Middlesex County, CT Homes

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  /10

  $175,000

  • Land
  • 2.2 Acres
  • $79,545 per Acre

  86 Bushy Hill Rd, Ivoryton, CT 06442

  Welcome to Ivoryton-a borough so rich in charm it practically begs to be the setting of your next chapter. Just up the road from the historic Ivoryton Playhouse, one of the country's longest-running theaters, this 2.2-acre lot places you right where culture and countryside meet. Imagine catching a Broadway-quality show just minutes from your front porch, then strolling to The Blue Hound Cookery

  

  Michael Marsden

  Compass Connecticut, LLC

  (860) 845-1408

  86 Bushy Hill Rd, Ivoryton, CT 06442
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  /35

  $1,100 - $2,200 per month plus fees

  Woodrow Wilson Apartments

  Studio - 2 Beds

  339 Hunting Hill Ave, Middletown, CT 06457

  Originally built in 1931 as Woodrow Wilson High School, the building was converted into apartments in 1985. Woodrow Wilson Apartments has 66 apartments which include studio, one and two bedroom units. Features include fully applianced kitchens, new windows with mini-blinds, an elevator, laundry facilities, intercom, and parking. A non-smoking building; no pets allowed. For additional photos of

  339 Hunting Hill Ave, Middletown, CT 06457
• 

  $810,000 Sold Oct 27, 2025

  • 2,555 Sq Ft
  • $317/SF
  • 132 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1880

  34 West Ave, Essex, CT 06426

  Prime location in the heart of Essex village. Walk to Downtown Essex restaurants, quaint shops, marinas and the CT River. This well appointed home offers both charm and modern amenities. Central location- close to everything- yet a private setting. It's cozy yet expansive. Featuring hardwood floors throughout, built-ins, and a wall of windows that leads to a captivating semi-circular screened in

  Meghan Flood William Raveis Real Estate

  34 West Ave, Essex, CT 06426
• 

  Est $468,484 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,676 Sq Ft

  116 Long Hill Rd, Clinton, CT 06413

  116 Long Hill Rd, Clinton, CT 06413
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  /27

  $660,000

  • Land
  • 38.56 Acres
  • $17,116 per Acre

  0 Gildersleeve Rd, Portland, CT 06480

  Rare 38.56-Acre Parcel with Golf Course Views - Portland, CT Attention developers, investors, and visionaries-this is your opportunity to own a prime 38.56-acre parcel in scenic Portland, Connecticut. With stunning views overlooking a nearby golf course, this expansive property offers incredible subdivision potential or the perfect setting for a private estate. This raw piece of land is a blank

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 981-0331

  0 Gildersleeve Rd, Portland, CT 06480
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  /7

  $1,700 total monthly price

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

  26 Sunset Terrace Unit C16, Essex, CT 06426

  This charming 1-bedroom, 1-bath rental in Essex provides a comfortable and updated living space. Recently renovated, it features bright living areas and a modernized bathroom. Located in a quiet neighborhood close to Essex Village, this home provides easy access to local shops, dining, and scenic spots. A great option for anyone looking for a welcoming place to settle in.

  Mantas Laureckis William Raveis Real Estate

  26 Sunset Terrace Unit C16, Essex, CT 06426
• 

  $187,000 Sold Oct 24, 2025

  • 1,057 Sq Ft
  • $177/SF
  • 7 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1973

  2212 Cromwell Hills Dr Unit 2212, Cromwell, CT 06416

  Discover easy living in this spacious and well-maintained 2-bedroom, 2 bathroom ranch-style condo. Situated in a desirable community, this unit offers a functional single-level layout with an open-concept living and dining area filled with plenty of natural light offering a great space to relax or entertain. Enjoy the ease of a covered carport located directly below the building, keeping your

  Monika Pietras William Pitt Sotheby's Int'l

  2212 Cromwell Hills Dr Unit 2212, Cromwell, CT 06416
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  Not Listed For Sale

