Middlesex County, CT Homes

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  /37

  $499,990

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,996 Sq Ft

  82 Depot Hill Rd, East Hampton, CT 06424

  Situated on an impressive 4.04-acre lot surrounded by natural beauty, this 3-bedroom, 2-bathroom Cape offers character, and comfortable living. Step inside to a sun-filled living room featuring a cozy fireplace centerpiece. Adjacent is the dining room, which offers direct access to the kitchen for effortless entertaining. The eat-in kitchen boasts clean tile flooring, generous cabinetry storage,

  Olivia Evans KEY Real Estate Services LLC

  82 Depot Hill Rd, East Hampton, CT 06424
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  /9

  $2,150 Per Month

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

  20 Erin St Unit 1, Middletown, CT 06457

  All utilities included!! 1st floor apartment with spacious eat in kitchen, Full basement use w/ access off of kitchen with washer/dryer hookups. Backyard and off street parking!

  Jennifer Gondola Farnam Realty Group

  20 Erin St Unit 1, Middletown, CT 06457
• 

  $397,000

  Sold Jul 31, 2026

  32 Maple St, Rockfall, CT 06481

  • 3 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Built 1942

  Last Sold Summary

  • 3% Above List Price
  • $297/SF
  • 38 Days On Market

  Current Estimated Value $382,356

  Last Listing Agent Margaret Curry William Raveis Real Estate

  32 Maple St, Rockfall, CT 06481
• 

  Est $1,207,286

  Not Listed For Sale

  27 Morgan Park, Clinton, CT 06413

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft
  • Built 2005

  27 Morgan Park, Clinton, CT 06413

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Delilah Lord Carbutti & Co., Realtors
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  /37

  $559,000

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  28 Deep Hollow Rd, Chester, CT 06412

  This beautifully maintained 1890 Farm House in coveted Deep Hollow Road is a rare opportunity and has been a labor of love over the time that the sellers have lived here. This 1.04 acre property on "The Hollow" consists of a house, an oversized 24' x 24' garage/shop, antique "pony" barn with authentic outhouse and custom built service barn suited for a man cave, cigar lounge or whatever else you

  Tom Pentalow Property Shoppe, LLC

  28 Deep Hollow Rd, Chester, CT 06412
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  /13

  $1,700 Per Month

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

  7 Stephens Ct, Clinton, CT 06413

  First floor one bedroom apartment located on a private cul-de-sac. Privately set yet convenient to town, beaches, shopping and commuting routes. Bright eat-in kitchen and spacious living room. The generous bedroom features hardwood flooring, a large walk-in closet, and full bathroom. Meticulously grounds that create a peaceful place to relax and enjoy the outdoors. *Please Note - Rent is $1,700

  Craig Milton Re/Max Valley Shore

  7 Stephens Ct, Clinton, CT 06413
• 

  $280,000

  Sold Oct 08, 2025

  675 Newfield St Unit 19, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,712 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Above List Price
  • $164/SF
  • 3 Days On Market

  Current Estimated Value $294,397

  Last Listing Agent Zhe Feng Eagle Eye Realty PLLC

  675 Newfield St Unit 19, Middletown, CT 06457
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  Est $293,463

  Not Listed For Sale

  10 Stirling Ct, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft
  • Built 1971

  10 Stirling Ct, Middletown, CT 06457

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Denise Walsh William Raveis Real Estate
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  /20

  $899,000

  • 4 Beds
  • 0.5 Baths
  • 925 Sq Ft

  105 Shore Rd, Clinton, CT 06413

  Quintessential summer waterfront cottage lovingly owned by the same family for 88 years. Enjoy four bedrooms and sleeping porch option. Large Sandy beachfront. Long Island Sound views from dining room, living room, enclosed 400sf porch and upstairs bedroom. Paneling in bedrooms and hardwood floors on lower level. Also nearby access to Clinton Town Beach and Hammonasset State Park. Outlet mall and

  Louisa Ketron Berkshire Hathaway NE Prop.

