Middlesex County, CT Homes

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  $699,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,304 Sq Ft

  4 Hunters Ridge Rd, Killingworth, CT 06419

  Inspired by the timeless architecture of the Solomon Richardson House at Old Sturbridge Village, this exceptional 1989 saltbox reproduction beautifully blends early American design with modern comfort. Prominently set on 2.1 acres in a cul-de-sac neighborhood in rural Killingworth, this 3-bedroom, 2.5-bath home offers charm, craftsmanship, and serene surroundings. A stunning entryway welcomes you

  

  Shelly Cumpstone

  Coldwell Banker Realty

  (860) 854-1827

  4 Hunters Ridge Rd, Killingworth, CT 06419
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  $2,350 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft
  • House for Rent

  12 Nutmeg Dr, Clinton, CT 06413

  Welcome to 12 Nutmeg Dr in Clinton, a 3 bed 1 bath ranch centrally located to schools, parks and the beach! The home offers nice updates like newer carpet and flooring, as well as clean and efficient propane heating. Available as an unfurnished yearly lease, this home has oversized shared spaces, with a bright unfilled living area, and a large living space off of the kitchen. A cleared level yard

  

  Dylan Walter

  William Raveis Real Estate

  (860) 943-4732

  12 Nutmeg Dr, Clinton, CT 06413
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  $645,000 Sold Jan 12, 2026

  41 Day School Dr, Middlefield, CT 06455

  • 3 Beds
  • 2.5 Baths
  • 2,949 Sq Ft
  • Built 1996

  Last Sold Summary

  • 6% Below List Price
  • $219/SF
  • 47 Days On Market

  Current Estimated Value $649,626

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  41 Day School Dr, Middlefield, CT 06455
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  Est $195,878 Not Listed For Sale

  1261 Washington St Unit 2, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 1,109 Sq Ft
  • Built 1985

  1261 Washington St Unit 2, Middletown, CT 06457

  Last Sold Summary

  • 15% Above List Price
  • $153/SF
  • 1 Day On Market

  Last Sold Price $170,000

  Last Listing Agent Xylia DiBianco Carbutti & Co., Realtors
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  $1,895,000

  • 4 Beds
  • 4.5 Baths
  • 5,610 Sq Ft

  108 Westbrook Rd, Essex, CT 06426

  Amazing custom built Nantucket style Cape situated on sprawling grounds, terraced high above a picturesque great yard & overseen by natural highlands. The setting is nothing but breathtaking! Inclusive is an inground Gunite pool engulfed by the primary hardscape which walks-out from the lower level & is situated high above the great yard. A magnificent carriage house featuring a 4 bay garage &

  

  Kevin Geysen

  William Pitt Sotheby's Int'l

  (860) 321-5635

  108 Westbrook Rd, Essex, CT 06426
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  $1,800 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  252 Main St Unit A3, Portland, CT 06480

  Spacious 1-bedroom apartment for rent in the heart of downtown Portland! Located on the second floor in the rear of a well-maintained multi-use building (Dagle & Dagle business in the front), this private unit offers both comfort and convenience. The remodeled eat-in kitchen features a charming built-in hutch and plenty of space for dining. The bathroom has been updated with a brand-new shower.

  

  Cheryl Zalewski

  eXp Realty

  (860) 362-3503

  252 Main St Unit A3, Portland, CT 06480
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  $340,000 Sold Mar 12, 2026

  38 Old Middletown Ave, East Hampton, CT 06424

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft
  • Built 1974

  Last Sold Summary

  • $244/SF
  • 51 Days On Market

  Current Estimated Value $339,242

  Last Listing Agent Mark Reyher Reyher Real Estate

  38 Old Middletown Ave, East Hampton, CT 06424
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  Est $251,841 Not Listed For Sale

  190 Spencer Dr, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1952

  190 Spencer Dr, Middletown, CT 06457

  Last Sold Summary

  • 5% Above List Price
  • $263/SF
  • 7 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Thomas Mele Dorrance Realty
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  $1,125,000

  • 4 Beds
  • 2 Baths
  • 1,722 Sq Ft

  144 Shore Rd, Clinton, CT 06413

  Nestled on the pristine Clinton Shoreline this extraordinary beach community offers an unparalleled coastal living experience. Imagine waking up to the gentle sound of waves, this is more than a home; it's a private sanctuary where the rhythm of the tides becomes the soundtrack to your life. Step inside and discover a meticulously designed completely renovated "open-concept floor plan" a gourmet

