Quick Middletown CT MLS Search

Browse All Middletown CT Between $400K - $500K Properties for Sale

$449,900
3 Beds 3 Baths 24194846 MLS
Welcome to this beautifully maintained, original-owner Colonial, perfectly nestled on a quiet cul-de-sac in Middletown's highly sought-after Westfield neighborhood! From the moment you step inside, you'll be welcomed by an abundance of natural light, gleaming hardwood floors, and a bright, open floor plan designed for both comfortable everyday living and effortless entertaining. The main level offers spacious gathering areas, convenient first-floor laundry, a half bath, and a flexible room that can easily serve as a home office, playroom, den, or additional living space to fit your lifestyle. Upstairs, you'll find three generously sized bedrooms and two full bathrooms, including an exceptional primary suite featuring an oversized bedroom, an expansive walk-in closet, and a private en-suite bath-your own peaceful retreat at the end of the day. Step outside and enjoy the beautiful deck beneath the gazebo while overlooking the large, level yard-perfect for entertaining, gardening, pets, or creating lasting memories with family and friends. The full unfinished basement offers approximately 1,000sq.ft of potential, giving you the opportunity to create a home gym, media room, recreation space, or whatever you've been dreaming of. Lovingly cared for by its original owners, this home offers the perfect combination of pride of ownership, timeless charm, and endless possibilities. Schedule your private showing today and experience everything this exceptional home has to offer!

279 Congdon St, Middletown

$419,000
9 Beds 5 Baths 24190092 MLS
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 business on the ground floor while collecting steady rental income from the apartments upstairs. The commercial spaces enjoy excellent street frontage and high visibility along busy East Main Street, providing strong exposure for retail, office, or service-oriented businesses-with one of the commercial units already featuring a dedicated kitchen. The 3 residential units offer versatile 1, 2, and 3 bedroom layouts, each featuring 1 full bathroom. These units offer strong rental appeal in a highly desirable location. Situated within walking distance to restaurants, shopping, entertainment, public transportation, and local amenities, this property benefits from Middletown's vibrant atmosphere. Whether you're looking to expand your investment portfolio, generate multiple income streams, or establish your business while collecting residential rental income, this versatile property offers outstanding potential. Convenient access to Route 9, I-91, Wesleyan University, and surrounding communities. Make an appointment today to view this property!

71 E Main St, Middletown

$480,000
3 Beds 3 Baths 24188018 MLS
Nestled in the highly desirable South Farms neighborhood, this well-maintained home is filled with quality features and timeless appeal. Car enthusiasts and hobbyists will appreciate the impressive 4-car garage, offering exceptional space for vehicles, storage, or the perfect workshop. The spacious eat-in kitchen features granite countertops, abundant cabinetry, and generous workspace for cooking and entertaining. Throughout the home, you'll find an abundance of closet space in each of the 3 bedrooms. Hardwood floors lie beneath the carpeting, offering the opportunity to restore their original beauty. The expansive finished basement, complete with a full bath, additional laundry room, and cozy gas fireplace, provides the perfect setting for entertaining, relaxing, or creating the ultimate recreation space. The sunroom off the kitchen can also be used for a home office. A second gas fireplace in the living room adds warmth and charm, making this home inviting in every season. Step outside to enjoy the deck, complete with a retractable awning for shade on sunny days. Additional highlights include a full-house generator, walk-up attic, central A/C, laundry on the main floor and exceptional storage space throughout the home. Take advantage of all that Middletown has to offer with its many restaurants, cultural centers, and shopping. Close to I-91 and Rt 9. This home presents an exceptional opportunity for its next owner. Don't miss your chance to make it yours!

