Middlesex, CT Homes

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  /40

  $949,000

  • 4 Beds
  • 2 Baths
  • 2,249 Sq Ft

  86 Chalker Beach Rd, Old Saybrook, CT 06475

  Welcome to Year-Round Beach Living with Room to Spare! Welcome to 86 Chalker Beach Rd. Do you desire a year-round beach home with plenty of space? Look no further! Welcome to 86 Chalker Beach Rd-your gateway to coastal living in one of Old Saybrook's most vibrant beach communities. With nearly 2,300 square feet of living space, this rare find offers four spacious bedrooms and two full bathrooms,

  

  Jodi Serapilia

  William Raveis Real Estate

  (860) 809-5460

  86 Chalker Beach Rd, Old Saybrook, CT 06475
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• 

  

  

  /40

  $3,200 per month

  • 3 Beds
  • 1.5 Baths
  • 1,784 Sq Ft
  • House for Rent

  50 Longwood Dr, Colchester, CT 06415

  Nestled in a peaceful wooded setting within the Lake Hayward community, this modern home offers the perfect escape with plenty of space to unwind. Located just a half-hour drive from Mohegan Sun and Mystic Seaport, the property is less than a mile from the lake, where you'll find three beautiful lakefront beaches, swimming areas, tennis and basketball courts, and a playground. Whether you're

  

  Joyce Covone

  Berkshire Hathaway NE Prop.

  (860) 697-9887

  50 Longwood Dr, Colchester, CT 06415
• 

  $1,230,000 Sold Jun 17, 2025

  • 2,557 Sq Ft
  • $481/SF
  • 0 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1966

  5 Cromwell Ct, Old Saybrook, CT 06475

  Welcome to the relaxed coastal lifestyle you've been dreaming of. Nestled in the prestigious North Cove community, this charming Cape Cod-style home offers comfort, space, and the perfect setting for a peaceful, yet active, life by the water. Built in 1966 and lovingly maintained this 2,600 square foot home is set on a beautifully landscaped .48-acre lot at the end of a quiet cul-de-sac, just a

  Joel Lucas Coldwell Banker Realty

  5 Cromwell Ct, Old Saybrook, CT 06475
• 

  Est $524,792 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  25 Deep Hollow Rd, Chester, CT 06412

  25 Deep Hollow Rd, Chester, CT 06412
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  /33

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft

  95 Training Hill Rd, Middletown, CT 06457

  Welcome to 95 Training Hill Road - Where Comfort Meets Convenience in Middletown! Discover this beautifully updated ranch-style gem in one of Middletown's most desirable areas. Featuring 4 spacious bedrooms and 2 full bathrooms, this home is perfect for anyone seeking style, space, and functionality. Step inside to an inviting open floor plan that flows effortlessly from room to room - ideal

  

  Guillermo Araujo

  Five Stars Realty

  (860) 935-6055

  95 Training Hill Rd, Middletown, CT 06457
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  /20

  $2,600 per month

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

  2 Porges Rd, East Haddam, CT 06423

  Newly renovated 1-bedroom, 1-bath apartment with air conditioning and all utilities-including internet-fully included. This bright, single-level unit features large glass doors that fill the space with natural light, no stairs, and a private backyard perfect for relaxing or entertaining. Conveniently located just up the road from the Goodspeed Opera House, the Gelston House, and Route 9, this

  

  Cory Tyler

  Berkshire Hathaway NE Prop.