  00 Tater Hill Rd, East Haddam, CT 06423

  00 Tater Hill Rd, East Haddam, CT 06423
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  /39

  $2,500,000

  • 10 Beds
  • 8.5 Baths
  • 6,588 Sq Ft

  10 & 12 Firetower Rd, Killingworth, CT 06419

  Turn into the driveway and the stunning surroundings will melt your stress away. A rare find of two properties on 20+ acres of exquisite grounds bordered by Chatfield Hollow Park and includes a private residence, caretaker's dwelling, and a cabin that feels like you're miles away in a wilderness lodge. The primary residence, a 5 bedroom, 3 bath mid-century modern with an infinity-edge pool that

  

  Betsy Anderson

  William Pitt Sotheby's Int'l

  (860) 517-8016

  10 & 12 Firetower Rd, Killingworth, CT 06419
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  /4

  $1,500 - $1,900 per month plus fees

  On Ward Apartments

  1 - 2 Beds

  38 Ward St, Middletown, CT 06457

  Nestled in the heart of one of Connecticut’s most vibrant and historic cities, 38 Ward Street offers a blend of comfort, character, and convenience. Whether you're a first-time homebuyer, a growing family, or simply looking for a peaceful retreat, this home has it allKey Features:Spacious Layout: Enjoy generous living space with bright and airy rooms throughout.Charming

  38 Ward St, Middletown, CT 06457
• 

  $1,235,000 Sold Oct 24, 2025

  • 1,941 Sq Ft
  • $636/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1930

  19 Neptune Dr, Old Saybrook, CT 06475

  Welcome to 19 Neptune Drive, a beautifully rebuilt Cape Cod-style home in the sought-after Knollwood Beach Association. Completely reconstructed in 2022, this residence blends coastal charm w/modern updates, offering 1,914sqft of thoughtfully designed living space & water views just a short walk to the beach. Step inside to find an inviting open floor plan filled w/natural light & finished

  Mark Riesbeck Berkshire Hathaway NE Prop.

  19 Neptune Dr, Old Saybrook, CT 06475
• 

  Est $2,999,852 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 6,978 Sq Ft

  14 Rackett Ln, Essex, CT 06426

  14 Rackett Ln, Essex, CT 06426
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  /40

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 3,912 Sq Ft

  67 Hayden Hill Rd, Haddam, CT 06438

  **ELEGANT OASIS - A Rare Gem!** Experience the perfect blend of sophistication & functionality in this highly customized 3-BD, 2.5-BTH Cape, nestled on a picturesque 1.35-acre landscaped lot in a serene neighborhood. Every inch of this exceptional home has been thoughtfully & lovingly designed to invite large gatherings, fun entertaining, & making special memories. Fully renovated & expanded in

  

  Sandra Blevins

  William Raveis Real Estate

  (860) 775-6788

  67 Hayden Hill Rd, Haddam, CT 06438
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  /2

  $1,750 total monthly price

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

  26 Sunset Terrace Unit B6, Essex, CT 06426

  This charming 2-bedroom, 1-bath rental in Essex provides a comfortable and updated living space. Recently renovated, it features bright living areas and a modernized bathroom. Located in a quiet neighborhood close to Essex Village, this home provides easy access to local shops, dining, and scenic spots. A great option for anyone looking for a welcoming place to settle in.

