16,647

Middletown, CT Homes

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  • /37

    $289,900

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,249 Sq Ft

    177 Front St, Middletown, CT 06457

    Welcome to 177 Front Street, a charming farmhouse-style home in Middletown's desirable Farm Hill District. This 3-bedroom, 1.5-bath home offers a functional layout with comfortable living space, a formal dining room, and plenty of natural light throughout. Recent updates include fresh interior paint, newer Stainless Steel appliances and countertops, and freshly painted wood cabinetry, giving the

    Thomas Cody Align Realty LLC

    177 Front St, Middletown, CT 06457
  • /8

    $1,550 Per Month

    • 4 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    14 Portland St Unit 1, Middletown, CT 06457

    Welcome to 14 Portland Street #1 in Middletown! This spacious 3-bedroom, 1-bath rental offers approximately 1,000 square feet of comfortable living space. Conveniently located near downtown Middletown, local shops, restaurants, highways, and area amenities. The unit features a functional layout with generously sized rooms and plenty of natural light. Offered at $1,550 per month and ready for its

    Santo Gulino William Raveis Real Estate

    14 Portland St Unit 1, Middletown, CT 06457
  • 23 Mckenna Dr, Middletown, CT 06457

    $160,000

    Sold Aug 11, 2026

    23 Mckenna Dr, Middletown, CT 06457

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Below List Price
    • $133/SF
    • 4 Days On Market

    Last Listing Agent Kelvin Wilson Berkshire Hathaway NE Prop.

    23 Mckenna Dr, Middletown, CT 06457
    • 37 Roberts St, Middletown, CT 06457

      Est $338,013

      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

      • 26 Days On Market

      Last Listing Agent Taylor Spadacenta Real Broker CT, LLC

  • /16

    $375,000

    Pending
    • 6 Beds
    • 2 Baths
    • 1,924 Sq Ft

    108 Maple St, Middletown, CT 06457

    WELCOME TO THIS BEAUTIFULLY REFRESHED PROPERTY OFFERING CLASSIC CHARM, COMFORTABLE LIVING SPACES, AND EXCELLENT OUTDOOR APPEAL. THE INVITING EXTERIOR FEATURES A GENEROUS TWO-STORY COVERED PORCH, PROVIDING THE PERFECT SPOT TO ENJOY YOUR MORNING COFFEE, RELAX, OR ENTERTAIN GUESTS. THE ATTRACTIVE GRAY SIDING, CRISP WHITE TRIM, LANDSCAPED BEDS, AND WELL-MAINTAINED LAWN CREATE WONDERFUL CURB APPEAL.

    Donna Ricci Coldwell Banker Realty

    108 Maple St, Middletown, CT 06457
  • /10

    $1,550 Per Month

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

    542 Main St Unit 3B, Middletown, CT 06457

    Welcome to Middletown at Main - a collection of newly renovated apartments, thoughtfully curated for modern living. 542 Main St., Unit 3B offers a stylish and efficient one bedroom 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. The in-unit

    Jordan Ostrofsky LPT Realty

    542 Main St Unit 3B, Middletown, CT 06457
  • 111 Dekoven Dr Unit 1105, Middletown, CT 06457

    $147,000

    Sold Apr 30, 2026

    111 Dekoven Dr Unit 1105, Middletown, CT 06457

    • 1 Bed
    • 1.5 Baths
    • 752 Sq Ft
    • Built 1989

    Last Sold Summary

    • 2% Below List Price
    • $195/SF
    • 7 Days On Market

    Current Estimated Value $151,412

    Last Listing Agent Mark Toledo Berkshire Hathaway NE Prop.

