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$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
$900,000
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
$779,000
6 Beds ⋅ 4 Baths ⋅ 24199581 MLS
A truly extraordinary residence where distinctive architecture, exceptional privacy and sophisticated design come together to create a home unlike any other. Privately set on 3.5 acres, this beautifully renovated contemporary offers more than 5,500 square feet of impressive living space, with soaring interiors, walls of windows and an abundance of natural light creating a seamless connection to the surrounding landscape. The beautifully designed kitchen features quartz countertops, stainless steel appliances, double ovens, and generous space for gathering and entertaining. Two striking stone fireplaces serve as dramatic focal points, adding warmth, texture and character to the home's expansive living spaces. Offering six bedrooms and three-and-a-half beautifully renovated baths, the versatile floor plan provides exceptional flexibility for today's lifestyle. With its generous proportions and abundance of private and flexible spaces, the home is ideally suited for multigenerational living, extended family, guests, or those seeking dedicated space for a home office or home-based business. A fabulous loft provides yet another versatile area for a family room, office or game room. The spacious primary suite offers a walk-in closet, beautifully updated bath and private patio overlooking the peaceful surroundings. Throughout the home, meticulous details, interesting architectural elements and thoughtfully designed spaces create a sense of character rarely found in

44 Chamberlain Hill Rd, 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
$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
$410,000
6 Beds ⋅ 2 Baths ⋅ 24188066 MLS
Turnkey multifamily for owner occupied or 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
$399,900
6 Beds ⋅ 2 Baths ⋅ 24202328 MLS
Welcome to this character-filled, turn-of-the-century two-family Colonial in the heart of Middletown, ideally located directly across from Wesleyan University and within walking distance of downtown, restaurants, shops, and public transportation. Each spacious unit offers three bedrooms, a generous living room with a fireplace, beautiful built-in cabinetry, wood flooring, and French doors opening to a sunroom. Large, open kitchens with walk-in pantries provide ample space and functionality, while charming period details throughout reflect the home's original character. The first-floor unit is vacant and move-in ready, while the second-floor unit is currently tenant-occupied, offering immediate rental income. A new roof adds significant value, while the interiors still provide opportunities for updates and personal touches. Situated on a corner lot with two separate driveways accessed from different streets, plus a convenient walkout basement. An excellent opportunity for an owner-occupant or investor!

108 High St, Middletown
$390,000
7 Beds ⋅ 2 Baths ⋅ 24188106 MLS
Owner occupied or investors! 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
$374,500
6 Beds ⋅ 2 Baths ⋅ 24202551 MLS
Welcome to this beautifully remodeled two-family home ideally located within walking distance of vibrant downtown Middletown! This property offers the perfect blend of modern updates, spacious living, and unbeatable convenience. Both units have been fully remodeled with new appliances and updates throughout, making this an excellent opportunity for an owner-occupant, investor, or multi-generational living arrangement. Enjoy the added charm and versatility of enclosed back porches, perfect for relaxing, extra storage. A standout feature is the walk-up attic, offering approximately 650 additional square feet of living space-an incredible opportunity to create additional bedrooms, an office, recreation room, or whatever best suits your needs. Natural gas heat and hot water, separate utilities. Common laundry area in the basement with brand new washer and dryer. Step outside and enjoy everything Middletown has to offer, with parks, restaurants, shops, and downtown attractions all just a short walk away. Located in the heart of a lively and growing community, this home combines convenience, character, and future potential. Move-in ready, fully updated, and in a fantastic location-this is a two-family opportunity you won't want to miss!

74 Grove St, Middletown

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