Middlesex, CT Homes

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  $369,900

  • 4 Beds
  • 1.5 Baths
  • 2,005 Sq Ft

  175 Lincoln St, Middletown, CT 06457

  Step into timeless elegance with this spacious single-family Colonial, built in the 1800s & rich with historic charm. Located just minutes from downtown Middletown, Wesleyan University & Middlesex Hospital, this home offers the perfect blend of convenience & character. Featuring 4 nice sized bedrooms, this home boasts high ceilings, original woodwork & a warm inviting layout. The detached garage

  Michelle Mazzotta eXp Realty

  175 Lincoln St, Middletown, CT 06457
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  /25

  $2,100 per month

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

  179 Butternut St Unit A, Middletown, CT 06457

  Welcome to The Flats@MTown West! This brand new 1-bedroom apartment is perfect for luxurious and modern living in Middletown, CT. Step inside and be dazzled by unique and detailed finishes to an exquisite apartment. The thoughtfully designed kitchen features granite countertops, stainless appliances that add to the elegance of the layout. You'll also encounter, hardwood floors, a tastefully tiled

  Scott Nardozzi Cavanaugh & Company LLC

  179 Butternut St Unit A, Middletown, CT 06457
• 

  $320,000 Sold Jun 27, 2025

  • 960 Sq Ft
  • $333/SF
  • 114 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  155 Dorothy Dr, Middletown, CT 06457

  Welcome to this charming 3-bedroom, 2-bathroom ranch home offering 960 sq. ft. of main-level living space plus a full basement for added versatility. Nestled on a dead-end road in the center of South Farms district of Middletown, this home provides plenty of outdoor space, including a semi-private backyard and new deck - perfect for relaxation and entertaining! Inside, the inviting living room

  Devon Taylor Assael Dave Jones Realty, LLC

  155 Dorothy Dr, Middletown, CT 06457
• 

  Est $205,070 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 857 Sq Ft

  8 Hillside Ct, Middletown, CT 06457

  8 Hillside Ct, Middletown, CT 06457
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  /10

  $225,000

  • 4 Beds
  • 2 Baths
  • 2,054 Sq Ft

  15 Wall St, Middletown, CT 06457

  Step into this generously sized Colonial, offering four spacious bedrooms and a flexible floor plan. The inviting living room flows seamlessly into a formal dining room-perfect for entertaining. Enjoy cooking in the large eat-in kitchen, complete with sliders that lead out to a private deck, ideal for outdoor dining and relaxation. Upstairs, you'll find four well-proportioned bedrooms, providing

  Lisa Sader-Goede Aspen Realty Group

  15 Wall St, Middletown, CT 06457
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  /24

  $1,875 per month

  • 4 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Apartment for Rent

  76 Spring St Unit 2, Middletown, CT 06457

  NEWLY renovated 4 Bedroom unit near downtown Middletown! This second floor unit is over 1500 square feet and has gleaming hardwood floors. Updated kitchen & living area. Washer/Dryer hookups in basement with separate utilities. Each unit has high efficiency/on demand heat & hot water natural gas. Lots of windows throughout the sun filled rooms. Each unit has been newly renovated. Off street

  Lina Delis William Raveis Real Estate

  76 Spring St Unit 2, Middletown, CT 06457
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  $250,000 Sold Jun 27, 2025

  • Land
  • 22 Acres
  • $11,574 per Acre

  • 18 Days On Market

  0 Arbutus St Unit 24075922, Middletown, CT 06457

  What would it mean to own a piece of untouched nature-where every tree, every quiet moment, and every breath of fresh air belongs to you? This 21.6-acre wooded lot in Middletown's sought-after South Farms area offers the rare chance to build not just a home, but a sanctuary. Surrounded by the beauty and serenity of nature, this property is a blank canvas for your imagination. Picture a custom

  Debbie Huscher Real Broker CT, LLC

  0 Arbutus St Unit 24075922, Middletown, CT 06457
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  Est $320,379 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,470 Sq Ft

  76 Hunting Hill Ave, Middletown, CT 06457

  76 Hunting Hill Ave, Middletown, CT 06457
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  /13

  $360,000

  • 6 Beds
  • 3 Baths
  • 2,622 Sq Ft

  23 Portland St, Middletown, CT 06457

  This is a fantastic, possible owner-occupied investment opportunity! This spacious 3 family house with back yard is available now, in heart of downtown Middletown. The 2nd and 3rd floors are already rented, providing immediate income. The 2nd-floor kitchen has been recently renovated with updated counters and cabinets. Each unit has separate electrical panels, boilers, and water heaters, all of