  Mantas Laureckis William Raveis Real Estate

  26 Sunset Terrace Unit B6, Essex, CT 06426
• 

  $635,000 Sold Oct 24, 2025

  • 1,989 Sq Ft
  • $319/SF
  • 25 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1988

  15 Colonial Dr, Killingworth, CT 06419

  OFFERS REQUESTED BY 9 pm SUNDAY 9/28. This property offers tranquility without sacrificing convenience. Pristine landscaping with a private driveway off a cul-de-sac, 4.65 acres abut a 30+ acre reserve with meadow views. The home has been immaculately updated and renovated. The vaulted living room features floor to ceiling windows and a fireplace with marble surround. Light filled throughout, the

  Laurie Trulock Compass Connecticut, LLC

  15 Colonial Dr, Killingworth, CT 06419
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  Est $1,039,585 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,864 Sq Ft

  61 Cedar Lake Rd, Deep River, CT 06417

  61 Cedar Lake Rd, Deep River, CT 06417
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  /39

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,133 Sq Ft

  6 Landing Hill Rd, East Haddam, CT 06423

  This renovated c.1899 Colonial blends timeless character with modern updates, offering sweeping views of the Connecticut River. Set on a landscaped 0.89-acre lot in East Haddam Village, the home is within walking distance of the Goodspeed Opera House, Gelston House, and the vibrant Theater District. The classic exterior with companion barn, stonework, and patios creates an inviting setting for

  

  Laura Marozsan

  Berkshire Hathaway NE Prop.

  (860) 909-8506

  6 Landing Hill Rd, East Haddam, CT 06423
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  /21

  $1,800 - $2,000 per month plus fees

  Apartment for Rent

  2 Beds

  70 Pond Meadow Rd, Ivoryton, CT 06442

  Freshly Painted second floor unit, 2 bedrooms/1 bathroom

  70 Pond Meadow Rd, Ivoryton, CT 06442
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  $166,000 Sold Oct 24, 2025

  • 576 Sq Ft
  • $288/SF
  • 13 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1981

  1469 Boston Post Rd Unit 19, Westbrook, CT 06498

  Welcome to Ocean View Village, where easy living meets a desirable shoreline location. This move-in ready condo features a spacious bedroom with abundant natural light, a full bath, and an open living/dining area that opens to a private deck. With updated flooring, ample closet space, and a layout designed for comfort, this home combines convenience and style just minutes from beaches,

  Daniel Draffan Carbutti & Co., Realtors

  1469 Boston Post Rd Unit 19, Westbrook, CT 06498
• 

  Est $837,220 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 5,032 Sq Ft

  7 Smith Farm Rd, Cromwell, CT 06416

  7 Smith Farm Rd, Cromwell, CT 06416
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  /40

  $525,000

  • 3 Beds
  • 2 Baths
  • 2,113 Sq Ft

  16 Walkley Hill Rd, Haddam, CT 06438

  Welcome to your perfect family retreat in Haddam/Higganum! This beautifully updated three-bedroom, two-bath home combines historic charm with modern upgrades, offering a spacious layout, renovated kitchen and bathrooms, and a large yard for outdoor living. Located just a mile from the Higganum Center, it features an open floor plan that is ideal for entertaining. The bright living room, featuring

  

  Nick Prevost

  William Raveis Real Estate

  (860) 815-8045

  16 Walkley Hill Rd, Haddam, CT 06438
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  /17

  $1,950 total monthly price

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft
  • House for Rent

  157 Woodland Dr Unit 157, Cromwell, CT 06416

  Bright and happy condo unit on the top floor. Heat and hot water included in monthly rent. Spacious living room with hardwood floors, vaulted ceiling and access to the balcony.Kitchen offers neutral oak cabinets, tiles and connects with dining room area. 2 bedrooms, 2 full baths. Unit freshly painted in today's colors and ready to move in Landlord is looking for 700 credit score, 30 per cent

  Margo Mikunda Complete Real Estate

  157 Woodland Dr Unit 157, Cromwell, CT 06416
• 

  $315,000 Sold Oct 24, 2025

  • 1,254 Sq Ft
  • $251/SF
  • 17 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1948

  563 Main St, Cromwell, CT 06416

  Welcome to this 2-bedroom, 1-bath Cape, a home that offers comfort and simplicity in a convenient location. Filled with natural light, the main living spaces feel warm and inviting, while hardwood floors bring a touch of character throughout. The layout is practical and easy to maintain, making it a great fit for everyday living. Outside, the level backyard provides plenty of space for gardening,

