Middletown, CT Homes

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  $359,000

  • 2 Beds
  • 1 Bath
  • 1,414 Sq Ft

  74 West St, Middletown, CT 06457

  Charming Cape with great potential and thoughtful updates! This inviting 2-bedroom, 1-bath home offers classic character with room to grow. The main level features two bedrooms, including a very large primary bedroom with ample closet space, providing convenient one-floor living. The finished second floor is currently being used as a flex-space, 3rd bedroom potential. With a little ingenuity,

  Michelle Pirruccio Carl Guild & Associates

  74 West St, Middletown, CT 06457
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  $1,500 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  652 High St, Middletown, CT 06457

  ! AVAILABLE IMMEDIATELY ! SUPERB 2ND FL, (2) BDR RENTAL OFFERING WITHIN MIDDLETOWN'S DOWNTOWN DISTRICT. UNIT IS POISED FOR MULTIPLE YEARS OF TENANT ENJOYMENT WITH ITS FRESH PAINT, REFINISHED HDWD FLOORING THROUGHOUT, NEW OR NEWER KITCHEN APPLIANCES, ENERGY-EFFICIENT WINDOWS, GAS-FIRED HEAT AND HOT WATER -AND- A WONDERFUL BATHROOM OFFERING A DEEP SOAKING TUB -PLUS- SEPARATE TILED SHOWER. IMMEDIATE

  Joseph Fasone Sunset Creek Realty, LLC

  652 High St, Middletown, CT 06457
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  $384,000 Sold May 08, 2026

  8 Macdonough Place, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,740 Sq Ft
  • Built 1923

  Last Sold Summary

  • $221/SF
  • 44 Days On Market

  Current Estimated Value $382,912

  Last Listing Agent Patricia Flynn Sterling REALTORS

  8 Macdonough Place, Middletown, CT 06457
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  Est $550,153 Not Listed For Sale

  795 Pine St, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,212 Sq Ft
  • Built 2007

  795 Pine St, Middletown, CT 06457

  Last Sold Summary

  • 10% Above List Price
  • $226/SF
  • 4 Days On Market

  • Last Sold Price $500,000
  • Apr 04, 2024

  Last Listing Agent Robert Durato Sentry Real Estate
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  $140,000

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft

  227 Burgundy Hill Ln Unit 227, Middletown, CT 06457

  Second Floor Townhouse style condo conveniently located in Middletown's Westfield area. Unit features 2 bedrooms, large living with vaulted ceilings, additional loft space could be used as 3rd bed or office space, in unit laundry, exterior storage closet, and balcony. Condo complex features inground pool, and is on direct access to the areas walking/biking trails, city bus line, and just minutes

  Michelle Manter Berkshire Hathaway NE Prop.

  227 Burgundy Hill Ln Unit 227, Middletown, CT 06457
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  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  36 Walnut St Unit 2, Middletown, CT 06457

  Bright and cheerful 2-bedroom, 1-bath apartment featuring a spacious kitchen with plenty of cabinets, hardwood floors, and great natural light throughout. Both bedrooms offer large walk-in closets, and the living room provides plenty of space for relaxing or dining. Includes off-street parking and access through a back entrance.

  Michael Bernard Ironclad Real Estate

  36 Walnut St Unit 2, Middletown, CT 06457
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  $500,000 Sold Jul 28, 2025

  26 Reno Dr, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,264 Sq Ft
  • Built 1999

  Last Sold Summary

  • $221/SF
  • 45 Days On Market

  Current Estimated Value $520,911

  Last Listing Agent Michelle MacNeil William Raveis Real Estate

  26 Reno Dr, Middletown, CT 06457
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  Est $465,005 Not Listed For Sale

  53 Mulberry Ln, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,783 Sq Ft
  • Built 1994

  53 Mulberry Ln, Middletown, CT 06457

  Last Sold Summary

  • 13% Above List Price
  • $230/SF
  • 3 Days On Market

  • Last Sold Price $410,000
  • Oct 20, 2023

  Last Listing Agent Tracey Precourt Century 21 Clemens Group
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  $750,000

  • Land
  • 7.5 Acres
  • $100,000 per Acre

  0 Middle St, Middletown, CT 06457

  7.5 Acres Commercial Industrial Land. Zoning: IOP (Industrial Office Park including office, warehouse, industrial & recreation. This parcel is going to be split off of a larger piece consisting of 28.96 acres. 8 acres of abutting residential land off Bell Street available for assemblage * Total Potential Assemblage: 41 acres * Immediate Access: Minutes to I-91 (Exit 20) Highly flexible IOP zoning

