Middletown, CT Homes

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  $499,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  2 Nathan Hale Rd, Middletown, CT 06457

  Experience one-floor living at its finest at Nathan Hale Estates, a private-way community nestled in Middletown, Connecticut, built by Silvin Homes and offering modern comfort, quality craftsmanship, and peaceful surroundings. Entering from the covered front porch, you're welcomed into a thoughtfully designed layout. Features include a convenient laundry room and two well-appointed secondary

  Jenna Talbot RE/MAX One

  2 Nathan Hale Rd, Middletown, CT 06457
• 

  $800,000

  Sold Sep 02, 2025

  98 Ryefield Rd, Middletown, CT 06457

  • 3 Beds
  • 6 Baths
  • 4,863 Sq Ft
  • Built 1995

  Last Sold Summary

  • 6% Below List Price
  • $165/SF
  • 58 Days On Market

  Current Estimated Value $881,735

  Last Listing Agent Stacey McPherson KW Legacy Partners

  98 Ryefield Rd, Middletown, CT 06457
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  Est $622,049

  Not Listed For Sale

  35 Mcgrath Dr, Middletown, CT 06457

  • 4 Beds
  • 4 Baths
  • 3,488 Sq Ft
  • Built 1990

  35 Mcgrath Dr, Middletown, CT 06457

  Last Sold Summary

  • 107 Days On Market

  Last Listing Agent Frederick Ferguson Carl Guild & Associates
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  /40

  $224,900

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,206 Sq Ft

  78 Trolley Crossing Ln, Middletown, CT 06457

  Fabulous Opportunity to Own One of The Most Desirable Units in the Complex!! This Rarely Available End Unit Offers Exceptional Privacy & the Peaceful Setting You've Been Waiting For!! Beautifully Maintained, Move-In Ready Townhome Located In the Highly Sought After Trolley Crossing Community!! Freshly Painted Throughout Including Walls, Trim & Ceilings Creating a Bright & Inviting Feel!! New

  MaryJo Dunn William Raveis Real Estate

  78 Trolley Crossing Ln, Middletown, CT 06457
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  $225,000

  Sold Jan 09, 2026

  3 Trolley Crossing Ln, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,220 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Below List Price
  • $184/SF
  • 52 Days On Market

  Current Estimated Value $231,823

  Last Listing Agent Linda Muraski Century 21 Classic Homes

  3 Trolley Crossing Ln, Middletown, CT 06457
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  Est $291,882

  Not Listed For Sale

  171 Markham St, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,092 Sq Ft
  • Built 1950

  171 Markham St, Middletown, CT 06457

  Last Sold Summary

  • 109 Days On Market

  Last Listing Agent Arben Belica William Raveis Real Estate
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  /15

  $379,000

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  7 Reservoir Rd, Middletown, CT 06457

  Built in 1979, this beautifully updated Cape Cod offers the perfect blend of timeless charm and modern convenience. This move-in-ready home features an updated kitchen, three spacious bedrooms, and two full bathrooms, along with a flexible floor plan designed to accommodate a variety of lifestyles. Step outside to enjoy the stunning stamped concrete patio and expansive backyard-perfect for

  Michael Burke Clover Realty Group, LLC

  7 Reservoir Rd, Middletown, CT 06457
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  $124,000

  Sold Jul 31, 2026

  23 Burgundy Hill Ln, Middletown, CT 06457

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

  Last Sold Summary

  • 5% Below List Price
  • $168/SF
  • 27 Days On Market

  Current Estimated Value $130,357

  Last Listing Agent Michelle Mazzotta eXp Realty

  23 Burgundy Hill Ln, Middletown, CT 06457
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  Est $490,903

  Not Listed For Sale

  214 Plumb Rd, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,098 Sq Ft
  • Built 1967

  214 Plumb Rd, Middletown, CT 06457

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Debbie Huscher Real Broker CT, LLC
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  $299,900

  $50K PRICE DROP

  • 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
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  $167,700

  Sold Mar 19, 2026

  285 Carriage Crossing Ln Unit 285, Middletown, CT 06457

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

  Last Sold Summary

  • 5% Above List Price
  • $250/SF
  • 25 Days On Market

  Current Estimated Value $166,169

  Last Listing Agent Eric Ellison Better Homes and Gardens Real Estate Executive Real Estate

  285 Carriage Crossing Ln Unit 285, Middletown, CT 06457
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  Est $496,043

  Not Listed For Sale

  45 Sand Hill Rd, Middletown, CT 06457

  • 4 Beds
  • Built 2024

  45 Sand Hill Rd, Middletown, CT 06457

  Last Sold Summary

  • 337 Days On Market

  Last Listing Agent Dale Bunn Riverview Realty, LLC
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  /24

  $273,000

  Pending

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  65 Deerfield Ave, Middletown, CT 06457

  Welcome home to this lovingly maintained Cape Cod-style house with the convenience of one-floor living in the highly desireable South Farm neighborhood. This charming home features a spacious two-bedroom layout filled with natural sunlight throughout. The inviting eat-in kitchen is equipped with off-white cabinetry, stainless steel appliances, and a durable tiled floor, creating a bright and

  Emily Curtis William Raveis Real Estate

  65 Deerfield Ave, Middletown, CT 06457
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  $349,900

  Sold Aug 29, 2025

  153 Barbara Rd, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,242 Sq Ft
  • Built 1939

  Last Sold Summary

  • 17% Above List Price
  • $282/SF
  • 3 Days On Market

  Current Estimated Value $355,971

  Last Listing Agent Karen Mendes Berkshire Hathaway NE Prop.