    111 Dekoven Dr Unit 1105, Middletown, CT 06457
    • 1195 S Main St, Middletown, CT 06457

      Est $315,075

      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

      • 12 Days On Market

      Last Listing Agent Joe Fazzino eXp Realty

  • /28

    $199,900

    • 2 Beds
    • 2 Baths
    • 866 Sq Ft

    316 Carriage Crossing Ln Unit 316, Middletown, CT 06457

    Welcome to this bright and inviting condo offering comfortable, low-maintenance living! The open living and dining area features soaring vaulted ceilings, oversized windows that fill the space with natural light, and a cozy, wood burning fireplace with built-in shelving. Off the living room is a private outdoor space, perfect for enjoying your morning coffee or relaxing at the end of the day. The

    Jeff Petersen Century 21 AllPoints Realty

    316 Carriage Crossing Ln Unit 316, Middletown, CT 06457
  • /22

    $1,600 Per Month

    • 2 Beds
    • 1 Bath
    • 1,928 Sq Ft
    • Apartment for Rent

    58 Washington St Unit 2, Middletown, CT 06457

    Are you looking for a 2 bedroom rental in the heart of Middletown right off of Main Street? If so this is the unit for you. We are happy to offer this freshly painted 2nd floor unit that has an in unit washer/dryer, private balcony and off street parking for 1 car!. This unit offers natural gas heat and hot water. The owner is looking for very strong credit scores and references. Sorry no smoking

    Scott Nardozzi Cavanaugh & Company LLC

    58 Washington St Unit 2, Middletown, CT 06457
  • 12 Copper Beech Dr, Middletown, CT 06457

    $920,000

    Sold Jul 10, 2026

    12 Copper Beech Dr, Middletown, CT 06457

    • 4 Beds
    • 3.5 Baths
    • 4,393 Sq Ft
    • Built 2005

    Last Sold Summary

    • 1% Above List Price
    • $209/SF
    • 55 Days On Market

    Current Estimated Value $909,781

    Last Listing Agent Rob Rosa Berkshire Hathaway NE Prop.

    12 Copper Beech Dr, Middletown, CT 06457
    • 791 Long Hill Rd Unit F, Middletown, CT 06457

      Est $335,810

      Not Listed For Sale

      791 Long Hill Rd Unit F, Middletown, CT 06457

      • 2 Beds
      • 2.5 Baths
      • 1,449 Sq Ft
      • Built 1986
      791 Long Hill Rd Unit F, Middletown, CT 06457

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Stefania Bramato Berkshire Hathaway NE Prop.

  • /37

    $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
  • /14

    $1,525 Per Month

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

    17 Broad St Unit 1 East, Middletown, CT 06457

    Remodeled 1st Floor Apartment - Welcome home to a thoughtfully updated and move-in ready 1st floor apartment! The apartment features fresh paint throughout, beautiful hardwood flooring, an updated kitchen and bathroom, and brand-new appliances. There is off-street parking for one car and easy access to everything Middletown has to offer. Close RT 9, Middlesex Health, Wesleyan University, and

    Heather Kilbourn Cavanaugh & Company LLC

    17 Broad St Unit 1 East, Middletown, CT 06457
  • 33 Bartlett Hollow Unit 33, Middletown, CT 06457

    $460,000

    Sold Oct 30, 2025

    33 Bartlett Hollow Unit 33, Middletown, CT 06457

    • 2 Beds
    • 2 Baths
    • 1,401 Sq Ft
    • Built 2012

    Last Sold Summary

    • 2% Above List Price
    • $328/SF
    • 57 Days On Market

    Current Estimated Value $479,850

    Last Listing Agent Deborah Pach Compass Connecticut, LLC

    33 Bartlett Hollow Unit 33, Middletown, CT 06457
    • 70 Burgundy Hill Ln, Middletown, CT 06457

      Est $119,801

      Not Listed For Sale

      70 Burgundy Hill Ln, Middletown, CT 06457

      • 1 Bed
      • 1 Bath
      • 581 Sq Ft
      • Built 1987
      70 Burgundy Hill Ln, Middletown, CT 06457

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Michael Disla eXp Realty

  • /40

    $779,000

    Under Contract
    • 6 Beds
    • 3.5 Baths
    • 3,199 Sq Ft

    44 Chamberlain Hill Rd, Middletown, CT 06457

    A truly extraordinary residence where distinctive architecture, exceptional privacy and sophisticated design come together to create a home unlike any other. Privately set on 3.5 acres, this beautifully renovated contemporary offers more than 5,500 square feet of impressive living space, with soaring interiors, walls of windows and an abundance of natural light creating a seamless connection to

    Sharon Linder Berkshire Hathaway NE Prop.