  Nancy Newman LPT Realty

  0 Middle St, Middletown, CT 06457
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  $389,900 Sold Nov 25, 2025

  163 Basswood Dr, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1965

  Last Sold Summary

  • $232/SF
  • 20 Days On Market

  Current Estimated Value $398,851

  Last Listing Agent Betsy Purtell Purtell Realty LLC

  163 Basswood Dr, Middletown, CT 06457
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  Est $485,311 Not Listed For Sale

  97 Mcdowell Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 2,200 Sq Ft
  • Built 1989

  97 Mcdowell Rd, Middletown, CT 06457

  Last Sold Summary

  • 5% Above List Price
  • $210/SF
  • 56 Days On Market

  • Last Sold Price $462,500
  • Oct 30, 2024

  Last Listing Agent Ela Konferowicz Golden Key Realty LLC
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  $300,000 Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,283 Sq Ft

  78 Highland Ave, Middletown, CT 06457

  Well maintained and thoughtfully updated, this home offers a combination of space, functionality, and value that's getting harder to find. Hardwood floors run throughout much of the home, adding warmth and character, while the layout provides flexibility for a variety of living needs. The main level features an updated kitchen that connects comfortably to the living space, where a fireplace

  Rob Paskiewicz CT Home Pro, LLC

  78 Highland Ave, Middletown, CT 06457
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  $350,000 Sold Apr 29, 2026

  117 S Main St, Middletown, CT 06457

  • 6 Beds
  • 2 Baths
  • 2,555 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Above List Price
  • $137/SF
  • 7 Days On Market

  Current Estimated Value $386,375

  Last Listing Agent Mark Toledo Berkshire Hathaway NE Prop.

  117 S Main St, Middletown, CT 06457
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  Est $348,847 Not Listed For Sale

  76 Hunting Hill Ave, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • Built 1949

  76 Hunting Hill Ave, Middletown, CT 06457

  Last Sold Summary

  • 26% Above List Price
  • $188/SF
  • 8 Days On Market

  • Last Sold Price $276,000
  • May 29, 2024

  Last Listing Agent Betsy Purtell Purtell Realty LLC
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  $845,000

  • 4 Beds
  • 1.5 Baths
  • 2,070 Sq Ft

  110 Freeman Rd, Middletown, CT 06457

  VERY unique property. Use to be a goat farm. Contains 6 outbuildings consisting of a 3 bay open shed - perfect for storing just about anything, a 3 story red bank barn, a 1 car detached heated garage with an office and a furnace with a separate oil tank, a feed shed, a detached garage for the house and an outhouse. The home has 4 bedroom on the 2nd floor, a walk up attic that is floored , a large

  Pam Rizy Berkshire Hathaway NE Prop.

  110 Freeman Rd, Middletown, CT 06457
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  $220,000 Sold Aug 29, 2025

  300 Carriage Crossing Ln Unit 300, Middletown, CT 06457

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

  Last Sold Summary

  • 3% Above List Price
  • $254/SF
  • 30 Days On Market

  Current Estimated Value $226,984

  Last Listing Agent Leticia Rodriguez Casa Mia Realty Corporation

  300 Carriage Crossing Ln Unit 300, Middletown, CT 06457
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  Est $388,410 Not Listed For Sale

  4 Blue Spruce St, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,718 Sq Ft
  • Built 1972

  4 Blue Spruce St, Middletown, CT 06457

  Last Sold Summary

  • 5% Above List Price
  • $215/SF
  • 6 Days On Market

  • Last Sold Price $370,000
  • Sep 29, 2023

  Last Listing Agent Jim Treanor Jr ERA Treanor Real Estate
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  $350,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 2,226 Sq Ft

  38 Johnson St, Middletown, CT 06457

  Looking for a charming home? This one is dying to meet you! Welcome to this character-filled Middletown home blending classic details with thoughtful updates. Freshly painted with original wood trim and refinished hardwood floors, it offers warmth and charm throughout. The kitchen features newer appliances, an antique sink, and great natural light with porch access. A dedicated laundry room

  Britany Goyen BB Realty CT

  38 Johnson St, Middletown, CT 06457
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  $210,000 Sold Nov 26, 2025

  71 E Main St, Middletown, CT 06457

  • 6 Beds
  • 3 Baths
  • 3,110 Sq Ft
  • Built 1900

  Last Sold Summary

  • 25% Below List Price
  • $68/SF
  • 83 Days On Market

  Current Estimated Value $375,776

  Last Listing Agent Connor Wenchell VC Property Group, LLC

  71 E Main St, Middletown, CT 06457
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  Est $234,300 Not Listed For Sale