  Sacha Armstrong William Pitt Sotheby's Int'l

  23 Portland St, Middletown, CT 06457
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  /16

  $1,675 per month

  • 2 Beds
  • 2 Baths
  • 788 Sq Ft
  • Apartment for Rent

  666 Main St Unit A2, Middletown, CT 06457

  Welcome to Main Street, Middletown. This two bedroom apartment is newly updated with new flooring, paint, and bathrooms. It's located in the beautiful, historic town center with over seven walkable blocks of different restaurants, shops and dozens of choices of dining, art, music and entertainment. This beautiful apartment is located on the main floor, has its own private entrance with plenty of

  Laura Milano Seabury Hill REALTORS

  666 Main St Unit A2, Middletown, CT 06457
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  $195,000 Sold Jun 24, 2025

  • 1,680 Sq Ft
  • $116/SF
  • 40 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1976

  138 Rising Trail Dr, Middletown, CT 06457

  Welcome to 138 Rising Trail! Step inside this 4 level unit. The main level features a fully appliance kitchen, dining room and a sunken living room with an abundance of natural lighting along with a guest bathroom. The 2nd floor you will find 2 bedrooms, a full bathroom and the convenience of laundry, the 3rd floor is an additional bedroom along with extra space that is perfect for storage, gym

  Heather Fitzgerald YellowBrick Real Estate LLC

  138 Rising Trail Dr, Middletown, CT 06457
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  Est $389,404 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,718 Sq Ft

  4 Blue Spruce St, Middletown, CT 06457

  4 Blue Spruce St, Middletown, CT 06457
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  /21

  $289,999

  • 4 Beds
  • 1.5 Baths
  • 1,415 Sq Ft

  10 Silver St, Middletown, CT 06457

  Newly reduced and full of potential-10 Silver Street now comes with a $10,000 price improvement and buyers choice of $15,000 closing credit or full kitchen remodel. A sample rendering from Wren Kitchens is included to inspire your vision. Located in the heart of Middletown, this home offers charm, convenience, and flexible value-all just minutes from restaurants, shops, and Wesleyan University.

  Sacha Armstrong William Pitt Sotheby's Int'l

  10 Silver St, Middletown, CT 06457
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  /24

  $2,250 per month

  • 3 Beds
  • 1 Bath
  • 14,820 Sq Ft
  • House for Rent

  360 Main St Unit 3-B, Middletown, CT 06457

  Central downtown district. Home to Typhoon and Ford News deli at street level. Historic Pythian Building with an interesting ownership history as hotel and meeting place of the Pythian Knights. Large 3-bedroom unit on top floor. Open floor plan with kitchen, livingroom and full bath. It includes all utilities. There isn't any onsite parking for tenants. There are municipal parking lots nearby.

  Patricia Flynn Sterling REALTORS

  360 Main St Unit 3-B, Middletown, CT 06457
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  $250,000 Sold Jun 23, 2025

  • 1,132 Sq Ft
  • $221/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  6 Countryside Ln Unit 1, Middletown, CT 06457

  End unit in a quiet complex! This complex offers privacy and convenience with quick access to Rt 9 and Rt 17. On the main floor you will find a large living/dining room combo, a half bath on your way to the kitchen with newer stainless steel appliances. Upstairs you will find two generously sized bedrooms with plenty of closet space and a full bath. Bonus space in the finished basement with

  Jill Bright Putnam Agency Real Estate LLC

  6 Countryside Ln Unit 1, Middletown, CT 06457
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  Est $235,982 Not Listed For Sale

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

  15 Forest Glen Cir Unit 10, Middletown, CT 06457

  15 Forest Glen Cir Unit 10, Middletown, CT 06457
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  /7

  $129,000

  • Land
  • 3.58 Acres
  • $36,034 per Acre

  0 Mountain Laurel Dr, Middletown, CT 06457

  Build your dream home on this 3.5 acre approved building lot bordering open space. Last lot on a private cul-de-sac! Beautiful, wooded country setting for a home, yet only 1 mile from Rt 9 and 10 minutes to Downtown Middletown! Enter the lot down a picturesque driveway though the woods to a clearing with old stone walls and natural rock outcroppings. The open space for the cul-de-sac borders this

  Siobhan McLaughlin William Raveis Real Estate

  0 Mountain Laurel Dr, Middletown, CT 06457
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  /11

  $1,650 per month

  • 1 Bath
  • 476 Sq Ft
  • Apartment for Rent

  584 Main St Unit H, Middletown, CT 06457

  Discover these NEW luxury studio apartments, ideally located on the main street of a bustling college town. Perfectly blending comfort, convenience, and style, these modern studios that include a sophisticated retreat just steps from all the action. Each apartment features high-end finishes, sleek hardwood floors, large windows that flood the space with natural light, and contemporary kitchens

  Marianna Terenzio William Raveis Real Estate

  584 Main St Unit H, Middletown, CT 06457
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  $350,000 Sold Jun 23, 2025

  • 2,038 Sq Ft
  • $172/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  50 Andrew St, Middletown, CT 06457

  Deceiving is one way to describe this three bedroom, two bath Cape that offers a blend of living and functional separation ideal for multi-generational living. Or live in the main dwelling and rent out the one bedroom, one bath, in-law apartment in the basement. The second floor and living room were recently updated with new paint and carpeting. Second floor bathroom has been totally renovated.

