Middletown Real Estate

Recently Sold Listings in Middletown, CT

Welcome to your dedicated resource for viewing Sold listings in Middletown, CT. As local Middletown, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights home values, selling strategies, and options like cash offers. Start exploring the most recent sold properties in Middletown, CT below, or if you are looking to sell a home in Middletown, CT contact a local agent to discuss the possibilities.

< Back to all Homes for Sale in Middletown, CT

Be the First to Know About New Middletown Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Middletown Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Recently Sold in Middletown, CT

$1,875,000
4 Beds ⋅ 5 Baths ⋅ 24130406 MLS
Situated on almost 13 acres in the heart of CT, this stunning Colonial offers peace and nature while being located conveniently to everything including beaches, highways, Middlesex hospital, Wesleyan University, CT river, and Middletown's thriving downtown with an abundance of shops, restaurants and activities. An entertainer's paradise with a backyard oasis boasting a heated, gunite, in-ground pool with splash pad and jacuzzi, fireplace, wet bar with propane grill and flat top, and new wood fired steam sauna. The chef's kitchen features all GE Profile smart appliances, 2 hidden spice racks and has a walk-in pantry and an additional smaller one. The family room off the kitchen is a perfect link to the outdoor parties and features a hidden tv that is lowered out of the way of the patio entrance. The 21' high great room offers a floor to ceiling stone fireplace and windows flooding the home with natural light. An office with a gas fireplace is off the front foyer with a beautiful, crystal chandelier with a switch to lower it for cleaning. The first floor master suite has a slider to the patio and gorgeous ensuite and walk-in closet. The upper level features a bonus room and 3 bedrooms, all with ensuites and walk-in closets. The kitchen and all full baths have heated floors, surround sound speakers throughout the whole house, smart thermostats and appliances, heated garage, whole house water filtration with UV light, irrigation system, whole house generator plus much, much more.

120 Chamberlain Hill Rd, Middletown
$1,200,000
5 Beds ⋅ 5 Baths ⋅ 24024319 MLS
Lovingly maintained country estate with award-winning gardens, second guest home or opportunity for rental income, and serene heated in-ground gunite pool. Imagine living in this tranquil oasis but being just moments away from fabulous restaurants, art, entertainment, and all that being near a prestigious university offers! The Nehemiah Hubbard House is filled with charm, character, plus modern-day amenities. Marvel at hand hewn wide plank floors while exploring this 5 bedroom, 3 full 2 half bath home with modern day mudroom. Large eat-in kitchen with loads of prep-space and great entertainment flow. Opportunity for in-law in main home, au-pair suite, art studio, or work from home space. 2 greenhouses will fuel your inner gardener year-round. Lower-level walkout offers easy access to gardens and pool creating endless entertainment choices. This home has a newer roof and new mechanicals including a top-of-the line Buderus boiler! Only the 2nd time this property has been offered to the public in nearly 100 years. With over 10 combined acres including a building lot this property offers access to Wadsworth falls trails, this estate would make for an excellent horse property. Guesthouse features 2 bedrooms, 2 possible full baths. Adjoining barn is excellent storage for the car enthusiast or antique collector. Use for yourself or lease for additional income. Would make excellent living quarters for stable-hand, gardeners, and professionals.

15 Laurel Grove Rd, Middletown
$1,150,000
8 Beds ⋅ 9 Baths ⋅ 170575745 MLS
Welcome to The White Lion Manor. The manor is a perfect balance of tasteful, modern updates with grand colonial craftmanship. Enjoy the stunning front to back, whole house foyer with original millwork, gorgeous wood floors and a custom painted ceiling medallion. The living room is bright and welcoming with a hand painted statement wall and incomparable millwork. There's a 1st floor en suite with port hole windows, sun room and leads out to the pool. The oversized dining room with custom built ins, original moldings and one of the 6 fireplaces is ready for entertaining. The eat in kitchen area with butler's pantry is a chef's sanctuary. This home is currently being used as a 2nd home/retreat and as a highly rated AirBNB. To ensure a special experience for all, recent updates include: private entrance gate, refurbishment of pool and replaced pump, custom chimney caps, updated the electrical system, added generator hookup, updated CAIR, commercial grade dehumidifier, hard wire internet system and garage office for office manager. Professionally landscaped lawn and outdoor entertainment space includes walking trails, pool and jacuzzi. Located in Middletown, it's home to Wesleyan University, featured in The NY Times for it's "friendly" and "hip" vibe and awarded "Most Romantic Main Street". This idyllic 8 bedroom, 6+acre destination is 25 minutes from the CT shoreline and centrally located between Hartford and New Haven. Easy commute from Manhattan and just in time for summer!!

85 Flynn Ln, 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.