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 854-4742

  144 Shore Rd, Clinton, CT 06413
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  $2,000 total monthly price

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

  26 College St Unit 2, Clinton, CT 06413

  Located in a very convenient area, close to shopping, town beach, and 95, this 2 bedroom condo has had recent updates and is now available for an immediate rental. A fresh coat of paint throughout and new windows have revitalized this second floor unit. In addition to the living room measuring 17 x 12, the unit has a kitchen with stainless appliances and a comfortable eating area. There is even

  

  Shelly Cumpstone

  Coldwell Banker Realty

  (860) 809-2107

  26 College St Unit 2, Clinton, CT 06413
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  $1,725,000 Sold Dec 15, 2025

  20 Hemlock Dr, Essex, CT 06426

  • 4 Beds
  • 3.5 Baths
  • 4,162 Sq Ft
  • Built 1962

  Last Sold Summary

  • 22% Below List Price
  • $414/SF
  • 156 Days On Market

  Current Estimated Value $1,854,189

  Last Listing Agent Dee Hasuly KW Legacy Partners

  20 Hemlock Dr, Essex, CT 06426
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  Est $404,322 Not Listed For Sale

  16 Woodland Dr, Clinton, CT 06413

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft
  • Built 1969

  16 Woodland Dr, Clinton, CT 06413

  Last Sold Summary

  • 9% Above List Price
  • $184/SF
  • 141 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Gene Pica RE/MAX
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  $1,000,000

  • 6 Beds
  • 3 Baths
  • 2,522 Sq Ft

  176 Shore Rd, Clinton, CT 06413

  Unprecedented Investment or Family Compound with Private Beach Rights This is a rare and unparalleled opportunity to own a piece of paradise, featuring deeded rights to a private beach on the Long Island Sound and three distinct residences, making it an ideal family compound or a high-yield investment property. The Main Residence has been an Airbnb $500 per night. Completely updated and boasting

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 507-9240

  176 Shore Rd, Clinton, CT 06413
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  $1,655 - $3,120 total monthly price

  Brainerd Place

  Studio - 2 Beds

  69 Marlborough St, Portland, CT 06480

  Experience the perfect blend of history and modern elegance at Brainerd Place, a luxury apartment community built in historic Portland, CT. Where the charm of the past meets the sophistication of the present, our thoughtfully designed residences offer unparalleled comfort, state-of-the-art amenities, and timeless style. Immerse yourself in a setting that honors its heritage while providing the

  69 Marlborough St, Portland, CT 06480
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  $1,450,000 Sold Nov 17, 2025

  55 Main St, East Haddam, CT 06423

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft
  • Built 1850

  Last Sold Summary

  • 3% Below List Price
  • $630/SF
  • 147 Days On Market

  Current Estimated Value $1,424,406

  Last Listing Agent Sacha Armstrong William Pitt Sotheby's International Realty

  55 Main St, East Haddam, CT 06423
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  Est $732,547 Not Listed For Sale

  1 Docs Hill Rd, Westbrook, CT 06498

  • 2 Beds
  • 3 Baths
  • 1,951 Sq Ft
  • Built 1989

  1 Docs Hill Rd, Westbrook, CT 06498

  Last Sold Summary

  • 6% Above List Price
  • $355/SF
  • 126 Days On Market

  Last Sold Price $692,350

  Last Listing Agent Gigi Giordano Taylor Compass Connecticut, LLC
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  $650,000

  • 3 Beds
  • 3 Baths
  • 2,752 Sq Ft

  1 Ferry Rd, Chester, CT 06412

  An extraordinary offering in one of Connecticut's most beloved river towns. Stunning sunrises over unobstructed views of Chester Creek sets the tone for this rare piece of Chester history. The Bani Denison homestead dates to 1781 and once served as Chester's first post office. Thoughtfully restored, this classic embankment Colonial with Dutch kick gambrel style roof offers modern amenities while

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (860) 454-6525

  1 Ferry Rd, Chester, CT 06412
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  $2,700 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  98 W Main St, Chester, CT 06412

  Experience the charm of Chester Village right down the street with delightful shops and restaurants just moments away. Enjoy quick access to the highway for trips to the ocean and additional shopping. Step into this stunning remodeled 3 bedroom apartment and be the first to enjoy this gorgeous kitchen featuring custom cabinets, spacious island, leathered granite countertops, & stainless-steel

  Suzanne Walsh William Raveis Real Estate

  98 W Main St, Chester, CT 06412
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  $406,000 Sold Jan 06, 2026

  55 Lorelei Cir, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1966

  Last Sold Summary

  • 3% Above List Price
  • $251/SF
  • 9 Days On Market

  Current Estimated Value $403,531

  Last Listing Agent Michelle Pirruccio Carl Guild & Associates

  55 Lorelei Cir, Middletown, CT 06457
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  Est $320,900 Not Listed For Sale

