Middletown Real Estate

Homes for Sale in Middletown, CT Between $400,000 to $450,000

Welcome to your dedicated resource for Homes for Sale Between $400,000 to $450,000 in Middletown, CT. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Middletown, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $400,000 to $450,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Middletown, CT Homes for Sale Between $400,000 to $450,000

$437,900
3 Beds 2 Baths 24188898 MLS
Rarely does a home blend historic character, creative energy & walkable in-town living so effortlessly. Nestled on a beautifully landscaped corner lot just moments from Wesleyan University, vibrant downtown Middletown & the Connecticut River waterfront, this thoughtfully updated early-1900s home offers warmth, flexibility & timeless appeal. Featuring 3 bedrooms, 2 full baths & a versatile third-floor studio, the flexible layout is ideal for an artist's retreat, home office, guest suite or creative sanctuary. Original character shines throughout with exposed brick, custom built-ins & abundant natural light. The updated kitchen features a Viking 6-burner range & opens seamlessly to the living & dining areas, creating an inviting space for everyday living & entertaining. Significant updates include newer windows, roof & a tankless hot water heater, while the classic brownstone foundation reflects the home's enduring craftsmanship. Outside, enjoy the charm of your own private city homestead with mature perennial gardens, window boxes, a fenced corner lot, dedicated garden beds, a welcoming back porch & even a chicken coop. A detached garage with bonus studio space offers endless possibilities for hobbies, a workshop or additional workspace. Just a short stroll to downtown restaurants, shops, local schools, parks & the riverfront, this exceptional property offers the perfect balance of historic charm, modern comfort & an unbeatable in-town lifestyle.

598 High St, Middletown

$430,000
3 Beds 3 Baths 24190665 MLS
Classic Colonial on a picture-perfect lot with sweeping pastoral views in one of Middletown's most scenic settings! This home offers solid bones, generous room sizes, and loads of potential for anyone ready to add their own touches. The sun-filled living room offers oversized windows and flows easily into the dining area, while the beamed family room delivers warmth and character with wood paneling and a brick fireplace. The eat-in kitchen features ample counter space, stainless appliances, and a picture window overlooking the private backyard. A main-level laundry room and half bath add everyday convenience. Upstairs you'll find three comfortable bedrooms, including a spacious primary suite with its own private bath and double closets, plus a second full bath off the hall. The finished lower level adds fantastic flexible space with a large recreation room and dry bar - perfect for movie nights, a home office, or gym. Step outside and this property truly shines: an expansive deck with covered gazebo overlooks a sprawling, level backyard bordered by mature trees and open field views - a wonderful setting for entertaining or simply unwinding at the end of the day. Additional highlights include a two-car garage, mini-split systems for efficient heating and cooling, and a peaceful country feel just minutes from shopping, schools, and Route 9. Opportunities to own this view, space, and charm don't come along often. Bring your vision and make it home!

9 Round Hill Rd, Middletown

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.