Middletown Homes for Sale

Welcome to Middletown, Connecticut – a charming city nestled in the heart of Middlesex County, where rich history meets modern living! With its vibrant downtown, scenic parks, and a community spirit that welcomes all, Middletown offers a unique blend of suburban tranquility and urban convenience.

Middletown is renowned for its picturesque streets lined with historic homes and contemporary residences, making it an ideal place for families, professionals, and retirees alike. The city boasts a diverse range of homes for sale, from quaint colonial-style houses to modern condominiums and spacious single-family homes. Whether you're seeking a cozy starter home or a luxurious retreat, Middletown's real estate market has something to cater to every taste and budget.

The city's vibrant arts scene, highlighted by the renowned Wesleyan University, offers a plethora of cultural events, theaters, and galleries. Outdoor enthusiasts will appreciate the lush parks and the beautiful Connecticut River, perfect for kayaking, fishing, and leisurely strolls. With excellent schools, a variety of dining options, and convenient access to major highways, Middletown is not just a place to live; it’s a place to thrive.

If you’re considering a move to this delightful city, now is the perfect time to explore the homes for sale in Middletown. Discover the community that feels like home and experience the warmth of a city that truly embraces both its history and its future. Let us help you find your dream home in Middletown today!

Newest Middletown Homes for Sale

$609,000

3 Beds ⋅ 3 Baths ⋅ 24207436 MLS

Welcome to this gorgeous 3-bedroom, 3.5-bath Colonial nestled on a desirable cul-de-sac in a highly sought-after neighborhood. Filled with natural light, this beautifully updated home offers comfort, space, and functionality throughout. The home has been thoughtfully updated within the past two years.The inviting living room features beautiful flooring and flows seamlessly into the dining area, creating an ideal space for entertaining. The updated kitchen offers new appliances, abundant natural light, and convenient access to the sunroom-perfect for relaxing and enjoying the surroundings. The oversized family room provides plenty of space for quality time with family and friends.Upstairs, you'll find generously sized bedrooms, with updated carpeting throughout the second floor. The spacious primary suite features hardwood flooring, a ceiling fan, and a private bath with a Jacuzzi tub and separate standing shower. Additional ceiling fans throughout the home enhance comfort and airflow.The finished walkout basement adds valuable living space and includes a full bathroom, making it ideal for a media room, recreation area, home office, or entertaining space. Step outside to enjoy the beautiful backyard and patio, perfect for gatherings, outdoor dining, and summer celebrations.This wonderful home offers a great combination of updates, space, and location. The seller has spent $161,000 to keep the house updates. Don't miss the opportunity to make it your own dream home!

184 Rolling Grn, Middletown

$539,900

3 Beds ⋅ 3 Baths ⋅ 24207248 MLS

Welcome to Sylvan Run, a welcoming Westfield neighborhood where spacious homes, three cul-de-sacs and a convenient Middletown location come together. This beautifully updated Saltbox Colonial offers an impressive amount of living space with a layout designed for both everyday comfort and entertaining. Step inside to hardwood floors and a bright, inviting interior. The updated kitchen features granite countertops with stainless steel appliances. The open floor plan makes the stunning custom pellet stove fireplace the focal point of family room with vaulted ceilings adding to the spacious feel. Two sets of sliding doors connect the main living spaces to the expansive rear deck and fully fenced back yard. A formal dining room and living room provide even more flexibility on the main level. Upstairs, the spacious primary suite offers dual closets and an updated private bath. An open hallway overlooking the family room below enhances the homes bright, airy feel, while two additional generously sized bedrooms and full bath complete the second floor. Need even more space? The finished lower level offers exceptional versatility for a recreation room, home gym, office, media room or playroom along with a dedicated laundry room and cedar closet. Outside enjoy your evenings on the expansive deck overlooking the fenced backyard or take advantage of the Sylvan Run neighborhood - perfect for a stroll, bike ride or enjoy the picnic area.