  (860) 772-0481

  2 Porges Rd, East Haddam, CT 06423
• 

  $429,000 Sold Jun 16, 2025

  • 1,334 Sq Ft
  • $322/SF
  • 31 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1953

  15 Melody Ln, Ivoryton, CT 06442

  Discover the charm of easy living in this comfortable ranch-style home, perfectly situated in a quiet neighborhood yet just minutes from Essex village and major commuting routes. With two bedrooms plus an office that could easily serve as a third bedroom, this home is ideal for those downsizing or purchasing for the first time. Enjoy cooking in the beautifully updated kitchen with new appliances,

  Joel Lucas Coldwell Banker Realty

  15 Melody Ln, Ivoryton, CT 06442
• 

  Est $422,511 Not Listed For Sale

  • 6 Beds
  • 2 Baths
  • 2,314 Sq Ft

  77 S Front St, Middletown, CT 06457

  77 S Front St, Middletown, CT 06457
• 

  

  /38

  $419,900

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  106 Lorraine Terrace, Middletown, CT 06457

  COMPLETELY RENOVATED WOODLAND OASIS IN SOUGHT-AFTER WESTFIELD! This stunning split-level home sits on a private 0.47-acre lot blending modern luxury with natural charm. Freshly painted inside and out with new architectural roof and high-efficiency central AC. The showstopping kitchen features white-shaker cabinetry, granite countertops, stainless appliances, and herringbone blue tile backsplash.

  

  Romanee Ives

  Cornerstone Homes Plus, Inc.

  (860) 750-9769

  106 Lorraine Terrace, Middletown, CT 06457
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  /32

  $2,450 per month

  • 4 Beds
  • 1.5 Baths
  • 1,699 Sq Ft
  • House for Rent

  375 Main St, Deep River, CT 06417

  Charming 1950s Cape in the Heart of Deep River, CT Welcome to this delightful and well-maintained single-family Cape, ideally located in the scenic town of Deep River. This 4-bedroom, 1.5-bath rental blends classic charm with modern updates for comfortable everyday living. The inviting eat-in kitchen features timeless cabinetry, granite countertops, and room for casual dining. The spacious living

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 492-6271

  375 Main St, Deep River, CT 06417
• 

  $480,000 Sold Jun 16, 2025

  • 1,964 Sq Ft
  • $244/SF
  • 96 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1900

  24 Burr Ave, Middletown, CT 06457

  Welcome to this Beautifully Renovated 3 Family Home. Nestled in the heart of Middletown. This property is perfect for investors or Owner-Occupant. Looking for a turnkey property look no further! Conveniently situated near downtown Middletown, Middlesex Hospital and Wesleyan University.This property offers, easy access to shopping, dining, and entertainment.Newer siding and windows in 2010,Roof

  Shari Jones Coldwell Banker Realty

  24 Burr Ave, Middletown, CT 06457
• 

  Est $231,009 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,975 Sq Ft

  12 Pine Ct Unit 12, Cromwell, CT 06416

  12 Pine Ct Unit 12, Cromwell, CT 06416
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  /33

  $575,000

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  5 Aladdin Ave, Old Saybrook, CT 06475

  GET YOUR SPOT AT THE BEACH! The perfect getaway, just a short walk from the Chalker Beach Sandy Shoreline. Ready for love, sun, swim, and enjoying all the fun-with no traffic and plenty of relaxation right outside this home. A spacious deck overlooks a beautiful backyard, ideal for entertaining family and friends. Rinse off the day in the outdoor shower. Chalker Beach offers an abundance of

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 590-4441

  5 Aladdin Ave, Old Saybrook, CT 06475
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  /7

  $1,650 per month

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

  238 Main St, 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.

  (860) 854-2685

  238 Main St, Durham, CT 06422
• 

  $415,000 Sold Jun 16, 2025

  • 1,754 Sq Ft
  • $237/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1954

  33 Waverly Ave, Portland, CT 06480

  Every now and then, you walk into a home and everything just feels... right. There's a calm, a sense of ease, and an immediate invitation to imagine life here. This updated Cape brings that feeling to life-with hardwood floors throughout, thoughtful updates, and a layout that simply works. The kitchen is both stylish and functional, featuring dark gray cabinetry, Calacatta quartz counters, a

