Middlesex County, CT Homes

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  $1,795,000

  $100K PRICE DROP

  • 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 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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  /21

  $2,500 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,328 Sq Ft
  • House for Rent

  55 Liberty St, Chester, CT 06412

  Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its bustling restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an

  

  Janet Cronin-Rumanoff

  William Pitt Sotheby's Int'l

  (860) 981-0835

  55 Liberty St, Chester, CT 06412
• 

  $340,000

  Sold May 27, 2026

  1 Foley Rd, Portland, CT 06480

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1956

  Last Sold Summary

  • 17% Above List Price
  • $363/SF
  • 3 Days On Market

  Current Estimated Value $285,127

  Last Listing Agent Cheryl Zalewski eXp Realty

  1 Foley Rd, Portland, CT 06480
• 

  Est $642,147

  Not Listed For Sale

  10 Jack English Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,226 Sq Ft
  • Built 2023

  10 Jack English Dr, Middletown, CT 06457

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /40

  $419,900

  Under Contract

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  119 Main St, East Hampton, CT 06424

  Multiple offers received! Seller is requesting highest and best offers by 5:00 PM on Monday, June 22nd. The charm of a Cape Cod with the space, storage, and flexibility you've been searching for. Lovingly maintained and ready for its third owner, this East Hampton home is full of character, from the beautiful archways to the thoughtful updates throughout. The main level features a renovated

  

  Michelle Maldonado

  RE/MAX RISE

  (860) 364-6441

  119 Main St, East Hampton, CT 06424
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  /29

  Starting at $1,710

  Total Monthly Price

  • Studio - 2 Beds

  75 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

  Brainerd Place

  (860) 854-3101

  75 Marlborough St, Portland, CT 06480
• 

  $370,000

  Sold Jun 23, 2026

  31 Grandview Terrace, Portland, CT 06480

  • 2 Beds
  • 2.5 Baths
  • 2,169 Sq Ft
  • Built 1967

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 7 Days On Market

  Current Estimated Value $404,828

  Last Listing Agent Cheryl Zalewski eXp Realty

  31 Grandview Terrace, Portland, CT 06480
• 

  Est $708,081

  Not Listed For Sale

  382 Middlesex Turnpike, Old Saybrook, CT 06475

  382 Middlesex Turnpike, Old Saybrook, CT 06475

  Last Sold Summary

  • 468 Days On Market
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  /38

  $997,000

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

  144 Shore Rd, Clinton, CT 06413

  Living the Shoreline dream! Featuring 4 beds & 2 full baths 144 Shore Road, a beautifully remodeled coastal escape in the highly coveted Clinton Beach Association. Complete with deeded beach access and sweeping Long Island Sound views, this turn-key property perfectly blends modern luxury with timeless seaside charm.The main level features a bright, open-concept floor plan with an oversized

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 792-4174

  144 Shore Rd, Clinton, CT 06413
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  /2

  $3,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft
  • House for Rent

  7 Egypt Ln, Clinton, CT 06413

  This beautiful 2,632 sq ft colonial offers a rare short term rental opportunity (3-6 months) and features impressive architectural details throughout. A striking three story foyer sets the tone as you enter, leading to the formal living room perfect for entertaining, plus a spacious family room with custom built ins and a fireplace ideal for relaxing or gatherings. The modern, fully equipped

  

  Sharon O'Brien

  Hillside Properties

  (860) 590-4011

  7 Egypt Ln, Clinton, CT 06413
• 

  $444,000

  Sold May 15, 2026

  45 Crestwood Dr, East Hampton, CT 06424

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Above List Price
  • $206/SF
  • 2 Days On Market

  Current Estimated Value $421,213

  Last Listing Agent Rick Berkenstock CENTURY 21 AllPoints Realty

  45 Crestwood Dr, East Hampton, CT 06424
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  Not Listed For Sale

  51 Rising Trail Dr Unit 51, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,232 Sq Ft
  • Built 1976

  51 Rising Trail Dr Unit 51, Middletown, CT 06457

  Last Sold Summary

  • 7 Days On Market
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  /38

  $479,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,188 Sq Ft

  31 N Maple St, East Hampton, CT 06424

  Welcome to 31 N Maple Rd, East Hampton - where space, updates, and lifestyle come together in one of the area's most desirable settings. Well maintained and thoughtfully improved, this 4-bedroom, 2.5-bath home offers the kind of room and functionality today's buyers are searching for. From everyday living to hosting family and friends, the layout provides a comfortable flow with plenty of space

  

  James Harrington

  Carl Guild & Associates

  (860) 735-4661

  31 N Maple St, East Hampton, CT 06424
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  Starting at $1,797

  Total Monthly Price

  • 1 - 2 Beds

  100 Town Brooke, Middletown, CT 06457

  At Middletown Brook Apartment Homes, you'll be greeted by modern interiors and breathtaking views of the surrounding neighborhood. With high-end finishes and sophisticated design, your apartment is the perfect place to relax and unwind after a long day. Curl up on your cozy couch with a glass of wine or enjoy a romantic dinner for two in your spacious dining area. With a beautiful swimming pool

