Middlesex County, CT Homes

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  $1,150,000

  • 8 Beds
  • 6 Baths
  • 7,300 Sq Ft

  87 Main St, Deep River, CT 06417

  VC Property Group is proud to present a rare two-parcel assemblage in Deep River, Connecticut, featuring a newer construction single-family residence, a five-unit mixed-use building with four residential apartments and one retail unit, and a contiguous 0.30-acre vacant parcel. Located in the highly desirable Lower Connecticut River Valley, the property is just 0.4 miles from Downtown Deep River

  

  Anthony Velez

  VC Property Group, LLC

  87 Main St, Deep River, CT 06417
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  /8

  $1,700 Per Month

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

  238 Main St Unit B, Durham, CT 06422

  Convenient 2-bedroom, 1-bath apartment located right on Main Street in the heart of Durham. This freshly painted unit features brand-new flooring throughout and an open-concept layout that seamlessly connects the kitchen and living room-perfect for entertaining or relaxing. Enjoy the added convenience of in-unit laundry and easy access to local shops and restaurants. Ideal for anyone looking to

  

  Cory Tyler

  Berkshire Hathaway NE Prop.

  238 Main St Unit B, Durham, CT 06422
• 

  $485,000

  Sold Aug 06, 2026

  15 Mulberry Ln, Middletown, CT 06457

  • 3 Beds
  • 3 Baths
  • 1,813 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Above List Price
  • $268/SF
  • 7 Days On Market

  Current Estimated Value $481,763

  Last Listing Agent Noora Brown William Pitt Sotheby's Int'l

  15 Mulberry Ln, Middletown, CT 06457
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  Not Listed For Sale

  0 Freeman Rd, Middletown, CT 06457

  0 Freeman Rd, Middletown, CT 06457

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Barbara Puorro Puorro Realty Group
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  /18

  $649,900

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,654 Sq Ft

  15 Baxter Rd, Clinton, CT 06413

  GREAT PRICE ADJUSTMENT. LOCATION,LOCATION,LOCATION.RENOVATED RANCH STYLE HOME WITH THE LOFT. OVERSIZE DECK FACING THE BOULDER LAKE. PROPERTY WENT THROUGH RENOVATION IN 2023. OPEN CONCEPT OF LIVING .CORNER SLIDERS ARE GIVING PANORAMIC VIEW OF THE LAKE. RARE TO FIND SEPARATE SECOND HOME-MOBLE ON A PARCEL/TWO BEDROOM ,EATING KITHEN WITH BAY WINDOW/LAKE VIEW ,COULD PROVIDE ADDITIONAL LIVING SPACE OR

  

  Barbara Myslinski-Krucko

  William Raveis Real Estate

  15 Baxter Rd, Clinton, CT 06413
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  /31

  Starting at $1,793

  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

  75 Marlborough St, Portland, CT 06480
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  $400,000

  Sold Jul 27, 2026

  390 Ballfall Rd, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,092 Sq Ft
  • Built 1963

  Last Sold Summary

  • $191/SF
  • 19 Days On Market

  Current Estimated Value $402,185

  Last Listing Agent Rick Nassiff KW Legacy Partners

  390 Ballfall Rd, Middletown, CT 06457
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  Est $1,211,525

  Not Listed For Sale

  20 Navy Ln, Essex, CT 06426

  • 3 Beds
  • 2.5 Baths
  • 2,717 Sq Ft
  • Built 1976

  20 Navy Ln, Essex, CT 06426

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Susan Malan William Pitt Sotheby's Int'l
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  /40

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  39 Old Carriage Rd, Portland, CT 06480

  Welcome to this custom-built 4-bedroom, 2.5-bath Colonial, ideally situated on a beautiful corner lot! Offering timeless craftsmanship, spacious rooms, and endless potential, this well-maintained home is ready for its next chapter. Inside, you'll find hardwood floors, including all four bedrooms. The inviting front-to-back living room features a wood-burning fireplace, while the spacious family

  

  Cheryl Zalewski

  eXp Realty

  39 Old Carriage Rd, Portland, CT 06480
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  /13

  $1,700 Per Month

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

  43 Riverview Rd, Westbrook, CT 06498

  Enjoy comfortable coastal living in Westbrook, CT! This charming, spacious 3-bedroom, 1-full-bath home is situated just a short walk from Grove Beach. Features an expansive deck leading to a great yard, ideal for outdoor enjoyment. Conveniently located near local shops, dining, and commuter routes. Available for the academic year. Pets ok, rentSpree application preferred. The 3 season room will

  

  Nancy Potts

  Coldwell Banker Realty

  43 Riverview Rd, Westbrook, CT 06498
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  $430,000

  Sold Jul 30, 2026

  119 Main St, East Hampton, CT 06424

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $260/SF
  • 41 Days On Market