  Debbie Huscher Real Broker CT, LLC

  33 Waverly Ave, Portland, CT 06480
• 

  Est $277,959 Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 1,284 Sq Ft

  200 Skyview Dr Unit 200, Cromwell, CT 06416

  200 Skyview Dr Unit 200, Cromwell, CT 06416
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  /40

  $699,900 Pending

  • 2 Beds
  • 2.5 Baths
  • 3,750 Sq Ft

  74 High St, Portland, CT 06480

  Tucked away in nature yet minutes from downtown Portland, this stunning McGinley custom home offers over 3,750 sq ft of luxury living - with public utilities! Step into the grand foyer and fall in love with the open layout, soaring ceilings, sun-filled windows, and an oversized fireplace that anchors the space beautifully. The chef's kitchen boasts granite counters, an 8-foot island, double

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 413-1586

  74 High St, Portland, CT 06480
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  /32

  $3,500 per month

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Apartment for Rent

  725 Boston Post Rd, Old Saybrook, CT 06475

  Updated 4-Bedroom, 2-Bathroom Year-Round Rental in the Heart of Old Saybrook Enjoy the convenience of living just steps from downtown Old Saybrook, with easy access to restaurants, shops, and stunning beaches. This beautifully updated home features a newly renovated kitchen with an open-concept design, Corian countertops, stainless steel appliances, and a spacious island with additional seating.

  

  Nancy Potts

  Coldwell Banker Realty

  (860) 905-0075

  725 Boston Post Rd, Old Saybrook, CT 06475
• 

  $515,000 Sold Jun 16, 2025

  • 743 Sq Ft
  • $693/SF
  • 59 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1954

  28 Hammock Pkwy, Clinton, CT 06413

  Sought-After Harborview Cottage - Your Beachside Retreat Awaits! Escape to a serene and charming year-round cottage in the coveted Harborview neighborhood, a quiet, beachside oasis with stunning coastal views. Perfectly situated on a double lot with beach views from front and tranquil marsh vistas from the back. Enjoy the fresh air with a front courtyard porch and a back deck-ideal spots to relax

  Lynn Lehrman Re/Max Valley Shore

  28 Hammock Pkwy, Clinton, CT 06413
• 

  Not Listed For Sale

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

  161 E Main St Unit 102, Clinton, CT 06413

  161 E Main St Unit 102, Clinton, CT 06413
• 

  

  /27

  $299,000 Open Sat 1PM - 2:30PM

  • 3 Beds
  • 1.5 Baths
  • 1,314 Sq Ft

  240 Barbara Rd, Middletown, CT 06457

  Welcome to this charming Cape Cod-style gem! Built in 1947, this 3-bedroom, 1.5-bathroom home offers classic character and timeless appeal across 1,314 square feet of living space. The main level features a sun-filled living room with hardwood floors and a cozy fireplace, a traditional dining area, and a well-appointed kitchen with new flooring and updated appliances-including a new refrigerator,

  

  Stephanie Rush

  RE/MAX Legends

  (860) 962-7332

  240 Barbara Rd, Middletown, CT 06457
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  /31

  $3,500 per month

  • 3 Beds
  • 2 Baths
  • 2,402 Sq Ft
  • House for Rent

  40 Crestwood Dr, East Hampton, CT 06424

  Available August 1, 2025. Beautifully Updated Raised Ranch for Rent. This Furnished 3-bedroom, 2-bath raised ranch offers over 2,400 sq ft of living space on a serene, level acre lot. You'll love the beautifully remodeled kitchen featuring granite countertops, tile backsplash, stainless steel appliances, and breakfast bar island, perfect for everyday living and entertaining. The open layout flows

  

  Joyce Covone

  Berkshire Hathaway NE Prop.

