Middletown, CT Homes

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  /38

  $550,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,708 Sq Ft

  26 Tuscany Hills Dr, Middletown, CT 06457

  Welcome to 26 Tuscany Hills Drive, a beautifully maintained single-family ranch home loaded with charm and upgrades in this pet-friendly, 55+ active adult community! Rich hardwood floors grace the main living areas, while plush carpeting in both bedrooms adds warmth and comfort, creating an inviting atmosphere you'll love coming home to. The spacious living room features a cozy propane fireplace

  Heather Dacey William Raveis Real Estate

  26 Tuscany Hills Dr, Middletown, CT 06457
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  /40

  Starting at $1,670

  Total Monthly Price

  • 1 - 2 Beds

  121-122 Rose Cir, Middletown, CT 06457

  Offering spacious one and two bedroom flats, as well as two and three bedroom townhomes, Meadoway Gardens is conveniently located to shopping, restaurants, schools and the highway. Meadoway is a pedestrian friendly neighborhood with ample off-street parking. The grounds are professionally landscaped by Carabetta's 24 hour Maintenance Team who implement a landscaping plan to provide seasonal color

  Meadoway Gardens

  

  121-122 Rose Cir, Middletown, CT 06457
• 

  $325,000

  Sold Jan 29, 2026

  84 Camp St, Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 1,064 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Above List Price
  • $305/SF
  • 46 Days On Market

  Current Estimated Value $333,342

  Last Listing Agent Emily Curtis William Raveis Real Estate

  84 Camp St, Middletown, CT 06457
• 

  Not Listed For Sale

  896 East St, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2025

  896 East St, Middletown, CT 06457

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Geraldine Mattera Luxe Realty LLC
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  /34

  $1,300,000

  • 12 Beds
  • 8 Baths
  • 9,890 Sq Ft

  13 Portland St, Middletown, CT 06457

  Unique mixed-use opportunity in Middletown offering strong cash flow and flexible ownership potential. Property consists of a fully occupied 4-family, a fully occupied 2-family, and two 1,600 SF commercial garage/workshop spaces all situated on one lot with views of the Connecticut River and Arrigoni Bridge. One commercial space is leased, while the second vacant garage offers ideal owner-user

  Sacha Armstrong William Pitt Sotheby's International Realty

  13 Portland St, Middletown, CT 06457
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  /40

  Starting at $2,177

  Total Monthly Price

  • 2 Beds

  72 Forest Glen Cir, Middletown, CT 06457

  Welcome to Windshire Terrace Apartments in Middletown, CT! Our spacious two bedroom apartments, plus three bedroom townhome feature a cozy fireplace, perfect for relaxing on chilly evenings. Enjoy the convenience of having a washer and dryer right in your own unit, making laundry day a breeze. The walk-in closets provide ample storage space for all your belongings. With a prime location in

  Windshire Terrace

  

  72 Forest Glen Cir, Middletown, CT 06457
• 

  $747,925

  Sold May 14, 2026

  128 Webster Ln, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Above List Price
  • $481/SF
  • 14 Days On Market

  Last Listing Agent Sally Annino Berkshire Hathaway NE Prop.

  128 Webster Ln, Middletown, CT 06457
• 

  Est $239,459

  Not Listed For Sale

  289 Carriage Crossing Ln Unit 289, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Built 1988

  289 Carriage Crossing Ln Unit 289, Middletown, CT 06457

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Lauren Iraeta KW Legacy Partners
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  /35

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,352 Sq Ft

  104 Bell St, Middletown, CT 06457

  Welcome to 104 Bell Street - a rare find on 2.6 private acres in the heart of Middletown. This 4-bedroom, 2 full bath home offers a truly unique setting where you drive down a long, secluded driveway and cross a bridge over Sawmill Brook to arrive at your own private oasis. Fully updated throughout, this home features a renovated kitchen, updated bathrooms, new flooring, new 200-amp electrical

  Warren Juall HOMESELL

  104 Bell St, Middletown, CT 06457
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  /40

  Starting at $1,949

  Total Monthly Price

  • 1 - 3 Beds

  5 Town Colony Dr, Middletown, CT 06457

  Welcome to Northwoods East in Middletown, CT! Our one bedroom or three bedroom apartments offer the convenience of a private balcony or patio, perfect for enjoying the fresh air and sunshine. Inside, you'll find the convenience of a washer and dryer right in your unit, making laundry day a breeze. The spacious walk-in closets provide ample storage for all your belongings. With these amenities,