  105 Shore Rd, Clinton, CT 06413
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  /13

  $1,700 Per Month

  • 2 Beds
  • 1 Bath
  • 975 Sq Ft
  • Apartment for Rent

  166 College St Unit 2, Middletown, CT 06457

  Opportunity awaits at 166 College Street Rear in the heart of Middletown's Historic District. This charming two-bedroom rental offers an unbeatable location just steps from Wesleyan University and downtown Middletown's vibrant restaurants, shops, and entertainment. Heat and hot water are included in the rent, providing added value and convenience. Off-street parking is available. Enjoy the

  Santo Gulino William Raveis Real Estate

  166 College St Unit 2, Middletown, CT 06457
• 

  $195,000

  Sold Mar 10, 2026

  301 Carriage Crossing Ln Unit 301, Middletown, CT 06457

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft
  • Built 1988

  Last Sold Summary

  • 9% Above List Price
  • $257/SF
  • 35 Days On Market

  Current Estimated Value $194,897

  Last Listing Agent Steve Jones Jr KW Legacy Partners

  301 Carriage Crossing Ln Unit 301, Middletown, CT 06457
• 

  Est $328,978

  Not Listed For Sale

  420 Tater Hill Rd, East Haddam, CT 06423

  • 2 Beds
  • 1 Bath
  • 1,224 Sq Ft
  • Built 1973

  420 Tater Hill Rd, East Haddam, CT 06423

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent James Harrington Carl Guild & Associates
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  /9

  $250,000

  • 3 Beds
  • 1.5 Baths
  • 1,326 Sq Ft

  164 Airline Ave, Portland, CT 06480

  Calling all INVESTORS and BOATERS, as well as anyone else willing to give this cozy nest some TLC! Situated walking distance to the NEW River Bend Landing, a short distance to Birdon Marina and a hop, skip and a jump to the Members-Only Meriden Motor Boat Club, all this home needs, is a vision to bring this Cape to life! Brand new furnace and all new pipes; half bathroom has started a

  Vaiva Baltonis Coldwell Banker Realty

  164 Airline Ave, Portland, CT 06480
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  /14

  $2,150 Per Month

  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  10 Summit St Unit 1, East Hampton, CT 06424

  This must see beautifully furnished New York Style Loft Apartment is in a newly renovated converted factory located in the historical village center of East Hampton. These units are pet free, smoke free with open floor plans. They boast gorgeous gourmet kitchens with granite counter tops, stainless steel appliances, ceramic tile, vaulted ceilings and ceiling fans, exposed brick walls, token

  Alyssa Gambell William Raveis Real Estate

  10 Summit St Unit 1, East Hampton, CT 06424
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  $175,000

  Sold Jun 12, 2026

  0 Cedar Swamp Rd, Deep River, CT 06417

  • Land
  • 2.41 Acres
  • $72,614 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 14 Days On Market

  Last Listing Agent Rick Allen William Raveis Real Estate

  0 Cedar Swamp Rd, Deep River, CT 06417
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  Est $545,232

  Not Listed For Sale

  22 Hickory Hill Dr, Chester, CT 06412

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft
  • Built 1985

  22 Hickory Hill Dr, Chester, CT 06412

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent John Oliveri Property Works New England
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  /38

  $2,995,000

  • 4 Beds
  • 6 Baths
  • 4,926 Sq Ft

  288 Middlesex Ave, Chester, CT 06412

  Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by

  Nancy Mesham Coldwell Banker Realty

  288 Middlesex Ave, Chester, CT 06412
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  /16

  $1,900 Per Month

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

  2306 Cromwell Hills Dr, Cromwell, CT 06416

  This is a move in ready top floor, single level 2 bedrooms with 1.5 bathrooms in a desirable neighborhood at Cromwell Hills. The large master bedroom comes with a very spacious walk-in closet and a half bathroom. The unit is freshly painted with vinyl flooring in the living room extending to the second bedroom. The living room opens to a private balcony. There is coin laundry at the common space

  Felicia Otoo Century 21 Classic Homes

  2306 Cromwell Hills Dr, Cromwell, CT 06416
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  $460,000

  Sold Dec 02, 2025

  142 Greenview Terrace, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Above List Price
  • $278/SF
  • 7 Days On Market

  Current Estimated Value $441,686

  Last Listing Agent Jay Zaleski Commercial Real Estate Group

  142 Greenview Terrace, Middletown, CT 06457
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  Est $438,489

  Not Listed For Sale

  24 Main St, East Hampton, CT 06424

  • 3 Beds
  • 2.5 Baths
  • 1,774 Sq Ft
  • Built 1890

  24 Main St, East Hampton, CT 06424

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Amy Rio Better Homes and Gardens Real Estate Executive Real Estate
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  /9