  15 Forest Glen Cir Unit 10, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft
  • Built 1989

  15 Forest Glen Cir Unit 10, Middletown, CT 06457

  Last Sold Summary

  • 20% Above List Price
  • $183/SF
  • 5 Days On Market

  • Last Sold Price $195,000
  • Jan 04, 2024

  Last Listing Agent Stephen Mele Houlihan Lawrence
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  $229,900

  • 3 Beds
  • 1 Bath
  • 1,238 Sq Ft

  103 Grand St, Middletown, CT 06457

  Perfect opportunity for home ownership in Middletown! This 3 bedroom home offers an updated kitchen with quartz countertops and stainless steel appliances, large dining room perfect for entertaining, and beautiful living room arrangement with custom shiplap wall! Level lot with off street parking. Stop by for a showing today!

  Sylvia Narciso Bottom Line Realty

  103 Grand St, Middletown, CT 06457
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  $443,000 Sold Apr 24, 2026

  211 Boston Rd, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,596 Sq Ft
  • Built 1880

  Last Sold Summary

  • 11% Above List Price
  • $278/SF
  • 43 Days On Market

  Current Estimated Value $398,310

  Last Listing Agent Tina Lachance Berkshire Hathaway NE Prop.

  211 Boston Rd, Middletown, CT 06457
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  Est $385,964 Not Listed For Sale

  275 Middle St, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 1810

  275 Middle St, Middletown, CT 06457

  Last Sold Summary

  • 23% Above List Price
  • $158/SF
  • 83 Days On Market

  • Last Sold Price $315,000
  • Aug 21, 2024

  Last Listing Agent Brenden Hultgren Robert C White & Company LLC
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  $379,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft

  55 Saw Mill Rd, Middletown, CT 06457

  Set on a picturesque 1.4-acre lot and lovingly maintained by its original owner, 55 Saw Mill Road offers a rare opportunity to own a truly special property in Middletown. This home reflects years of meticulous care, with thoughtful upkeep evident throughout! One of the standout features is its exceptional setting-directly facing the Highland Pond Preserve. Enjoy peaceful views, natural beauty,

  Jeffrey Anderson William Pitt Sotheby's International Realty

  55 Saw Mill Rd, Middletown, CT 06457
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  $201,000 Sold Sep 18, 2025

  323 Carriage Crossing Ln, Middletown, CT 06457

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

  Last Sold Summary

  • 9% Above List Price
  • $300/SF
  • 27 Days On Market

  Current Estimated Value $195,626

  Last Listing Agent Carol Mancini William Pitt Sotheby's Int'l

  323 Carriage Crossing Ln, Middletown, CT 06457
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  Est $397,293 Not Listed For Sale

  271 Ridge Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  271 Ridge Rd, Middletown, CT 06457

  Last Sold Summary

  • 8% Above List Price
  • $264/SF
  • 19 Days On Market

  • Last Sold Price $369,000
  • Apr 03, 2024

  Last Listing Agent Edward Lawton iHeart Homes Real Estate LLC
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  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,309 Sq Ft

  11 Webster Ln Unit 6, Middletown, CT 06457

  Beautifully maintained single-family home located in a desirable 55+ community offering comfort, style & easy living. This open floor plan features a stunning kitchen with granite countertops, abundant cabinetry & a natural gas fireplace that creates a warm, inviting living space. Hardwood floors extend throughout the main level, including the spacious primary suite complete with a walk-in

  Michelle Mazzotta eXp Realty

  11 Webster Ln Unit 6, Middletown, CT 06457
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  $500,000 Sold Mar 18, 2026

  1 Jefferson Ave, Middletown, CT 06457

  • 5 Beds
  • 3 Baths
  • 3,546 Sq Ft
  • Built 1940

  Last Sold Summary

  • 11% Above List Price
  • $141/SF
  • 3 Days On Market

  Current Estimated Value $484,069

  Last Listing Agent Britany Goyen BB Realty CT

  1 Jefferson Ave, Middletown, CT 06457
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  Est $336,585 Not Listed For Sale

  455 West St, Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 1,604 Sq Ft
  • Built 1948

  455 West St, Middletown, CT 06457

  Last Sold Summary

  • 5% Above List Price
  • $200/SF
  • 21 Days On Market

  • Last Sold Price $320,000
  • Jul 08, 2024

  Last Listing Agent Ana Russo William Pitt
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  $364,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,052 Sq Ft

  160 Boston Rd, Middletown, CT 06457

  Step into timeless New England charm with this beautifully updated historic colonial farmhouse that perfectly blends classic character with modern comfort. Every corner of this home reflects care and craftsmanship, with thoughtful improvements that make it both beautiful and reliable for years to come. The property features a freshly updated exterior, structural enhancements, a newer roof (2024

  Emily Braman Berkshire Hathaway NE Prop.