897 East St, Middletown

$244,900

4 Beds ⋅ 1 Baths ⋅ 24205927 MLS

Set on a quiet dead-end street near Wesleyan University and downtown Middletown, 27 Fairview Ave is a classic 1934 Colonial with character, convenience, and potential. This estate property features 1,235 sq ft, 4 bedrooms, 1 full bath, (with room for a 2nd bath on the upper level) and walk-in attic space. MAJOR RECENT IMPROVEMENTS INCLUDE: NEW ROOF IN 2024 (stripped & reroofed=1 layer), NEW 200 AMP ELECTRICAL SERVICE IN 2025, a NEW OIL BOILER AND OIL TANK in 2025 as well as a NEW CEILING IN both the LIVING ROOM and ONE BEDROOM, all of which creates a strong starting point for a remodel. The traditional layout offers defined living spaces, a manageable footprint, and room to bring fresh ideas to the kitchen, bath, finishes, and overall design. Its central Middletown location provides easy access to nearby campus, downtown shops, restaurants, parks, and commuter routes. Best suited for an investor or contractor. This property will not qualify for FHA or VA financing. Cash, renovation loan or conventional financing only. This home to be sold strictly AS-IS. Seller will not make any repairs. Sale is subject to Probate Court approval.

27 Fairview Ave, Middletown

$549,900

3 Beds ⋅ 3 Baths ⋅ 24204996 MLS

Set well back from the road on 4.6 secluded acres, this beautifully maintained ranch combines generous one-level living with a bright, welcoming feel throughout. Large windows on all sides bring in abundant natural light and frame views of the expansive landscaping, lawn, and surrounding trees. The spacious remodeled kitchen anchors the home's everyday living, with beautifully crafted cabinetry, substantial granite countertops, a large custom center island, and generous workspace, complemented by expansive backyard views and seamless flow to the outdoor living space. The private bedroom wing includes a generous remodeled primary suite with hardwood floors, 3 spacious closets, and a modern private bath designed for the comfort, style, and functionality today's buyers expect. Just beyond the primary suite, a dedicated office with extensive built-ins offers flexible space for working from home, studying, meetings, or enjoying a hobby. The living and dining rooms flow together with warm hickory floors and custom millwork, while a thoughtfully designed mudroom/pantry just off the kitchen adds character and function with built-in cubbies and cabinetry. Outside, the broad, open lawn offers room to gather, play, garden, or enjoy the private setting. A Trex deck and paver patio extend the living space outdoors, creating an inviting place to relax or entertain. Meticulously cared for and truly move-in ready, this home feels spacious, comfortable, and private from the moment you arrive.

1446 Randolph Rd, Middletown

$429,900

3 Beds ⋅ 2 Baths ⋅ 24207126 MLS

Welcome to 18 Gibson Lane, ideally situated in Middletown's desirable Westfield section. This inviting 3 bedroom, 2 bath home offers an open floor plan designed for everyday living and easy entertaining. Enjoy the year round comfort of central air and natural gas heat. The spacious layout provides a wonderful opportunity to make this home your own. Conveniently located close to shopping, major roadways and Middletown's vibrant downtown, where you'll find an excellent selection of restaurants, cafes and local amenities. A great opportunity to own a one level home in a sought after area with convenience, comfort and an easy lifestyle. INTERIOR PHOTOS COMING SOON!

18 Gibson Ln, Middletown

$221,900

1 Beds ⋅ 1 Baths ⋅ 24206820 MLS

CUTE AS A BUTTON! This move-in ready home on almost an acre of land, has several wonderful updates! New boiler 2025, new oil tank 2024, chimney was rebuilt from the roof line up in 2025, wood stove in living room 2013, roof approx 14 years old, driveway sealed in June, flooring in the kitchen/dining room/living room & bedroom 2022, light fixtures 2022, bathroom exhaust fan 2025, blinds 2025, storm door 2023, water heater 2023, dishwasher 2024, oven range 2025, washer 2026, dryer 2022 and the town put in a new water meter a few weeks ago! PUBLIC WATER & SEWER. This home is well cared for, clean and just as nice as the photos show it to be. Beautiful yard! Quiet neighborhood in a fantastic part of town near the Cromwell line!

79 Plumb Rd, Middletown

$389,000

2 Beds ⋅ 3 Baths ⋅ 24205251 MLS

You'll fall in love with this move-in condition colonial located at the end of a cul-de-sac. The yard is level and partially fenced with a large deck ideal for three-season cookouts and relaxation. The bright interior has plenty of room for hosting gatherings. The recently remodeled kitchen adjoins the dining room so the cook can join the conversation. Upstairs are two bedrooms each with hardwood floors and their own newly remodeled baths. There's a full basement for exercising and storage ideal for future finishing. All this convenient to highways, shopping, and recreation. Don't miss this one!