  (959) 214-2735

  40 Crestwood Dr, East Hampton, CT 06424
• 

  $340,000 Sold Jun 13, 2025

  • 1,236 Sq Ft
  • $275/SF
  • 29 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  9 Berkshire Dr, East Hampton, CT 06424

  Welcome to this Wonderful spacious raised ranch - Retreat on a Cul-de-Sac! Tucked away in charming East Hampton CT, this 3-bedroom, 2-bath raised ranch offers the perfect blend of comfort, space, and convenience. Step inside to find hardwood floors throughout, a sun-filled living area, and an open layout that's ideal for both daily living and entertaining. The primary bedroom features its own en

  Laura Beth Collinson Carl Guild & Associates

  9 Berkshire Dr, East Hampton, CT 06424
• 

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  647 Ridgewood Lot#3 Rd, Middletown, CT 06457

  647 Ridgewood Lot#3 Rd, Middletown, CT 06457
• 

  

  /25

  $439,000 Under Contract

  • 5 Beds
  • 2 Baths
  • 2,740 Sq Ft

  65 Spring St, Rockfall, CT 06481

  Blending old and new, this gracious Colonial home welcomes you to explore and imagine the space and all of it's possibilities. Nestled on a private, lightly wooded 1.17 acre lot, the original 1890 home in the center has been expanded in the last 20 years with two major additions on either side, yielding 2740 square feet of living space with 5 bedrooms and 2 full baths (and room to add another to

  

  Claudia O'Connell

  William Raveis Real Estate

  (860) 419-7307

  65 Spring St, Rockfall, CT 06481
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  /43

  $2,025 - $3,845 per month

  Springside Middletown

  1-3 Beds

  1100 Springside Ln, Middletown, CT 06457

  Striking Design, a Rich Campus, and Exciting Middletown - 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
• 

  $557,650 Sold Jun 13, 2025

  • 1,985 Sq Ft
  • $281/SF
  • 29 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  107 Chestnut Hill Rd, Portland, CT 06480

  This single-family free-standing home is ready for a new owner! Located in the popular Bartlett Hill 55+ community, where there is plenty to do from enjoying the pool in the summer months to social events and clubs all year round. Great curb appeal with professional landscaping greets you as you step onto the covered front porch. Inside, the open floor plan is sunny and bright, featuring hardwood

  Nancy Stetson Coldwell Banker Realty

  107 Chestnut Hill Rd, Portland, CT 06480
• 

  Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,614 Sq Ft

  65 Long Hill Rd, East Hampton, CT 06424

  65 Long Hill Rd, East Hampton, CT 06424
• 

  

  /30

  $379,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,744 Sq Ft

  94 E Ridge Rd, Middletown, CT 06457

  Immaculate 3-Bedroom Home in a Peaceful Yet Convenient Location Welcome to this beautifully maintained 3-bedroom, 2.5-bath home nestled on a charming, easy-to-maintain lot. The main level features an open-concept layout with a bright and airy living room and dining area that seamlessly flows into the kitchen-perfect for everyday living and entertaining. Step through the sliding glass door to a

  

  Michelle MacNeil

  William Raveis Real Estate

  (860) 532-6860

  94 E Ridge Rd, Middletown, CT 06457
• 

  

  /19

  $1,675 per month

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

  359 S Main St Unit 2, Middletown, CT 06457

  This 2nd floor 2 bedroom unit was updated less than a year ago. With over 825 sq ft of living space just waiting for you to move in. Off Street parking is a plus. Heat is included in your monthly rental amount. We are first months rent and two months security deposit. Please no smoking/vaping or pets. A 1 garage bay is also available for an additional $100 per month. This unit is available for

  Scott Nardozzi Cavanaugh & Company LLC

  359 S Main St Unit 2, Middletown, CT 06457
• 

  $465,000 Sold Jun 13, 2025

  • 1,445 Sq Ft
  • $322/SF
  • 30 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1946

  7 Budney Hill, Ivoryton, CT 06442

  Step into the timeless charm with this beautifully updated 3 bedroom Cape Cod nestled in the heart of Ivoryton. Just a short walk to the historic Ivoryton Playhouse, this home combines classic style with thoughtful modern upgrades throughout. Inside you will find a sunlit living room featuring a cozy gas fireplace, hardwood floors that run throughout the home, adding warmth and character to every