  Carl Guild Carl Guild & Associates

  563 Main St, Cromwell, CT 06416
• 

  Est $438,102 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  111 Field Rd, Cromwell, CT 06416

  111 Field Rd, Cromwell, CT 06416
• 

  

  /40

  $549,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,222 Sq Ft

  25 Olde Orchard Rd, Clinton, CT 06413

  Best and Final due 10/21 by 7 pm!! Welcome to 25 Olde Orchard Road in Clinton, set in one of the town's most desirable neighborhoods, the home sits on 1.1 acres surrounded by other well-kept homes on larger lots. This 3-bedroom, 2.5-bath Colonial has been completely remodeled from top to bottom, blending clean modern updates with the warmth and comfort of home. The main level feels open and

  

  Dylan Walter

  William Raveis Real Estate

  (860) 730-9528

  25 Olde Orchard Rd, Clinton, CT 06413
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  /9

  $1,000 - $1,700 per month plus fees

  Apartment for Rent

  1 - 2 Beds

  562 Main St, Middletown, CT 06457

  562 Main St, Middletown, CT 06457
• 

  $420,000 Sold Oct 24, 2025

  • 1,590 Sq Ft
  • $264/SF
  • 14 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  311 Long Ln, Middletown, CT 06457

  Beautiful 3-bedroom, 2.5-bath Colonial with a fantastic layout inside and out. The updated kitchen features granite counters, stainless steel appliances, and ample cabinetry. The main level is highlighted by hardwood floors throughout and a bright and airy living room with a wood fireplace. The second level offers a spacious primary suite with a full bath and walk-in closet, along with two

  Sara Etienne eXp Realty

  311 Long Ln, Middletown, CT 06457
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  Est $528,448 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,160 Sq Ft

  2 Greendale Ave, Cromwell, CT 06416

  2 Greendale Ave, Cromwell, CT 06416
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  /33

  $242,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,430 Sq Ft

  234 S Main St Unit 414, Middletown, CT 06457

  With ceilings that soar, wood beams and wood floors; this property will make a lover of charm feel immediately at home. This amazing brick building is aptly on the National Register of Historic Places, blending a vintage feel and modern conveniences. A quick 10 minute walk will get you to Wesleyan University or downtown to a multitude of restaurants and activities. If you're more of a homebody,

  

  Sarah Murphy

  William Raveis Real Estate

  (860) 846-3466

  234 S Main St Unit 414, Middletown, CT 06457
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  /16

  $1,800 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,127 Sq Ft
  • Apartment for Rent

  175 Prospect St, Middletown, CT 06457

  This clean 2nd fl unit is close to downtown Middletown and short drive to Rt9 and 91. Gleaming hardwood floors and two balconies to enjoy the Middletown area

  Andre Holloman KW Legacy Partners

  175 Prospect St, Middletown, CT 06457
• 

  $325,000 Sold Oct 24, 2025

  • 1,264 Sq Ft
  • $257/SF
  • 63 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1900

  25 Waverly Ave, Portland, CT 06480

  Welcome to this spacious 3-bedroom, 1 full 2 half bath home that perfectly blends comfort, character, and potential. Tucked near the end of a quiet cul-de-sac, the property offers both privacy and convenience-just minutes to schools, shops, restaurants, golf courses, hiking trails, farmstands, and more. The exterior features a generous backyard and a detached two-car garage. Step inside and

  Carl Guild Carl Guild & Associates

  25 Waverly Ave, Portland, CT 06480
• 

  Est $387,247 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,218 Sq Ft

  20 Waverly Ave, Portland, CT 06480

  20 Waverly Ave, Portland, CT 06480
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  /34

  $250,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,314 Sq Ft

  156 Summer St Unit 156, Portland, CT 06480

  Welcome to Summer Meadow Condos! This half-duplex offers the perfect combination of comfort, convenience, and low-maintenance living. Step inside to an inviting open floor plan featuring a spacious living/dining area that flows seamlessly into a galley-style kitchen-perfect for both everyday living and entertaining. French doors off the living room fill the space with natural light and open to a

