Middletown, CT Homes

• 

  

  

  /29

  $235,000 Pending

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

  91 Trolley Crossing Ln Unit 91, Middletown, CT 06457

  Welcome to this well-maintained and move-in ready townhome located in the desirable Trolley Crossing community. This inviting home offers a spacious and functional layout with comfortable living spaces throughout. The main level features a bright and open living room with plenty of natural light, a dining area perfect for everyday meals or entertaining, and a well-appointed kitchen with ample

  Anthony Bethune Dreamview Properties, LLC

  91 Trolley Crossing Ln Unit 91, Middletown, CT 06457
• 

  

  

  /35

  Starting at $1,945

  Total Monthly Price

  • 1 - 3 Beds

  10 Town Place, Middletown, CT 06457

  Comfortable living without the luxury price tag. Newly updated 1, 2, and 3 bedroom apartment homes, some with stainless steel appliances, full-size washers & dryers, private patios and balconies, ample parking, and private entries.

  Town Place

  (959) 245-5159

  

  10 Town Place, Middletown, CT 06457
• 

  $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 $398,528

  Last Listing Agent rob link Sterling REALTORS

  4 Lorraine Terrace, Rockfall, CT 06481
• 

  Est $182,645 Not Listed For Sale

  263 Carriage Crossing Ln Unit 263, Middletown, CT 06457

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

  263 Carriage Crossing Ln Unit 263, Middletown, CT 06457

  Last Sold Summary

  • 1% Above List Price
  • $269/SF
  • 33 Days On Market

  • Last Sold Price $180,000
  • May 09, 2025

  Last Listing Agent Martin Piggot Boyden Real Estate Company,LLC
• 

  

  

  /32

  $429,900

  • 4 Beds
  • 2 Baths
  • 1,963 Sq Ft

  63 Millbrook Rd, Middletown, CT 06457

  Welcome home to rustic Connecticut charm paired with flexible living space and timeless character. You are greeted by a warm living area featuring exposed wood beams and a beautiful stone fireplace that anchors the space with cozy appeal. Just beyond, your kitchen offers an abundance of cabinetry, giving you ample storage and functionality for everyday living and entertaining. Step outside and

  Krystal Pulley Tier 1 Real Estate

  63 Millbrook Rd, Middletown, CT 06457
• 

  

  /7

  Starting at $1,700 Plus Fees

  • 2 - 3 Beds

  121 Rose Cir, Middletown, CT 06457

  Rose Gardens offers spacious one bedroom flats, two and three bedroom townhomes conveniently located in a pedestrian friendly neighborhood near shopping, restaurants, schools and highways. The professionally landscaped grounds offer seasonal color year-round, maintained by Carabetta's 24 hour Maintenance Team. Appliances are included in all the units which have hardwood floors throughout.

  Rose Gardens Apartments

  (860) 854-4124

  

  121 Rose Cir, Middletown, CT 06457
• 

  $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 $380,077

  Last Listing Agent Santo Gulino William Raveis Real Estate

  152 Old Mill Rd, Middletown, CT 06457
• 

  Est $320,754 Not Listed For Sale

  11 Butternut Knolls Unit 11, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,306 Sq Ft
  • Built 1989

  11 Butternut Knolls Unit 11, Middletown, CT 06457

  Last Sold Summary

  • $245/SF
  • 48 Days On Market

  • Last Sold Price $320,000
  • May 09, 2025

  Last Listing Agent Shawna Rohan eXp Realty
• 

  

  /38

  $434,900 Under Contract

  • 5 Beds
  • 3 Baths
  • 1,644 Sq Ft

  207 Timber Ridge Rd, Middletown, CT 06457

  Don't miss this beautiful Cape Cod featuring five bedrooms and three full baths. Well maintained and thoughtfully updated, this home has seen many renovations over the past three years and is filled with natural light throughout. The main floor offers two bedrooms, a comfortable living room, and a welcoming kitchen perfect for everyday cooking and gathering. The kitchen opens to a large deck,

  Himanshu Singh Singh Realty

  207 Timber Ridge Rd, Middletown, CT 06457
• 

  

  /20

  Starting at $975 Plus Fees

  • Studio

  104 Meetinghouse Ln, Middletown, CT 06457

  Our spacious and affordable studio apartments are a place you'll love to call home! Burgundy Apartments in Middletown are set amidst beautifully landscaped grounds located in the desirable Westlake area. We are a short drive to all your everyday needs and Routes 91 and 9 are easily accessible. Our studio apartments are packed with features including air conditioning, kitchen appliances, extra

  Burgundy Apartments

  (959) 245-2207

  

  104 Meetinghouse Ln, Middletown, CT 06457
• 

  $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 $319,991

  Last Listing Agent Theresa Bitondo Berkshire Hathaway NE Prop.