  Jennifer Capano William Raveis Real Estate

  7 Budney Hill, Ivoryton, CT 06442
• 

  Not Listed For Sale

  00 Dennison Rd, Essex, CT 06426

  00 Dennison Rd, Essex, CT 06426
• 

  

  /37

  $549,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,812 Sq Ft

  14 Meadowood Ln, Old Saybrook, CT 06475

  Make this warm, inviting home your own this spring! Ideally located in one of the most desirable neighborhoods in town and conveniently located a short walk to the high school and close to beaches and the village. This home offers a very flexible floor plan with hardwood floors, a new roof and recently replaced septic system. A spacious, private deck with a hot tub complete the package! Schedule

  

  Rick Allen

  William Raveis Real Estate

  (860) 773-4719

  14 Meadowood Ln, Old Saybrook, CT 06475
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  /16

  $1,691 - $4,491 per month

  Middletown Ridge Apartments

  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

  100 Town Ridge, Middletown, CT 06457
• 

  $550,000 Sold Jun 13, 2025

  • 1,744 Sq Ft
  • $315/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  192 Thompson Hill Rd, Portland, CT 06480

  Discover this stunning mid-century modern home set on 1.56 acres of partially fenced land with charming stone walls. Featuring three spacious bedrooms, including a luxurious primary suite with a private bath and glass sliders to a deck overlooking the serene backyard. The open floor plan is enhanced by floor-to-ceiling windows, flooding the space with natural light. The beautifully remodeled

  Lisa Golebiewski Coldwell Banker Realty

  192 Thompson Hill Rd, Portland, CT 06480
• 

  Est $814,395 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,784 Sq Ft

  541 Higganum Rd, Killingworth, CT 06419

  541 Higganum Rd, Killingworth, CT 06419
• 

  

  /39

  $715,000

  • 5 Beds
  • 3 Baths
  • 2,347 Sq Ft

  11 Liberty St, Clinton, CT 06413

  Updated Historic Cape Just Off the Town Green - Legal Rental & Artist Studio This beautifully updated antique Cape is a rare blend of history, charm, and modern functionality, ideally located on 1.29 private acres just steps from the town green. Enjoy easy access to the town beach, shops, outlets, and restaurants, while coming home to a serene and versatile retreat. The main residence offers

  

  Cory Tyler

  Berkshire Hathaway NE Prop.

  (860) 792-3533

  11 Liberty St, Clinton, CT 06413
• 

  

  /22

  $1,800 per month

  • 2 Beds
  • 1.5 Baths
  • 1,172 Sq Ft
  • House for Rent

  584 Main St Unit 2, Portland, CT 06480

  Spacious 2-Bedroom Rental with Garage & Storage!This well-kept 2-bedroom, 1.5-bath rental offers comfortable living with added convenience. The unit includes washer and dryer hookups, a 1-car detached garage, and basement space perfect for extra storage. Enjoy a functional layout with generous room sizes and a location close to local amenities, shopping, and major routes. A great opportunity for

  Amber Alcazar Coldwell Banker Realty

  584 Main St Unit 2, Portland, CT 06480
• 

  $450,000 Sold Jun 13, 2025

  • 2,448 Sq Ft
  • $184/SF
  • 26 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1976

  95 Maple Rd, Portland, CT 06480

  Don't miss this classic 4-bedroom Colonial located in Portland! This home features an open-concept living and dining area, an eat-in kitchen, and a cozy family room with a fireplace. Beautiful hardwood floors run throughout the main living spaces. Enjoy the convenience of first-floor laundry and relax in the sun-filled, year-round sunroom with skylights and southern exposure. Upstairs, you'll

  Michelle MacNeil William Raveis Real Estate

  95 Maple Rd, Portland, CT 06480
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 548 Sq Ft

  89 Lake Shore Dr, East Haddam, CT 06423

  89 Lake Shore Dr, East Haddam, CT 06423

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