  Middletown Brooke Apartments

  (860) 846-4439

  

  100 Town Brooke, Middletown, CT 06457
• 

  $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 $343,589

  Last Listing Agent Mark Reyher Reyher Real Estate

  38 Old Middletown Ave, East Hampton, CT 06424
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  Not Listed For Sale

  17 Oconnell Road Extension, Colchester, CT 06415

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 1986

  17 Oconnell Road Extension, Colchester, CT 06415

  Last Sold Summary

  • 22 Days On Market
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  /40

  $518,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  42 Parker Hill Rd, Killingworth, CT 06419

  Your private retreat awaits in one of Killingworth's most desirable areas. Set well back from the road on 4.2 secluded acres, this property offers a rare blend of privacy, natural beauty, and tranquility, with views of Murray Pond and abundant wildlife. This stylish split-level home features a distinctive design, highlighted by a hip roof over the two-story section and a complementary ranch-style

  

  Shelly Cumpstone

  Coldwell Banker Realty

  (860) 934-0301

  42 Parker Hill Rd, Killingworth, CT 06419
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  $1,900 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,057 Sq Ft
  • House for Rent

  2316 Cromwell Hills Dr, Cromwell, CT 06416

  Welcome to this spacious 2-bedroom, 1.5-bath condo offering 1,057 sq. ft. of comfortable living space in a highly convenient location. This well-laid-out home features generous room sizes, great natural light, and an easy-flowing floor plan perfect for everyday living. Enjoy the added value of heat and hot water included, helping keep monthly costs more manageable. The complex also offers a pool,

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  (860) 485-7296

  2316 Cromwell Hills Dr, Cromwell, CT 06416
• 

  $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 $668,022

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  41 Day School Dr, Middlefield, CT 06455
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  Est $388,065

  Not Listed For Sale

  17 Hills Ave, East Hampton, CT 06424

  • 2 Beds
  • 2 Baths
  • 1,054 Sq Ft
  • Built 1930

  17 Hills Ave, East Hampton, CT 06424

  Last Sold Summary

  • 3 Days On Market
• 

  

  /38

  $968,800

  Pending

  • 2 Beds
  • 2.5 Baths
  • 2,823 Sq Ft

  25 Sheffield St Unit 3, Old Saybrook, CT 06475

  Experience refined coastal living in this stunning end-unit townhome, completed in 2021 and ideally located in the heart of downtown Old Saybrook. This exceptional residence offers convenient access to dining, shopping, the Katharine Hepburn Cultural Arts Center, Saybrook Point Marina, and local beaches. Bathed in natural light, the home features a spacious open floor plan with gleaming hardwood

  

  Nick Prevost

  William Raveis Real Estate

  (860) 792-4053

  25 Sheffield St Unit 3, Old Saybrook, CT 06475
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  Starting at $1,400

  Total Monthly Price

  • Studio - 2 Beds

  131 Ridgefield Dr, Middletown, CT 06457

  ***Maintenance Team On-site*** At Ridgefield Apartments we offer studios, lofts, and one and two bedroom apartments. We invite you to take advantage of our quality apartment homes. We offer value, comfort, and convenience to our residents, We are located in the esteemed Westlake neighborhood nestled among the trees. Our features include a pleasant, professional, and accommodating maintenance and

  Ridgefield Apartments

  (475) 255-0337

  

  131 Ridgefield Dr, Middletown, CT 06457
• 

  $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 $1,817,660

  Last Listing Agent Dee Hasuly KW Legacy Partners

  20 Hemlock Dr, Essex, CT 06426
• 

  Est $359,668

  Not Listed For Sale

  104 Lantern Ct, Clinton, CT 06413

  • 1 Bed
  • 1.5 Baths
  • 1,592 Sq Ft
  • Built 2010

  104 Lantern Ct, Clinton, CT 06413

  Last Sold Summary

  • 46 Days On Market
• 

  

  /18

  $274,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  1218 Cromwell Hills Dr Unit 1218, Cromwell, CT 06416

  This 3 Bedroom 2 Full Bath condo is modern and ready to move in. Condo has a newer kitchen with granite counter-tops, stainless steel appliances, garbage disposal and professional faucet. Both full bathrooms are redone with tile shower walls and flooring. Large master bedroom with its own private bathroom, sliding door windows and a huge walk in closet large enough to fit any size wardrobe(almost

  