  Current Estimated Value $420,776

  Last Listing Agent Michelle Maldonado RE/MAX RISE

  119 Main St, East Hampton, CT 06424
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  Est $646,431

  Not Listed For Sale

  25 Kenilworth Dr, Clinton, CT 06413

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft
  • Built 1976

  25 Kenilworth Dr, Clinton, CT 06413

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Robert Teodosio William Raveis Real Estate
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  $484,900

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,892 Sq Ft

  16 Raymond Place, Cromwell, CT 06416

  A perfect home & perfect neighborhood! This move-in-ready 4 Bedroom, 2 Bath Cape offers 1,892 sq ft of living space, a 1-car garage, and amazing deck/backyard. The sun-filled Living Room features a beautiful fireplace, crown molding, recessed lighting, large picture window, and flows seamlessly into the remodeled Kitchen. The Kitchen boasts granite countertops, a peninsula w/seating for 4, and

  

  Jeff Coleman

  Hagel & Assoc. Real Estate

  16 Raymond Place, Cromwell, CT 06416
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  Starting at $1,607 Plus Fees

  • 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

  

  100 Town Brooke, Middletown, CT 06457
• 

  $530,000

  Sold Jul 31, 2026

  32 Franklin Rd, Cromwell, CT 06416

  • 3 Beds
  • 2 Baths
  • 2,014 Sq Ft
  • Built 1934

  Last Sold Summary

  • 6% Above List Price
  • $263/SF
  • 16 Days On Market

  Current Estimated Value $497,334

  Last Listing Agent Jeff Coleman Hagel & Assoc. Real Estate

  32 Franklin Rd, Cromwell, CT 06416
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  Est $367,952

  Not Listed For Sale

  8 Roberta Dr, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft
  • Built 1974

  8 Roberta Dr, Middletown, CT 06457

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Peter Nowak Ryze Realty Group LLC
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  /40

  $500,000

  • 2 Beds
  • 2.5 Baths
  • 1,503 Sq Ft

  19 Plumrose Ct, Portland, CT 06480

  Location, Location, Location! Welcome to the sought-after 55+ community of Bartlett Hill! This move-in ready Berkshire style home offers 1,503 sq. ft. of comfortable living on a quiet cul-de-sac, backing to peaceful woods for exceptional privacy. An inviting front porch, beautifully landscaped gardens, and charming curb appeal welcome you home. Inside, the open floor plan is perfect for everyday

  

  Cheryl Zalewski

  eXp Realty

  19 Plumrose Ct, Portland, CT 06480
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  /20

  $2,300 Per Month

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

  324 Main St Unit 1, Portland, CT 06480

  Modern 2-Bedroom Rental in Portland - Heat Included! Available now! This beautifully updated 2-bedroom, 1-bath unit in Portland offers style, convenience, and comfort-all for $2,300/month with heat included! Step inside to a completely renovated interior featuring brand-new flooring, fresh paint, and a sleek, modern kitchen with brand-new stainless steel appliances. The open living space is

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  324 Main St Unit 1, Portland, CT 06480
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  $460,000

  Sold Aug 05, 2026

  254 Park Rd, Haddam, CT 06438

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1940

  Last Sold Summary

  • 11% Above List Price
  • $256/SF
  • 3 Days On Market

  Current Estimated Value $412,089

  Last Listing Agent Amerra Ziyadeh William Pitt Sotheby's Int'l

  254 Park Rd, Haddam, CT 06438
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  Est $607,931

  Not Listed For Sale

  137 Main St, Chester, CT 06412

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft
  • Built 1915

  137 Main St, Chester, CT 06412

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l
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  /40

  $824,900

  $14K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,012 Sq Ft

  614 Route 81, Killingworth, CT 06419

  Sited on 6.4 private acres and set high above the road, this impressive 3,012-square-foot Colonial offers an exceptional combination of space, privacy, and functionality. A welcoming front porch, attached three car garage, beautifully landscaped grounds, flowering gardens, fruit trees, and stone walls create a picturesque setting. Designed with everyday living and entertaining in mind, the

  

  Shelly Cumpstone

  Coldwell Banker Realty

  614 Route 81, Killingworth, CT 06419
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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

  

  131 Ridgefield Dr, Middletown, CT 06457
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  $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 $442,848

  Last Listing Agent Rick Berkenstock CENTURY 21 AllPoints Realty

  45 Crestwood Dr, East Hampton, CT 06424
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  Est $1,610,063

  Not Listed For Sale

  6 Crosstrees Hill Rd, Essex, CT 06426

  • 5 Beds
  • 4.5 Baths
  • 5,071 Sq Ft
  • Built 1965

  6 Crosstrees Hill Rd, Essex, CT 06426

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Jennifer Caulfield William Pitt Sotheby's Int'l
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  /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

  25 Sheffield St Unit 3, Old Saybrook, CT 06475
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  /32

  $5,595 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,334 Sq Ft
  • House for Rent

  1 Priorwood Gardens Unit 1, Cromwell, CT 06416

  Fully furnished short term rental at the Town Homes of River Highlands (aka Cromwell's TPC). Luxurious 4 bedroom, 3 1/2 bath property. New kitchen appliances. Lovely, enclosed porch off of living room. Kitchen is open to den with double sided fireplace. Second floor includes two bedrooms, full bath, office area, and additional study area. Balcony overlooking the den and Living room. The

  

  Patricia Deperry

  Berkshire Hathaway NE Prop.

