Middletown, CT Homes

• 

  $505,000

  Sold Jun 30, 2026

  24 Meadowood Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 1,964 Sq Ft
  • Built 1965

  Last Sold Summary

  • 1% Above List Price
  • $257/SF
  • 5 Days On Market

  Current Estimated Value $498,576

  Last Listing Agent Mark Toledo Berkshire Hathaway NE Prop.

  24 Meadowood Dr, Middletown, CT 06457
• 

  Est $476,140

  Not Listed For Sale

  75 Knox Blvd, Middletown, CT 06457

  • 3 Beds
  • 3 Baths
  • 1,592 Sq Ft
  • Built 1983

  75 Knox Blvd, Middletown, CT 06457

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Rachael Cisz Serhant Connecticut, LLC
• 

  

  

  /28

  $219,900

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  868 Long Hill Rd, Middletown, CT 06457

  MULTIPLE OFFERS RECEIVED - PLEASE SUBMIT HIGHEST AND BEST BY END OF DAY MONDAY SEPT 7, 2026. Bring Your Vision to Wesleyan Hills! This is the kind of opportunity buyers love-a 3-bedroom, 11/2-bath townhouse in the desirable Wesleyan Hills community, priced more than $70,000 below other condos in the complex. If you've been looking for a home where you can put your own stamp on things and build

  Carol Wanat Rockoff Realty

  868 Long Hill Rd, Middletown, CT 06457
• 

  $1,875,000

  Sold Dec 22, 2025

  120 Chamberlain Hill Rd, Middletown, CT 06457

  • 4 Beds
  • 4.5 Baths
  • 5,661 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $331/SF
  • 67 Days On Market

  Current Estimated Value $1,880,559

  Last Listing Agent Jeff Petersen Century 21 AllPoints Realty

  120 Chamberlain Hill Rd, Middletown, CT 06457
• 

  Est $172,341

  Not Listed For Sale

  284 Carriage Crossing Ln, Middletown, CT 06457

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

  284 Carriage Crossing Ln, Middletown, CT 06457

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Nikki Defrancesco Coldwell Banker Realty
• 

  

  /24

  $299,900

  $50K PRICE DROP Pending

  • 4 Beds
  • 1 Bath
  • 1,509 Sq Ft

  475 Ballfall Rd, Middletown, CT 06457

  Welcome to this charming Colonial-style home set on a generous 3.3-acre lot, offering the perfect blend of comfort, space, and modern updates. The exterior showcases classic appeal with a welcoming front entry & an attached 2 car garage, all surrounded by open land that provides privacy and endless possibilities. Step inside to discover a beautifully updated kitchen featuring stainless steel

  Michelle Mazzotta eXp Realty

  475 Ballfall Rd, Middletown, CT 06457
• 

  $250,000

  Sold Apr 29, 2026

  7 Countryside Ln Unit 4, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Above List Price
  • $156/SF
  • 33 Days On Market

  Current Estimated Value $250,775

  Last Listing Agent Sally McMahon William Raveis Real Estate

  7 Countryside Ln Unit 4, Middletown, CT 06457
• 

  Est $186,922

  Not Listed For Sale

  126 Carriage Crossing Ln, Middletown, CT 06457

  • 1 Bed
  • 1 Bath
  • 670 Sq Ft
  • Built 1987

  126 Carriage Crossing Ln, Middletown, CT 06457

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Deborah Walden eXp Realty
• 

  

  /37

  $579,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft

  220 Randolph Rd, Middletown, CT 06457

  Welcome to 220 Randolph Rd - This spacious 4-bedroom, 2.5-bath Colonial offers the rare opportunity to enjoy 2.53 acres of privacy in the heart of Middletown. The first floor features a welcoming living room with a propane fireplace, an open-concept eat-in kitchen, and a convenient primary suite complete with a walk-in closet and a large en-suite bathroom featuring both a shower and jetted tub. A

  Alyssa Gambell William Raveis Real Estate

  220 Randolph Rd, Middletown, CT 06457
• 

  $365,000

  Sold Nov 19, 2025

  81 Dorothy Dr, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,346 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Above List Price
  • $271/SF
  • 29 Days On Market

  Current Estimated Value $377,633

  Last Listing Agent Nancy Newman LPT Realty

  81 Dorothy Dr, Middletown, CT 06457
• 

  Est $164,135

  Not Listed For Sale

  111 Dekoven Dr Unit 805, Middletown, CT 06457

  • 1 Bed
  • 1.5 Baths
  • 752 Sq Ft
  • Built 1989

  111 Dekoven Dr Unit 805, Middletown, CT 06457

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Jeremy Beamer Eagle Eye Realty PLLC
• 