    44 Chamberlain Hill Rd, Middletown, CT 06457
  • /25

    $2,100 Per Month

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

    682 Main St Unit 2F, Middletown, CT 06457

    Don't walk, run! Welcome to Middletown at Main-a collection of newly renovated apartments, thoughtfully curated for modern living. 682 Main St., Unit 2F offers a fresh, contemporary interior with an expansive open-concept living and dining area, abundant natural light, and stylish finishes throughout. The updated kitchen features granite countertops, soft-close white shaker cabinetry, stainless

    Jordan Ostrofsky LPT Realty

    682 Main St Unit 2F, Middletown, CT 06457
  • 390 Butternut St, Middletown, CT 06457

    $350,000

    Sold Sep 26, 2025

    390 Butternut St, Middletown, CT 06457

    • 3 Beds
    • 1.5 Baths
    • 1,721 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $203/SF
    • 31 Days On Market

    Current Estimated Value $361,026

    Last Listing Agent Scott Nardozzi Cavanaugh & Company LLC

    390 Butternut St, Middletown, CT 06457
  • /24

    $364,900

    Under Contract
    • 5 Beds
    • 3 Baths
    • 2,418 Sq Ft

    53 Spring St, Middletown, CT 06457

    This well maintained colonial, located just steps from the bustling downtown of Middletown, is ready for its new owner! Three units, all on different floors, offer flexible plans for owner-occupants and investors alike! The first and second floor units are comfortably controlled with high efficiency Navien units, both with a 2 bed/1 bath layout. The third unit is also natural gas, and provides a

    Frederick Ferguson Carl Guild & Associates

    53 Spring St, Middletown, CT 06457
  • /13

    $1,700 Per Month

    • 2 Beds
    • 2 Baths
    • 2,029 Sq Ft
    • Apartment for Rent

    59 Park Place, Middletown, CT 06457

    Bright spotless second floor unit in a large 2 family in downtown Middletown.Walk to university or downtown. Hardwood floors throughout .Spacious rooms. Off-street parking. Big yard!!.

    Vincent Engingro William Raveis Real Estate

    59 Park Place, Middletown, CT 06457
  • 914 Saybrook Rd, Middletown, CT 06457

    $380,000

    Sold May 28, 2026

    914 Saybrook Rd, Middletown, CT 06457

    • 4 Beds
    • 2 Baths
    • 1,634 Sq Ft
    • Built 1989

    Last Sold Summary

    • 9% Above List Price
    • $233/SF
    • 3 Days On Market

    Current Estimated Value $375,557

    Last Listing Agent Samuel Affhauser eXp Realty

    914 Saybrook Rd, Middletown, CT 06457
    • 111 Dekoven Dr Unit 905, Middletown, CT 06457

      Est $157,567

      Not Listed For Sale

      111 Dekoven Dr Unit 905, Middletown, CT 06457

      • 1 Bed
      • 1.5 Baths
      • 752 Sq Ft
      • Built 1989
      111 Dekoven Dr Unit 905, Middletown, CT 06457

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Adam Zak Century 21 Classic Homes

  • /40

    $359,999

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,537 Sq Ft

    123 Fisher Rd, Middletown, CT 06457

    Welcome to 123 Fisher Rd, a charming 3-bedroom, 2-bath Cape offering a flexible floor plan and plenty of space to suit today's lifestyle. One of the home's standout features is the main-level bedroom, which is currently being used as an additional living space. This versatile room provides an excellent opportunity for a family room, home office, den, or comfortable first-floor bedroom depending

