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$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
$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
$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
$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
$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
$649,900
9 Beds ⋅ 6 Baths ⋅ 24199960 MLS
Exceptional 3-Unit Mixed-Use Investment Opportunity A rare opportunity to own a well-maintained three-unit property offering townhouse-style living, private garages, excellent parking, and strong income-producing potential in the heart of Middletown. 227 East Main Street is an attractive investment opportunity for both seasoned investors and owner-occupants looking to build equity while generating rental income. The property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bathroom, and 1 half bathroom. The desirable layouts include bright, comfortable living spaces and eat-in kitchens, creating a residential feel that appeals to a broad range of tenants. One of the property's most compelling features is the private under-building garage for each unit, complete with direct access. This added convenience provides residents with the feel and functionality of a single-family home-an especially desirable feature in a multi-family property. Additional highlights include separate utilities, hardwood flooring, abundant natural light, basement storage, Washer dryer hook-ups in each unit, ample off-street parking, and a rear driveway providing convenient access behind the building. Separate utilities offer practical advantages for ownership and day-to-day management. Situated near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. Property being sold As Is. Agent owner related.

227 E Main St, Middletown

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