Middletown, CT Homes

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  $925,000 Open Sat 12PM - 3PM

  • 6 Beds
  • 3.5 Baths
  • 5,599 Sq Ft

  44 Chamberlain Hill Rd, Middletown, CT 06457

  Experience over 5,500 square feet of beautifully updated living space in this fully remodeled 6+ bedroom, 3.5-bath residence, perfectly situated on a quiet and expansive 8+ acre lot. Every detail has been thoughtfully upgraded, creating a truly move-in-ready home offering exceptional flexibility and design versatility. The expansive kitchen is the heart of the home, featuring elegant quartz

  Gary Peacock Berkshire Hathaway NE Prop.

  44 Chamberlain Hill Rd, Middletown, CT 06457
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  /13

  $1,475 total monthly price

  • 1 Bed
  • 1 Bath
  • 561 Sq Ft
  • House for Rent

  176 Burgundy Hill Ln Unit 176, Middletown, CT 06457

  Welcome Home to Comfort and Convenience! This first-floor condo at 176 Burgundy Hill Lane offers easy living with a bright, practical layout. The open Living and Dining area flows nicely into the kitchen, creating a comfortable space for both everyday living and entertaining. The spacious bedroom features a large closet, and the unit offers multiple additional closets to maximize storage. Sliders

  Clare Guest William Raveis Real Estate

  176 Burgundy Hill Ln Unit 176, Middletown, CT 06457
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  $395,000 Sold Jul 21, 2025

  116 Front St, Middletown, CT 06457

  • 6 Beds
  • 2 Baths
  • 2,579 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $153/SF
  • 30 Days On Market

  Current Estimated Value $392,286

  Last Listing Agent Michelle Mazzotta eXp Realty

  116 Front St, Middletown, CT 06457
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  Est $216,595 Not Listed For Sale

  1 Forest Glen Cir Unit 17, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Built 1989

  1 Forest Glen Cir Unit 17, Middletown, CT 06457

  Last Sold Summary

  • 18% Above List Price
  • $197/SF
  • 2 Days On Market

  Last Sold Price $183,000

  Last Listing Agent Lisa Orcutt Simply Sold Real Estate
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  /21

  $164,900 Under Contract

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

  45 Mckenna Dr, Middletown, CT 06457

  OWNER OCCUPANTS ONLY. CAN'T BE RENTED. NO INVESTORS. CASH ONLY! THIS IS A CO-OP: BUYERS OWN A SHARE AND MUST COMPLETE AN APPLICATION. Bright and move in ready, this end unit townhouse in the Wadsworth Grove Co-op offers three bedrooms, 1.5 baths and an inviting open layout. Hardwood floors flow through the main and upper levels, and the freshly painted interior features new crown molding and a

  Christian Salaman Coldwell Banker Realty

  45 Mckenna Dr, Middletown, CT 06457
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  /50

  $1,400 - $1,700 per month plus fees

  Willowcrest

  1 - 2 Beds

  63 Stoneycrest Dr, Middletown, CT 06457

  NO Application Fee! Some income restrictions apply. INCLUDES HEAT AND HOT WATER! Call for any rental specials. Spacious 1, 2 and 3 bedroom apartments in a convenient location and pedestrian friendly neighborhood. Property includes a landscaping plan that provides for seasonal color with the grounds professionally maintained by Carabetta's Maintenance Team. Amenities include 24-Hour Maintenance

  63 Stoneycrest Dr, Middletown, CT 06457
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  $634,000 Sold Aug 04, 2025

  896 East St, Middletown, CT 06457

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

  Last Sold Summary

  • 7% Below List Price
  • $264/SF
  • 68 Days On Market

  Last Listing Agent Geraldine Mattera Luxe Realty LLC

  896 East St, Middletown, CT 06457
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  Est $235,652 Not Listed For Sale

  2 Forest Glen Cir Unit 3, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Built 1989

  2 Forest Glen Cir Unit 3, Middletown, CT 06457

  Last Sold Summary

  • 5% Above List Price
  • $241/SF
  • 55 Days On Market

  Last Sold Price $224,000

  Last Listing Agent Nikki Trocchio Calcagni Real Estate
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  /31

  $185,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft

  159 Carriage Crossing Ln Unit 159, Middletown, CT 06457

  Welcome to this beautifully maintained condominium in sought-after Carriage Crossing, one of Middletown's premier communities at an affordable price. This sun-filled home offers effortless living with soaring 16-foot ceilings, expansive windows, and a unique contemporary layout. The open living and dining area features a cozy wood-burning fireplace with a stylish spiral staircase to a versatile

