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$1,100,000
1 Baths ⋅ 24164387 MLS
High-Yield Multi-Asset Investment Opportunity, CT | Positioned in Middletown, this rare, income-producing portfolio features two 2-family homes (4 total units), a 2,898 sq ft workshop, and two additional land parcels-delivering multiple revenue streams and value-add potential. Each residential building offers approximately 1,380 sq ft and has been capital-improved with new roofs, new windows, updated electrical, and modernized plumbing, significantly reducing near-term CapEx. All structures are connected to natural gas, enhancing operational efficiency and tenant appeal. * 4-unit rental configuration with strong, consistent income potential * Additional monetization opportunity via the heated workshop (ideal for contractor lease, storage income, or owner use) * Two separate vacant parcels (.08 & .02 acres) create development or resale upside (buyer to perform due diligence) * Ability to increase rents to market for improved NOI and long-term appreciation. Situated on a combined .25-acre footprint, this asset offers flexibility to scale returns-whether through rent optimization, auxiliary income from the workshop, or future development of excess land. Ideal for investors seeking: * Cash flow + appreciation potential * Multiple exit strategies (hold, expand, or subdivide/sell parcels) Income-generating opportunity with built-in upside in a strong rental market.

Portland Street, Middletown
$315,000
4 Beds ⋅ 1 Baths ⋅ 24163941 MLS
Welcome to this charming Colonial-style home set on a generous 3.3-acre lot, offering the perfect blend of comfort, space, and modern updates. The exterior showcases classic appeal with a welcoming front entry & an attached 2 car garage, all surrounded by open land that provides privacy and endless possibilities. Step inside to discover a beautifully updated kitchen featuring stainless steel appliances, ample cabinetry, and sleek countertops, ideal for both everyday living & entertaining. The main level offers the convenience of a primary bedroom & first-floor laundry, creating an easy and functional layout for homeowners. The renovated bathroom is tastefully finished with modern fixtures and stylish tile work, adding a touch of luxury to your daily routine. Upstairs, you'll find three additional bedrooms, providing plenty of space for family, guests, or a home office setup. With its spacious acreage, thoughtful updates & conveniently located near local amenities, shopping & major routes, this home offers a unique opportunity to enjoy peaceful living while still having all the modern conveniences you need. **Conventional or cash offers only.**

475 Ballfall Rd, Middletown
$209,900
3 Beds ⋅ 2 Baths ⋅ 24163396 MLS
This classic 1900 Colonial at 103 Prospect Street offers a chance to bring new life to a well-loved home in a convenient Middletown location. With 1,160 square feet of living space, three bedrooms, and two full baths, the layout is simple and functional, ready for someone with vision to make it their own. The home does require work, making it a great project for investors, renovators, or buyers looking to build equity over time. Set on a manageable lot, this property is part of an estate and is being sold as-is. If you've been waiting for an opportunity to create something from the ground up, this could be the one worth exploring! as is, where is, with remaining contents at closing. Subject to probate approval

103 Prospect St, Middletown
$499,900
3 Beds ⋅ 2 Baths ⋅ 24159033 MLS
This 1,500 sq ft ranch-style home, built by Silvin Homes, offers thoughtfully designed one-level living with an open-concept layout ideal for everyday living and entertaining. The spacious living area flows seamlessly into the kitchen with a center island and ample cabinetry, creating a welcoming gathering space. The private primary suite features a custom full bath and walk-in closet and is set apart for added privacy, while two additional generously sized bedrooms and a second full bath provide flexibility for guests or home office needs. A dedicated laundry area and convenient entryway from the attached one-car garage enhance everyday functionality. Nathan Hale Estates is a thoughtfully planned residential community in Middletown, Connecticut, offering a quiet neighborhood setting while remaining conveniently close to shopping, dining, schools, parks, and major commuter routes. The central location provides easy access to the shoreline, making this an ideal place for you and your family. The builder offers generous allowances, allowing buyers to thoughtfully curate finishes and selections. Builder requires a one-time construction-to-permanent loan, financed by Elm Tree Funding.

Lot 3 Nathan Hale, Middletown
$299,609
4 Beds ⋅ 2 Baths ⋅ 24158805 MLS
Welcome to this inviting contemporary home in Middletown offering the perfect blend of comfort, style, and convenience. This well maintained 4 bedroom, 2 bath residence features 1,328 square feet of thoughtfully designed living space ideal for today's lifestyle. Step inside to discover an updated kitchen with modern finishes, providing a functional and attractive space for everyday living and entertaining. Both bathrooms have been tastefully updated, adding a fresh, move in ready feel throughout the home. The flexible floor plan offers four bedrooms, giving plenty of room for family, guests, or a home office. One of the home's most convenient features is the second floor laundry, making daily chores easier and more efficient. With its contemporary style, smart layout, and desirable updates, this home offers a fantastic opportunity to enjoy comfortable living in a convenient location close to shopping, dining, parks, and major commuting routes. Don't miss your chance to make this beautiful Middletown home your own.