  Northwoods East

  

  5 Town Colony Dr, Middletown, CT 06457
• 

  $450,000

  Sold Nov 21, 2025

  90 Briarwood Ln, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Built 1996

  Last Sold Summary

  • $298/SF
  • 31 Days On Market

  Current Estimated Value $467,865

  Last Listing Agent Lori Geraci BHGRE Gaetano Marra Homes

  90 Briarwood Ln, Middletown, CT 06457
• 

  Not Listed For Sale

  8K Rising Trail Ct, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,232 Sq Ft
  • Built 1976

  8K Rising Trail Ct, Middletown, CT 06457

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Jim Treanor Jr ERA Treanor Real Estate
• 

  

  /17

  $589,900

  New Construction $40K PRICE INCREASE

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

  137 Webster Ln Unit 2-42, Middletown, CT 06457

  Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "MARTIN II," Under CONSTRUCTION! Now with many new UPGRADES - available for occupancy in early 2027 Located in the highly sought-after Westfield section of Middletown, this beautiful 1,430 sq. ft. home has the convenience of single-floor living with top-of-the-line features and Elegant Design:

  Phyllis Bysiewicz Berkshire Hathaway NE Prop.

  137 Webster Ln Unit 2-42, Middletown, CT 06457
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  /27

  Starting at $1,600 Plus Fees

  • 1 - 3 Beds

  305 S Main St, Middletown, CT 06457

  Stunning remodeled units available now! Call/text manager for details! Don't miss out on this opportunity!

  The Wilcox

  305 S Main St, Middletown, CT 06457
• 

  $505,000

  Sold May 22, 2026

  58 Morning Glory Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,360 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Above List Price
  • $214/SF
  • 8 Days On Market

  Current Estimated Value $503,164

  Last Listing Agent Mark Toledo Berkshire Hathaway NE Prop.

  58 Morning Glory Dr, Middletown, CT 06457
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  Not Listed For Sale

  311 Main Street Extension, Middletown, CT 06457

  • Built 1936

  311 Main Street Extension, Middletown, CT 06457

  Last Sold Summary

  • 144 Days On Market

  Last Listing Agent Patrick Savarese LPT Realty
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  /32

  $549,000

  New Construction Pending

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  18 Talcott Ridge Dr, Middletown, CT 06457

  Award-winning builder, Reinhard Von Hollander proudly presents "The Cameron", one of his most sought-after models; sure to please the most discerning buyer. Quality and design meet as the home features a customizable, open floor plan, presenting future homeowners with an opportunity to make the space truly their own. It comes with 3 bedrooms and 2 full baths, including a spacious primary suite.

  Nick DeLuca eXp Realty

  18 Talcott Ridge Dr, Middletown, CT 06457
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  Starting at $1,133

  Total Monthly Price

  • Studio - 2 Beds

  352 Newfield St, Middletown, CT 06457

  Stoneycrest Towers is a 50 year old and older community offering spacious studio, one and two bedroom apartments in a pedestrian friendly neighborhood within close proximity to shopping, restaurants, bus lines and highways. A Resident Service Coordinator is onsite for the residents during business hours, located in the property's community room. All units are handicap accessible via elevators.

  Stoneycrest Tower

  

  352 Newfield St, Middletown, CT 06457
• 

  $330,000

  Sold May 22, 2026

  207 Pearl St, Middletown, CT 06457

  • 6 Beds
  • 2 Baths
  • 1,818 Sq Ft
  • Built 1900

  Last Sold Summary

  • $182/SF
  • 96 Days On Market

  Current Estimated Value $330,454

  Last Listing Agent Wendi Zuk Homes Plus of Connecticut

  207 Pearl St, Middletown, CT 06457
• 

  Est $636,307

  Not Listed For Sale

  10 Jack English Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,226 Sq Ft
  • Built 2023

  10 Jack English Dr, Middletown, CT 06457

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Vik Khandai Dave Jones Realty, LLC
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  /40

