 2.3 secluded acres with 400 feet of direct frontage on Wright's Pond, this home is a nature lover's paradise. Whether you enjoy fishing, canoeing, paddle boating, or bird

  Gigi Giordano Taylor Compass Connecticut, LLC

  157 Pine Lake Rd, Westbrook, CT 06498
• 

  

  /16

  $1,725 per month

  • 1 Bath
  • 460 Sq Ft
  • House for Rent

  358 Toby Hill Rd, Westbrook, CT 06498

  Absolutely adorable fully furnished loft apartment over owner's garage on quiet, peaceful road in Westbrook! This cozy home has been rented in the past with rave reviews. Enjoy the comfort of your own space - living area, kitchen with refrigerator and stove top, full bath with shower stall and sleeping area separated by a half wall. HEAT, A/C, ELECTRIC, WATER, WI-FI, CABLE ALL INCLUDED!!!!!!!!!

  Lisa Genovali Re/Max Valley Shore

  358 Toby Hill Rd, Westbrook, CT 06498
• 

  $850,000 Sold Jul 01, 2025

  • 1,717 Sq Ft
  • $495/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  124 Old Salt Works Rd, Westbrook, CT 06498

  Welcome to 124 Old Salt Works Rd, a beautifully updated 3-bedroom, 2-bathroom Cape-style home in a sought-after shoreline community! Just steps from the beach, this home offers the perfect blend of charm, modern updates, and relaxing coastal vibes. Step inside to discover an open-concept kitchen featuring granite countertops, stainless steel appliances, and custom white cabinetry. The adjacent

  Joseph Malerba eXp Realty

  124 Old Salt Works Rd, Westbrook, CT 06498
• 

  Est $707,530 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,064 Sq Ft

  27 Broadway S, Westbrook, CT 06498

  27 Broadway S, Westbrook, CT 06498

Showing Results 1 - 40, Page 1 of 18