  85 Meech Rd, Middletown, CT 06457
• 

  Not Listed For Sale

  311 Main Street Extension, Middletown, CT 06457

  • Built 1936

  311 Main Street Extension, Middletown, CT 06457

  Last Sold Summary

  • $28/SF
  • 144 Days On Market

  • Last Sold Price $225,000
  • Apr 01, 2025

  Last Listing Agent Patrick Savarese LPT Realty
• 

  

  /39

  $233,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,209 Sq Ft

  8 Inverness Square, Middletown, CT 06457

  ***MULTIPLE OFFERS - HIGHEST & BEST BY MONDAY, APRIL 27TH, by 12pm***Welcome home to this spacious 3-bedroom PLUS office/playroom single-family PUD home in the highly sought-after Highland at Westlake community. Mature arborvitaes line the front and sides of the property, enhancing curb appeal while creating a private, inviting setting. Newer floors throughout! Step inside and be pleasantly

  Karen Klein Coldwell Banker Realty

  8 Inverness Square, Middletown, CT 06457
• 

  

  /11

  Starting at $25 Plus Fees

  • 1 - 2 Beds

  65 Church St, Middletown, CT 06457

  Project-based Section 8 Housing for the Elderly (62 and older) and Persons with Disabilities. Rent is based on adjusted monthly income.

  South Green Apartments

  (860) 775-6410

  

  65 Church St, Middletown, CT 06457
• 

  $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 $221,248

  Last Listing Agent Martin Piggot Boyden Real Estate Company,LLC

  30 Orange Rd Unit 30, Middletown, CT 06457
• 

  Not Listed For Sale

  00 Livingston Rd, Middletown, CT 06457

  00 Livingston Rd, Middletown, CT 06457

  Last Sold Summary

  • $2/SF
  • 172 Days On Market

  • Last Sold Price $145,000
  • Mar 13, 2024

  Last Listing Agent Tim O'Hara William Raveis Real Estate
• 

  

  /35

  $465,000

  • 3 Beds
  • 2 Baths
  • 2,176 Sq Ft

  408 Maromas Rd, Middletown, CT 06457

  Immaculate 3-bedroom, 2-bath ranch offering a bright, lifestyle-focused layout across two levels. The main level showcases a spacious eat-in kitchen with granite countertops and opens directly to a low-maintenance composite deck-perfect for morning coffee or easy outdoor dining. Next on the main level is a sun-filled living room with cathedral ceilings and multiple windows, creating an airy,

  Sandy Fehrs Lamacchia Realty

  408 Maromas Rd, Middletown, CT 06457
• 

  

  /11

  Starting at $1,475

  Total Monthly Price

  • 1 Bed

  121-131 Butternut St, Middletown, CT 06457

  Come see why Highview Apartments is so popular. Our spacious one and two bedroom apartments feature eat-in kitchens, a large deck and on-site laundry facilities. All of our apartments are carpeted and include appliances and blinds for your convenience. Don’t forget about free heat and hot water. On-site maintenance provides prompt courteous service for your every need. Walking distance to

  Highview Apartments

  (959) 208-4565

  

  121-131 Butternut St, Middletown, CT 06457
• 

  $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
• 

  Not Listed For Sale

  0 Kelsey St, Middletown, CT 06457

  0 Kelsey St, Middletown, CT 06457

  Last Sold Summary

  • $2/SF
  • 117 Days On Market

  • Last Sold Price $153,400
  • Oct 24, 2023

  Last Listing Agent Dale Bunn Riverview Realty, LLC
• 

  

  /40

  $449,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft

  75 Azalea Dr, Middletown, CT 06457

  Welcome to 75 Azalea Drive in Middletown, a beautifully remodeled home that blends modern upgrades with comfortable living in a well-established neighborhood. Set on a generous 0.72-acre lot, this 2,088 sq ft home offers peaceful indoor and outdoor living. From the moment you step inside, you'll notice the attention to detail and quality craftsmanship throughout. The heart of the home is the