    Courtney LeBlanc Dave Jones Realty, LLC

    123 Fisher Rd, Middletown, CT 06457
  • /13

    $1,500 Per Month

    • 1 Bath
    • 450 Sq Ft
    • Apartment for Rent

    542 Main St Unit 2A, Middletown, CT 06457

    Welcome to Middletown at Main - a collection of newly renovated apartments, thoughtfully curated for modern living. 542 Main St., Unit 2A offers a fresh, modern living space right in the heart of downtown Middletown. Thoughtfully designed with both style and convenience in mind, this inviting apartment features an updated kitchen with sleek cabinetry, Quartz countertops, and a dishwasher, along

    Jordan Ostrofsky LPT Realty

    542 Main St Unit 2A, Middletown, CT 06457
  • 100 Jack English Dr, Middletown, CT 06457

    $555,000

    Sold Nov 10, 2025

    100 Jack English Dr, Middletown, CT 06457

    • 4 Beds
    • 2.5 Baths
    • 2,219 Sq Ft
    • Built 2019

    Last Sold Summary

    • 1% Above List Price
    • $250/SF
    • 5 Days On Market

    Current Estimated Value $592,523

    Last Listing Agent Tracy Wilson Lamacchia Realty

    100 Jack English Dr, Middletown, CT 06457
    • 75 Westmont Dr, Middletown, CT 06457

      Est $381,149

      Not Listed For Sale

      75 Westmont Dr, Middletown, CT 06457

      • 4 Beds
      • 2.5 Baths
      • 1,550 Sq Ft
      • Built 1965
      75 Westmont Dr, Middletown, CT 06457

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Beverly Rodriguez Five Stars Realty

  • /5

    $499,900

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    4 Nathan Hale Rd, Middletown, CT 06457

    This 1,500 sq ft ranch-style home, built by Silvin Homes, offers thoughtfully designed one-level living with an open-concept layout ideal for everyday living and entertaining. The spacious living area flows seamlessly into the kitchen with a center island and ample cabinetry, creating a welcoming gathering space. The private primary suite features a custom full bath and walk-in closet and is set

    Jenna Talbot RE/MAX One

    4 Nathan Hale Rd, Middletown, CT 06457
  • /14

    $1,782 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    1185 Randolph Rd Unit Back Apartment, Middletown, CT 06457

    Spacious 2-bedroom, 1.5-bath apartment in Middletown! This unique two-level unit features an open main living, dining, and kitchen area with included appliances, plus convenient in-unit laundry. Enjoy an additional flexible space perfect for storage, a playroom, or a home office. Upstairs, you'll find two comfortable bedrooms with generous closets and extra storage, along with a spacious full

    Michael Bernard Ironclad Real Estate

    1185 Randolph Rd Unit Back Apartment, Middletown, CT 06457
  • 80 Russell St, Middletown, CT 06457

    $350,000

    Sold Dec 08, 2025

    80 Russell St, Middletown, CT 06457

    • 4 Beds
    • 3 Baths
    • 2,089 Sq Ft
    • Built 1999

    Last Sold Summary

    • $168/SF
    • 135 Days On Market

    Current Estimated Value $384,317

    Last Listing Agent Santo Gulino William Raveis Real Estate

    80 Russell St, Middletown, CT 06457
    • 1478 Bartholomew Rd, Middletown, CT 06457

      Est $629,417

      Not Listed For Sale

      1478 Bartholomew Rd, Middletown, CT 06457

      • 4 Beds
      • 4 Baths
      • 2,382 Sq Ft
      • Built 2001
      1478 Bartholomew Rd, Middletown, CT 06457

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Tanya Bottaro Real Broker CT, LLC

  • /40

    $569,900

    • 4 Beds
    • 2.5 Baths
    • 3,169 Sq Ft

    62 Greenview Terrace, Middletown, CT 06457

    Welcome to 62 Greenview Terrace, a beautifully maintained 3-4 bedroom, 2.5-bath Colonial nestled in the desirable Riverbend community of Middletown. Immaculately clean and thoughtfully cared for, this spacious home offers an ideal combination of comfort, functionality, storage, and privacy in a quiet neighborhood with a convenient location. The main level features a welcoming two-story foyer with