779 Ridge Rd, Middletown

$499,999
4 Beds 3 Baths 24183267 MLS
****Highest and Best by Monday July 13 at 5:00pm.**** This beautifully maintained Colonial, tucked away on a quiet cul-de-sac, in the highly sought after Riverbend development is a must-see! Filled with natural light and abundant storage, this home also features two spacious decks for relaxing and entertaining. The sun-filled eat-in kitchen boasts soaring ceilings that extend to the second floor, creating an open and airy feel. Large windows flood the space with light, while direct access to the upper deck and adjoining family room make it ideal for everyday living and gatherings. The main level also offers a spacious living room with oversized windows that flows seamlessly into the formal dining room. Upstairs, the primary suite features a walk-in closet and a private full bath. Two additional bedrooms each include walk-in closets and share a full bath, while a fourth bedroom is currently being used as a home office. A conveniently located second-floor laundry room adds to the home's functionality. The finished lower level offers a generous recreation room with walkout access to the lower deck, along with entry to a third garage bay that provides exceptional space for storage, a workshop, or hobby area. With abundant storage throughout, versatile living spaces, and a desirable cul-de-sac location, this home is ready to impress. It's only minutes away from I-91 and Route 9 so commuting is no problem. HOA includes grounds maintenance and snow removal of common areas only.

175 Rolling Grn, Middletown

$414,900
2 Beds 3 Baths 24188911 MLS
Turn-key home in the sought-after Riverbend Community in Middletown's desirable Westfield neighborhood offers suburban tranquility with excellent convenience. Inside, soaring ceilings grace the living and dining areas, a fireplace adds warmth to the living room, and hardwood floors flow through the main spaces. Large dining area flows to the kitchen and living room, perfect for entertaining. The stunning white eating kitchen features tile flooring while the two bedrooms with the vaulted ceilings and a remodeled primary bath create comfortable retreats. Relax or entertain on the oversized composite deck steps down to the fully fenced backyard with dedicated play area complete with playscape. Walk out finished lower level includes flexible space that can easily serve as a 3rd bedroom; has a full bath, and extra storage. Enjoy the two-car garage Just minutes from vibrant downtown Middletown, you'll enjoy shops, boutiques, and popular restaurants, while the nearby Mattabesset multi-use trail is perfect for walking and biking. Golfers appreciate the short drive to Miner Hills Golf Course, you will love the proximity to Veterans Memorial Park with its new pool & splash pad plus the excellent Champions Skating Center in Cromwell just five to six miles away. Route 9 access makes Connecticut's beautiful beaches and shoreline towns only 25-30 minutes away. This move-in-ready home delivers convenient access to downtown, recreation, and the shoreline.

38 Wildflower Ln, Middletown

$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

$485,000
3 Beds 3 Baths 24184294 MLS
Nestled at the end of a quiet cul-de-sac, this beautifully maintained Colonial offers the perfect blend of privacy, comfort, and timeless charm on nearly an acre of professionally landscaped grounds surrounded by nature. A welcoming front porch framed by classic pillars invites you inside, while the expansive two-tier Trex deck creates an ideal setting for outdoor entertaining and offers ample space for a future pool. Additional exterior features include a storage shed. Step inside to discover gleaming Brazilian cherry hardwood floors, a cozy living room with a fireplace, and a formal dining room accented by elegant crown molding and a stylish chandelier. The spacious eat-in kitchen is equipped with newer appliances and sliders that lead directly to the deck, seamlessly connecting indoor and outdoor living. A convenient half bath completes the main level. Upstairs, you'll find three generously sized bedrooms featuring vaulted ceilings and brand-new carpeting throughout. The primary suite offers a walk-in closet and private full bath, while a second full bath serves the additional bedrooms. The partially finished basement provides valuable flex space perfect for a recreation room, home office, gym, or media area. Additional highlights include central air conditioning, whole-house generator, a two-car garage, and meticulous ownership evidenced by consistent maintenance and care throughout the years. MULTIPLE OFFERS HIGHEST AND BEST BY 7/6 AT 5 PM