  Santo Gulino William Raveis Real Estate

  75 Azalea Dr, Middletown, CT 06457
• 

  

  /4

  Starting at $1,500 Plus Fees

  • 1 - 2 Beds

  38 Ward St, Middletown, CT 06457

  Nestled in the heart of one of Connecticut’s most vibrant and historic cities, 38 Ward Street offers a blend of comfort, character, and convenience. Whether you're a first-time homebuyer, a growing family, or simply looking for a peaceful retreat, this home has it allKey Features:Spacious Layout: Enjoy generous living space with bright and airy rooms throughout.Charming

  On Ward Apartments

  (475) 255-1758

  

  38 Ward St, Middletown, CT 06457
• 

  $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 $420,428

  Last Listing Agent Debbie Huscher Real Broker CT, LLC

  1018 Long Hill Rd, Middletown, CT 06457
• 

  Est $238,457 Not Listed For Sale

  3 Countryside Ln Unit 2, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft
  • Built 1987

  3 Countryside Ln Unit 2, Middletown, CT 06457

  Last Sold Summary

  • 7% Above List Price
  • $204/SF
  • 2 Days On Market

  • Last Sold Price $222,000
  • Jul 21, 2023

  Last Listing Agent Caitlin Cavanaugh Cavanaugh & Company LLC
• 

  /2

  $409,100

  • 3 Beds
  • 2 Baths
  • 1,934 Sq Ft

  5 Lorraine Terrace, Middletown, CT 06457

  REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 2000, this two story home offers approximately 1934 finished square feet, three bedrooms and two full baths, fireplace, covered front porch, fully finished basement and attached one car garage. This home sits on an approximate 11326 sqft lot. "As is" cash only sale with no

  Sherry Price Realhome Services & Solutions

  5 Lorraine Terrace, Middletown, CT 06457
• 

  

  /9

  Starting at $1,300 Plus Fees

  • 1 Bed

  562 Main St, Middletown, CT 06457

  Located on vibrant Main St, downtown Middletown just a walk away from shops, restaurants, and entertainment. Walking distance to a grocery market and convenience store. On the bus route. Lease terms: One year. Water is included. The renter pays directly for electricity and heat. No smoking building and no pets allowed.

  (860) 852-6189

  562 Main St, Middletown, CT 06457
• 

  $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 $355,408

  Last Listing Agent Colin Taylor Better Homes and Gardens Real Estate Executive Real Estate

  50 Andrew St, Middletown, CT 06457
• 

  Not Listed For Sale

  42 Mckenna Dr, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1968

  42 Mckenna Dr, Middletown, CT 06457

  Last Sold Summary

  • $99/SF
  • 54 Days On Market

  • Last Sold Price $119,000
  • Apr 25, 2023

  Last Listing Agent Stephanie Starr Berkshire Hathaway Home Services
• 

  

  /28

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft

  103 Prospect St, Middletown, CT 06457

  This classic 1900 Colonial at 103 Prospect Street offers a chance to bring new life to a well-loved home in a convenient Middletown location. With 1,160 square feet of living space, three bedrooms, and two full baths, the layout is simple and functional, ready for someone with vision to make it their own. The home does require work, making it a great project for investors, renovators, or buyers

  Carl Guild Carl Guild & Associates

  103 Prospect St, Middletown, CT 06457
• 

  

  /18

  $2,011 Plus Fees

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • House for Rent

  286 Mile Ln, Middletown, CT 06457

  Property Id: 2521266Run do not walk to see this stunning home Gorgeous at every turn. From the beautiful hardwood floors, updated kitchen and baths, open floor plan and oversized kitchen - one will be impressed. "Is this a model home?" It shows like one. The oversized master offers a large closet/dressing area perfect for an en suite bath if desired. This beautiful abode sits on a

