16,733

Middletown, CT Homes

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  • /40

    $799,900

    $25K PRICE DROP Under Contract
    • 5 Beds
    • 4.5 Baths
    • 4,560 Sq Ft

    66 Sachem Dr, Middletown, CT 06457

    STUNNING 5-bedroom, 4.5-bath Colonial set on almost 2 private acres in a peaceful cul-de-sac setting. Enter into an elegant dining space with a sun-filled bay window, which flows into a phenomenal, fully remodeled kitchen with shaker-style cabinetry, quartz countertops, an impressive 9-foot island, and plenty of space for casual dining or a cozy sitting area. The kitchen opens to a large family

    Tracey Precourt Century 21 Clemens Group

    66 Sachem Dr, Middletown, CT 06457
  • /16

    $2,199 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Townhouse for Rent

    27 Woodside Cir Unit 33, Middletown, CT 06457

    Fully renovated top to the bottom. Very quiet residential neighborhood. Lots of yard in the front and back. Tons of parking space. 3 bedrooms and 2 full bathrooms. Open concept living, dining and kitchen. Hardwood floors throughout the house. Mud room. Tons of storage in the basement. Tenant pays for all the utilities.

    Naima Mazouzi Eagle Eye Realty PLLC

    27 Woodside Cir Unit 33, Middletown, CT 06457
  • 85 Spencer Dr, Middletown, CT 06457

    $430,000

    Sold Nov 06, 2025

    85 Spencer Dr, Middletown, CT 06457

    • 5 Beds
    • 2 Baths
    • 1,965 Sq Ft
    • Built 1952

    Last Sold Summary

    • 2% Below List Price
    • $219/SF
    • 18 Days On Market

    Current Estimated Value $441,590

    Last Listing Agent Andrea Thomas SB Realty Group, LLC

    85 Spencer Dr, Middletown, CT 06457
  • /21

    $364,900

    $10K PRICE DROP Pending
    • 5 Beds
    • 2 Baths
    • 2,243 Sq Ft

    121 Saybrook Rd, Middletown, CT 06457

    Come see this two family investment property in the heart of Middletown, offering over 2,200 sq. ft. of living space. Each unit is thoughtfully laid out and provides comfortable, functional living. The first floor unit features three bedrooms, a full bathroom, and spacious living and dining areas. The second-floor unit offers two bedrooms, one full bathroom, and access to a full walk-up attic

    Michael Reiman William Raveis Real Estate

    121 Saybrook Rd, Middletown, CT 06457
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    $2,000 Per Month

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

    582 Main St, Middletown, CT 06457

    Spacious and updated 3-bedroom, 1-bath apartment offering approximately 1,200 square feet of living space in a convenient Main Street location. This second-floor unit features generous room sizes, updated finishes, and easy access to local restaurants, shopping, parks, and downtown amenities. Commuters will appreciate the quick access to major highways. A great opportunity to enjoy comfortable

    Corey Briggs William Raveis Real Estate

    582 Main St, Middletown, CT 06457
  • 94 Cynthia Ln Unit C6, Middletown, CT 06457

    $217,000

    Sold Oct 29, 2025

    94 Cynthia Ln Unit C6, Middletown, CT 06457

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

    Last Sold Summary

    • 3% Above List Price
    • $235/SF
    • 4 Days On Market

    Current Estimated Value $225,960

    Last Listing Agent David Borges The Borges Group LLC

    94 Cynthia Ln Unit C6, Middletown, CT 06457
  • /40

    $325,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 1,564 Sq Ft

    162 Old Middle St, Middletown, CT 06457

    This charming ranch offers the perfect blend of comfort, space, and flexibility! Step inside to a welcoming family room featuring a cozy wood-burning fireplace, perfect for relaxing evenings at home. The updated kitchen boasts granite countertops, newer appliances, and opens beautifully to the dining room/sunroom area, creating a bright and inviting space for everyday living and entertaining.

