Middletown, CT Homes

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  /40

  $199,000

  • 2 Beds
  • 1.5 Baths
  • 1,510 Sq Ft

  201 College St Unit 10, Middletown, CT 06457

  Welcome to a bright and updated townhouse-style condo offering a comfortable layout and several features that set it apart. The first floor has been refreshed with luxury vinyl plank flooring and includes a spacious living area, dining space, and modern-style kitchen. Upstairs, two bedrooms are accompanied by a versatile bonus room featuring a vaulted ceiling and skylight, offering an ideal spot

  Doug Hagen Starr Team at LPT Realty

  201 College St Unit 10, Middletown, CT 06457
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  /13

  $1,100 Per Month

  • 1 Bath
  • 300 Sq Ft
  • Apartment for Rent

  696 Main St Unit B1, Middletown, CT 06457

  Be part of the vibrant downtown Middletown community! Located above the bakery putting out the best cupcakes in the state and just a few feet from some of Middletown's most well known restaurants and gathering spots, this 2nd floor, studio apartment has heat, electric and hot water included in your monthly rental amount. There is new laminate flooring throughout, large closets as well as coin

  Scott Nardozzi Cavanaugh & Company LLC

  696 Main St Unit B1, Middletown, CT 06457
• 

  $256,000

  Sold Jun 26, 2026

  248 Carriage Crossing Ln Unit 248, Middletown, CT 06457

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

  Last Sold Summary

  • 7% Above List Price
  • $269/SF
  • 9 Days On Market

  Current Estimated Value $252,469

  Last Listing Agent Jared Tedesco Litchfield County Real Estate

  248 Carriage Crossing Ln Unit 248, Middletown, CT 06457
• 

  Est $213,914

  Not Listed For Sale

  93 Grand St, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 647 Sq Ft
  • Built 1900

  93 Grand St, Middletown, CT 06457

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Lauren Iraeta KW Legacy Partners
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  /40

  $589,000

  Open Sat 1PM - 3PM Coming Soon

  • 2 Beds
  • 2.5 Baths
  • 2,054 Sq Ft

  35 Sonoma Ln, Middletown, CT 06457

  Homes in Sonoma Woods don't come available often, and Unit 35 offers one of the largest models in this sought-after 55+ Middletown community. With 2 bedrooms, 2.5 baths, walkout basement with an exercise or craft room, and nearly 2,000 sq ft of living space, this home delivers the ease of condo living without giving up the space you want. The comfortable main level features a fireplace and a

  Devon Taylor Assael Dave Jones Realty, LLC

  35 Sonoma Ln, Middletown, CT 06457
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  /7

  $1,100 Per Month

  • 1 Bath
  • 300 Sq Ft
  • Apartment for Rent

  696 Main St Unit A2, Middletown, CT 06457

  Be part of the vibrant downtown Middletown community! Located above the bakery putting out the best cupcakes in the state and just a few feet from some of Middletown's most well known restaurants and gathering spots, this 2nd floor, studio apartment has heat, electric and hot water included in your monthly rental amount. There is new laminate flooring throughout, large closets as well as coin

  Scott Nardozzi Cavanaugh & Company LLC

  696 Main St Unit A2, Middletown, CT 06457
• 

  $195,000

  Sold Jul 09, 2026

  221 Carriage Crossing Ln Unit 221, Middletown, CT 06457

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

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 38 Days On Market

  Current Estimated Value $199,140

  Last Listing Agent Tracy Molloy Coldwell Banker Realty

  221 Carriage Crossing Ln Unit 221, Middletown, CT 06457
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  Est $563,517

  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

  • 4 Days On Market

  Last Listing Agent Robert Durato Sentry Real Estate
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  /40

  $599,900

  $245K PRICE DROP

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

  110 Freeman Rd, Middletown, CT 06457

  THIS IS AN IDEAL HOME FOR BUYERS SEEKING A PROPERTY WITH EXTRAORDINARY STORAGE, WORKSHOP, HOBBY OR EQUESTRIAN POTENTIAL !! Step back in time while enjoying the comfort of modern updates in this distinctive 1868 home in Middletown's desirable South Farms area. Set on a property rich in character, history, and functionality, this unique home offers 3 bedrooms, 1 1/2 baths, an upstairs office, and a

  Pam Rizy Berkshire Hathaway NE Prop.