  153 Barbara Rd, Middletown, CT 06457
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  Est $331,280

  Not Listed For Sale

  35 Arnold St, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,109 Sq Ft
  • Built 1938

  35 Arnold St, Middletown, CT 06457

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Jaime Russo Calcagni Real Estate
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  /40

  $649,900

  $25K PRICE DROP

  • 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
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  $325,000

  Sold Oct 08, 2025

  181 Fowler Ave, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Above List Price
  • $198/SF
  • 8 Days On Market

  Current Estimated Value $338,263

  Last Listing Agent Mikell Foggitt Margaret Bennett Realty

  181 Fowler Ave, Middletown, CT 06457
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  Est $684,646

  Not Listed For Sale

  41 Annello Way, Middletown, CT 06457

  • 5 Beds
  • 3.5 Baths
  • 3,121 Sq Ft
  • Built 2006

  41 Annello Way, Middletown, CT 06457

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Stefania Bramato Berkshire Hathaway NE Prop.
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  $174,500

  $25K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,054 Sq Ft

  201 College St Unit 22, Middletown, CT 06457

  Welcome to Hamilton Court! This beautifully remodeled 2 bedroom, 1.5 bath townhouse offers stylish updates, low-maintenance living, and an unbeatable location just one block from Wesleyan University. Renovated within the last year, this move-in-ready home features a remodeled kitchen with updated appliances, renovated bathrooms, new flooring, brand-new carpeting, freshly painted walls and trim,

  kathleen mullins Real Broker CT, LLC

  201 College St Unit 22, Middletown, CT 06457
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  $200,000

  Sold Aug 28, 2025

  92 Cynthia Ln Unit E1, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Built 1977

  Last Sold Summary

  • 9% Below List Price
  • $215/SF
  • 29 Days On Market

  Current Estimated Value $213,485

  Last Listing Agent Matt Diamond Houlihan Lawrence WD

  92 Cynthia Ln Unit E1, Middletown, CT 06457
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  Est $222,898

  Not Listed For Sale

  111 Dekoven Dr Unit 1201, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,034 Sq Ft
  • Built 1989

  111 Dekoven Dr Unit 1201, Middletown, CT 06457

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Margaret Foran Berkshire Hathaway NE Prop.
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  $799,000

  • 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
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  $281,000

  Sold Jul 09, 2026

  183 Carriage Crossing Ln Unit 183, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Above List Price
  • $255/SF
  • 27 Days On Market

  Current Estimated Value $253,836

  Last Listing Agent Amy Balko RE/MAX Right Choice

  183 Carriage Crossing Ln Unit 183, Middletown, CT 06457
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  Est $473,082

  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
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  $385,000

  • 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
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  $225,000

  Sold Jan 06, 2026

  130 Carriage Crossing Ln Unit 130, Middletown, CT 06457

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

  Last Sold Summary

  • 6% Below List Price
  • $268/SF
  • 21 Days On Market

  Current Estimated Value $228,201

  Last Listing Agent Michael DuMouchel Berkshire Hathaway NE Prop.

  130 Carriage Crossing Ln Unit 130, Middletown, CT 06457
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  Est $169,615

  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
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  $299,609

  • 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
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  $345,000

  Sold May 20, 2026

  166 Ridge Rd, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,488 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Above List Price
  • $232/SF
  • 8 Days On Market

  Current Estimated Value $340,837

  Last Listing Agent Laura Russo Regency Real Estate, LLC

  166 Ridge Rd, Middletown, CT 06457
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  Est $183,119

  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
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  $198,000

  Sold Sep 04, 2025

  110 Trolley Crossing Ln, Middletown, CT 06457

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

  Last Sold Summary

  • 7% Above List Price
  • $230/SF
  • 48 Days On Market

  Current Estimated Value $196,626

  Last Listing Agent Euna Cho Naples Realty Group, LLC

  110 Trolley Crossing Ln, Middletown, CT 06457
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  Est $162,564

  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
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  $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 $477,703

  Last Listing Agent Mark Toledo Berkshire Hathaway NE Prop.

  24 Meadowood Dr, Middletown, CT 06457
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  Est $169,317

  Not Listed For Sale

  1251 Washington St Unit 6, Middletown, CT 06457

  • 1 Bed
  • 1 Bath
  • 806 Sq Ft
  • Built 1985

  1251 Washington St Unit 6, Middletown, CT 06457

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Rachel Welch William Raveis Real Estate
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  $363,000

  Sold Aug 15, 2025

  44 Durwin St, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 1,490 Sq Ft
  • Built 1951

  Last Sold Summary

  • 12% Above List Price
  • $244/SF
  • 17 Days On Market

  Current Estimated Value $369,786

  Last Listing Agent Scott Sasinouski LPT Realty

  44 Durwin St, Middletown, CT 06457
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  Est $275,036

  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
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  $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 $1,904,190

  Last Listing Agent Jeff Petersen Century 21 AllPoints Realty

  120 Chamberlain Hill Rd, Middletown, CT 06457
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  Est $499,588

  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
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  $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 $250,124

  Last Listing Agent Sally McMahon William Raveis Real Estate

  7 Countryside Ln Unit 4, Middletown, CT 06457
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  Est $545,368

  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.

Showing Results 441 - 480, Page 12 of 18