    Samantha Celentano Coldwell Banker Realty

    162 Old Middle St, Middletown, CT 06457
  • /9

    $1,650 Per Month

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

    104 Burgundy Hill Ln Unit 104, Middletown, CT 06457

    2 bedroom 1 bathroom condo with good parking and great location neer 91, route 9 and cromwell/middletown line. This. Wont. Last. Owner is licensed realtor in CT.

    Geoff Luxenberg Century 21 Classic Homes

    104 Burgundy Hill Ln Unit 104, Middletown, CT 06457
  • 753 Long Hill Rd Unit A, Middletown, CT 06457

    $306,000

    Sold Dec 12, 2025

    753 Long Hill Rd Unit A, Middletown, CT 06457

    • 2 Beds
    • 2.5 Baths
    • 1,449 Sq Ft
    • Built 1986

    Last Sold Summary

    • 9% Above List Price
    • $211/SF
    • 30 Days On Market

    Last Listing Agent Tracy Cooley Berkshire Hathaway NE Prop.

    753 Long Hill Rd Unit A, Middletown, CT 06457
  • /40

    $849,900

    $25K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,452 Sq Ft

    29 Copper Beech Dr, Middletown, CT 06457

    Tucked away on a quiet, highly desirable cul-de-sac of only 7 homes in the sought-after South Farms district, this beautifully crafted 5-bedroom, 3.5-bathroom colonial features a stunning brick-front facade and exceptional curb appeal. Boasting a coveted 3-car attached garage, the home greets you with an abundance of natural light and gleaming hardwood floors flowing seamlessly throughout the

    Stefania Bramato Berkshire Hathaway NE Prop.

    29 Copper Beech Dr, Middletown, CT 06457
  • /18

    $2,200 Per Month

    • 4 Beds
    • 1 Bath
    • 1,207 Sq Ft
    • Apartment for Rent

    207 E Main St, Middletown, CT 06457

    Now available a rarely found 4 bedroom rental at a n affordable price! Located at 207 East Main Street this unit is now available for its next occupants. Boasting 4 good size bedrooms this unit offes the convince of being located near amenities including groceries, public transportation, medical facilities, and restaurants, Located minutes from downtown Middletown, and offering easy highway

    Anthony LaCava Berkshire Hathaway NE Prop.

    207 E Main St, Middletown, CT 06457
  • 80 Birchwood Dr, Middletown, CT 06457

    $275,000

    Sold Jan 23, 2026

    80 Birchwood Dr, Middletown, CT 06457

    • 3 Beds
    • 1 Bath
    • 950 Sq Ft
    • Built 1961

    Last Sold Summary

    • 1% Below List Price
    • $289/SF
    • 11 Days On Market

    Current Estimated Value $287,128

    Last Listing Agent Thomas Mele Social & Co Realty

    80 Birchwood Dr, Middletown, CT 06457
  • /5

    $149,900

    Pending
    • 2 Beds
    • 1 Bath
    • 709 Sq Ft

    205 Burgundy Hill Ln Unit 205, Middletown, CT 06457

    Beautifully renovated first-floor 2-bedroom condo available in the desirable Peppermill Village community on West Lake Drive. This bright, move-in ready unit offers modern updates, convenience, and low-maintenance living. The fully updated kitchen features new cabinetry, quartz countertops, updated fixtures, and stylish finishes throughout. Recent renovations also include new flooring, an updated

    Lindsey Eberle Connecticut Real Estate Group LLC

    205 Burgundy Hill Ln Unit 205, Middletown, CT 06457
  • /12

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,180 Sq Ft
    • House for Rent

    1 Alicia Ln Unit B, Middletown, CT 06457

    Heat, central AC & electric INCLUDED! This newly constructed, beautiful apartment built in 2021 has 3 bedrooms, 2 full gorgeous bathrooms, modern kitchen with granite countertops & stainless steel appliances. Large main bedroom suite on 2nd floor with cathedral ceilings, double closets, huge master bathroom & tons of natural lighting. Luxury vinyl flooring throughout, washer & dryer included,