  Michele Devanney ERA Hart Sargis-Breen

  159 Carriage Crossing Ln Unit 159, Middletown, CT 06457
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  $3,100 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • House for Rent

  932 Saybrook Rd, Middletown, CT 06457

  Lovely 3 Bed/2 Bath Cape available immediately for rent in Middletown. The lot is set back on 1.25 acres, offering a perfect getaway in a quiet neighborhood surrounded by nature. The main floor features an open concept hosting the Living Room/Dining Room, a Full Bath w/ a new mirror/medicine cabinet, and a Kitchen w/ stainless steel appliances and newly restained cabinets and countertops. The

  Eric Ellison Executive Real Estate Inc.

  932 Saybrook Rd, Middletown, CT 06457
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  $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 $392,067

  Last Listing Agent rob link Sterling REALTORS

  4 Lorraine Terrace, Rockfall, CT 06481
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  Est $233,051 Not Listed For Sale

  14 Forest Glen Cir Unit 3, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Built 1989

  14 Forest Glen Cir Unit 3, Middletown, CT 06457

  Last Sold Summary

  • 11% Above List Price
  • $226/SF
  • 2 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Paula Fahy Ostop William Raveis Real Estate
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  /26

  $169,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft

  118 Carriage Crossing Ln, Middletown, CT 06457

  Welcome to this ranch style condo in the vibrant Carriage Crossing Complex where modern comfort meets resort-style living! This unit is in a super convenient secluded location on the second floor, steps to parking right out front! This bright 1 bedroom, 1 bath end unit with loft features an open floor plan with a sun filled living room highlighted by soaring vaulted ceilings, oversized windows,

  Lauren Iraeta KW Legacy Partners

  118 Carriage Crossing Ln, Middletown, CT 06457
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  /40

  $1,675 - $2,495 total monthly price

  Northwoods East

  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,

  5 Town Colony Dr, Middletown, CT 06457
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  $330,000 Sold Apr 08, 2025

  676 Saybrook Rd, Middletown, CT 06457

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $215/SF
  • 34 Days On Market

  Current Estimated Value $337,215

  Last Listing Agent Shari DiDomenico Berkshire Hathaway NE Prop.

  676 Saybrook Rd, Middletown, CT 06457
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  Est $221,943 Not Listed For Sale

  1 Forest Glen Cir Unit 13, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Built 1989

  1 Forest Glen Cir Unit 13, Middletown, CT 06457

  Last Sold Summary

  • 43% Above List Price
  • $167/SF
  • 1 Day On Market

  Last Sold Price $155,000

  Last Listing Agent Maria Gaudet Lamacchia Realty
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  $384,000 Under Contract

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

  8 Macdonough Place, Middletown, CT 06457

  Eager to get a jump on the 2026 Spring Market? Better get a move to a very special in-town offering. This early 20th century gambrel colonial, built in 1923 embraces its vintage charms and architectural detail with elan. Its ownership history shows an appreciation and sensitivity to its wood detail: original wood trim detail and moldings, plus hardwood flooring throughout. While owned just four

  Patricia Flynn Sterling REALTORS

  8 Macdonough Place, Middletown, CT 06457
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  $1,600 total monthly price

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

  161 Burgundy Hill Ln Unit 161, Middletown, CT 06457

  Charming 1br/1ba with loft conveniently located in Middletown. 3rd floor walk-up apartment. Fresh paint and carpet with sliding door to wood deck. Wall unit A/C. 1 parking space included and communal laundry room. Renter responsible for all utilities and renter's insurance. Each applicant over the age of 18 must complete a credit/background check through rentspree. Rent Spree charges

  Gerard Sullivan Coldwell Banker Realty

  161 Burgundy Hill Ln Unit 161, Middletown, CT 06457
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  $355,000 Sold Aug 29, 2025

  152 Old Mill Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft
  • Built 1969

  Last Sold Summary

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

  Current Estimated Value $368,124

  Last Listing Agent Santo Gulino William Raveis Real Estate

  152 Old Mill Rd, Middletown, CT 06457
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  Est $383,259 Not Listed For Sale

  56 Autumn Ln, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,486 Sq Ft
  • Built 2012

  56 Autumn Ln, Middletown, CT 06457

  Last Sold Summary

  • 13% Above List Price
  • $229/SF
  • 8 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Jonathan Zuromski Real Broker CT, LLC
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  /5

  $16,000

  • Land
  • 0.13 Acre
  • $123,077 per Acre

  0 Dunn St Unit 24162046, Middletown, CT 06457

  Residential lot located off Butternut Street in Middletown on Dunn Street, offering an opportunity for buyers, builders, or investors looking to secure land in an established area. Conveniently situated near local amenities, shopping, dining, parks, and commuter routes. Buyers are encouraged to perform their own due diligence regarding zoning, utilities, wetlands, frontage, and buildability.

