Quick Middletown CT MLS Search

Browse All Middletown CT Historical Properties for Sale

130 Spencer Dr, Middletown
$349,000
5 Beds ⋅ 2 Baths ⋅ 24201926 MLS
Perfect 3-Bedroom Home Layout with 2 Bonus Flex Rooms/Offices! Welcome to this spacious 1952 Middletown Colonial, where classic charm meets low-maintenance living in a quiet neighborhood. Step inside a welcoming foyer with an entry closet that opens into a sun-drenched living area highlighted by a large bay window. The home features stunning hardwood floors throughout, flowing into a functional kitchen complete with natural wood cabinets, Corian countertops, a matching backsplash, and durable laminate flooring. Designed for effortless lifestyle flexibility, the main level hosts two bedrooms, including the primary bedroom, alongside a full bathroom with a tub/shower. Upstairs, you will find three additional bedrooms, perfect for a home office or private gym, and a second full bathroom with a tub/shower. The expansive basement is perfect for a hobbyist equipped with a dedicated tool workbench, storage shelving, and a laundry area with a washer and dryer. Outside, the home has low-maintenance vinyl siding and a cleared, level rear yard with mature landscaping and a handy tool shed. This prime location keeps you tranquil at home while placing you just minutes from Wesleyan University, downtown restaurants, nightlife, and scenic walks at Harborpark or Wadsworth Falls State Park. Commuting is a breeze with instant access to Route 9 and Route 66. This turn-key five-bedroom gem blends comfort, space, and ultimate Connecticut convenience.

130 Spencer Dr, Middletown

85 Oakcliff Rd, Middletown
$555,000
4 Beds ⋅ 3 Baths ⋅ 24198723 MLS
Welcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable Middletown neighborhood, privately set back from the road. Featuring an updated kitchen, new windows throughout, remodeled baths and a finished walk-out basement with a full bathroom this home offers space, flexibility and privacy. The finished lower level provides potential for an in-law apartment or separate living space, subject to town approval, making it ideal for extended family, guests, a home office or recreation. The expansive deck overlooks a beautiful yard for entertaining, a game of catch or running with your favorite four legged pal. Close to major highways, 20 minutes from Downtown Hartford, 35 minutes to New Haven, 45 minutes to CT Casinos, a little over an hour to the Rhode Island line and minutes from Wesleyan University, great shopping and restaurants in downtown Middletown! Major updates include: Brand New Septic- 2019 Kitchen remodeled - 2024 All windows replaced - 2024 Basement remodeled - 2023 Garage doors replaced - 2023 Full bathroom remodeled - 2022 AC air handler & condenser - 2021 Electrical upgrades & generator hookup - 2021 Well pump - 2021 Front door - 2021 Paver walkway & gutter/fascia improvements - 2020 Chimney repair & cap - approx. 2019 Boiler -2014 With a private setting, extensive updates, 4 bedrooms, 2.5 baths and a versatile walk-out lower level, this Middletown Colonial is ready to welcome its next owner!

85 Oakcliff Rd, Middletown

71 E Main St, Middletown
$419,000
8 Beds ⋅ 4 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

27 Pleasant St, Middletown
$679,900
24175820 MLS
Exceptional opportunity to own a beautifully maintained commercial property in one of Middletown's most desirable and visible locations. Currently operating as a professional attorney's office, this versatile building offers endless potential for professional, medical, office, boutique, or mixed-use possibilities. Perfectly positioned across from the historic town green and hospital, and just moments from downtown restaurants, shops, and major commuter routes, the location offers outstanding convenience and exposure. Blending timeless historic charm with modern updates, the property features an inviting entrance, impressive grand staircase, and a tastefully updated interior that preserves elements of the home's original character while incorporating modern finishes and functionality. Dedicated off-street parking, with charging for your EV, provides added convenience for clients and staff. The upper level offers exceptional flexibility with an updated full kitchen featuring quartz countertops, a luxurious full bath with a full tile shower, and two bedrooms. Ideal for an owner-occupant or live/work setup, you can simply walk downstairs to work each day. The sellers have also obtained city approval for a future rooftop expansion, creating the opportunity for an upscale rooftop terrace or executive entertaining space overlooking the downtown setting. A rare landmark-style property combining character, convenience, and future potential in an unbeatable location.

27 Pleasant St, Middletown

13 Portland St, Middletown
$1,300,000
8 Baths ⋅ 24174579 MLS
Exceptional mixed-use investment opportunity in Middletown, with views of CT River and landmark Arrigoni Bridge. Offering strong in-place cash flow with immediate upside potential. Features six fully occupied residential apartments (2-1bds, 2-2bds, 2-3bds) plus two 1,600 square foot commercial garage/workshop spaces, creating strong stability. One commercial garage is currently leased, while the second vacant garage presents a compelling opportunity for an owner-user or investor seeking additional income. If you're a contractor, workshop operator, have storage needs, or small business owner, the vacant commercial space (currently listed for rent) allows a buyer to occupy the space while offsetting ownership costs through the residential income stream. The residential apartments have been updated over time, have newer boilers/water heaters and offer a strong unit mix of one-, two-, and three-bedroom layouts with broad tenant appeal. Property features off-street parking, and excellent access to Route 9, downtown Middletown, shopping, restaurants, and commuter routes. * 8 total income-producing spaces * 6 fully leased residential apartments * 2 commercial garage/workshop units * One leased commercial space + one vacant 1,600 SF commercial unit * Owner-user opportunity (act soon before rented) * Minutes from Route 9 * Walk to downtown and Wesleyan - This is a rare, stable cash flow, turnkey opportunity!!!! Property to be conveyed in as-is condition.

13 Portland St, Middletown

668 Main St, Middletown
$2,249,500
21 Baths ⋅ 24165225 MLS
Investors dream - fully leased with value add potential! 18-unit corner brick building located on Main Street in the heart of Downtown Middletown, steps from gourmet restaurants and boutiques. Originally built in 1850, this 11,232 SQ FT building consists of 17 residential units and one ground level retail space. The retail space is leased to a mobile carrier/retailer through 2028 with annual rent escalation, allowing the new owner to focus on executing on the business plan for the 17 residential units. The building features four rare 2 beds, 2 bath units, seven 1-bedroom units, and six studio apartments. The building is currently fully leased, giving the new Owner an opportunity to capture the incredible rent upside over time while collecting rent income. The building has all separate gas boilers, huge unfinished basement and shared electricity. The units feature great layouts with nice natural light, high ceilings and large bedrooms with good closet space. The current owner has recently replaced some of the units windows, appliances and carpeting. Easy access to route 9 and a short drive/walk to Wesleyan University. This corner brick building is located near the beautiful, historic town center with over 7 walkable blocks of different restaurants and shops, featuring dozens of choices of dining, art, music, entertainment and unique finds. Neighborhood attractions include: Perkatory Coffee Roasters; Eli Cannons Tap Room; The Whey Station; Luce. Become part of this exciting tow

668 Main St, 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.

Middletown Historical Real Estate

Our website features the best real estate search for historical 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!

How much is your home worth?

Get instant property value now!