  35 Arnold St, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,109 Sq Ft
  • Built 1938

  35 Arnold St, Middletown, CT 06457

  Last Sold Summary

  • 4% Above List Price
  • $280/SF
  • 48 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Jaime Russo Calcagni Real Estate
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  $329,900 Pending

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

  30 Larkspur Dr, Cromwell, CT 06416

  Beautifully remodeled 3-bedroom, 1.5-bath END UNIT townhome located in the highly desirable Oxford Park community, where comfort meets convenience and wonderful community amenities await. This spacious home is truly move-in ready and thoughtfully updated throughout. As you step inside, you'll immediately notice the care and attention to detail. The main level features gorgeous hardwood floors

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 813-2530

  30 Larkspur Dr, Cromwell, CT 06416
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  $1,844 - $3,740 total monthly price

  Springside Middletown

  1 - 3 Beds

  1100 Springside Ln, Middletown, CT 06457

  "Connecticut's Best New Rental Community" as awarded by the CT Home Builder and Remodeler's Association. Discover Springside Middletown, a brand-new apartment community that features a one-of-a-kind central amenity village, as well as a choice of multi-story rental townhomes and traditional single-level apartment homes.

  1100 Springside Ln, Middletown, CT 06457
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  $51,000 Sold Mar 31, 2025

  50 Riverside Dr, Clinton, CT 06413

  • 800 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $64/SF
  • 17 Days On Market

  Last Listing Agent Noreen Brennan-Rowe William Raveis Real Estate

  50 Riverside Dr, Clinton, CT 06413
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  Est $566,175 Not Listed For Sale

  45 Dolbia Hill Rd, East Haddam, CT 06423

  • 3 Beds
  • 2.5 Baths
  • 2,069 Sq Ft
  • Built 1998

  45 Dolbia Hill Rd, East Haddam, CT 06423

  Last Sold Summary

  • 10% Above List Price
  • $249/SF
  • 67 Days On Market

  Last Sold Price $515,000

  Last Listing Agent Alan Spotlow William Raveis Real Estate
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  $850,000

  • 4 Beds
  • 2 Baths
  • 8,382 Sq Ft

  26 Ferry Rd, Chester, CT 06412

  Located in the Town of Chester, this mixed-use property presents a rare opportunity to acquire a distinctive asset in one of Connecticut's most desirable markets. As it stands, the property consists of approximately 5,000 square feet of commercial space, including one loading dock, three (3) garages, and an oversized on-site parking lot, supporting a wide range of operational and occupancy needs.

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1600

  26 Ferry Rd, Chester, CT 06412
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  $2,200 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  96 W Main St Unit 98, Chester, CT 06412

  Be the first to rent this charming, remodeled apartment! Nestled near the quaint village of Chester, you'll be close to shops and restaurants while still enjoying a peaceful, countryside ambiance. The apartment has modern amenities, including split units for heating & central air, new stainless-steel appliances, & granite countertops, making it both stylish and functional. Open floor plan for the

  Suzanne Walsh William Raveis Real Estate

  96 W Main St Unit 98, Chester, CT 06412
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  $174,000 Sold Aug 21, 2025

  1 Brush Pasture Ln Unit 109, Portland, CT 06480

  • 1 Bed
  • 1 Bath
  • 832 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $209/SF
  • 50 Days On Market

  Current Estimated Value $174,512

  Last Listing Agent Maria Phillips William Raveis Real Estate

  1 Brush Pasture Ln Unit 109, Portland, CT 06480
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  Est $338,251 Not Listed For Sale

  14 Chittenden Hill Rd, Clinton, CT 06413

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 1939

  14 Chittenden Hill Rd, Clinton, CT 06413

  Last Sold Summary

  • 7% Above List Price
  • $397/SF
  • 86 Days On Market

  Last Sold Price $317,500

  Last Listing Agent Phoebe Schreiner William Pitt
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  $1,350,000

  • 7 Beds
  • 6 Baths
  • 3,787 Sq Ft

  87 Main St, Deep River, CT 06417

  VC Property Group is proud to present a two-parcel assemblage in Deep River, Connecticut, offering stabilized mixed-use income with residential value and land optionality. The assemblage includes: 87 Main Street - a parcel improved with: a Newer Construction Single Family Residence and a 5-unit mixed-use building (four residential apartments and one retail unit) 55 Prospect Street - a contiguous

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1057

  87 Main St, Deep River, CT 06417
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  $1,450 - $2,000 per month plus fees