34 Inverness Ln, 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
$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
$599,609
2 Baths ⋅ 24152111 MLS
Located along the highly visible Newfield Street corridor, 609 Newfield Street is a converted mid-century ranch now used as professional office space. Originally built in 1950 as a single family home, the 1,500 sq ft building has been fully adapted for commercial use and currently houses Innovative Properties. The layout provides multiple private offices, meeting areas, and a welcoming reception space. The 1.09-acre lot offers ample off-street parking and room for exterior improvements. Its flexible design also makes the property a strong candidate for group home use. The owner is willing to complete modifications or provide a credit for required updates. Owner financing is available. Located within Middletown's NPC zone, the property supports a wide variety of professional, service, and light retail uses, including medical, dental, legal, salon, specialty retail, or care-based operations. With strong drive-by exposure on Route 3, convenient neighborhood access, and close proximity to local schools and amenities, 609 Newfield Street offers excellent visibility and adaptability for a business or organization seeking a ready-to-occupy space in one of Middletown's most active commercial corridors. AGENT OWNER

609 Newfield St, Middletown
$100,000
24149149 MLS
This scenic and beautiful lot has a stream running through it. The location is spectacular on this very quiet street located minutes to interstate 91 makes travel super easy. No test have been done.

Bell St, Middletown
$350,000
24149097 MLS
21.46 Acres Commercial Industrial Land. Lot is behind the 7.5 acre lot also for sale.Zoning: IOP (Industrial Office Park including office, warehouse, industrial & recreation. This parcel is going to be split off of a larger piece consisting of 28.96 acres. 8 acres of abutting residential land off Bell Street available for assemblage * Total Potential Assemblage: 41 acres * Immediate Access: Minutes to I-91 (Exit 20) Highly flexible IOP zoning allows multiple development strategies Large contiguous acreage suitable for corporate campus, distribution, flex-industrial, mixed-use, or recreational. Strong highway access for logistics, employees, and regional connectivity. Middletown's central CT location supports Hartford-New Haven corridor growth

Middle St, Middletown
$750,000
24149055 MLS
41.99 acres including 3 separate lots.Commercial Industrial Land. Zoning: IOP (Industrial Office Park including office, warehouse, industrial & recreation. 7.88 acres residential lot is abutting and on Bell St. Immediate Access: Minutes to I-91 (Exit 20) Highly flexible IOP zoning allows multiple development strategies Large contiguous acreage suitable for corporate campus, distribution, flex-industrial, mixed-use, or recreational. Strong highway access for logistics, employees, and regional connectivity. Middletown's central CT location supports Hartford-New Haven corridor growth

Middle St, Middletown
$649,900
2 Beds ⋅ 2 Baths ⋅ 24133669 MLS
Experience Carefree Living at Founders' Ridge - the Premier 55+ Award-Winning Community! Introducing our newest Model Home -our sought after "KIRBY II", now available for early 2027 occupancy! This is the last Kirby at this price point! Nestled in the highly desirable Westfield section of Middletown, this thoughtfully designed 1,555 sq. ft. single-level home offers both luxury and ease in one perfect package. Elegant Interior Features include stunning white cabinetry, quartz countertops, and a walk-in pantry for style and function. Hardwood flooring throughout the main living areas, with tile in baths and laundry for durability. A bright bay window in the front room offers sweeping views and a private rear patio is ideal for relaxing or entertaining. Comfort All Year Long: Enjoy the convenience of natural gas heating and central A/C. Some photos shown are of similar homes and may include upgrades. Agent/Owner related.

145 Webster Ln Unit 2-41, Middletown
$975,000
10 Baths ⋅ 24133406 MLS
Escape overpriced city markets of Manhattan, Brooklyn, Bridgeport and Stamford and invest in opportunity of Middletown, Connecticut. Just two hours from Manhattan, 504 Main Street offers rare versatility and long-term upside: a restored 1888 brick landmark with six total units - two prime commercial storefronts and four bright, character-filled apartments overlooking Middletown's vibrant Main Street. The building blends historic charm with smart upgrades, sun-soaked interiors, renovated kitchens and baths, in unit laundry in 2 units and soaring ceilings amplify the space and craftsmanship. A geothermal HVAC system with Nest controls keeps operating costs low, and private off-street parking is an added bonus for tenants or owner. 2 store fronts offer a long term committed tenant on one side and flexibilty on the other side. Steps from acclaimed dining, boutique shops, live music, CT river, year-round community events, and Wesleyan University, this property draws a consistent, quality tenant base - from professors and grad students to professionals seeking charm, community and convenience. 504 Main is a compelling alternative to inflated city assets - a chance to own income-producing property, bring your business here or make your home here! Middletown's main street was named one of America's "Most Romantic Main Streets, highlighting its love affair with food, river vistas and New England charm. Also highlighted in the New York Times praising its vibrance and accessibly to NYC