  (908) 212-9877

  286 Mile Ln, Middletown, CT 06457
• 

  $230,000 Sold Dec 12, 2025

  137 Knowles Ave Unit 137, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 1,128 Sq Ft
  • Built 1989

  Last Sold Summary

  • 4% Below List Price
  • $204/SF
  • 44 Days On Market

  Current Estimated Value $231,746

  Last Listing Agent Wynne Lord Coldwell Banker Realty

  137 Knowles Ave Unit 137, Middletown, CT 06457
• 

  Not Listed For Sale

  00 Kelsey St, Middletown, CT 06457

  00 Kelsey St, Middletown, CT 06457

  Last Sold Summary

  • 290 Days On Market

  • Last Sold Price $95,000
  • Jul 21, 2023

  Last Listing Agent Patricia Holmes Berkshire Hathaway Home Services
• 

  

  /40

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,836 Sq Ft

  325 Barbara Rd, Middletown, CT 06457

  You're not seeing things-this home is priced to move! Welcome to easy, one-level living in a highly desirable, walkable neighborhood in Middletown, Connecticut. This charming ranch-style home offers 3 bedrooms, 1.2 baths, and an attached one-car garage, delivering both comfort and convenience. Set on a beautiful third-of-an-acre lot, the property features a brand-new white peastone patio &

  Erik Sousa William Raveis Real Estate

  325 Barbara Rd, Middletown, CT 06457
• 

  

  /8

  $2,450 Plus Fees

  • 3 Beds
  • 2 Baths
  • House for Rent

  53 Braeburn Ln, Middletown, CT 06457

  Property Id: 9987093 beds and 2 full bath , finished basement with another small roomClose to shopping and eating places, close to major highways 2 car garage, nice front and back yard for outdoor living Tenant responsible for , electricity, water and sewer , snow and lawn1st, last , security, required at lease sign.. total at lease sign is 6750$

  (413) 288-4820

  53 Braeburn Ln, Middletown, CT 06457
• 

  $189,909 Sold Oct 16, 2025

  18 Bacon Ave, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $167/SF
  • 2 Days On Market

  Current Estimated Value $196,605

  Last Listing Agent Keith Murphy Innovative Properties

  18 Bacon Ave, Middletown, CT 06457
• 

  /2

  Est $391,127 Not Listed For Sale

  272 S Main St, Middletown, CT 06457

  • Studio
  • 2 Baths
  • 2,164 Sq Ft
  • Built 1988

  272 S Main St, Middletown, CT 06457

  Last Sold Summary

  • 6% Below List Price
  • $171/SF

  • Last Sold Price $369,000

  Last Listing Agent Kris Cole Waterhouse Realty LLC
• 

  

  /21

  $708,768 Pending

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  128 Webster Ln, Middletown, CT 06457

  Founders' Ridge Award-Winning 55+ Adult Community! Introducing our model home, the "KIRBY II at 128 Webster Lane has 1,555 square feet of one-level living in the highly sought-after Westfield section of Middletown. This home features many high-end upgrades, including 9-foot ceilings, white wood cabinets with quartz countertops, hardwood floors in the living areas and bedrooms, and tile In the

  Sally Annino Berkshire Hathaway NE Prop.

  128 Webster Ln, Middletown, CT 06457
• 

  

  /20

  $1,800 Plus Fees

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  128 Grand St, Middletown, CT 06457

  Property Id: 2450251Spacious Unit 3 - Two-Bedroom Apartment for Rent This spacious two-bedroom apartment is available now and ready for move-in! The unit includes a dishwasher, washer, and dryer for your convenience. The apartment is pet-friendly and offers parking. Cold flat.Features:• 2 Bedrooms• Dishwasher• Washer & Dryer in unit• Pet Friendly •

  (860) 854-8011

  128 Grand St, Middletown, CT 06457
• 

  $429,000 Sold Feb 06, 2026

  77 Lindsey Rd, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,890 Sq Ft
  • Built 1988

  Last Sold Summary

  • 10% Below List Price
  • $227/SF
  • 180 Days On Market

  Current Estimated Value $442,647

  Last Listing Agent Sandy Orsie Berkshire Hathaway NE Prop.

  77 Lindsey Rd, Middletown, CT 06457
• 

  Est $445,241 Not Listed For Sale

  2 Lakeside Ave, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 2,223 Sq Ft
  • Built 2009

  2 Lakeside Ave, Middletown, CT 06457

  Last Sold Summary

  • 6% Above List Price
  • $189/SF
  • 92 Days On Market

  • Last Sold Price $420,000
  • Jan 17, 2025

  Last Listing Agent Gina Torre Real Broker CT, LLC

Showing Results 81 - 120, Page 3 of 18