  StoneGate Apartments

  1 - 2 Beds

  1150-1160 S Main St, Middletown, CT 06457

  Stonegate Apartments – Middletown, CTWelcome to Stonegate Apartments, where comfort and convenience meet. Our spacious apartments are designed for easy living, with heat and hot water included in your rent so you can enjoy peace of mind all year round.Relax and unwind with our community amenities, including a sparkling outdoor pool, a fully equipped fitness center, and a lively

  1150-1160 S Main St, Middletown, CT 06457
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  $749,900 Sold Jul 16, 2025

  17 Partridge Hill Ln, Essex, CT 06426

  • 4 Beds
  • 2.5 Baths
  • 2,976 Sq Ft
  • Built 1967

  Last Sold Summary

  • $252/SF
  • 27 Days On Market

  Current Estimated Value $791,218

  Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

  17 Partridge Hill Ln, Essex, CT 06426
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  Est $410,296 Not Listed For Sale

  198 Ross Rd, Rockfall, CT 06481

  • 3 Beds
  • 1.5 Baths
  • 1,364 Sq Ft
  • Built 1958

  198 Ross Rd, Rockfall, CT 06481

  Last Sold Summary

  • 3% Above List Price
  • $293/SF
  • 24 Days On Market

  Last Sold Price $399,000

  Last Listing Agent Maya Brown Coldwell Banker Realty
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  $675,000 Pending

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  2 Pequot Trail, Old Saybrook, CT 06475

  Welcome to 2 Pequot Trail, perfectly positioned within Old Saybrook's desirable Indian Town Association, this beautifully maintained coastal ranch offers a rare opportunity to enjoy shoreline living in one of the area's most established waterfront neighborhoods. This stunning home captures the relaxed charm and lifestyle that make Indian Town and Old Saybrook at large, so sought after. Completely

  

  Dylan Walter

  William Raveis Real Estate

  (860) 909-8203

  2 Pequot Trail, Old Saybrook, CT 06475
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  $1,675 total monthly price

  • 1 Bed
  • 1.5 Baths
  • 776 Sq Ft
  • Townhouse for Rent

  14 Country Squire Dr Unit 14B, Cromwell, CT 06416

  One bedroom Loft style with carport will be ready for May 1st! 15 x14 living room has double sliders to deck, kitchen features stainless steel appliances, pantry storage, subway tile backsplash & island with granite! 17x12 bedroom with walk-in closet & updated full bath. Wood floors on both levels. Open floor plan with separate dining area, large storage closet & remodeled 1/2 bath on main level.

  Eileen England eXp Realty

  14 Country Squire Dr Unit 14B, Cromwell, CT 06416
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  $675,000 Sold Feb 20, 2026

  99 Maple Ave, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Above List Price
  • $577/SF
  • 34 Days On Market

  Current Estimated Value $636,670

  Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l

  99 Maple Ave, Old Saybrook, CT 06475
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  Est $283,954 Not Listed For Sale

  7 Railroad Ave, East Hampton, CT 06424

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1910

  7 Railroad Ave, East Hampton, CT 06424

  Last Sold Summary

  • 14% Above List Price
  • $208/SF
  • 57 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Kara Pedersen Carl Guild & Associates
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  $525,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  56 Coles Rd, Middletown, CT 06457

  Come see this beautiful 4 bedroom, 2.5 bathroom Colonial with a 2-car garage, built in 1996 and ideally located on .41 acres in a quiet cul-de-sac setting before it is SOLD! The remodeled kitchen features granite countertops, a large center island with breakfast bar, and opens seamlessly to a cozy fireplaced family room with sliders to the back deck and a bright living room with hardwood

  

  Cheryl Zalewski

  eXp Realty

  (860) 579-1457

  56 Coles Rd, Middletown, CT 06457
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  $2,085 - $3,080 total monthly price

  The Landon of Cromwell

  1 - 2 Beds

  150 Country Squire Dr, Cromwell, CT 06416

  Welcome Home to The Landon of Cromwell!

  150 Country Squire Dr, Cromwell, CT 06416
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  $300,000 Sold Sep 19, 2025

  23 Lexington Place S, Durham, CT 06422

  • 2 Beds
  • 2.5 Baths
  • 1,686 Sq Ft
  • Built 1997

  Last Sold Summary

  • $178/SF
  • 174 Days On Market

  Current Estimated Value $305,035

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  23 Lexington Place S, Durham, CT 06422
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  Est $348,685 Not Listed For Sale

  1001 Middle St, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,066 Sq Ft
  • Built 1960

  1001 Middle St, Middletown, CT 06457

  Last Sold Summary

  • 5% Above List Price
  • $312/SF
  • 20 Days On Market

  Last Sold Price $333,000

  Last Listing Agent Chad Crookes Statewide Premier Prop. LLC

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