  John David Brewer Exceptional Real Estate LLC

  0 Dunn St Unit 24162046, Middletown, CT 06457
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  /24

  $1,850 per month plus fees

  Apartment for Rent

  1 Bed

  141 Bridge St, Middletown, CT 06457

  Welcome to 141 Bridge Street, a beautifully reimagined four-unit residence where modern design, everyday comfort, and effortless convenience come together seamlessly. The property includes two spacious one-bedroom units, one two-bedroom unit, and one three-bedroom unit, each thoughtfully designed with high-end finishes and private entrances for added privacy. Inside every unit, you’ll find sleek

  141 Bridge St, Middletown, CT 06457
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  $315,000 Sold Nov 25, 2025

  85 Meech Rd, Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 1,267 Sq Ft
  • Built 1953

  Last Sold Summary

  • 5% Above List Price
  • $249/SF
  • 4 Days On Market

  Current Estimated Value $312,461

  Last Listing Agent Theresa Bitondo Berkshire Hathaway NE Prop.

  85 Meech Rd, Middletown, CT 06457
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  Est $270,644 Not Listed For Sale

  25 W Silver St, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,138 Sq Ft
  • Built 2007

  25 W Silver St, Middletown, CT 06457

  Last Sold Summary

  • 4% Above List Price
  • $228/SF
  • 4 Days On Market

  Last Sold Price $259,000

  Last Listing Agent Brittany O'Hara William Raveis Real Estate
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  /15

  $1,200,000

  • Land
  • 29.37 Acres
  • $40,858 per Acre

  0 Country Club Rd and Massa Tom Rd Rd E, Middletown, CT 06457

  29.37 Acres/ 14 lots of unique Wooded land rolling hills, lush forests. ATTENTION BUYERS /BUILDERS ENDLESS OPPORTUNITY TO EXPLORING DEVELOPMENT POTENTIAL this raw piece of land is a blank canvas ready for your vision. Easy access to nearby school's shops and highways.

  Irene Smaga Global Real Estate Services, LLC

  0 Country Club Rd and Massa Tom Rd Rd E, Middletown, CT 06457
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  $1,675 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Apartment for Rent

  1 Russell St Unit 18, Middletown, CT 06457

  Beautiful newly painted 2 floor style spacious apartment with 2 bathrooms in beautiful brick building with in unit laundry and easy parking. This. Wont. Last. Text owner/agent for showing details

  Geoff Luxenberg Century 21 Classic Homes

  1 Russell St Unit 18, Middletown, CT 06457
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  $225,000 Sold Dec 15, 2025

  30 Orange Rd Unit 30, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 880 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Above List Price
  • $256/SF
  • 9 Days On Market

  Current Estimated Value $219,178

  Last Listing Agent Martin Piggot Boyden Real Estate Company,LLC

  30 Orange Rd Unit 30, Middletown, CT 06457
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  Est $284,152 Not Listed For Sale

  49 Silver St, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft
  • Built 1935

  49 Silver St, Middletown, CT 06457

  Last Sold Summary

  • 58% Above List Price
  • $115/SF
  • 2 Days On Market

  Last Sold Price $180,000

  Last Listing Agent Keith Murphy Innovative Properties
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  $399,900 Under Contract

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

  211 Boston Rd, Middletown, CT 06457

  Colonial Farmhouse with detached 3 car garage and possible in-law suite. Two buildings for the price of one. Charming front covered porch and back deck southerly facing guarantee every drop of sunshine for your pleasure. You will enjoy the hardwood flooring throughout these 2 bedrooms, one full and one-half bathroom historic home. Utilize a third room on the second floor as a third bedroom. The

  Tina Lachance Berkshire Hathaway NE Prop.