  $465,000

  New Construction Open Sat 10AM - 12PM

  • 2 Beds
  • 2.5 Baths
  • 1,525 Sq Ft

  61 West St Unit 15, Middletown, CT 06457

  Experience elevated living in this brand-new luxury townhome, thoughtfully designed with quality craftmanship, modern finishes, and an open concept layout ideal for everyday living and entertaining. This is a spacious 2 bedroom 2.5 bath home. The chef-inspired kitchen showcases GE stainless steel appliances, white shaker cabinetry, premium quartz countertops, sleek black hardware, and

  Milena Mineri Social & Co Realty

  61 West St Unit 15, Middletown, CT 06457
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  /35

  Starting at $1,500 Plus Fees

  • 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

  Woodrow Wilson Apartments

  

  339 Hunting Hill Ave, Middletown, CT 06457
• 

  $305,000

  Sold Dec 12, 2025

  37 Front St, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,384 Sq Ft
  • Built 1924

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 5 Days On Market

  Current Estimated Value $317,117

  Last Listing Agent Brenda Hanley Berkshire Hathaway NE Prop.

  37 Front St, Middletown, CT 06457
• 

  Not Listed For Sale

  51 Rising Trail Dr Unit 51, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,232 Sq Ft
  • Built 1976

  51 Rising Trail Dr Unit 51, Middletown, CT 06457

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Allison Hughes William Raveis Real Estate
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  /40

  $309,000

  Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,246 Sq Ft

  34 Franklin St, Middletown, CT 06457

  Move right in! 34 Franklin Street is a well-cared-for Middletown split-level offering 3 bedrooms, 1 fully renovated bath, and 966 sq ft of comfortable living. Highlights include hardwood flooring, an eat-in kitchen with sliders to a huge covered deck, and a spa-style bathroom with a walk-in shower, built-in seat, and skylight. Outside, enjoy a private, fenced 0.16-acre yard with mature trees and

  Chaz Koch William Raveis Real Estate

  34 Franklin St, Middletown, CT 06457
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  /35

  Starting at $1,450 Plus Fees

  • 1 - 2 Beds

  1150-1160 S Main St, Middletown, CT 06457

  Stonegate Apartments – Middletown, CTWelcome to Stonegate Apartments, where comfort and convenience meet. Our spacious apartments are designed for easy living, with heat and hot water included in your rent so you can enjoy peace of mind all year round.Relax and unwind with our community amenities, including a sparkling outdoor pool, a fully equipped fitness center, and a lively

  StoneGate Apartments

  1150-1160 S Main St, Middletown, CT 06457
• 

  $585,000

  Sold Nov 18, 2025

  23 Falmouth Ct, Middletown, CT 06457

  • 5 Beds
  • 2.5 Baths
  • 2,760 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $212/SF
  • 74 Days On Market

  Current Estimated Value $619,741

  Last Listing Agent Kristin Callahan eXp Realty

  23 Falmouth Ct, Middletown, CT 06457
• 

  Not Listed For Sale

  503 Cambridge Common Unit 503, Middletown, CT 06457

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft
  • Built 1988

  503 Cambridge Common Unit 503, Middletown, CT 06457

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Kelly Harvey Best Real Estate Brokerage LLC
• 

  

  /35

  $375,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,446 Sq Ft

  72 Durant Terrace, Middletown, CT 06457

  Built in 2010 and meticulously maintained, this Cape-style home offers the perfect blend of comfort, flexibility, and peace of mind. From the moment you arrive, you'll appreciate that everything has already been done for you - simply move in and enjoy. Inside, hardwood floors flow throughout the main level, where the versatile layout is designed to fit a variety of lifestyles. The spacious

  Michelle Pirruccio Carl Guild & Associates

  72 Durant Terrace, Middletown, CT 06457
• 

  

  /35

  Starting at $1,941

  Total Monthly Price

  • 1 - 3 Beds

  10 Town Place, Middletown, CT 06457

  Comfortable living without the luxury price tag. Newly updated 1, 2, and 3 bedroom apartment homes, some with stainless steel appliances, full-size washers & dryers, private patios and balconies, ample parking, and private entries.

