Middletown Real Estate

Welcome to Middletown, a charming city nestled in Middlesex County, Connecticut. Middletown is a vibrant community with a rich history and a promising future, making it an ideal place to call home.

Known for its picturesque downtown area, Middletown offers a perfect blend of small-town charm and urban convenience. Residents enjoy a variety of local shops, restaurants, and cultural attractions, creating a lively atmosphere that caters to all interests.

Nature enthusiasts will appreciate the city's proximity to the Connecticut River, where outdoor activities such as boating, fishing, and hiking can be enjoyed year-round. For those seeking a more relaxed pace, Middletown's numerous parks and green spaces provide the perfect setting for a leisurely stroll or a quiet afternoon picnic.

With a strong sense of community and a diverse population, Middletown offers a welcoming environment for residents of all ages. The city's top-rated schools, healthcare facilities, and recreational amenities make it an ideal place to raise a family or enjoy retirement.

Whether you're looking to buy, rent, or invest in real estate, Middletown has something for everyone. Come discover the beauty and charm of this historic city in the heart of Connecticut.

Newest Listings in Middletown

$180,000

3 Beds ⋅ 2 Baths ⋅ 24194531 MLS ⋅ Beacon Hill Towne Homes BLDG.

Investment Opportunity! This spacious condo is being sold as-is and offers excellent potential for investors or buyers looking to build sweat equity. The unit features gleaming hardwood floors throughout, a partially finished basement offering additional living or storage space, and a finished attic that adds even more usable square footage. A convenient 1.5 bath layout rounds out the floor plan. Enjoy community amenities including access to a sparkling in-ground pool. Conveniently located near I-91 and Route 9, offering easy access for commuters. With its combination of extra finished space, low-maintenance hardwood flooring, and community amenities, this unit presents a strong opportunity for value-add renovation or rental income. Sold as-is.

106 Rising Trail Dr Unit 106, Middletown

$395,000

3 Beds ⋅ 3 Baths ⋅ 24194117 MLS

Welcome home to this charming property located at the end of a peaceful cul-de-sac. This residence features three bedrooms, including a primary bedroom with an ensuite full bathroom. There are two updated full bathrooms in total, along with a convenient half bath. As you enter, you'll notice the gleaming hardwood floors that flow throughout the main living areas. The kitchen is thoughtfully designed with granite countertops, maple wood cabinets, and stainless steel appliances, offering a great setup for everyday cooking. The dining area seamlessly connects to the cozy living space, which features a gas fireplace and a mini-split system, providing an additional heating and cooling option for year-round comfort. From the dining area, sliding doors open to a patio with Trex decking, complete with a retractable awning, perfect for providing shade when needed and easily rolled back for sunny days. The two-car garage provides direct access to a finished basement area that includes a half bathroom and laundry facilities, enhancing the home's functionality. Energy-efficient solar panels ensure excellent coverage, leading to no current electric bill. Step outside to discover a private walking path accessible right from your backyard. This home is fully move-in ready, waiting for you to create lasting memories.

3 Yellow Pine Cir, Middletown

$539,999

3 Beds ⋅ 3 Baths ⋅ 24191099 MLS

Welcome to this beautifully updated 3-bedroom Contemporary retreat, perfectly situated on a lush, private lot. A charming wraparound covered front porch welcomes you home and offers the perfect space to relax, unwind, or gather with family and friends. Inside, you'll find 1,604 square feet of thoughtfully designed living space featuring soaring vaulted ceilings, abundant natural light, beautiful wall-to-wall luxury vinyl plank (LVT) flooring, three bathrooms, and a spacious primary suite with an updated en-suite bathroom complete with a relaxing Jacuzzi tub. More than $60K in renovations have been completed within the past year, including a new roof, new siding, a new balcony, a freshly stained deck, and numerous additional updates, making this home truly move-in ready. The finished lower level expands your living space with a cozy family room centered around a fireplace. Adjacent to the family room is an unfinished area already equipped with plumbing, offering a true blank canvas for your vision. Whether you dream of a future kitchenette, home office, guest suite, multigenerational living space, or a potential in-law setup (subject to local approvals), the possibilities are endless.Step outside to your own backyard oasis. Surrounded by mature trees & lush greenery, the expansive deck, brand-new above-ground pool, and newly built balcony create a private, resort-like setting that's perfect for morning coffee, summer pool parties,or relaxing evenings under the stars...