  1 Priorwood Gardens Unit 1, Cromwell, CT 06416
• 

  $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 $352,102

  Last Listing Agent Mark Reyher Reyher Real Estate

  38 Old Middletown Ave, East Hampton, CT 06424
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  Est $498,660

  Not Listed For Sale

  19 Heritage Brook Dr, East Haddam, CT 06423

  • 4 Beds
  • 2.5 Baths
  • 2,046 Sq Ft
  • Built 1998

  19 Heritage Brook Dr, East Haddam, CT 06423

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Donald Sagarino Coldwell Banker Realty
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  /18

  $249,900

  $50K 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

  1218 Cromwell Hills Dr Unit 1218, Cromwell, CT 06416
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  Starting at $1,691 Plus Fees

  • 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

  

  100 Town Ridge, Middletown, CT 06457
• 

  $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 $665,041

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  41 Day School Dr, Middlefield, CT 06455
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  Est $241,955

  Not Listed For Sale

  93 Trolley Crossing Ln, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,206 Sq Ft
  • Built 1987

  93 Trolley Crossing Ln, Middletown, CT 06457

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Euna Cho Naples Realty Group, LLC
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  /38

  $875,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,134 Sq Ft

  24 W Point Rd, East Hampton, CT 06424

  Lakefront living at its finest! This charming 3-bedroom, 1.5-bath dormered Cape/Bungalow offers the perfect blend of character, comfort, and breathtaking waterfront views. Wake up each morning to the beauty of the lake and enjoy boating, fishing, kayaking, paddleboarding, or simply relaxing along your own picturesque shoreline. The expansive waterfront yard is ideal for entertaining, complete

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  24 W Point Rd, East Hampton, CT 06424
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  /33

  $2,500 Per Month

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

  84 Waterside Ln Unit A, Clinton, CT 06413

  Welcome to a hidden gem tucked away on Waterside Lane in Clinton. This adorable PUD community offers a nostalgic, picturesque escape reminiscent of a classic 1950s beachside neighborhood. The incredible care and pride of ownership shine throughout this entire development, which boasts beautiful views of the Long Island Sound and is just steps away from Clinton Beach. 84A Waterside Lane is a

  

  Nancy Potts

  Coldwell Banker Realty

  84 Waterside Ln Unit A, Clinton, CT 06413
• 

  $250,000

  Sold Aug 07, 2026

  98 Rising Trail Dr, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,505 Sq Ft
  • Built 1976

  Last Sold Summary

  • 4% Above List Price
  • $166/SF
  • 60 Days On Market

  Current Estimated Value $236,984

  Last Listing Agent Kelley Vanacore Century 21 AllPoints Realty

  98 Rising Trail Dr, Middletown, CT 06457
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  Est $732,933

  Not Listed For Sale

  15 Westwood Rd, Ivoryton, CT 06442

  • 3 Beds
  • 2.5 Baths
  • 2,597 Sq Ft
  • Built 1994

  15 Westwood Rd, Ivoryton, CT 06442

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  /40

  $524,900

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,952 Sq Ft

  1020 Bartholomew Rd, Middletown, CT 06457

  Welcome to your own PRIVATE RETREAT! Nestled on a SECLUDED 4.5-ACRE LOT, this well-built RANCH-STYLE HOME offers the perfect blend of PRIVACY, COMFORT, and OPPORTUNITY. Enjoy TRUE ONE-LEVEL LIVING featuring 3 BEDROOMS and 2.5 BATHS, including a PRIMARY SUITE with its own FULL BATH. The layout is both FUNCTIONAL and SPACIOUS, highlighted by a LARGE FAMILY ROOM complete with a FIREPLACE, MINI SPLIT

  

  Ramon Matos

  Matos Level Eminent Realty

  1020 Bartholomew Rd, Middletown, CT 06457
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  /67

  Starting at $2,176

  Total Monthly Price

  • 1 - 2 Beds

  150 Country Squire Dr, Cromwell, CT 06416

  Welcome Home to The Landon of Cromwell!

  The Landon of Cromwell

  

  150 Country Squire Dr, Cromwell, CT 06416
• 

  $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 $1,852,032

  Last Listing Agent Dee Hasuly KW Legacy Partners

  20 Hemlock Dr, Essex, CT 06426
• 

  Est $127,538

  Not Listed For Sale

  264 Burgundy Hill Ln, Middletown, CT 06457

  • 1 Bed
  • 1 Bath
  • 729 Sq Ft
  • Built 1987

  264 Burgundy Hill Ln, Middletown, CT 06457

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Amy Rio Better Homes and Gardens Real Estate Executive Real Estate

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