  $879,000

  New Construction Pending

  • 4 Beds
  • 2.5 Baths
  • 3,311 Sq Ft

  2 Stone Bridge Dr Unit Lot 2, Durham, CT 06422

  Welcome to 48 Stonebridge Drive! Construction is underway on this 3,311 sq ft Farmhouse Colonial that offers the perfect blend of classic charm with modern elements. The home's exterior impresses with its inviting front porch and sought after design features such as the black exterior windows and mix of vinyl styles. This home offers not only exceptional curb appeal but also everyday

  Dori Degennaro William Raveis Real Estate

  2 Stone Bridge Dr Unit Lot 2, Durham, CT 06422
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  /13

  $1,995 Per Month

  • 2 Beds
  • 1 Bath
  • 6,573 Sq Ft
  • Apartment for Rent

  170 Pearl St Unit B, Middletown, CT 06457

  Newly renovated first-floor apartment offering two bedrooms, one full bathroom and a modern open-concept layout. The updated kitchen connects seamlessly with the main living space, and a private in-unit washer and dryer provides added convenience. Ideally located near downtown Middletown, Wesleyan University, Middlesex Health, local dining and shopping, with easy access to Route 9. On-street

  Michelle Mandel Carl Guild & Associates

  170 Pearl St Unit B, Middletown, CT 06457
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  $692,609

  Sold Nov 07, 2025

  37 Primrose Ln, Cromwell, CT 06416

  • 3 Beds
  • 2.5 Baths
  • 2,246 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Above List Price
  • $308/SF
  • 1 Day On Market

  Last Listing Agent Daniela Volo Calcagni Real Estate

  37 Primrose Ln, Cromwell, CT 06416
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  Est $378,653

  Not Listed For Sale

  25 Arnold St, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1964

  25 Arnold St, Middletown, CT 06457

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Carl Guild Carl Guild & Associates
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  /3

  $619,900

  New Construction Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,151 Sq Ft

  3 Freya Ln, East Hampton, CT 06424

  Lake Overlook Estates en enclave of 12 homesites with stunning seasonal views of Lake Pocotopaug. This beautiful Cape offers it all. You will enjoy the classic historic Cape look on the exterior, framed by a brick center chimney. The inside is wow! You walk into an oversized entry boasting an open staircase offering vaulted ceilings in entry and 2 story front/flex room. You will make your way to

  Mark Toledo Berkshire Hathaway NE Prop.

  3 Freya Ln, East Hampton, CT 06424
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  /29

  $2,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft
  • House for Rent

  151 Chapman Beach Rd, Westbrook, CT 06498

  THIS IS AN ACADEMIC LEASE, NOT AN ANNUAL LEASE! Live by the water & walk to your private beach! This Furnished home is located in the Chapman Beach Association. Available from September 8, 2026 to May 29, 2027. A Charming 3 bedroom furnished home. The Primary bedroom has a queen size bed & the other 2 bedrooms have full size beds. The primary bedroom has a sitting area with water views. The first

  Susan Clifford Coldwell Banker Realty

  151 Chapman Beach Rd, Westbrook, CT 06498
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  $520,000

  Sold Jan 30, 2026

  120 Scenic View Dr, Middletown, CT 06457

  • 4 Beds
  • 3.5 Baths
  • 3,833 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $136/SF
  • 146 Days On Market

  Current Estimated Value $564,525

  Last Listing Agent Meghan Hess Real Broker CT, LLC

  120 Scenic View Dr, Middletown, CT 06457
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  Est $581,684

  Not Listed For Sale

  7 Windsor Oval, Old Saybrook, CT 06475

  • 3 Beds
  • 1 Bath
  • 1,856 Sq Ft
  • Built 1961

  7 Windsor Oval, Old Saybrook, CT 06475

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Joel Lucas Coldwell Banker Realty
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  /26

  $610,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 3,168 Sq Ft

  22 Hill Top Dr, Durham, CT 06422

  Welcome to a home where there's room to spread out, gather together, and create lasting memories. Tucked away on a picturesque cul-de-sac just minutes from town, this spacious 4-bedroom Cape offers the perfect blend of charm, comfort, and flexibility. Thoughtfully designed for everyday living, the first floor features an inviting family room with exposed wood beam ceilings and a brick fireplace,

  Debbie Huscher Real Broker CT, LLC

  22 Hill Top Dr, Durham, CT 06422
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  /14

  $3,300 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft
  • House for Rent

  29 Kelsey Rd, Clinton, CT 06413

  Direct Waterfront in desirable Harbor View Association with your own private dock! Amazing unobstructed sunset views in this 3 bedroom Ranch style home with 2 car garage. Steps to the Private Association Beaches and Clinton Town Beach! Set on a double lot that goes to the water, leading to your own private dock where you can fish, crab, kayak, or boat ride out to the open water of Long Island

  Pam Kadamus William Pitt Sotheby's Int'l

  29 Kelsey Rd, Clinton, CT 06413
• 

  $707,500

  Sold Dec 19, 2025

  355 Main St, Old Saybrook, CT 06475

  • 3 Beds
  • 1.5 Baths
  • 2,194 Sq Ft
  • Built 1919

  Last Sold Summary

  • 6% Below List Price
  • $322/SF
  • 187 Days On Market

  Current Estimated Value $777,862

  Last Listing Agent Paula Stuart Berkshire Hathaway NE Prop.