  160 Boston Rd, Middletown, CT 06457
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  $264,000 Sold Aug 28, 2025

  23 Rising Trail Dr Unit C, Middletown, CT 06457

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

  Last Sold Summary

  • 2% Above List Price
  • $236/SF
  • 13 Days On Market

  Last Listing Agent Carrie Vass Brainerd Carbutti & Co., Realtors

  23 Rising Trail Dr Unit C, Middletown, CT 06457
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  Est $327,377 Not Listed For Sale

  37 Roberts St, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1919

  37 Roberts St, Middletown, CT 06457

  Last Sold Summary

  • 7% Above List Price
  • $246/SF
  • 26 Days On Market

  • Last Sold Price $306,500
  • Jan 15, 2025

  Last Listing Agent Taylor Spadacenta Real Broker CT, LLC
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  $217,500 Under Contract

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

  36 Rising Trail Dr Unit 36, Middletown, CT 06457

  Prime location near the pool & clubhouse - just in time for Summer! Welcome to 36 Rising Trail Drive, a beautifully maintained condo nestled in the desirable Westlake area of Middletown. This spacious unit offers a bright and open layout with generous living and dining areas, perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, ample counter space, and

  Kervin Figaro Five Stars Realty

  36 Rising Trail Dr Unit 36, Middletown, CT 06457
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  $325,000 Sold Oct 07, 2025

  24 Stantack Rd, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Built 1966

  Last Sold Summary

  • 14% Above List Price
  • $231/SF
  • 26 Days On Market

  Current Estimated Value $353,530

  Last Listing Agent Kevin Green Berkshire Hathaway NE Prop.

  24 Stantack Rd, Middletown, CT 06457
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  Est $179,539 Not Listed For Sale

  19 Trolley Crossing Ln, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Built 1987

  19 Trolley Crossing Ln, Middletown, CT 06457

  Last Sold Summary

  • 6% Above List Price
  • $197/SF
  • 32 Days On Market

  • Last Sold Price $169,500
  • May 22, 2023

  Last Listing Agent Geoff Luxenberg Century 21 Classic Homes
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  $1,500,000 Pending

  • 1 Bed
  • 1 Bath
  • 11,033 Sq Ft

  530 Main St, Middletown, CT 06457

  Prime Mixed-Use Investment Opportunity - Downtown Middletown, CT. This asset currently produces 9.7 cap annually, features a total of 16 units, including 4 retail storefronts and 12 on1-bedroom residential apartments. The retail spaces are currently occupied by established neighborhood businesses, including a grocery store, Boost Mobile, a barber shop, and a convenience store-providing steady

  Geni Silva Ethos Rlty, LLC

  530 Main St, Middletown, CT 06457
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  $425,000 Sold Oct 14, 2025

  80 Pond Place, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • Built 1995

  Last Sold Summary

  • 9% Above List Price
  • $254/SF
  • 4 Days On Market

  Current Estimated Value $438,576

  Last Listing Agent Robin Thurston Coldwell Banker Realty

  80 Pond Place, Middletown, CT 06457
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  Est $302,267 Not Listed For Sale

  1195 S Main St, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Built 1900

  1195 S Main St, Middletown, CT 06457

  Last Sold Summary

  • 6% Above List Price
  • $224/SF
  • 12 Days On Market

  • Last Sold Price $285,000
  • Aug 27, 2024

  Last Listing Agent Joe Fazzino eXp Realty
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  /23

  $479,900

  • 3 Beds
  • 3 Baths
  • 2,030 Sq Ft

  25 Pleasant View Dr, Middletown, CT 06457

  Welcome to 25 Pleasant View Drive in the highly desirable Westfield section of Middletown. A completely updated home nestled on a quiet cul-de-sac, offering the perfect blend of comfort, style and functionality. This inviting property features large, sun filled rooms and beautiful hardwood floors throughout the main living areas, adding warmth and appeal. The spacious living room is highlighted

  Gregory Domingue Coldwell Banker Realty

  25 Pleasant View Dr, Middletown, CT 06457
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  $520,000 Sold Oct 27, 2025

  16 Snow Ridge S, Middletown, CT 06457

  • 4 Beds
  • 2.5 Baths
  • 2,813 Sq Ft
  • Built 1989

  Last Sold Summary

  • 8% Below List Price
  • $185/SF
  • 92 Days On Market

  Current Estimated Value $553,658

  Last Listing Agent Justin Marino Marino Realty LLC

  16 Snow Ridge S, Middletown, CT 06457

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