  110 Freeman Rd, Middletown, CT 06457
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  /4

  $1,500 Per Month

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

  20 Erin St Unit 2, Middletown, CT 06457

  All utilities incuded!! Close to Middletown's great restaurants and less than a mile from Wesleyan University!

  Jennifer Gondola Farnam Realty Group

  20 Erin St Unit 2, Middletown, CT 06457
• 

  $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 $501,392

  Last Listing Agent Britany Goyen BB Realty CT

  1 Jefferson Ave, Middletown, CT 06457
• 

  Est $482,796

  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

  • 3 Days On Market

  Last Listing Agent Tracey Precourt Century 21 Clemens Group
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  /33

  $1,395,000

  • 21 Beds
  • 9 Baths
  • 10,629 Sq Ft

  61 E Main St, Middletown, CT 06457

  Two-building mixed-use investment opportunity in Middletown. The offering includes 61 East Main Street with four apartments and two storefronts, plus a separate three-apartment building at 2-6 Flower Street, offering a more private off Main street setting. Six apartments are occupied, while the seventh is being updated with a new kitchen and bathroom. Upon completion and lease-up at the projected

  Sacha Armstrong William Pitt Sotheby's International Realty

  61 E Main St, Middletown, CT 06457
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  /9

  $2,150 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  20 Erin St Unit 1, Middletown, CT 06457

  All utilities included!! 1st floor apartment with spacious eat in kitchen, Full basement use w/ access off of kitchen with washer/dryer hookups. Backyard and off street parking!

  Jennifer Gondola Farnam Realty Group

  20 Erin St Unit 1, Middletown, CT 06457
• 

  $640,000

  Sold May 29, 2026

  886 East St, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,390 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $268/SF
  • 2 Days On Market

  Last Listing Agent Geraldine Mattera Luxe Realty LLC

  886 East St, Middletown, CT 06457
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  Est $513,375

  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

  • 56 Days On Market

  Last Listing Agent Ela Konferowicz Golden Key Realty LLC
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  /20

  $390,000

  $15K PRICE DROP

  • 7 Beds
  • 2 Baths
  • 2,476 Sq Ft

  194 Liberty St, Middletown, CT 06457

  Owner occupied or investors! Fully renovated investment opportunity in the heart of Middletown! This well-maintained 7 bedrooms 2 bath, multifamily property has been completely remodeled and offers immediate cash flow with tenants already in place. Each unit is currently rented, providing strong and stable rental income from day one. Updates include modern kitchens, renovated bathrooms, updated

  Amiyra Beauduy Century 21 Scala Group

  194 Liberty St, Middletown, CT 06457
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  /13

  $1,700 Per Month

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

  166 College St Unit 2, Middletown, CT 06457

  Opportunity awaits at 166 College Street Rear in the heart of Middletown's Historic District. This charming two-bedroom rental offers an unbeatable location just steps from Wesleyan University and downtown Middletown's vibrant restaurants, shops, and entertainment. Heat and hot water are included in the rent, providing added value and convenience. Off-street parking is available. Enjoy the

  Santo Gulino William Raveis Real Estate

  166 College St Unit 2, Middletown, CT 06457
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  $499,900

  Sold Aug 03, 2026

  1 Nathan Hale Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 2026

  Last Sold Summary

  • $325/SF
  • 53 Days On Market

  Last Listing Agent Jenna Talbot RE/MAX One

  1 Nathan Hale Rd, Middletown, CT 06457
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  Est $365,456

  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

  • 8 Days On Market

  Last Listing Agent Betsy Purtell Purtell Realty LLC
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  /12

