Rarely does an opportunity come along that offers this level of flexibility, lifestyle, and income potential all in one exceptional property. Completely renovated from top to bottom just a few years ago, this stunning home combines modern finishes, thoughtful design, and turnkey convenience with virtually every major component already updated - allowing you to focus on enjoying the property rather than maintaining it. Whether you're seeking a spacious owner-occupied residence, a multigenerational setup, or a high-performing investment, the possibilities here are remarkable. The current upper-level short-term rental is generating over $50,000 annually and has become a favorite among guests thanks to its unique character, custom artwork, inviting atmosphere, and unbeatable location. Situated in one of Middletown's most desirable areas, you'll enjoy the ability to walk to Wesleyan University, vibrant downtown Middletown, award-winning restaurants, boutique shopping, breweries, entertainment venues, and the scenic Connecticut River waterfront and Riverwalk. Commuters will appreciate convenient access to Routes 9, 66, 91, and other major thoroughfares. Outside, the property continues to impress with extensive parking, a newly paved driveway, beautiful landscaping, multiple new decks, private patio spaces, and a luxurious outdoor retreat featuring a hot tub lounge area complete with television, privacy shades, and a resort-like feel perfect for relaxing or entertaining.
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.
Charming and well-located two-family home in the heart of Central Connecticut! This quaint property features two 1-bedroom, 1-bath units, making it an ideal opportunity for an owner-occupant or investor alike. Recent exterior improvements include a new deck and exterior staircase to the second floor. Approximately four years ago, the home was upgraded to efficient on-demand heat and hot water systems for each apartment. An unbeatable location just a short walk to Middlesex Health and close to Wesleyan University, vibrant downtown Middletown, and the scenic Connecticut River. Convenient, comfortable, and full of potential-don't miss this versatile property! More photos soon!
Welcome to 118 Grove Street, a well-maintained two-family property located in the heart of Middletown. Situated on a quiet corner lot in a desirable neighborhood, this home is just minutes from downtown Middletown and Wesleyan University. This property is easy to manage and ideal for both owner-occupants and investors, featuring natural gas, separate utilities, two electric panels, and laundry in each unit. The first-floor unit offers two bedrooms, one full bath, and a formal dining room accented with beautiful crown molding and classic charm throughout. The second-floor unit is a spacious one-bedroom, one-bath layout featuring abundant natural light and a comfortable, functional floor plan. Whether you are looking to expand your investment portfolio or occupy one unit while generating rental income from the other, this property presents a fantastic opportunity. Schedule your showing today! Agent is related to Seller.
Updated two-family in a fantastic Middletown location just minutes from Wesleyan University, downtown shopping, and Route 9 - great for an owner-occupant or investor, with one unit delivered open at the end of the month and ready for immediate occupancy. Recent improvements have all the major boxes checked: brand new roof, brand new water heaters, plus updated kitchens, updated baths, and newer flooring throughout - all completed within the last five years. Everything is properly split for hassle-free two-family living: separate natural gas heat with two boilers, two electric panels, and two gas meters - no shared utilities, clean books, easy management. The first-floor unit features in-unit laundry, while both units offer a comfortable layout with multiple bedrooms, a full bath, eat-in kitchen, and a covered front porch overlooking the neighborhood. Outside you'll find a private off-street driveway with parking for multiple vehicles, a level yard, mature shade trees, and a metal storage shed for added convenience. Whether you're looking to offset your mortgage with rental income, expand your investment portfolio, or set up a multi-generational living arrangement, 37-39 Hotchkiss delivers strong fundamentals, modern updates, and a prime walkable location near one of Connecticut's premier university towns. Don't miss this one! Agent Owner
Turnkey mixed use investment opportunity at 227 East Main Street! This well-maintained three-family property features townhouse-style units, offering enhanced privacy and a highly desirable layout for tenants. With strong rental income potential and separate utilities, this is an ideal opportunity for investors or owner-occupants alike. Each unit spans multiple levels and offers 3 bedrooms with 1 full bath, and 1 half bath along with a spacious living room and eat-in kitchen. The townhouse-style design provides a single-family feel within a multi-family setting-an attractive feature that helps drive tenant demand. The property showcases classic charm with hardwood floors, generous natural light, and functional layouts throughout. A standout feature of this property is that each unit includes its own under-house garage, providing direct access and added convenience-a rare and highly sought-after amenity for tenants in this area. The property also includes additional basement space for storage and laundry hookups. Conveniently located near downtown Middletown with easy access to shopping, dining, parks, and major commuter routes. Close proximity to Wesleyan University and Middlesex Hospital on bus line. Agent owner related.
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.
PERMIT IN HAND READY TO BUILD! In the heart of Middletown and within walking distance to countless amenities, 54 Washington Street offers both location and opportunity. Once home to the Italian American Club, the building carries a unique history and is now ready for a new vision. This spectacular building has received zoning approval to convert this once community/event space to residential units. Take advantage of the already in place engineered 18-unit build-out plans with extra room for a super, the possibilities are endless. Not only does this building have engineered plans, but it is also stamped for electrical and plumbing. With all major systems professionally designed, code-compliant, and permit ready, this property allows seamless transition straight into the build phase. The opportunities are endless for the savvy investor looking to maximize value in a prime location. 18 parking spots town approved across the street next to the police station !
Middletown is located in Connecticut. Middletown, Connecticut has a population of 47,164. Middletown is less family-centric than the surrounding county with 22.78% of the households containing married families with children. The county average for households married with children is 27.85%.
The median household income in Middletown, Connecticut is $67,485. The median household income for the surrounding county is $90,833 compared to the national median of $69,021. The median age of people living in Middletown is 39.5 years.
The average high temperature in July is 84.1 degrees, with an average low temperature in January of 18.7 degrees. The average rainfall is approximately 47.6 inches per year, with 34.7 inches of snow per year.