  

  /40

  $649,900

  $25K PRICE DROP Under Contract

  • 4 Beds
  • 4 Baths
  • 2,671 Sq Ft

  76 Thimble Rock Rd, Middletown, CT 06457

  Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and

  Carl Guild Carl Guild & Associates

  76 Thimble Rock Rd, Middletown, CT 06457
• 

  $248,000

  Sold Jan 29, 2026

  88 Carriage Crossing Ln, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Above List Price
  • $261/SF
  • 25 Days On Market

  Current Estimated Value $254,348

  Last Listing Agent Mary Jean Agostini RE/MAX Right Choice

  88 Carriage Crossing Ln, Middletown, CT 06457
• 

  Est $270,812

  Not Listed For Sale

  2 Inverness Square, Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 2,312 Sq Ft
  • Built 1971

  2 Inverness Square, Middletown, CT 06457

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Linda Conchado Century 21 AllPoints Realty
• 

  

  /33

  $699,000

  $100K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 4,271 Sq Ft

  20 Chimney Hill Rd, Middletown, CT 06457

  Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering

  Joe Koontz eXp Realty

  20 Chimney Hill Rd, Middletown, CT 06457
• 

  $377,000

  Sold May 29, 2026

  32 Burr Ave, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,854 Sq Ft
  • Built 1928

  Last Sold Summary

  • 1% Below List Price
  • $203/SF
  • 19 Days On Market

  Current Estimated Value $371,418

  Last Listing Agent Michelle Mazzotta eXp Realty

  32 Burr Ave, Middletown, CT 06457
• 

  Est $495,912

  Not Listed For Sale

  654 Wadsworth St, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 2,905 Sq Ft
  • Built 1993

  654 Wadsworth St, Middletown, CT 06457

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Carlos Neves Real Estate Professionals LLC
• 

  

  /4

  $429,900

  Pending

  • 6 Beds
  • 3 Baths
  • 2,760 Sq Ft

  82 Westfield St, Middletown, CT 06457

  3 unit property for sale. Great investment opportunity or for owner occupant. Separate utilities. Some updates. Convenient to shopping, restaurants, highway access, recreation and entertainment.

  Phil Ledwith Century 21 AllPoints Realty

  82 Westfield St, Middletown, CT 06457
• 

  $415,000

  Sold Mar 13, 2026

  95 Training Hill Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Below List Price
  • $270/SF
  • 70 Days On Market

  Current Estimated Value $428,750

  Last Listing Agent Guillermo Araujo Five Stars Realty

  95 Training Hill Rd, Middletown, CT 06457
• 

  Est $531,892

  Not Listed For Sale

  565 Newfield St Unit 30, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,436 Sq Ft
  • Built 1991

  565 Newfield St Unit 30, Middletown, CT 06457

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Marybeth Barrett Berkshire Hathaway NE Prop.
• 

  

  /33

  $385,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  49 George St, Middletown, CT 06457

  Welcome home to this beautifully remodeled 3 bedroom, 2 full bath home that's truly move in ready! Enjoy relaxing on the inviting front porch or entertaining in the fenced backyard. The updated kitchen features stainless steel appliances, plenty of cabinet and counter space, and room for meal preparation. The spacious living room offers a cozy fireplace and new flooring, creating a warm and

  Lori Shaer eXp Realty

  49 George St, Middletown, CT 06457
• 

  $330,000

  Sold Aug 28, 2026

  37 Hotchkiss St, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,616 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $204/SF
  • 116 Days On Market

  Current Estimated Value $296,485

  Last Listing Agent Warren Juall HOMESELL

  37 Hotchkiss St, Middletown, CT 06457
• 

  Est $348,600

  Not Listed For Sale

  49 Hunting Hill Ave, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft
  • Built 1941

  49 Hunting Hill Ave, Middletown, CT 06457

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Natuzza Dimasi William Raveis Real Estate
• 

  

  /7

  $289,609

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,328 Sq Ft

  33 Inverness Ln, Middletown, CT 06457

  Welcome to this spacious move in ready four bedroom, two bath home located in the desirable Highland section of Middletown. This well maintained property features an updated kitchen with granite countertops and stainless steel appliances, offering both style and functionality. The first floor includes laminate flooring throughout the main living areas, while the bedrooms feature carpeting for