  Colin Taylor Executive Real Estate Inc.

  50 Andrew St, Middletown, CT 06457
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  Est $376,839 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  271 Ridge Rd, Middletown, CT 06457

  271 Ridge Rd, Middletown, CT 06457
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  /6

  $135,000

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft

  225 Burgundy Hill Ln, Middletown, CT 06457

  Welcome to Peppermill Village! This adorable two bedroom, one bath, condo is ideal for an investor or owner occupied! Large bedrooms with ample closet space and a spacious living room with newly installed vinyl flooring throughout. This unit has an assigned parking spot and visitor spaces for guests! This complex offers washer and dryer units in the basement for added convivence! Pet friendly!

  Maria Convertito Regency Real Estate, LLC

  225 Burgundy Hill Ln, Middletown, CT 06457
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  /9

  $1,319 per month

  • 1 Bed
  • 1 Bath
  • Apartment for Rent

  251 Court St, Middletown, CT 06459

  Rick Rivera Rental Housing Deals

  251 Court St, Middletown, CT 06459
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  $243,700 Sold Jun 23, 2025

  • 1,306 Sq Ft
  • $187/SF
  • 30 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  2 Butternut Knolls Unit 2, Middletown, CT 06457

  Rarely available Townhouse style condo in Butternut Knoll with fantastic location near Wesleyan and vibrant Downtown! This bright and sunny unit features nicely sized bedrooms with high ceilings and double closets, skylight, private patio, central heat and air plus garage parking. The main floor includes a roomy living area with bay window and breakfast bar. The kitchen includes a dining area

  Pauline Webb William Raveis Real Estate

  2 Butternut Knolls Unit 2, Middletown, CT 06457
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  Est $330,457 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,604 Sq Ft

  455 West St, Middletown, CT 06457

  455 West St, Middletown, CT 06457
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  /5

  $159,900

  • Land
  • 4.40 Acres
  • $36,341 per Acre

  174 Old Road Dr, Middletown, CT 06457

  Gorgeous lot! Previous home on property was demolished after fire. The views are incredible of Higby Mountain!

  Nancy Newman LPT Realty

  174 Old Road Dr, Middletown, CT 06457
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  $570,000 Sold Jun 23, 2025

  • 3,756 Sq Ft
  • $152/SF
  • 46 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1988

  36 Mcgrath Dr, Middletown, CT 06457

  Welcome to your dream home! This spacious Colonial offers the perfect blend of comfort, style, and convenience. Inside, you'll find a thoughtfully designed layout ideal for both entertaining and everyday living. The main floor features a bright, eat-in kitchen, a formal dining room for special occasions, a cozy living room, a welcoming family room, and a private office - all complemented by a

  Tom Derick Executive Real Estate Inc.

  36 Mcgrath Dr, Middletown, CT 06457
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  Est $179,553 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft

  19 Trolley Crossing Ln, Middletown, CT 06457

  19 Trolley Crossing Ln, Middletown, CT 06457
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  /11

  $525,000

  • Land
  • 26 Acres
  • $19,864 per Acre

  0 Arbutus St Unit 24065180, Middletown, CT 06457

  **26+ Acres of Unique Land** These 3 parcels are found in a picturesque rural setting, the expansive 26+ acres provides a unique opportunity (previous site work completed years ago). The land is easily accessible providing convenient travel to RTs 9 and 17 and to nearby downtown Middletown. Surround yourself with stunning landscapes, including rolling hills, lush forests....this property is a

  Heather Kilbourn Cavanaugh & Company LLC

  0 Arbutus St Unit 24065180, Middletown, CT 06457
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  $502,500 Sold Jun 20, 2025

  • 2,064 Sq Ft
  • $243/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1999

  31 Sherman Lee Dr, Middletown, CT 06457

  Welcome to this beautifully updated 3-bedroom, 2.5-bath home nestled on a peaceful cul-de-sac in one of Middletown's most desirable neighborhoods. Move-in ready, this home blends style, space, and comfort with standout features inside and out. Step inside to find newly installed hardwood floors flowing throughout a bright, inviting interior. The heart of the home is a stunning renovated kitchen,

  Matt Donafrio GRL & Realtors, LLC

  31 Sherman Lee Dr, Middletown, CT 06457
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  Est $391,658 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft

  17 Yellow Hill Rd, Middletown, CT 06457

  17 Yellow Hill Rd, Middletown, CT 06457
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  /3

  $619,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  605 Higby Rd, Middletown, CT 06457

  The Colonial - offering a classic Colonial look. The first floor offers an open floor plan with great room and kitchen located in the entire back of home and a large dining room. The beautiful staircase is set to the side with open railings, a large window and window seat. The second floor offers a large primary bedroom suite and walk in closet and en suite with walk in tile shower. One will also

  Mark Toledo Berkshire Hathaway NE Prop.