1512 Country Club Rd, Middletown

$239,900

2 Beds ⋅ 2 Baths ⋅ 24193840 MLS ⋅ Cedar Ridge BLDG.

This lovely move in ready unit, is set within a peaceful and quiet complex. On the main level you with find a large living room, dining room combination, 1/2 bath, pretty kitchen with plenty of cabinets, and a brand new refrigerator and oven hood. Also, the door off the kitchen will lead you right out onto your pretty deck for some relaxation time and grilling. Upstairs you will find the primary and 2nd bedrooms, along with a spacious full bath. There are pull down stairs, as well as an attic fan. The basement is large and ready for your special touches to create a workout room, office, or whatever may be suitable for you. Located close to highway access, both route 17 as well as Routh 9, Middlesex Community College, plenty of restaurants, shopping, banking, and just about anything else that you may need. C'mon and make your appointment today, as this very clean unit will surely not last long. Lucky will be the new owner for this truly great unit!

10 Countryside Ln Unit 5, Middletown

$688,000

4 Beds ⋅ 3 Baths ⋅ 24193869 MLS

Welcome home to this beautifully maintained 5-bedroom, 2.5-bath Colonial, ideally located in the heart of vibrant Middletown. Enjoy easy access to Middletown's many wonderful restaurants and downtown charm, with Middlesex Health, Wesleyan University, and the scenic CT River all just minutes away. Freshly painted throughout, this turn-key home is ready for you to move right in! The main level offers a wonderful flow for both everyday living and entertaining. The spacious eat-in kitchen features a center island and a sunlit breakfast nook with a skylight, creating the perfect spot to enjoy your morning coffee or casual meals. The kitchen opens seamlessly into the inviting great room, complete with a cozy fireplace and a built-in sound system, creating the ideal setting for gatherings, movie nights, or relaxing at home. A separate living room and formal dining room provide additional space for hosting family and friends. A standout feature of this home is the impressive 500-square-foot first-floor fifth bedroom, traditionally designed as a media room. Complete with surround sound and a projector, this exceptional space is perfect for movie nights and entertaining. Its generous size also makes it an ideal primary or guest bedroom, home office, playroom, or recreation room-offering incredible flexibility. Upstairs, you'll find four generously sized bedrooms and well-appointed bathrooms, providing plenty of room for family, guests, or additional workspace.

166 Mccormick Ln, Middletown

$209,000

2 Beds ⋅ 2 Baths ⋅ 24193843 MLS ⋅ Hamlin Court BLDG.

This freshly painted townhouse-style condo offers 2 bedrooms, 1.5 bathrooms, newer windows, updated appliances, newer flooring throughout, and an open-concept layout. The main level features a spacious living room that flows into the dining area and kitchen, along with access to a private terrace. The kitchen includes tile flooring, a mosaic tile backsplash, and appliances replaced within the past three years. Upstairs are two bedrooms with spacious closets, a full bathroom, and convenient in-unit laundry with a new washer and dryer. Previously rented for $1,900 per month, this investor-friendly unit offers strong income potential. Additional features include a dedicated storage unit, one assigned parking space, and visitor parking. Ideally located within walking distance of Downtown Middletown, Wesleyan University, and Middlesex Hospital, with easy access to restaurants, shopping, and major commuter routes.

201 College St Unit 20, Middletown

$85,000

24192347 MLS

Approved 0.42-acre building lot offering the opportunity to build your custom single family or two family home. Public water, public sewer, and natural gas are available at the street. Ideally located just minutes from downtown Middletown, shopping, restaurants, parks, and major highways, this property offers the perfect combination of convenience and potential. Don't miss this opportunity to bring your vision to life!

