Middlesex County, CT Homes

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  $675,000

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  60 Watch Hill Dr, Middletown, CT 06457

  Welcome to the peaceful and charming Watch Hill Estates community, where elevated living meets timeless elegance. Perched high atop a scenic hill, this stunning Colonial offers sweeping panoramic views stretching across Middletown and Durham, creating a truly breathtaking everyday backdrop. Meticulously maintained and completely turnkey, this exceptional residence blends refined comfort with

  Stephanie Liriano Redfin Corporation

  60 Watch Hill Dr, Middletown, CT 06457
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  /15

  $1,900

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  67 W Main St, Clinton, CT 06413

  Beautiful apartment available July1st.. Hardwood floors, stainless appliances, granite countertops. Great location close to I-95, Hammonassett State Park and the Clinton beaches. This apartment is located on the 2nd level. No pets, no smoking allowed. Credit check, two months security required.

  67 W Main St, Clinton, CT 06413
• 

  $426,000

  Sold Aug 26, 2025

  18 Beach Park Rd, Clinton, CT 06413

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $296/SF
  • 30 Days On Market

  Current Estimated Value $466,117

  Last Listing Agent Gary Damato Press/Cuozzo Realtors

  18 Beach Park Rd, Clinton, CT 06413
• 

  Est $600,762

  Not Listed For Sale

  29 Stephanie Ct, Durham, CT 06422

  • 4 Beds
  • 2.5 Baths
  • 2,446 Sq Ft
  • Built 1997

  29 Stephanie Ct, Durham, CT 06422

  Last Sold Summary

  • 6 Days On Market
• 

  

  

  /26

  $549,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,321 Sq Ft

  121 Bartholomew Rd, Middletown, CT 06457

  Amazing home! This beautiful abode sits on a 1.23 acre Currier & Ives setting. One will be impressed with the gorgeous landscaping, gardens and wooded, private setting. The oversized deck and fenced-in yard is the icing on the cake. The architectural detailing on the exterior offers brick facade, gables and sloped roof lines that sets the stage for the amazing interior of this home. One will walk

  Mark Toledo Berkshire Hathaway NE Prop.

  121 Bartholomew Rd, Middletown, CT 06457
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  /8

  $1,395 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  460 Main St Unit 11, Middletown, CT 06457

  Available for $1,395 per month, this beautifully updated end-unit apartment offers 1 bedroom and 1 full bathroom with a blend of charm and modern finishes. The unit features stunning quartzite countertops, a decorative fireplace, and washer hookups for added convenience. Heat and water are included in the rent; tenant is responsible for electricity. Enjoy the privacy of an end unit while being

  Santo Gulino William Raveis Real Estate

  460 Main St Unit 11, Middletown, CT 06457
• 

  $505,000

  Sold May 22, 2026

  58 Morning Glory Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,360 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Above List Price
  • $214/SF
  • 8 Days On Market

  Current Estimated Value $487,417

  Last Listing Agent Mark Toledo Berkshire Hathaway NE Prop.

  58 Morning Glory Dr, Middletown, CT 06457
• 

  Est $617,404

  Not Listed For Sale

  37 Menunketesuck Rd, Westbrook, CT 06498

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1930

  37 Menunketesuck Rd, Westbrook, CT 06498

  Last Sold Summary

  • 33 Days On Market
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  /28

  $359,000

  Pending

  • 2 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  18 Augusta Cir, Moodus, CT 06469

  Welcome to resort living at Banner Country Club Estates! With an in-ground pool, tennis / pickleball courts, an on-site restaurant, & scenic walking trails, every day feels like a vacation. Seamlessly integrated into the sprawling grounds, 18 Augusta is an architecturally striking townhouse with a unique floorplan that blends sophisticated form with everyday function. Offering the option of

  Tommy Connors Redfin Corporation

  18 Augusta Cir, Moodus, CT 06469
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  /8

  $1,350

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft
  • House for Rent

  157 Main St, Deep River, CT 06417

  Just renovated one-bedroom apartment located in the center of the quaint village of Deep River; brand new galley kitchen; living room, full bath and bedroom with spacious closets; new flooring and paint throughout; tenant pays heat/electric; walk to shops, restaurants, and laundromat; off-street parking; easy access to route 9, route 95, shoreline points and Middletown area; no dogs allowed; no