  

  Cheryl Zalewski

  eXp Realty

  (860) 467-0352

  156 Summer St Unit 156, Portland, CT 06480
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  /15

  $1,950 - $1,995 per month plus fees

  Bridge Road Commons

  1 Bed

  105 Bridge Rd, Haddam, CT 06438

  Experience modern living in the heart of Haddam, CT, where our open concept apartment units seamlessly blend comfort and style. Nestled in this picturesque town, our community features a clubhouse and inviting outdoor spaces, offering a perfect backdrop to enjoy Haddam's quaint charm. With scenic trails, historic landmarks, and the gentle flow of the nearby Connecticut River, Bridge Road Commons

  105 Bridge Rd, Haddam, CT 06438
• 

  $315,000 Sold Oct 24, 2025

  • 1,744 Sq Ft
  • $181/SF
  • 26 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  31 Wynwood Dr Unit 31, Cromwell, CT 06416

  Welcome to 31 Wynwood Drive! An expansive 3 Bedroom, 2-1/2 Bath, end unit Townhouse w/1,744 sq ft of living and a 1 car att'd garage, and an unbeatable location in highly coveted Fox Meadows! It offers comfort, style, and convenience at every turn. The main living area is fantastic as the Dining Room seamlessly flows into the inviting Living Room w/attractive gas fireplace, and sliders to your

  Jeff Coleman Hagel & Assoc. Real Estate

  31 Wynwood Dr Unit 31, Cromwell, CT 06416
• 

  Est $636,012 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  10 Wexford Ln, Cromwell, CT 06416

  10 Wexford Ln, Cromwell, CT 06416
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  /39

  $599,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,564 Sq Ft

  593 Route 148, Killingworth, CT 06419

  Offers received. Deadline for offers is 5 pm Sunday. This home will not disappoint and is a pleasure to show!!! Charming Renovated Farmhouse on Nearly 5 Acres. A timeless classic reimagined with modern comforts, this beautifully renovated vintage farmhouse blends character and charm with thoughtful updates throughout. The stunning chef's kitchen features GE Cafe appliances, abundant cabinetry, a

  

  Cathy Lynch

  Coldwell Banker Realty

  (860) 370-3312

  593 Route 148, Killingworth, CT 06419
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  /15

  $2,500 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,117 Sq Ft
  • House for Rent

  10 Plains Rd, Moodus, CT 06469

  Welcome home to this lovely 3-bedroom, 1-bath Colonial nestled in the heart of East Haddam. Filled with warmth and character, this home offers the perfect blend of old-fashioned charm and modern comfort. The bright kitchen and inviting living spaces make it easy to feel right at home. Upstairs, you'll find three comfortable bedrooms and a full bath, all updated and ready for you to move right

  Abby Ondras Carl Guild & Associates

  10 Plains Rd, Moodus, CT 06469
• 

  $1,100,000 Sold Oct 24, 2025

  • 1,353 Sq Ft
  • $813/SF
  • 45 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  51 Sunrise Rd, Westbrook, CT 06498

  Charming, rare find, water front New England Beach home. The views are breath taking! Watch the sunrise and sunset from your Bedroom suit balcony, your Kitchen, Living room or Den. All while having a view of a large beach, Long Island sound and Duck Island. Imagine being able to wake up every day living this experience. The kitchen has a beautiful granite island with stools for your comfort and

  Darlene White Coldwell Banker Realty

  51 Sunrise Rd, Westbrook, CT 06498
• 

  Est $235,842 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft

  2 Forest Glen Cir Unit 7, Middletown, CT 06457

  2 Forest Glen Cir Unit 7, Middletown, CT 06457

Showing Results 201 - 240, Page 6 of 18