46 Clarence Ct, Middletown

$280,000

3 Beds ⋅ 2 Baths ⋅ 24206413 MLS

Beautifully renovated and ready for its next chapter, this charming 3-bedroom, 2-bath home offers comfortable living with modern updates throughout. The main living spaces provide a warm and inviting setting, while three bedrooms upstairs offer privacy and plenty of room to spread out. The spacious primary bedroom features vaulted ceilings, adding an open and airy feel. Conveniently located near major highways, this home is an excellent choice for commuters while still being close to shopping, dining, and everyday conveniences. With thoughtful renovations already completed, there's nothing left to do but move in and enjoy!

6 Hillside Ct, Middletown

$379,900

3 Beds ⋅ 2 Baths ⋅ 24205306 MLS

Well maintained 3 bedroom home with flexible floor plan. 1 bedroom on the first floor, as well as 2 full baths, Living room, and eat-in kitchen. The second floor has 2 additional bedrooms. 1st Floor Laundry. New Furnace. Splits for air condioning. 200 amp elec. Panel w/ Generator hook up. New detached 3 car garage with loft are above.

64 Ryan St, Middletown

$379,900

3 Beds ⋅ 2 Baths ⋅ 24206199 MLS

FULLY UPDATED & TURN KEY! Welcome to 672 East Main Street, a beautifully renovated home offering extensive update inside and out. This meticulously maintained property features a new roof, siding, windows, front door, flooring, interior paint, kitchen cabinets, updated kitchen and bathrooms, and so much more. Enjoy the convenience of a dedicated washer and dryer located on the main floor, making everyday living easy and convenient without the need to go up or down. Outside, enjoy new landscaping, a new concrete walkway, and a new back patio, creating a fresh and welcoming exterior. Located close to everything, with easy access to Route 9 and just minutes from Downtown Middletown, you'll enjoy convenient access to shopping, dining, entertainment, and everyday amenities. With so many major improvements already completed, this home is truly move-in ready and turn-key. Just unpack, settle in, and enjoy!

672 E Main St, Middletown

$689,000

2 Beds ⋅ 2 Baths ⋅ 24205132 MLS

Expect the best! Carefree living at Founders' Ridge, the premier award-winning 55+ community in Central Connecticut! Introducing the highly sought-after Kirby II model home, now available for IMMEDIATE occupancy. This is the last Kirby II available at this price point. Located in Middletown's desirable Westfield section, this thoughtfully designed 1,555-square-foot, single-level home offers an ideal blend of comfort, style, and convenience. Inside, you'll find elegant white cabinetry, quartz countertops, and a spacious walk-in pantry that combine beauty with functionality. Hardwood flooring flows throughout the main living areas, while the bathrooms and laundry room feature durable tile flooring. A bright bay window in the front room fills the space with natural light and offers sweeping views. Outside, the private rear patio provides the perfect setting for relaxing or entertaining. Additional highlights include natural gas heating and central air conditioning for year-round comfort. Some photos are of similar homes and may include optional upgrades. Agent/owner related.

Unit 2-41 Webster Ln Unit 145, Middletown

$119,000

1 Beds ⋅ 1 Baths ⋅ 24204389 MLS

*** BRAND NEW MOBILE HOME - Modern, Stylish & Ready for You! *** Be the first to call 500 Washington Street #9 home! Located in Middletown Mobile Home Park, this brand-new 1-bedroom, 1-full-bath mobile home offers fresh, modern living with everything new from the start. A welcoming 6' front porch adds charm and the perfect spot to relax outdoors. Inside, enjoy a bright, thoughtfully designed interior featuring a beautiful kitchen with new stainless steel appliances, including refrigerator, dishwasher, microwave/hood vent, and upgraded smooth-top electric range. With 200-amp electrical service and an efficient, easy-to-maintain layout, this home offers comfort, convenience, and the peace of mind that comes with owning brand new. Mobile home scheduled to be delivered onsite October 9, 2026, with anticipated move-in availability October 30, 2026. Why renovate when you can start fresh? Don't miss this opportunity to be the very first owner-schedule your showing and make #9 yours! ***Note: Home to be delivered and installed onsite. Sketch is a rendering of the New Mobile Home Model. Colors and Details may differ. New Mobile Home on Pad Site - Taxes to be determined. Purchaser to verify with local municipality.***

500 Washington St Unit #9, 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.