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423 Main St, Middletown
$3,990,000
4 Baths ⋅ 24182009 MLS
Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts.

423 Main 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

51-57 S Main St, Middletown
$1,695,000
1 Baths ⋅ 24157523 MLS
The perfectly situated and meticulously maintained medical/office campus at 51 & 57 South Main Street in Middletown is now being offered for sale. The properties will have 6,618sf available for occupancy at the time of sale leaving ample room for a new owner and their medical practice or an investor bringing a new tenant/tenants with them. The properties are located directly across the street from Middlesex Hospital offering healthcare providers the convenience of just a quick walk to and from their procedures. The shared 30+ car parking area was freshly paved and striped less than a year ago and there is no deferred maintenance to speak of. The lone tenant at the properties is on a triple net lease relieving ownership of a portion of the maintenance, property tax and insurance burden. Financials and interior photos are available upon request. -Location: The properties are located directly across from Middlesex Hospital's main campus -Well Maintained: The current owner operated his ENT practice here for decades and has taken meticulous care and great pride in the upkeep of the properties -Income: The lone medical tenant pays good rent on a landlord-friendly triple net lease -Convenience: The campus is located just off of CT Route 9 which connects to I-91, I-95 and I-84 -Value-Add: 1,772sf basement at 57 South Main can be converted to paid tenant storage or possibly addit

51-57 S Main St, Middletown

942 Washington St, Middletown
$1,500,000
2 Baths ⋅ 24196708 MLS
942 Washington Street presents a prime commercial investment opportunity in the heart of Middletown's busiest retail corridor. Positioned on the heavily traveled Route 66, with an average daily traffic count of approximately 20,000 cars, this property offers exceptional visibility and exposure for investors and end users alike. Surrounded by national retailers including Wendy's, McDonald's, AutoZone, and Home Depot, the location benefits from strong neighboring businesses and consistent consumer traffic. This high-profile commercial property is ideal for retail, restaurant, or service uses, or for redevelopment, and represents a valuable addition to any investment portfolio. Washington Street remains one of Middletown's most active commercial corridors, offering convenient access, strong demographics, and long-term growth potential. Don't miss the chance to secure a property in one of the city's most sought-after business locations.

942 Washington St, Middletown

61 E Main St, Middletown
$1,395,000
21 Beds ⋅ 9 Baths ⋅ 24206879 MLS
Two-building mixed-use investment opportunity in Middletown. The offering includes 61 East Main Street with four apartments and two storefronts, plus a separate three-apartment building at 2-6 Flower Street, offering a more private off Main street setting. Six apartments are occupied, while the seventh is being updated with a new kitchen and bathroom. Upon completion and lease-up at the projected rent, the property is expected to offer an approximately 9% cap rate, that's before any income from the two vacant storefronts. Zoned MXI, the storefronts have previously operated as a clothing store, salon and convenience store in past years, offering flexible possibilities subject to zoning guidelines. Additional features include private off-street parking space, wood flooring, same ownership since 2014, units updated/repaired over ownership for housing voucher compliance/inspections, separate utilities, a yard area and visible East Main Street frontage. With a Walk Score of 74, the property is close to Downtown Middletown, restaurants, shops, services, Wesleyan University, the riverfront, public transportation and Route 9. Two buildings, one investment and multiple opportunities to increase income!!! Interior pics will be added prior to active date.

61 E Main St, Middletown

480 Main St, Middletown
$1,300,000
10 Baths ⋅ 24184246 MLS
Welcome to 480 Main Street, Middletown - a rare investment opportunity in the heart of Downtown Middletown! This stunning brick mixed-use building blends timeless character with strong income-producing potential. Featuring 8 spacious residential units, each offering 900+ square feet, soaring ceilings, beautiful hardwood flooring, functional built-ins, and oversized layouts that tenants love. Seven of the Eight residential units have been updated, and many feature newer hot water heaters, helping minimize future capital expenses. The property is anchored by two commercial storefronts, including a 3,100 SF space and a 1,100 SF (long-term tenant). Commercial tenants contribute approximately 40% of CAM expenses, creating additional value for ownership. Featuring classic brick construction, a well-maintained roof, and a prime downtown location, 480 Main Street offers a rare blend of character, stability, and investment potential. Located just steps from restaurants, shopping, and entertainment, this is an excellent opportunity to own a standout mixed-use asset in the heart of Middletown

480 Main St, Middletown

480 Main St, Middletown
$1,300,000
8 Beds ⋅ 10 Baths ⋅ 24182655 MLS
Welcome to 480 Main Street, Middletown - a rare investment opportunity in the heart of Downtown Middletown! This stunning brick mixed-use building blends timeless character with strong income-producing potential. Featuring 8 spacious residential units, each offering 900+ square feet, soaring ceilings, beautiful hardwood flooring, functional built-ins, and oversized layouts that tenants love. Seven of the Eight residential units have been updated, and many feature newer hot water heaters, helping minimize future capital expenses. The property is anchored by two commercial storefronts, including a 3,100 SF space and a 1,100 SF (long-term tenant). Commercial tenants contribute approximately 40% of CAM expenses, creating additional value for ownership. Featuring classic brick construction, a well-maintained roof, and a prime downtown location, 480 Main Street offers a rare blend of character, stability, and investment potential. Located just steps from restaurants, shopping, and entertainment, this is an excellent opportunity to own a standout mixed-use asset in the heart of Middletown