    Michelle Mazzotta eXp Realty

    1 Alicia Ln Unit B, Middletown, CT 06457
  • 83 Julia Terrace, Middletown, CT 06457

    $320,000

    Sold Sep 08, 2025

    83 Julia Terrace, Middletown, CT 06457

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft
    • Built 1975

    Last Sold Summary

    • $280/SF
    • 27 Days On Market

    Current Estimated Value $336,896

    Last Listing Agent Rick Selph Selph Realty, LLC

    83 Julia Terrace, Middletown, CT 06457
  • /6

    $149,000

    • 4 Beds
    • 1 Bath
    • 1,765 Sq Ft

    7 Evergreen Ave, Middletown, CT 06457

    Investor opportunity with great potential on a charming street. This property has been substantially gutted and requires a complete renovation, including plumbing, HVAC, windows, roof, and repairs related to a roof leak. The layout offers excellent possibilities, with an open floorplan- high ceilings on the first floor and area for a full bath or laundry, three to four bedrooms on second floor,

    Carly LuciƩr Our Home Realty Advisors

    7 Evergreen Ave, Middletown, CT 06457
  • /9

    $1,232 Per Month

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

    278 Chamberlain Rd Unit Lower Studio, Middletown, CT 06457

    Welcome to the lower-level studio at 278 Chamberlain Road. This unit features a large open-concept layout with space for a bedroom, living, and dining area all in one. Enjoy a spacious walk-in closet, a well-equipped kitchen with full-size fridge, stove, sink, and ample cabinet space, plus a full bathroom with a tub/shower combo and a charming pink vanity. A cozy and versatile studio with great

    Michael Bernard Ironclad Real Estate

    278 Chamberlain Rd Unit Lower Studio, Middletown, CT 06457
  • 0 Freeman Rd, Middletown, CT 06457

    $75,000

    Sold Aug 08, 2025

    0 Freeman Rd, Middletown, CT 06457

    • Land
    • 3 Acres
    • $25,000 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 38 Days On Market

    Last Listing Agent Barbara Puorro Puorro Realty Group

    0 Freeman Rd, Middletown, CT 06457
  • /2

    $100,000

    • Land
    • 8.18 Acres
    • $12,225 per Acre

    0 Bell St Unit 24149149, Middletown, CT 06457

    This scenic and beautiful lot has a stream running through it. The location is spectacular on this very quiet street located minutes to interstate 91 makes travel super easy. No test have been done.

    Nancy Newman LPT Realty

    0 Bell St Unit 24149149, Middletown, CT 06457
  • /13

    $1,430 Per Month

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

    666 Main St Unit A1, Middletown, CT 06457

    Bright and Inviting 1 bedroom Apartment This first floor apartment has its own private entrance. The rent is $1430.00 The apartment is located in the heart of Middletown's historic downtown district, you will be surrounded by seven walkable blocks of restaurants, shops, art, music, and entertainment. Additional Details: Fresh updates: Landlord to provide professional painting and necessary

    Laura Milano Seabury Hill REALTORS

    666 Main St Unit A1, Middletown, CT 06457
  • 118 Carriage Crossing Ln, Middletown, CT 06457

    $169,000

    Sold May 07, 2026

    118 Carriage Crossing Ln, Middletown, CT 06457

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

    Last Sold Summary

    • $222/SF
    • 93 Days On Market

    Current Estimated Value $173,912

    Last Listing Agent Lauren Iraeta KW Legacy Partners

    118 Carriage Crossing Ln, Middletown, CT 06457
  • /17

    $259,000

    $6K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,280 Sq Ft

    3 Flower St, Middletown, CT 06457

    Move right into this centrally located Middletown home! This 3 bedroom, 1 full bath home offers comfort, many updates, and timeless character in the heart of Middletown. Inside, you'll find a spacious living room perfect for entertaining lots of family and friends, along with touches of classic 1900s charm including a beautiful wood staircase and original railing details that add warmth and

    Leah Schroeder KW Legacy Partners

    3 Flower St, Middletown, CT 06457
  • /19

    $1,750 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,442 Sq Ft
    • House for Rent