  $419,000

  Pending

  • 8 Beds
  • 4 Baths
  • 3,110 Sq Ft

  71 E Main St, Middletown, CT 06457

  Exceptional mixed-use investment opportunity convenient to downtown Middletown! This property features 2 commercial units and 3 residential units, offering a balanced blend of commercial and residential income that makes it an ideal addition to any investor's portfolio. Both commercial spaces are currently vacant, making this an excellent opportunity for someone who wants to open their own

  Levi Judqin Brass Moon Realty

  71 E Main St, Middletown, CT 06457
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  /13

  $1,995 Per Month

  • 2 Beds
  • 1 Bath
  • 6,573 Sq Ft
  • Apartment for Rent

  170 Pearl St Unit B, Middletown, CT 06457

  Newly renovated first-floor apartment offering two bedrooms, one full bathroom and a modern open-concept layout. The updated kitchen connects seamlessly with the main living space, and a private in-unit washer and dryer provides added convenience. Ideally located near downtown Middletown, Wesleyan University, Middlesex Health, local dining and shopping, with easy access to Route 9. On-street

  Michelle Mandel Carl Guild & Associates

  170 Pearl St Unit B, Middletown, CT 06457
• 

  $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 $360,229

  Last Listing Agent Kevin Green Berkshire Hathaway NE Prop.

  24 Stantack Rd, Middletown, CT 06457
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  Est $415,062

  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

  • 6 Days On Market

  Last Listing Agent Jim Treanor Jr ERA Treanor Real Estate
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  /23

  $410,000

  Open House 10/03 $89K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 3,319 Sq Ft

  1511 Country Club Rd, Middletown, CT 06457

  Welcome to 1511 Country Club Rd, a charming 2-bedroom Cape with the possibility of 5- bedrooms offering comfort, character, and exceptional versatility. This inviting home has a Brand new septic system and features a flexible layout with a private in-law suite or separate living space-perfect for multi-generational living, guests, a private home office or income possibility. Step outside to enjoy

  Dean Brockert Maverick Realty

  1511 Country Club Rd, Middletown, CT 06457
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  /13

  $1,995 Per Month

  • 2 Beds
  • 1 Bath
  • 6,573 Sq Ft
  • Apartment for Rent

  170 Pearl St Unit A, Middletown, CT 06457

  Completely renovated first-floor two-bedroom apartment featuring an open floor plan and modern finishes throughout. The kitchen flows into the main living area, creating a functional layout, while an in-unit washer and dryer adds everyday convenience. Located near downtown Middletown, Wesleyan University, Middlesex Health, restaurants, shopping and Route 9. On-street parking only. No smoking.

  Michelle Mandel Carl Guild & Associates

  170 Pearl St Unit A, Middletown, CT 06457
• 

  $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 $451,758

  Last Listing Agent Robin Thurston Coldwell Banker Realty

  80 Pond Place, Middletown, CT 06457
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  Est $247,104

  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

  • 5 Days On Market

  Last Listing Agent Stephen Mele Houlihan Lawrence
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  /40

  $199,900

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

  95 Trolley Crossing Ln, Middletown, CT 06457

  This townhouse style condo is in a great location with easy access to both Hartford and New Haven. Close to the Rt 9 and I-91 highway ramps. This 2 bedroom 1 1/2 bath unit is in need of updating but well worth the efforts. Ready for your upgrades, along with a private deck in the complex. Key features include: - Parking: 2-car garage plus 2 dedicated driveway spaces in front of the garage,

  Roger Lavoie LAER Realty Partners

  95 Trolley Crossing Ln, Middletown, CT 06457
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  /17

  $2,400 Per Month

  • 3 Beds
  • 1 Bath
  • 1,203 Sq Ft
  • House for Rent

  324 Washington St Unit . 2, Middletown, CT 06457

  This beautifully renovated, fully furnished apartment is conveniently located to downtown Middletown and sits directly across the street from Wesleyan University. With everything included right down to dishes and linens, this is a great opportunity for a faculty or corporate rental. This 3 bedroom/1 bath unit features an updated kitchen with soft gray shaker cabinetry, quartz counters and

  Richard Conary Berkshire Hathaway NE Prop.