  Town Place

  

  10 Town Place, Middletown, CT 06457
• 

  $408,000

  Sold Oct 15, 2025

  22 Belvidere Terrace, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,960 Sq Ft
  • Built 1937

  Last Sold Summary

  • 2% Above List Price
  • $208/SF
  • 43 Days On Market

  Current Estimated Value $453,573

  Last Listing Agent Michelle MacNeil William Raveis Real Estate

  22 Belvidere Terrace, Middletown, CT 06457
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  Not Listed For Sale

  00 Livingston Rd, Middletown, CT 06457

  00 Livingston Rd, Middletown, CT 06457

  Last Sold Summary

  • 172 Days On Market

  Last Listing Agent Tim O'Hara William Raveis Real Estate
• 

  

  /17

  $549,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,761 Sq Ft

  3 Nathan Hale Rd, Middletown, CT 06457

  Welcome to Nathan Hale Estates, Middletown's thoughtfully designed private-way community built by Silvin Homes, where timeless design, quality craftsmanship, and modern comfort come together effortlessly. This beautifully designed new construction colonial offers an elegant open-concept layout with thoughtfully created living spaces and high-end finishes. The main level features a beautifully

  Jenna Talbot RE/MAX One

  3 Nathan Hale Rd, Middletown, CT 06457
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  /36

  Starting at $500

  Total Monthly Price

  • 2 Beds

  80 Ferry St, Middletown, CT 06457

  Discover a community that inspires a lifestyle of convenience while elevating the standard of affordable apartment living. Nestled in the riverfront city of Middletown, CT, Wharfside Commons is just minutes from top-rated dining, exciting outdoor ventures, and local craft breweries! Find your home among thoughtfully designed amenities, sleek interiors, and spacious one, two, and three-bedroom

  Wharfside Commons

  

  80 Ferry St, Middletown, CT 06457
• 

  $404,900

  Sold Feb 02, 2026

  4 Lorraine Terrace, Rockfall, CT 06481

  • 3 Beds
  • 1.5 Baths
  • 1,672 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $242/SF
  • 21 Days On Market

  Current Estimated Value $406,032

  Last Listing Agent rob link Sterling REALTORS

  4 Lorraine Terrace, Rockfall, CT 06481
• 

  Not Listed For Sale

  0 Kelsey St, Middletown, CT 06457

  0 Kelsey St, Middletown, CT 06457

  Last Sold Summary

  • 117 Days On Market

  Last Listing Agent Dale Bunn Riverview Realty, LLC
• 

  

  /15

  $162,900

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  23 Mckenna Dr, Middletown, CT 06457

  Welcome to your new home in the Wadsworth Grove Co-op Community! This 3-bedroom, 1.5-bath property is super comfy and has everything you need. Step inside and you'll find a clean, open layout that lets in tons of natural light, perfect for making the refinished hardwood floors (and all the other new flooring!) really shine. Just off the living room, there's a lovely private patio with beautiful

  Kelvin Wilson Berkshire Hathaway NE Prop.

  23 Mckenna Dr, Middletown, CT 06457
• 

  

  /31

  Starting at $1,250 Plus Fees

  • Studio - 1 Bed

  62 Loveland St, Middletown, CT 06457

  Contemporary one bedroom apartment in beautiful brick building originally built as an elementary school in 1936. Studio apartment with high ceilings, large windows, and storage loft. Kitchen with stove, dishwasher, refrigerator. Full bath.Coin laundry in building. Parking. Intercom entry. No pets, Non-smoking building. Within walking distance to Wesleyan University, Middlesex Hospital, and

  Stillman School Apartments

  

  62 Loveland St, Middletown, CT 06457
• 

  $660,000

  Sold Jul 08, 2026

  60 Watch Hill Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft
  • Built 1999

  Last Sold Summary

  • 2% Below List Price
  • $307/SF
  • 48 Days On Market

  Current Estimated Value $678,271

  Last Listing Agent Stephanie Liriano Redfin Corporation

  60 Watch Hill Dr, Middletown, CT 06457
• 

  Est $242,740

  Not Listed For Sale

  6 Countryside Ln Unit 2, Middletown, CT 06457

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

  6 Countryside Ln Unit 2, Middletown, CT 06457

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Heather Kilbourn Cavanaugh & Company LLC

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