  157 Main St, Deep River, CT 06417
• 

  $200,000

  Sold Jun 02, 2026

  1101 Cromwell Hills Dr Unit 1101, Cromwell, CT 06416

  • 2 Beds
  • 1.5 Baths
  • 1,057 Sq Ft
  • Built 1973

  Last Sold Summary

  • 10% Above List Price
  • $189/SF
  • 4 Days On Market

  Current Estimated Value $178,575

  Last Listing Agent Joe Fazzino eXp Realty

  1101 Cromwell Hills Dr Unit 1101, Cromwell, CT 06416
• 

  Est $577,996

  Not Listed For Sale

  107 Chestnut Hill Rd, Portland, CT 06480

  • 2 Beds
  • 2.5 Baths
  • 1,985 Sq Ft
  • Built 2004

  107 Chestnut Hill Rd, Portland, CT 06480

  Last Sold Summary

  • 29 Days On Market
• 

  

  /31

  $479,900

  $20K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  24 Meadowood Dr, Middletown, CT 06457

  WOW! Do not miss out on this spectacular 4 bedroom home located in the Westfield section of Middletown. This beautiful abode sits on a gorgeous level landscaped lot on a quiet cul-de-sac street. The exterior boasts a front porch with brick front accent, a manicured picturesque yard with double patios, large deck, above ground pool and beautiful plantings and flowers. Amazing space to enjoy

  Mark Toledo Berkshire Hathaway NE Prop.

  24 Meadowood Dr, Middletown, CT 06457
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  /4

  $1,300 Per Month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  1500 Boston Post Rd Unit 10, Old Saybrook, CT 06475

  Studio unit includes heat, hot water, electricity, cable, and internet. Recently remodeled. Clean and freshly painted. Private bath. Parking available. Conveniently located. Walking distance to beach.

  Brian Botti Botti Realty

  1500 Boston Post Rd Unit 10, Old Saybrook, CT 06475
• 

  $330,000

  Sold May 22, 2026

  207 Pearl St, Middletown, CT 06457

  • 6 Beds
  • 2 Baths
  • 1,818 Sq Ft
  • Built 1900

  Last Sold Summary

  • $182/SF
  • 96 Days On Market

  Current Estimated Value $324,445

  Last Listing Agent Wendi Zuk Homes Plus of Connecticut

  207 Pearl St, Middletown, CT 06457
• 

  Est $464,219

  Not Listed For Sale

  95 Maple Rd, Portland, CT 06480

  • 4 Beds
  • 1.5 Baths
  • 2,448 Sq Ft
  • Built 1976

  95 Maple Rd, Portland, CT 06480

  Last Sold Summary

  • 26 Days On Market
• 

  

  /40

  $429,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  217 Middle Haddam Rd, East Hampton, CT 06480

  Welcome to your private New England retreat in the heart of Middle Haddam. Nestled along a scenic country road and just moments from the 1,000 acres of trails, river views, and natural beauty of Hurd State Park, this impeccably maintained 3-bedroom, 2.5-bath Colonial offers the perfect blend of peaceful surroundings and modern comfort. Pride of ownership shines throughout this move-in ready home,

  Dean Long III William Raveis Real Estate

  217 Middle Haddam Rd, East Hampton, CT 06480
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  /15

  $2,227

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  200 Main St Unit 1, Portland, CT 06480

  200 Main St Unit 1, Portland, CT 06480
• 

  $295,000

  Sold Jul 15, 2025

  153 Ballfall Rd, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft
  • Built 1944

  Last Sold Summary

  • 2% Below List Price
  • $329/SF
  • 17 Days On Market

  Current Estimated Value $301,187

  Last Listing Agent Joshua Brown KW Legacy Partners

  153 Ballfall Rd, Middletown, CT 06457
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  Est $534,170

  Not Listed For Sale

  32 Great Hill Pond Rd, Portland, CT 06480

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft
  • Built 1989

  32 Great Hill Pond Rd, Portland, CT 06480

  Last Sold Summary

  • 48 Days On Market
• 

  

  /31

  $2,850,000

  Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,900 Sq Ft

  99 Shore Rd, Clinton, CT 06413

  Experience beachfront living at its finest in this exquisitely designed coastal oasis offering over 2,900 square feet of refined luxury. Thoughtfully crafted to maximize breathtaking ocean views, this stunning residence seamlessly blends elegant design with relaxed waterfront living. The gourmet kitchen is a chef's dream, featuring premium Bertazzoni appliances, granite countertops, and a

  Lori Valimont Berkshire Hathaway NE Prop.