  605 Higby Rd, Middletown, CT 06457
• 

  $219,000 Sold Jun 20, 2025

  • 1,147 Sq Ft
  • $191/SF
  • 49 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  234 S Main St Unit 303, Middletown, CT 06457

  Let me know your thoughts! Welcome to 234 S Main St, Unit 303-a charming 2-bedroom, 2-bath condo in a beautifully maintained building that's proudly listed on the National Register of Historic Places. With exposed brick, massive timber beams, and unique plank ceilings, this 120-year-old treasure blends timeless character with modern comfort. Inside, you'll find 1,147 sq ft of easy, one-level

  Devon Taylor Assael Dave Jones Realty, LLC

  234 S Main St Unit 303, Middletown, CT 06457
• 

  Est $189,584 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 862 Sq Ft

  606 Congdon St W Unit 2, Middletown, CT 06457

  606 Congdon St W Unit 2, Middletown, CT 06457
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  /3

  $634,900 New Construction

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

  604 Higby Rd, Middletown, CT 06457

  The Ranch. One floor living at its best offering old world charm with all the modern conveniences. Approximately 8'x8' front covered porch leads you to the dramatic entry of this abode. The large primary suite will impress with large walk in closet, spacious en suite offering an oversized walk in tile shower and vanity with double sinks. The great room is amazing with large kitchen and island

  Mark Toledo Berkshire Hathaway NE Prop.

  604 Higby Rd, Middletown, CT 06457
• 

  $692,000 Sold Jun 20, 2025

  • 4,382 Sq Ft
  • $158/SF
  • 91 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2000

  34 Watch Hill Dr, Middletown, CT 06457

  Set high on Watch Hill, this stunning 3-4 bedroom, 2.5-bath Colonial offers breathtaking views and over 4,382 SqFt of living space on a 1.04-acre lot. The main level features gorgeous hardwood floors, a formal dining room, and a spacious living room with a cozy wood-burning fireplace. The chef's kitchen is a dream, with granite countertops, stainless steel appliances, a wall oven, a glass

  Joe Cafasso mygoodagent

  34 Watch Hill Dr, Middletown, CT 06457
• 

  Est $320,578 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,449 Sq Ft

  791 Long Hill Rd Unit F, Middletown, CT 06457

  791 Long Hill Rd Unit F, Middletown, CT 06457
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  /3

  $619,900 New Construction

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

  603 Higby Rd, Middletown, CT 06457

  This beautiful Cape with 1st floor primary offers it all. You will enjoy the classic historic Cape look on the exterior, framed by a center chimney with a brick-look style. 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 the back of the home which is one entire great room

  Mark Toledo Berkshire Hathaway NE Prop.

  603 Higby Rd, Middletown, CT 06457
• 

  $350,000 Sold Jun 20, 2025

  • 1,959 Sq Ft
  • $179/SF
  • 149 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  233 Barbara Rd, Middletown, CT 06457

  Tudor-Style Home simply oozing with charm in Middletown, CT! Step into timeless elegance with this vintage 1930 built home that offers an abundance of charm, space, and unique features. Nestled in a cute Middletown neighborhood, this residence is the perfect blend of classic details and modern conveniences. Key Features: Expansive Family Room with soaring cathedral ceilings and wood floors create

  Lisa McCarthy Coldwell Banker Realty

  233 Barbara Rd, Middletown, CT 06457
• 

  Est $273,274 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,729 Sq Ft

  7 W Meadow Ln Unit 6, Middletown, CT 06457

  7 W Meadow Ln Unit 6, Middletown, CT 06457
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  /3

  $632,400 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  602 Higby Rd, Middletown, CT 06457

  Expanded Colonial I - this stately home offers a spacious and dramatic first floor with two story entry and double sided balcony overlook. The large kitchen is open to eating area and large great room. One will enjoy a mudroom, first floor office and fantastic sized dining room. This amazing abode offers plenty of large windows throughout letting the outside in. The upstairs offers an oversized

  Mark Toledo Berkshire Hathaway NE Prop.

  602 Higby Rd, Middletown, CT 06457

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