672 E Main St, Middletown

$365,000

2 Beds ⋅ 2 Baths ⋅ 24191334 MLS

***Highest and Best by Monday July 27th at 50pm***Turnkey two-family investment opportunity on a quiet residential street in Middletown. Built in 1900 and offering 1,654 sq. ft. across two self-contained units, this property brings in reliable rental income with minimal upkeep thanks to durable vinyl siding and an architectural shingle roof. Combined the units offer 2 bedrooms and 2 full baths, plus additional flex space in each unit ideal for a home office or storage. The upstairs unit's primary bedroom includes its own walk-in closet, and each unit has private laundry hookups - a major draw for tenants. Recent updates include new luxury vinyl plank flooring and a modern kitchen island in one unit, while the other retains warm hardwood floors and classic charm. Large double-hung windows keep every room bright. Each unit enjoys its own private deck, and parking accommodates up to 4-6 vehicles across two parking areas. The 0.19-acre lot also includes a shared, fenced backyard.

200 E Ridge Rd, Middletown

$425,000

3 Beds ⋅ 3 Baths ⋅ 24192475 MLS

HIGHEST AND BEST by 5pm Friday July24th. Seller reserves the right to accept an offer at any time prior to the deadline. Nestled near the end of a quiet dead-end road, this beautifully maintained 3-bedroom ranch offers peaceful country living with picturesque pasture views. Stunning perennial gardens, designed by a master gardener, provide exceptional curb appeal and seasonal color. Hardwood floors run through the bedrooms, hallway, and formal dining room. The inviting living room features a wood-burning fireplace and bay window overlooking the front gardens, while the dining room's picture window captures the scenic farmland beyond. The primary suite includes a private full bath. A spacious family room with sliders opens to a bright sunroom and deck, creating the perfect space to relax or entertain while enjoying the tranquil backyard. First-floor laundry, an attached two-car garage, solar panels, and a whole-house generator add comfort and convenience. The walk-out lower level features a second fireplace with a wood stove, dry bar, workshop, pool table, secure safe, abundant storage, and unfinished space for future expansion. A wonderful opportunity to enjoy one-level living in a beautiful country setting.

85 Ten Acre Rd, Middletown

$229,900

3 Beds ⋅ 1 Baths ⋅ 24192281 MLS

Welcome to 21 Inverness Ln. Make this spacious 3 bedroom your new home. This home is nestled in the sought-after Highland Lake Community. The home features an open floor plan with generous sized rooms. Upon entering, you'll be met with an updated kitchen and a comfortable dining area. The adjacent family room features laminate flooring and sliders to a private fenced in patio complete with a pergola to shield you from the sun on scorching hot summer days. The upstairs features 3 spacious bedrooms, updated full bathroom, laundry nook and an area for den, office or media play. The 2-car garage also has an additional storage area off the back. You can enjoy single family home living without the extensive yard work. This home is waiting for your next summer party. Highest and best Sunday, 7/26 by 5:00 PM.

21 Inverness Ln, Middletown

$370,000

3 Beds ⋅ 2 Baths ⋅ 24190857 MLS

Beautifully maintained ranch offering the perfect blend of comfort, style, and functionality! This move-in-ready home features 3 spacious bedrooms and 2 full bathrooms, including a generous primary suite with a private en-suite bath. The bright and inviting living spaces are ideal for both everyday living and entertaining. A true highlight of the home is the stunning full-glass sunroom overlooking the expansive backyard, creating the perfect space to enjoy your morning coffee, unwind after a long day, or host family and friends year-round. An attached one-car garage and enclosed patio provide additional flexible space for entertaining, hobbies, or relaxing in every season. Conveniently located with central air conditioning and a thoughtfully designed layout, this home offers comfort, versatility, and pride of ownership throughout. Whether you're a first-time homebuyer, looking to downsize, or searching for your next home, this exceptional property is ready to welcome its new owners. Don't miss this incredible opportunity-schedule your private showing today!

417 Mile Ln, Middletown

$245,000

3 Beds ⋅ 2 Baths ⋅ 24192257 MLS ⋅ Beacon Hill Towne Homes BLDG.

Just renovated. Kitchen has just been remodeled with new counters, white cabinets, white backsplash and stainless steel appliances. 1st floor is tile floor and there is a pellet stove in corner of livingroom. 1/2 bath on main level has new toilet and vanity. 2nd level offers 2 bedrooms with walk in closets and laundry in hall. Floor's just refinished. 3rd level offers 3rd bedroom and a finished room that could be study, playroom or storage. Town records lists this as a 2 bedroom but incorrect. Carport in driveway and room for another car. Diagonally located across from pool.

45 Rising Trail Dr Unit 45, Middletown

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