  324 Washington St Unit . 2, Middletown, CT 06457
• 

  $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 $577,983

  Last Listing Agent Justin Marino Marino Realty LLC

  16 Snow Ridge S, Middletown, CT 06457
• 

  Est $395,703

  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

  • 83 Days On Market

  Last Listing Agent Brenden Hultgren Robert C White & Company LLC
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  /17

  $315,000

  $30K PRICE DROP Pending

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  175 Newfield St, Middletown, CT 06457

  It has style, it has grace, it has a new roof (3 years old) - you will absolutely love this place!! THIS is the cape you've been waiting for! Ideal floorplan - the primary bedroom on the first floor faces the backyard; the relaxing living room has a wood burning fireplace; the renovated full bathroom has a bathtub; the beautifully modernized kitchen is fully applianced and the separate dining

  Vaiva Baltonis Coldwell Banker Realty

  175 Newfield St, Middletown, CT 06457
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  /14

  $1,500 Per Month

  • 1 Bath
  • 450 Sq Ft
  • Apartment for Rent

  542 Main St Unit 3A, Middletown, CT 06457

  Welcome to Middletown at Main - a collection of newly renovated apartments, thoughtfully curated for modern living. 542 Main St., Unit 3A offers a stylish and efficient studio layout with fresh finishes and all the conveniences you're looking for. The bright, open living space is complemented by a modern kitchen featuring sleek cabinetry, stone countertops, and a dishwasher. An in-unit washer and

  Jordan Ostrofsky LPT Realty

  542 Main St Unit 3A, Middletown, CT 06457
• 

  $450,000

  Sold May 29, 2026

  259 Pearl St, Middletown, CT 06457

  • 9 Beds
  • 3 Baths
  • 3,906 Sq Ft
  • Built 1917

  Last Sold Summary

  • 14% Above List Price
  • $115/SF
  • 6 Days On Market

  Current Estimated Value $454,667

  Last Listing Agent Mike Rethis Coldwell Banker Realty

  259 Pearl St, Middletown, CT 06457
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  Est $408,321

  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

  • 19 Days On Market

  Last Listing Agent Edward Lawton iHeart Homes Real Estate LLC
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  /39

  $549,900

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,537 Sq Ft

  1446 Randolph Rd, Middletown, CT 06457

  Set well back from the road on 4.6 secluded acres, this beautifully maintained ranch combines generous one-level living with a bright, welcoming feel throughout. Large windows on all sides bring in abundant natural light and frame views of the expansive landscaping, lawn, and surrounding trees. The spacious remodeled kitchen anchors the home's everyday living, with beautifully crafted cabinetry,

  Jay Smolenski Berkshire Hathaway NE Prop.

  1446 Randolph Rd, Middletown, CT 06457
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  /32

  $1,600 Per Month

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

  54 Oak St Unit 11, Middletown, CT 06457

  Welcome to 54 Oak Street. This lovely 3 room, first floor corner apartment with a large eat in kitchen with all stainless steel appliances (oven range, range hood, refrigerator & dishwasher), large living room and huge bedroom with generous closets and a full bath is ready to go. Beautifully remodeled. Centrally located in a secure building with Intercom, it is within walking distance to Wesleyan

  Barbara Coyle William Raveis Real Estate

  54 Oak St Unit 11, Middletown, CT 06457
• 

  $375,000

  Sold Nov 04, 2025

  122 Newfield St Unit 2A, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,576 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Above List Price
  • $238/SF
  • 24 Days On Market

  Last Listing Agent Beth Cantor Coldwell Banker Realty

  122 Newfield St Unit 2A, Middletown, CT 06457
• 

  Est $358,006

  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

  • 21 Days On Market

  Last Listing Agent Ana Russo William Pitt Sotheby's Int'l

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