  Frank Fonteyn

  Prestige Realty Group

  (860) 650-1442

  1218 Cromwell Hills Dr Unit 1218, Cromwell, CT 06416
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  /24

  $3,900 Per Month

  • 3 Beds
  • 2 Baths
  • 2,176 Sq Ft
  • House for Rent

  32 West Ave, Essex, CT 06426

  Welcome home to this beautifully rebuilt barn-style residence, where timeless character meets modern convenience. This unique 3-bedroom, 2-bath home offers a spacious and inviting layout filled with charm and architectural appeal. The interior blends rustic elegance with contemporary finishes, creating a warm and comfortable living environment. Enjoy the efficiency and reliability of natural gas

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  (860) 743-1270

  32 West Ave, Essex, CT 06426
• 

  $778,522

  Sold Jun 15, 2026

  27 Primrose Ln, Cromwell, CT 06416

  • 3 Beds
  • 2.5 Baths
  • 2,329 Sq Ft
  • Built 2026

  Last Sold Summary

  • 10% Above List Price
  • $334/SF
  • 0 Days On Market

  Last Listing Agent Daniela Volo Calcagni Real Estate

  27 Primrose Ln, Cromwell, CT 06416
• 

  Est $1,160,144

  Not Listed For Sale

  180 Plains Rd, Haddam, CT 06438

  • 4 Beds
  • 4.5 Baths
  • 3,930 Sq Ft
  • Built 2008

  180 Plains Rd, Haddam, CT 06438

  Last Sold Summary

  • 43 Days On Market
• 

  

  /14

  $850,000

  Pending

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

  26 Ferry Rd, Chester, CT 06412

  Located in the Town of Chester, this residential 2 Family property presents a rare opportunity to acquire a multifamily property in one of Connecticut's most desirable markets. The property consists of two 2-bedroom residential apartments. The improvements are situated on over 2 acres of land. Waterhouse Brook flows directly through the site, creating a tranquil backdrop, while the property

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1600

  26 Ferry Rd, Chester, CT 06412
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  Starting at $1,621

  Total Monthly Price

  • 1 - 3 Beds

  100 Town Ridge, Middletown, CT 06457

  Middletown Ridge Apartments is a pet-friendly community located in the Town Ridge neighborhood near Cromwell, CT, within close proximity to Hartford. Our community offers the perfect blend of comfort and convenience, with spacious floor plans, modern amenities, and a prime location just minutes from everything you need.Each of our one, two, and three-bedroom apartments are designed with your

  Middletown Ridge Apartments

  (475) 255-2858

  

  100 Town Ridge, Middletown, CT 06457
• 

  $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 $1,474,316

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

  55 Main St, East Haddam, CT 06423
• 

  Est $394,614

  Not Listed For Sale

  10 Brainerd Dr, Portland, CT 06480

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1956

  10 Brainerd Dr, Portland, CT 06480

  Last Sold Summary

  • 13 Days On Market
• 

  

  /37

  $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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  Starting at $2,106

  Total Monthly Price

  • 1 - 2 Beds

  150 Country Squire Dr, Cromwell, CT 06416

  Welcome Home to The Landon of Cromwell!

  The Landon of Cromwell

  (860) 846-3329

  

  150 Country Squire Dr, Cromwell, CT 06416
• 

  $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 $419,101

  Last Listing Agent Michelle Pirruccio Carl Guild & Associates

  55 Lorelei Cir, Middletown, CT 06457
• 

  Est $459,414

  Not Listed For Sale

  96 River Rd, Clinton, CT 06413

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 2001

  96 River Rd, Clinton, CT 06413

  Last Sold Summary

  • 36 Days On Market
• 

  

  /37

  $550,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,583 Sq Ft

  43 Flynn Ln, Middletown, CT 06457

  Located in the desirable Westfield section of Middletown, this well cared for home offers one of the lowest fire taxes in town and sits on a beautiful 1.25 acre lot. Lovingly owned since 2004, the Seller has raised their family here, creating a warm and inviting home ready for its next chapter. The main level features hardwood floors and a dramatic cathedral ceiling in the living room with an

  

  Linda O'Hara

  William Raveis Real Estate

  (860) 864-4128

  43 Flynn Ln, Middletown, CT 06457
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  Starting at $2,155

  Total Monthly Price

  • 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.

  Springside Middletown

  (860) 854-3267

  

  1100 Springside Ln, Middletown, CT 06457
• 

  $239,000

  Sold May 26, 2026

  280 E Main St Unit B5, Clinton, CT 06413

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $207/SF
  • 53 Days On Market

  Last Listing Agent Antonella Vertucci William Pitt Sotheby's Int'l

  280 E Main St Unit B5, Clinton, CT 06413
• 

  Est $463,958

  Not Listed For Sale

  23 Silver St, Middletown, CT 06457

  • 5 Beds
  • 2 Baths
  • 2,262 Sq Ft
  • Built 2023

  23 Silver St, Middletown, CT 06457

  Last Sold Summary

  • 45 Days On Market

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