    Joseph Snell Luxe Realty LLC

    62 Greenview Terrace, Middletown, CT 06457
  • /13

    $2,250 Per Month

    • 4 Beds
    • 1.5 Baths
    • 3,784 Sq Ft
    • Apartment for Rent

    14 Pease Ave Unit 5, Middletown, CT 06457

    Fully renovated 4 bedroom 1.5 bath available for lease. Nothing to do but move in to this spacious, bright and updated unit! Heat and hot water are included in the monthly rent, onsite laundry, and conveniently located close to shopping and dining!

    Jaimie Andrews Bottom Line Realty

    14 Pease Ave Unit 5, Middletown, CT 06457
  • 66 East St, Middletown, CT 06457

    $365,000

    Sold Aug 10, 2026

    66 East St, Middletown, CT 06457

    • 3 Beds
    • 1.5 Baths
    • 1,514 Sq Ft
    • Built 1964

    Last Sold Summary

    • 4% Above List Price
    • $241/SF
    • 17 Days On Market

    Current Estimated Value $353,362

    Last Listing Agent Sally McMahon William Raveis Real Estate

    66 East St, Middletown, CT 06457
    • 565 Newfield St Unit 7, Middletown, CT 06457

      Est $298,919

      Not Listed For Sale

      565 Newfield St Unit 7, Middletown, CT 06457

      • 2 Beds
      • 1.5 Baths
      • 1,436 Sq Ft
      • Built 1991
      565 Newfield St Unit 7, Middletown, CT 06457

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Scott Nardozzi Cavanaugh & Company LLC

  • /31

    $317,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,776 Sq Ft

    70 Bielefield Rd, Middletown, CT 06457

    Move right in to this well-maintained raised ranch offering comfortable living and a functional floor plan. Enter through the street-level foyer, where you'll find access to the attached garage, a full bathroom, laundry area, utility room, and a versatile room that is perfect for a home office, den, workout room, or man cave. The main level features a bright eat-in kitchen, a spacious living

    Olga Acosta Century 21 AllPoints Realty

    70 Bielefield Rd, Middletown, CT 06457
  • 63 Meadowood Dr, Middletown, CT 06457

    $525,000

    Sold Jan 21, 2026

    63 Meadowood Dr, Middletown, CT 06457

    • 4 Beds
    • 3 Baths
    • 3,339 Sq Ft
    • Built 1965

    Last Sold Summary

    • 5% Above List Price
    • $157/SF
    • 11 Days On Market

    Current Estimated Value $543,003

    Last Listing Agent Joseph Harvey Best Real Estate Brokerage LLC

    63 Meadowood Dr, Middletown, CT 06457
    • 21 Portland St, Middletown, CT 06457

      Est $199,652

      Not Listed For Sale

      21 Portland St, Middletown, CT 06457

      • 2 Beds
      • 1 Bath
      • 791 Sq Ft
      • Built 1900
      21 Portland St, Middletown, CT 06457

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Amy Rio Better Homes and Gardens Real Estate Executive Real Estate

  • /37

    $379,900

    Open House 10/03
    • 2 Beds
    • 1 Bath
    • 1,188 Sq Ft

    142 Crystal Lake Rd, Middletown, CT 06457

    LAKEFRONT LIVING ON CRYSTAL LAKE! Welcome to 142 Crystal Lake Road, where everyday living feels like a getaway. Set directly on picturesque Crystal Lake, this charming 2-bedroom, 1-bath home offers the rare opportunity to enjoy waterfront living right from your own backyard. Step inside and you'll find 1,188 square feet of comfortable living space with a warm, inviting feel. The home features an

    Jessica Fedorich Stone Crest Realty LLC

    142 Crystal Lake Rd, Middletown, CT 06457

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