  Keith Murphy Innovative Properties

  33 Inverness Ln, Middletown, CT 06457
• 

  $349,900

  Sold Sep 25, 2026

  125 Stevens Ln, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1953

  Last Sold Summary

  • $210/SF
  • 77 Days On Market

  Current Estimated Value $352,719

  Last Listing Agent Wilson Lamas Regency Real Estate, LLC

  125 Stevens Ln, Middletown, CT 06457
• 

  Est $522,765

  Not Listed For Sale

  113 Scenic View Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,127 Sq Ft
  • Built 2006

  113 Scenic View Dr, Middletown, CT 06457

  Last Sold Summary

  • 111 Days On Market

  Last Listing Agent Dennis Gan Berkshire Hathaway NE Prop.
• 

  $425,000

  Sold May 01, 2026

  314 Timber Ridge Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1992

  Last Sold Summary

  • 12% Above List Price
  • $322/SF
  • 23 Days On Market

  Current Estimated Value $423,162

  Last Listing Agent Alana Wall-Galvin Suburban Homes & Condos

  314 Timber Ridge Rd, Middletown, CT 06457
• 

  Est $514,413

  Not Listed For Sale

  26 Elizabeth Ln, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,124 Sq Ft
  • Built 2000

  26 Elizabeth Ln, Middletown, CT 06457

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Tanya Bottaro Real Broker CT, LLC
• 

  $227,000

  Sold Jul 02, 2026

  56 Trolley Crossing Ln, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,136 Sq Ft
  • Built 1987

  Last Sold Summary

  • 14% Above List Price
  • $200/SF
  • 6 Days On Market

  Current Estimated Value $226,356

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

  56 Trolley Crossing Ln, Middletown, CT 06457
• 

  Est $401,472

  Not Listed For Sale

  598 E Main St, Middletown, CT 06457

  • 5 Beds
  • 2 Baths
  • 2,640 Sq Ft
  • Built 1850

  598 E Main St, Middletown, CT 06457

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Karly Worth Call It Closed Realty
• 

  $315,000

  Sold Jul 01, 2026

  1136 Randolph Rd, Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 1,028 Sq Ft
  • Built 1900

  Last Sold Summary

  • 5% Above List Price
  • $306/SF
  • 41 Days On Market

  Current Estimated Value $311,025

  Last Listing Agent Giulia Terese Hagel & Assoc. Real Estate

  1136 Randolph Rd, Middletown, CT 06457
• 

  Est $205,234

  Not Listed For Sale

  111 Dekoven Dr Unit 302, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • Built 1989

  111 Dekoven Dr Unit 302, Middletown, CT 06457

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Kim Rose Dave Jones Realty, LLC
• 

  $530,000

  Sold Jul 02, 2026

  26 Greenview Terrace, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Above List Price
  • $204/SF
  • 3 Days On Market

  Current Estimated Value $527,624

  Last Listing Agent Maryann Stanley Century 21 AllPoints Realty

  26 Greenview Terrace, Middletown, CT 06457
• 

  Est $498,557

  Not Listed For Sale

  31 Sherman Lee Dr, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,064 Sq Ft
  • Built 1999

  31 Sherman Lee Dr, Middletown, CT 06457

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Matt Donafrio GRL & Realtors, LLC
• 

  $525,000

  Sold Aug 20, 2026

  315 E Ridge Rd, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,645 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Above List Price
  • $198/SF
  • 38 Days On Market

  Current Estimated Value $492,898

  Last Listing Agent Lori Vogel William Raveis Real Estate

  315 E Ridge Rd, Middletown, CT 06457
• 

  Est $243,363

  Not Listed For Sale

  55 Rising Trail Dr, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1976

  55 Rising Trail Dr, Middletown, CT 06457

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Joshua Cataldo Compass Connecticut, LLC
• 

  $235,000

  Sold Sep 30, 2025

  11 Countryside Ln Unit 2, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Above List Price
  • $216/SF
  • 33 Days On Market

  Last Listing Agent Kristen Faraci Better Living Realty, LLC

  11 Countryside Ln Unit 2, Middletown, CT 06457
• 

  Est $507,796

  Not Listed For Sale

  510 Arbutus St, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 2,653 Sq Ft
  • Built 1948

  510 Arbutus St, Middletown, CT 06457

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Andrew Walker Compass Connecticut, LLC
• 

  $410,000

  Sold Oct 17, 2025

  60 Hemlock Place, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,285 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Above List Price
  • $319/SF
  • 6 Days On Market

  Current Estimated Value $415,027

  Last Listing Agent Richard Santana Cedar View Realty LLC

  60 Hemlock Place, Middletown, CT 06457
• 

  Est $508,112

  Not Listed For Sale

  70 Birchwood Dr, Middletown, CT 06457

  • 4 Beds
  • 3 Baths
  • 2,404 Sq Ft
  • Built 1961

  70 Birchwood Dr, Middletown, CT 06457

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Jennifer Hussey Century 21 Clemens Group

Showing Results 481 - 520, Page 13 of 18