117 David Dr, Middletown

$497,900
4 Beds 4 Baths 24179489 MLS
Experience the perfect blend of historic charm and modern comfort in this exceptional Colonial home. From the moment you enter the spacious foyer, you'll be captivated by the craftsmanship, warmth, and timeless elegance that define this residence. The formal dining room, living room, and sunroom showcase remarkable original plaster crown molding, a rare architectural detail that highlights the home's rich character. The beautifully updated kitchen features soapstone countertops, stainless steel appliances, and a classic swinging door that opens to the dining room. Just beyond, a private balcony provides the perfect setting for morning coffee or evening relaxation. A stylishly renovated half bath is conveniently located near the rear entry. The inviting living room centers around a gas-insert fireplace accented by stunning Art Deco sconces, while the adjacent sunroom offers terracotta tile flooring and abundant natural light, creating an ideal retreat for reading, relaxing, or enjoying the changing seasons. The home features four bedrooms and three-and-a-half bathrooms. The spacious primary suite includes a beautifully appointed full bath with a large tiled shower. Two additional bedrooms share a charming period-inspired full bath complete with the original tub, sink, and elegant vintage fixtures. The finished walk-up attic serves as a generous fourth bedroom and includes additional flexible space ideal for a home office, hobby room, studio, or extra storage.

46 Bretton Rd, Middletown

$499,900
3 Beds 2 Baths 24179107 MLS
Experience one-floor living at its finest at Nathan Hale Estates, a private-way community nestled in Middletown, Connecticut, built by Silvin Homes and offering modern comfort, quality craftsmanship, and peaceful surroundings. Entering from the covered front porch, you're welcomed into a thoughtfully designed layout. Features include a convenient laundry room and two well-appointed secondary bedrooms connected by a Jack-and-Jill style full bath. The home then leads you into a stunning open-concept design perfect for everyday living and entertaining. A chef-inspired kitchen complete with a large island fit for entertaining flows seamlessly into an expansive family room featuring a cozy gas fireplace and direct access to the backyard patio. Privately situated, the luxurious primary suite offers spacious walk-in closets and a beautifully designed primary bath complete with a walk-in shower. Additional features include high-end luxury vinyl flooring throughout the main living areas, carpeting in the bedrooms, tile in the bathrooms, energy-efficient systems, central air, and quality finishes throughout. Generous builder allowances allow buyers to personalize appliances, tile, flooring, cabinetry, and granite countertops. Conveniently located near shopping, dining, parks, major commuter routes, and the Connecticut shoreline. Optional two-car garage upgrade available. Builder requires a one-time construction-to-permanent loan financed by Elm Tree Funding.

Lot 2 Nathan Hale, Middletown

$499,900
3 Beds 2 Baths 24178985 MLS
Experience one-floor living at its finest at Nathan Hale Estates, a private-way community nestled in Middletown, Connecticut, built by Silvin Homes and offering modern comfort, quality craftsmanship, and peaceful surroundings. Entering from the covered front porch, you're welcomed into a thoughtfully designed layout. Features include a convenient laundry room and two well-appointed secondary bedrooms connected by a Jack-and-Jill style full bath. The home then leads you into a stunning open-concept design perfect for everyday living and entertaining. A chef-inspired kitchen complete with a large island fit for entertaining flows seamlessly into an expansive family room featuring a cozy gas fireplace and direct access to the backyard patio. Privately situated, the luxurious primary suite offers spacious walk-in closets and a beautifully designed primary bath complete with a walk-in shower. Additional features include high-end luxury vinyl flooring throughout the main living areas, carpeting in the bedrooms, tile in the bathrooms, energy-efficient systems, central air, and quality finishes throughout. Generous builder allowances allow buyers to personalize appliances, tile, flooring, cabinetry, and granite countertops. Conveniently located near shopping, dining, parks, major commuter routes, and the Connecticut shoreline. Optional two-car garage upgrade available. Builder requires a one-time construction-to-permanent loan financed by Elm Tree Funding.

Lot 1 Nathan Hale, Middletown

Start Your Search

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.

Between $400K - $500K Middletown Real Estate

Our website features the best real estate search for between $400k - $500k properties available in Middletown and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!