504 Main St, Middletown
$589,900
2 Beds ⋅ 2 Baths ⋅ 24123204 MLS
Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "MARTIN II," Under CONSTRUCTION! Now with many new UPGRADES - available for occupancy in early 2027 Located in the highly sought-after Westfield section of Middletown, this beautiful 1,430 sq. ft. home has the convenience of single-floor living with top-of-the-line features and Elegant Design: Enjoy the sophistication of wood cabinetry with granite countertops and a walk-in pantry. Hardwood floors flow through out the main living areas, while tile flooring is featured in the baths and laundry room. A deck at the rear of the home creates the perfect space to relax and entertain. The home is equipped with natural gas and central A/C for year-round comfort. Some photos similar and depict some upgrades. Agent/Owner related. Come see why our motto is "Choose a Carefree Lifestyle!"

137 Webster Ln Unit 2-42, Middletown
$399,900
2 Baths ⋅ 24131954 MLS
Location, Location, Location! Nice 1482sf retail building in the heart of Main St. Middletown. High traffic area, property currently being used as smoke shop, but can fit many other retail needs. Building is Zoned B-1. Currently being leased until Nov.2026

346 Main St, Middletown
$217,500
3 Beds ⋅ 2 Baths ⋅ 24111633 MLS
Prime location near the pool & clubhouse - just in time for Summer! Welcome to 36 Rising Trail Drive, a beautifully maintained condo nestled in the desirable Westlake area of Middletown. This spacious unit offers a bright and open layout with generous living and dining areas, perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, ample counter space, and appliances. Upstairs, you'll find comfortably sized bedrooms, with plenty of closet space. Additional highlights include in-unit laundry, a private patio for outdoor relaxation, and convenient Carport. Located in a quiet, well-managed complex with easy access to shopping, restaurants, and major highways-this home offers the perfect blend of comfort, style, and location. Don't miss the opportunity to make it yours!

36 Rising Trail Dr Unit 36, Middletown
$999,999
24130767 MLS
Position your business for success at 575 Main Street, a full-floor office condominium offering over 7,800 square feet of modern, light-filled workspace in downtown Middletown. This suite thoughtfully balances private offices, open collaboration areas, and meeting rooms, all serviced by an elevator and ADA-compliant restrooms. Meticulously maintained by a single tenant since 2008, it combines immediate professional appeal with long-term reliability. Ideally located just minutes from Middlesex Hospital, Wesleyan University, Pratt & Whitney, and the Superior Court, the property is part of a federally designated Opportunity Zone and sits within Middletown's Riverfront Redevelopment, offering both strategic value and growth potential. With a Walk Score of 93, vibrant downtown amenities, and convenient access to Route 9, 575 Main Street represents a rare opportunity to secure a premier office condominium in one of Connecticut's most dynamic markets. Owner Financing Available

575 Main St Unit STE 2, Middletown
$935,000
24130959 MLS
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 its 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 the major systems professionally designed, code compliant, and permit ready, this property allows seamless transition straight to 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 police station

54 Washington St, Middletown
$479,900
2 Baths ⋅ 24053933 MLS
*** Prime Commercial Property for Sale - 110 Coe Ave, Middletown, CT *** Discover an exceptional investment opportunity with this versatile commercial property. Ideal for a wide range of business ventures, this property allows both flexibility and prime location appeal. Featuring a spacious interior, ample parking, and excellent visibility, it's perfectly suited for retail, office, or mixed-use development. Ideally positioned in Middletown with easy access to I-91 and so close to Route 9. Conveniently located near Middlesex Hospital, one of the top medical facilities in the region, providing heathcare and attracting a steady flow of traffic. In close proximity to Wesleyan University, Middlesex Community College, Xavier High School and local Middletown schools, offering potential customer base and employee convenience. Directly next to Tradewinds Shopping Center with Restaurants, Retail Shops and Car Wash. This property is perfect for retail stores, medical offices, a professional facility, or a mixed-use development. Take advantage of this rare opportunity to own a prime piece of Middletown's commercial real estate. Whether you're expanding your business or looking for a new investment, 110 Coe Ave has the perfect blend of location, flexibility, and potential.

110 Coe Ave, Middletown

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