    131 Eastern Dr, Middletown, CT 06457

    A peaceful retreat close to everything Middletown has to offer. The main floor opens up the way a rental rarely does. Open floor plan, large living room, updated flooring throughout, and a half bath that keeps things practical. Upstairs has two bedrooms, a full bath, and a bonus room that works as an office, guest space, or whatever fits your life. Out back you have a deck and a large shared yard

    Nick Gilham Real Broker CT, LLC

    131 Eastern Dr, Middletown, CT 06457
  • 268 Bell St, Middletown, CT 06457

    $400,000

    Sold Jun 04, 2026

    268 Bell St, Middletown, CT 06457

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1967

    Last Sold Summary

    • 11% Below List Price
    • $347/SF
    • 5 Days On Market

    Current Estimated Value $443,164

    Last Listing Agent Laura Bitondo Berkshire Hathaway NE Prop.

    268 Bell St, Middletown, CT 06457
  • /40

    $785,000

    Pending
    • 4 Beds
    • 3 Baths
    • 3,054 Sq Ft

    33 Knoll Ridge Ct, Middletown, CT 06457

    This beautifully designed home offers the perfect blend of comfort, flexibility, and multigenerational living. The main level features impressive 9-foot ceilings that create an open, airy feel . The kitchen has loads of counters as well as an island and dining area which leads to a large trex deck boasting a panoramic view. A spacious primary suite serves as a private retreat with a separate

    Nancy Currlin William Raveis Real Estate

    33 Knoll Ridge Ct, Middletown, CT 06457
  • /7

    $1,450 Per Month

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

    23 Clinton Ave, Middletown, CT 06457

    Spacious 3-bedroom, 1-bath apartment located in Middletown's desirable Highlands area. This bright and well-maintained unit offers generously sized bedrooms, a comfortable living area, and convenient access to downtown, shopping, restaurants, Wesleyan University, and major highways. Additional storage available in the basement and attic areas. Natural gas heat and hot water. Monthly rent is

    Santo Gulino William Raveis Real Estate

    23 Clinton Ave, Middletown, CT 06457
  • 106 Northview Dr, Middletown, CT 06457

    $647,000

    Sold Jul 18, 2025

    106 Northview Dr, Middletown, CT 06457

    • 3 Beds
    • 2.5 Baths
    • 2,612 Sq Ft
    • Built 2007

    Last Sold Summary

    • $248/SF
    • 20 Days On Market

    Current Estimated Value $694,692

    Last Listing Agent George Muniz Keller Williams NY Realty

    106 Northview Dr, Middletown, CT 06457
  • /28

    $220,000

    Open Sat 11AM - 1PM
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    5 Carriage Crossing Ln, Middletown, CT 06457

    PHOTO'S ARE NOW AVAILABLE! Welcome to 5 Carriage Crossing, a desirable first floor end-unit condo in the welcoming Carriage Crossing community of Middletown, CT. This well maintained 2 bedroom, 2 bath condominium offers the perfect blend of comfort, convenience, and low maintenance living. Filled with natural light, the spacious floor plan provides an inviting atmosphere for everyday living and

    kathleen mullins Real Broker CT, LLC

    5 Carriage Crossing Ln, Middletown, CT 06457
  • /13

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 3,784 Sq Ft
    • Apartment for Rent

    14 Pease Ave Unit 3, Middletown, CT 06457

    Charming 1-bedroom with an extra bonus room, great for a home office. This 2nd-floor apartment offers beautiful hardwood flooring throughout and the convenience of heat and hot water included in the rent. Located close to local shops, restaurants, and entertainment, and quick access to highway. Heat & Hot Water included in monthly rent.

    Jaimie Andrews Bottom Line Realty

    14 Pease Ave Unit 3, Middletown, CT 06457
  • 8 Macdonough Place, Middletown, CT 06457

    $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 $382,351

    Last Listing Agent Patricia Flynn Sterling REALTORS

    8 Macdonough Place, Middletown, CT 06457

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