  99 Shore Rd, Clinton, CT 06413
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  /15

  $1,282 Per Month

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

  31 Warwick St Unit 33, Middletown, CT 06457

  Charming 1-bedroom, 1-bath rear apartment featuring a spacious living area, abundant natural light, full-size appliances, and ample storage. Tucked away at the back of the property, this cozy home offers a quiet setting with a versatile layout and comfortable living spaces.

  Michael Bernard Ironclad Real Estate

  31 Warwick St Unit 33, Middletown, CT 06457
• 

  $1,150,000

  Sold Mar 16, 2026

  121R Stage Coach Rd, Durham, CT 06422

  • 4 Beds
  • 3.5 Baths
  • 6,979 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $165/SF
  • 122 Days On Market

  Current Estimated Value $1,260,988

  Last Listing Agent Mark McElrath William Pitt Sotheby's Int'l

  121R Stage Coach Rd, Durham, CT 06422
• 

  Est $369,824

  Not Listed For Sale

  21 Tuccitto Rd, Portland, CT 06480

  • 4 Beds
  • 1.5 Baths
  • 1,593 Sq Ft
  • Built 1953

  21 Tuccitto Rd, Portland, CT 06480

  Last Sold Summary

  • 42 Days On Market
• 

  

  /40

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 4,132 Sq Ft

  46 Tavern Cir, Middletown, CT 06457

  Fantastic home located in Westfield Hills community with plenty of space to roam. This 3/4 bedroom home offers it all. The first floor boasts a large open kitchen with good size eating area, formal dining room, front to back great room and first floor family room with fireplace. All of this leading out to a stunning landscaped yard for enjoying those summer outings or just a relaxing Zen moment.

  Mark Toledo Berkshire Hathaway NE Prop.

  46 Tavern Cir, Middletown, CT 06457
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  /15

  $1,600

  Total Monthly Price

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

  31 Burr Ave Unit 1st Floor, Middletown, CT 06457

  31 Burr Ave Unit 1st Floor, Middletown, CT 06457
• 

  $499,275

  Sold Nov 07, 2025

  15 Chatham Fields Rd, East Hampton, CT 06424

  • 4 Beds
  • 2.5 Baths
  • 2,328 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Above List Price
  • $214/SF
  • 41 Days On Market

  Current Estimated Value $525,974

  Last Listing Agent Laurie Murray KW Legacy Partners

  15 Chatham Fields Rd, East Hampton, CT 06424
• 

  Est $609,182

  Not Listed For Sale

  69 Essex Rd, Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1957

  69 Essex Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 44 Days On Market
• 

  

  /40

  $599,900

  $40K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,989 Sq Ft

  159 Bear Swamp Rd, East Hampton, CT 06424

  Welcome to 159 Bear Swamp Road, a truly one-of-a-kind country contemporary set on 2.73 private, wooded acres. Set well back from the road and surrounded by nature, this property offers a rare sense of seclusion and tranquility while still close to town! Offering over 3,000 square feet of living space, the home features 4 beds, 3 full baths, and a flexible floor plan that could easily accommodate

  Carl Guild Carl Guild & Associates

  159 Bear Swamp Rd, East Hampton, CT 06424
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  /19

  $2,400 Per Month

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

  38 Seabreeze Rd, Old Saybrook, CT 06475

  This spectacular home with a fantastic location is an Academic Rental; from September 15, 2026 through May 15, 2027. Living in this Old Saybrook home is comfortable, near the beach and close to town with shopping and dining. Only a few steps to Cornfield Point, walk the quiet neighborhood and enjoy the gorgeous sunsets. This home is a perfect place of peaceful, tranquil days and evenings, with

  Terry McDonald McDonald Real Estate, LLC

  38 Seabreeze Rd, Old Saybrook, CT 06475
• 

  $305,000

  Sold Dec 12, 2025

  37 Front St, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,384 Sq Ft
  • Built 1924

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 5 Days On Market

  Current Estimated Value $317,751

  Last Listing Agent Brenda Hanley Berkshire Hathaway NE Prop.