  211 Boston Rd, Middletown, CT 06457
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  $2,100 - $3,600 total monthly price

  Windshire Terrace

  2 - 3 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

  72 Forest Glen Cir, Middletown, CT 06457
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  $754,537 Sold Jul 16, 2025

  127 Webster Ln Unit 2-44, Middletown, CT 06457

  • 2 Beds
  • 2.5 Baths
  • 2,195 Sq Ft
  • Built 2024

  Last Sold Summary

  • 6% Above List Price
  • $344/SF
  • 334 Days On Market

  Last Listing Agent Sally Annino Berkshire Hathaway NE Prop.

  127 Webster Ln Unit 2-44, Middletown, CT 06457
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  Est $241,066 Not Listed For Sale

  9 Clinton Ave, Middletown, CT 06457

  • 5 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • Built 1900

  9 Clinton Ave, Middletown, CT 06457

  Last Sold Summary

  • 21% Above List Price
  • $92/SF
  • 5 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Frank Balisciano Coldwell Banker Realty
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  /29

  $149,900

  • 1 Bed
  • 1.5 Baths
  • 752 Sq Ft

  111 Dekoven Dr Unit 1105, Middletown, CT 06457

  Rarely available one bedroom at Rivers Edge with stunning views of the CT River and the CT River valley. Plenty of space in this abode including private laundry in unit. Lots of closet space. 1 1/2 baths. Monthly fees includes air conditioning, heating, water, sewer, grounds maintenance, indoor pool, fitness center in building, prime parking spot and more. Truly a fantastic urban location. This

  Mark Toledo Berkshire Hathaway NE Prop.

  111 Dekoven Dr Unit 1105, Middletown, CT 06457
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  $1,800 total monthly price

  • 2 Beds
  • 1 Bath
  • 824 Sq Ft
  • Apartment for Rent

  7 Walnut St Unit 1, Middletown, CT 06457

  Welcome to this updated 2-bedroom apartment offering a comfortable and modern living space. The kitchen features granite countertops, stainless steel appliances, and a gas stove, providing both style and functionality. The bathroom includes tiled shower walls and sleek black fixtures for a clean, contemporary look. Black matte finishes throughout the unit add a subtle modern touch. Additional

  Jenny Bermeo Golden Ribbon Realty

  7 Walnut St Unit 1, Middletown, CT 06457
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  $400,000 Sold Aug 22, 2025

  1018 Long Hill Rd, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,084 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Above List Price
  • $192/SF
  • 35 Days On Market

  Current Estimated Value $403,659

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  1018 Long Hill Rd, Middletown, CT 06457
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  Est $447,177 Not Listed For Sale

  84 Mccormick Ln, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 2,276 Sq Ft
  • Built 1989

  84 Mccormick Ln, Middletown, CT 06457

  Last Sold Summary

  • 16% Above List Price
  • $170/SF
  • 21 Days On Market

  Last Sold Price $386,000

  Last Listing Agent Teri Lewis William Pitt
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  /3

  $599,900 Under Contract

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

  3 Sisk St, Middletown, CT 06457

  3 beautiful home sites in a fantastic location of the Westfield section of Middletown. This beautiful Cape offers it all. You will enjoy the classic historic Cape look on the exterior, framed by a brick center chimney. 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

  Mark Toledo Berkshire Hathaway NE Prop.

  3 Sisk St, Middletown, CT 06457
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  /15

  $1,450 - $1,500 per month plus fees

  Birchwood Apartments

  1 Bed

  400 Washington St, Middletown, CT 06457

  Out with the old, in with the new. Come see Middletown's newly renovated, re-developed community Located in the heart of Middletown! Birchwood Realty offers an exceptional lifestyle with amenities at your disposal that range from dramatic eight-foot ceilings to professional management and maintenance teams - and everything in between. The apartments in Birchwood Realty are unparalleled with any

  400 Washington St, Middletown, CT 06457
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  $350,000 Sold Jun 23, 2025

  50 Andrew St, Middletown, CT 06457

  • 4 Beds
  • 3 Baths
  • 2,038 Sq Ft
  • Built 1988

  Last Sold Summary

  • $172/SF
  • 15 Days On Market

  Current Estimated Value $349,569

  Last Listing Agent Colin Taylor Executive Real Estate Inc.

  50 Andrew St, Middletown, CT 06457
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  Est $194,497 Not Listed For Sale

  111 Dekoven Dr Unit 206, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft
  • Built 1989

  111 Dekoven Dr Unit 206, Middletown, CT 06457

  Last Sold Summary

  • 11% Above List Price
  • $168/SF
  • 38 Days On Market

  Last Sold Price $175,000

  Last Listing Agent Natalie Grant Nat's Honey Bee Real Estate

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