480 Main St, Middletown

13-15 Portland St, Middletown
$1,300,000
12 Beds ⋅ 8 Baths ⋅ 24178851 MLS
Unique mixed-use opportunity in Middletown offering strong cash flow and flexible ownership potential. Property consists of a fully occupied 4-family, a fully occupied 2-family, and two 1,600 SF commercial garage/workshop spaces all situated on one lot with views of the Connecticut River and Arrigoni Bridge. One commercial space is leased, while the second vacant garage offers ideal owner-user potential for contractors, storage, workshop space, or additional rental income. Projected 8.2% cap at current occupancy, with stabilization potential of approximately 9.4-9.8% upon lease of the 2nd garage. Residential units feature a desirable mix of 1-, 2-, and 3-bedroom layouts with updates completed over time, including newer boilers and water heaters. Off-street parking, minutes to Route 9, downtown Middletown, and walking distance to Wesleyan University. Property conveyed as-is.

13-15 Portland 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

1409 Millbrook Rd, Middletown
$1,295,000
4 Beds ⋅ 4 Baths ⋅ 24187574 MLS
Nestled on an extraordinary 39-acre estate with breathtaking panoramic views, this stunning custom log home offers the perfect blend of rustic elegance, modern comfort, and exceptional investment potential. Originally built in 2005 with an addition completed in 2014, the home features 4 bedrooms and 3 full bathrooms. The interior showcases soaring cathedral ceilings, beautiful tile flooring, ceiling fans throughout, and a dramatic two-sided fireplace that serves as a focal point for multiple living areas. German-engineered windows with roll shutters & premium German doors provide exceptional quality. Kitchen features new appliances & an open concept. 2 bedrooms with full bathrooms on the main level offer one-floor living options. The lower level includes 2 oversized garages providing abundant storage, workshop space, and room for recreational equipment. A wood/storage shed adds even more utility. This home is in pristine condition with brand new well, new water heater, and 2 central air units. The property consists of three separately deeded parcels presenting a rare opportunity for future investment, development, or resale. The land features rolling acreage, mature trees, open spaces, and a picturesque man-made pond. Whether you're seeking a private retreat, recreational haven, family compound, or property with investment upside, this one-of-a-kind estate delivers stunning natural beauty, exceptional craftsmanship, and limitless possibilities.

1409 Millbrook Rd, Middletown

145 Monarca Dr, Middletown
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 24202531 MLS
A one-of-a-kind custom-built new construction home that must be experienced in person to be appreciated. This modern contemporary farmhouse-style ranch sits on 2.38 acres of private land, positioned at the end of a cul-de-sac on a private road. From the moment you arrive, the exterior makes a lasting impression. Stone walls frame the driveway, guiding you past a thoughtfully designed approach w/a waterfall element & circular drive. The home's facade showcases board & batten siding, stone & striking black windows, gutters & trim. A covered front entry with a custom-built on-site front door & oversized 10-ft garage doors complete the curb appeal. Inside, every detail has been carefully designed & executed. Custom paneled walls conceal hidden features, including a discreet foyer closet & a hidden half bath accessed through the paneling along w/built-in storage for convenience. The open-concept living space is breathtaking, highlighted by soaring ceilings, exposed beams & a stunning central fireplace that anchors the home. The chef's kitchen is both beautiful & functional, featuring high-end cabinetry, a farmhouse sink, a large center island w/waterfall quartz edges & additional storage below. 1 wing of the home includes 2 guest bedrooms, a full bath & a cleverly enclosed laundry area finished walnut, keeping it completely out of sight. The primary suite offers a luxurious bath w/a walk-in shower, double vanities, walk-in closet, & a unique double-seater, lay-down soaking tub.

145 Monarca Dr, Middletown

516 Washington St Unit 1, Middletown
$1,000,000
24189275 MLS
Exceptional commercial opportunity in one of Middletown's busiest retail corridors. Situated on approximately 0.47 acres, this 5,115 SF commercial building offers outstanding visibility with average daily traffic counts of approximately 20,000 vehicles. Currently operating as an auto repair facility with five vehicle lifts, the property is well-suited for continued automotive use or redevelopment. Located in the desirable B-2 General Commercial Zone, this site offers tremendous flexibility for a variety of commercial uses, making it an excellent investment or development opportunity. Surrounded by established national and local businesses, the property benefits from strong exposure, convenient access to major roadways, and a thriving commercial environment. Whether you're looking to expand your existing business, invest in an income-producing property, or redevelop a prime commercial site, this is a rare opportunity to secure a highly visible location in one of Middletown's most sought-after business districts.

516 Washington St Unit 1, Middletown

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