  37 Front St, Middletown, CT 06457
• 

  Est $6,405,664

  Not Listed For Sale

  91 N Cove Rd, Old Saybrook, CT 06475

  • 6 Beds
  • 8 Baths
  • 5,592 Sq Ft
  • Built 1732

  91 N Cove Rd, Old Saybrook, CT 06475

  Last Sold Summary

  • 4 Days On Market
• 

  

  /40

  $699,000

  • 3 Beds
  • 4 Baths
  • 2,859 Sq Ft

  235 Middle Haddam Rd, Portland, CT 06480

  Surrounded on three sides by the 90-acre Palmer-Taylor Preserve, this one-of-a-kind home offers an extraordinary combination of history, privacy, and natural beauty. Originally built in 1979 and thoughtfully expanded over the years, the residence incorporates an early 20th-century guesthouse once associated with the Taylor family of nearby St. Clements Castle, creating a home unlike any other.

  Carl Guild Carl Guild & Associates

  235 Middle Haddam Rd, Portland, CT 06480
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  /11

  $2,295

  Total Monthly Price

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

  27 N Main St, Essex, CT 06442

  Two bedroom townhouse apartment with garage storage; new flooring; new stainless appliances with granite countertops; eat-in kitchen with slider to private deck; 1.5 baths; washer/dryer hookups; located in park like setting in beautiful New England village of Ivoryton, with easy access to I-95 and Route 9; pet ok with approval; $30 for application fee includes credit score, proof of income,

  27 N Main St, Essex, CT 06442
• 

  $176,000

  Sold Oct 29, 2025

  6 Country Club Trail, Killingworth, CT 06419

  • 2 Beds
  • 2 Baths
  • 1,045 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Above List Price
  • $168/SF
  • 10 Days On Market

  Last Listing Agent Shelly Cumpstone Coldwell Banker Realty

  6 Country Club Trail, Killingworth, CT 06419
• 

  Est $702,060

  Not Listed For Sale

  100 Sheffield St Unit D4, Old Saybrook, CT 06475

  • 2 Beds
  • 2.5 Baths
  • 2,002 Sq Ft
  • Built 1976

  100 Sheffield St Unit D4, Old Saybrook, CT 06475

  Last Sold Summary

  • 62 Days On Market
• 

  

  /40

  $825,000

  • 6 Beds
  • 3 Baths
  • 4,184 Sq Ft

  163 Main St, Deep River, CT 06417

  Rare mixed-use investment opportunity located in the heart of desirable Deep River Village. Positioned directly on Main Street, this 5-unit asset offers a strong blend of residential and commercial income within one of the Connecticut shoreline region's most sought-after rental and retail markets. The property consists of 3 residential apartments and 2 commercial storefronts occupied by long-term

  Connor Wenchell VC Property Group, LLC

  163 Main St, Deep River, CT 06417
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  /8

  $1,350 Per Month

  • 1 Bed
  • 1 Bath
  • 563 Sq Ft
  • Apartment for Rent

  135 Burgundy Hill Ln Unit 135, Middletown, CT 06457

  Nice condo in a quiet location.

  Barbara Peloquin G & W Real Estate

  135 Burgundy Hill Ln Unit 135, Middletown, CT 06457
• 

  $585,000

  Sold Nov 18, 2025

  23 Falmouth Ct, Middletown, CT 06457

  • 5 Beds
  • 2.5 Baths
  • 2,760 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $212/SF
  • 74 Days On Market

  Current Estimated Value $622,265

  Last Listing Agent Kristin Callahan eXp Realty

  23 Falmouth Ct, Middletown, CT 06457
• 

  Est $881,031

  Not Listed For Sale

  17 Cricket Ct, Old Saybrook, CT 06475

  • 3 Beds
  • 2.5 Baths
  • 1,761 Sq Ft
  • Built 1976

  17 Cricket Ct, Old Saybrook, CT 06475

  Last Sold Summary

  • 2 Days On Market

Showing Results 241 - 280, Page 7 of 18