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$419,000
9 Beds ⋅ 5 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
$420,000
6 Beds ⋅ 2 Baths ⋅ 24188066 MLS
Turnkey multifamily investment opportunity in a desirable Middletown location! This fully remodeled property offers strong income potential with updated units featuring modern kitchens, renovated bathrooms, new flooring, and contemporary finishes throughout. The building has been well maintained and provides an excellent opportunity for investors seeking a low-maintenance asset with immediate cash flow. Conveniently located near downtown Middletown, shopping, restaurants, schools, parks, and major highways, making it attractive to tenants and ensuring long-term rental demand. Whether you're expanding your portfolio or acquiring your first investment property, this move-in-ready multifamily is an opportunity you won't want to miss. Being SOLD AS-IS.

163 Pearl St, Middletown
$405,000
7 Beds ⋅ 2 Baths ⋅ 24188106 MLS
Fully renovated investment opportunity in the heart of Middletown! This well-maintained 7 bedrooms 2 bath, multifamily property has been completely remodeled and offers immediate cash flow with tenants already in place. Each unit is currently rented, providing strong and stable rental income from day one. Updates include modern kitchens, renovated bathrooms, updated flooring, fixtures, and mechanical improvements throughout. The property has been thoughtfully upgraded while maintaining its charm and functionality. Ideal for investors seeking a turnkey asset with reliable tenants and minimal deferred maintenance. Conveniently located near shopping, restaurants, schools, public transportation, and major highways. Don't miss this opportunity to add a fully occupied, income-producing property to your portfolio. Being SOLD AS-IS.

194 Liberty St, Middletown
$349,900
6 Beds ⋅ 2 Baths ⋅ 24187894 MLS
It's not easy to find a 2 family with 3 bedrooms on each level and it includes ALL separate utilties and each unit has c/a. Each tenant pays their own utilities. The first floor is leased until July 2027 and the 2nd floor lease is up Sept. 1st, 2026. The furnaces, electrical, hot water tanks have all been updated.

10-12 Glover Pl, 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
$749,900
9 Beds ⋅ 6 Baths ⋅ 24171799 MLS
Outstanding Mixed-Use Investment Opportunity at 227 East Main Street, Middletown, CT Now offered at a newly reduced price, 227 East Main Street presents an exceptional opportunity for investors or owner-occupants seeking strong income potential and long-term value. This well-maintained mixed-use property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bath, 1 half bath, bright living spaces, and eat-in kitchens-highly desirable layouts that help attract and retain tenants. A standout feature is that each unit includes its own private under-house garage with direct access, creating the convenience and feel of a single-family home. The property also offers ample off-street parking and a driveway behind the building, providing easy access and added convenience for residents and guests. Separate utilities, hardwood floors, abundant natural light, and additional basement storage further enhance the property's appeal and ease of management. Ideally located near downtown Middletown, shopping, dining, parks, major commuter routes, Wesleyan University, and Middlesex Health, this property benefits from strong rental demand and excellent accessibility. With its price improvement, desirable townhouse-style units, private garages, ample parking, and proven income-producing potential, 227 East Main Street is a compelling investment opportunity in the heart of Middletown. Agent owner related.

227 E Main St, Middletown
$1,100,000
8 Beds ⋅ 4 Baths ⋅ 24163304 MLS
Exceptional Multi-Family Investment Opportunity in CT! Located in desirable Middletown, this unique property package offers two two-family homes-for a total of four income-producing units-along with a versatile 2,898 sq ft workshop and two additional vacant land parcels. Each residential building offers approximately 1,380 sq ft with new roofs, new windows, upgraded electrical, and modernized plumbing-providing peace of mind for years to come. All properties are connected to natural gas, adding efficiency and convenience. One unit has been fully renovated, supplies to renovate the other units are located in the workshop. The standout feature is the expansive heated workshop with electricity and plumbing already in place, opening the door to endless possibilities-ideal for contractors, hobbyists, storage, or potential additional income use. Set on a combined .25-acre lot, plus two separate parcels (.08 and .02 acres), this offering provides flexibility rarely found * Expand your portfolio with strong rental income potential * Build on the additional lot (buyer to do due diligence) * Or enjoy extra outdoor space as a private side yard. Whether you're an investor looking for solid cash flow or an owner-occupant seeking supplemental income, this property delivers versatility, updates, and long-term value in one compelling package.

Portland Street, Middletown
$829,000
6 Beds ⋅ 4 Baths ⋅ 24148860 MLS
Experience over 5,500 square feet of beautifully updated living space in this fully remodeled 6+ bedroom, 3.5-bath residence, perfectly situated on a quiet and expansive 8+ acre lot. Every detail has been thoughtfully upgraded, creating a truly move-in-ready home offering exceptional flexibility and design versatility. The expansive kitchen is the heart of the home, featuring elegant quartz countertops, stainless steel appliances, a double oven, and generous prep and storage space-ideal for both everyday living and entertaining. Large windows and glass doors throughout flood the interior with natural light, enhancing the open-concept layout and spacious living areas. Designed with flexibility in mind, the floor plan offers multiple configuration options, including potential for a private secondary living area-perfect for multi-generational living, guests, or home-based business needs. Interior highlights include: * Large loft with adjoining office space * Two fireplaces * Hardwood flooring * High-end luxury vinyl plank flooring in key living areas The primary suite provides a peaceful retreat, complete with a spacious 7x10 walk-in closet and a beautifully designed bath featuring dual vanities and a custom tile shower. Step outside to enjoy the large deck just off the kitchen and dining area-an ideal setting for relaxing evenings or hosting gatherings.

44 Chamberlain Hill Rd, Middletown

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