  355 Main St, Old Saybrook, CT 06475
• 

  Est $331,106

  Not Listed For Sale

  10 Walnut St, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 2,657 Sq Ft
  • Built 1916

  10 Walnut St, Middletown, CT 06457

  Last Sold Summary

  • 159 Days On Market

  Last Listing Agent David Tigner Radiant New Horizon Homes, LLC
• 

  

  /19

  $289,900

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,196 Sq Ft

  1 Canterbury Ct Unit 2, Middletown, CT 06457

  Rare Laurel Ridge Opportunity! This beautifully updated, and move in condition unit is located in a small quiet complex in the Wesleyan Hills section of town. No work to do Just enjoy your space featuring a modern style updated kitchen with dark wood cabinetry, granite counters and stainless appliances. Sit back and relax in the living room with French door access to your private deck with views

  Mark Massaro Coldwell Banker Realty

  1 Canterbury Ct Unit 2, Middletown, CT 06457
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  /12

  $1,900 Per Month

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

  70 Pond Meadow Rd Unit 24125470, Ivoryton, CT 06442

  Freshly Painted 2 bedrooms/1 bathroom unit located in a quite complex Tenant responsible for electric/Internet Landlord is responsible for landscaping/snow/water good credit, no pets, and no smoking 1 year lease, 2 months Security deposit and first month rent due at lease signing

  Amru Abo-Alaial RE/MAX One

  70 Pond Meadow Rd Unit 24125470, Ivoryton, CT 06442
• 

  $616,000

  Sold Jul 14, 2026

  16 Sypher Rd, Chester, CT 06412

  • 2 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Above List Price
  • $357/SF
  • 42 Days On Market

  Current Estimated Value $602,323

  Last Listing Agent Peg Mitchel Coldwell Banker Realty

  16 Sypher Rd, Chester, CT 06412
• 

  Est $418,929

  Not Listed For Sale

  15 Blue Grass Dr, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,872 Sq Ft
  • Built 1972

  15 Blue Grass Dr, Middletown, CT 06457

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Steve Jones Jr KW Legacy Partners
• 

  

  /40

  $550,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 3,188 Sq Ft

  15 Payne Blvd, Portland, CT 06480

  Set on a beautifully landscaped .57-acre lot, 15 Payne Boulevard is a distinctive 3-bedroom Colonial offering possible 4th-bedroom flexibility and finished space across four levels. Hardwood floors lead through the main level, where a wood-burning fireplace anchors the living room and the formal dining room, eat-in kitchen, renovated half bath, first-floor laundry, and private office create a

  Mustafa Muaremi Coldwell Banker Realty

  15 Payne Blvd, Portland, CT 06480
• 

  

  /20

  $2,300 Per Month

  • 1 Bed
  • 1.5 Baths
  • 800 Sq Ft
  • Apartment for Rent

  100 W Main St Unit B, Chester, CT 06412

  Available 9/1/26! Taking applications now. Something special is happening at 100 W Main. This brand-new residence brings together thoughtful design, beautiful finishes, and the ease of modern living, all just minutes from the heart of Chester Village. **Unit B** has a style all its own. The bright, open living space centers around a beautifully finished kitchen with quartz countertops, a generous

  Aschly Daggett VC Property Group, LLC

  100 W Main St Unit B, Chester, CT 06412
• 

  $845,558

  Sold Dec 23, 2025

  6 Highland Terrace, East Hampton, CT 06424

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft
  • Built 2025

  Last Sold Summary

  • 43% Above List Price
  • $321/SF
  • 6 Days On Market

  Last Listing Agent Mark Toledo Berkshire Hathaway NE Prop.

  6 Highland Terrace, East Hampton, CT 06424
• 

  Est $451,500

  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

  Last Listing Agent Yvonne Bailey I'Lann Realty, LLC

Showing Results 641 - 680, Page 17 of 18