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$585,000
4 Beds 3 Baths 24198723 MLS
Welcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable Middletown neighborhood, privately set back from the road. Featuring an updated kitchen, new windows throughout, remodeled baths and a finished walk-out basement with a full bathroom this home offers space, flexibility and privacy. The finished lower level provides potential for an in-law apartment or separate living space, subject to town approval, making it ideal for extended family, guests, a home office or recreation. The expansive deck overlooks a beautiful yard for entertaining, a game of catch or running with your favorite four legged pal. Close to major highways, 20 minutes from Downtown Hartford, 35 minutes to New Haven, 45 minutes to CT Casinos, a little over an hour to the Rhode Island line and minutes from Wesleyan University, great shopping and restaurants in downtown Middletown! Major updates include: Brand New Septic- 2019 Kitchen remodeled - 2024 All windows replaced - 2024 Basement remodeled - 2023 Garage doors replaced - 2023 Full bathroom remodeled - 2022 AC air handler & condenser - 2021 Electrical upgrades & generator hookup - 2021 Well pump - 2021 Front door - 2021 Paver walkway & gutter/fascia improvements - 2020 Chimney repair & cap - approx. 2019 Boiler -2014 With a private setting, extensive updates, 4 bedrooms, 2.5 baths and a versatile walk-out lower level, this Middletown Colonial is ready to welcome its next owner!

85 Oakcliff Rd, Middletown

$317,000
2 Beds 2 Baths 24194383 MLS
Move right in to this well-maintained raised ranch offering comfortable living and a functional floor plan. Enter through the street-level foyer, where you'll find access to the attached garage, a full bathroom, laundry area, utility room, and a versatile room that is perfect for a home office, den, workout room, or man cave. The main level features a bright eat-in kitchen, a spacious living room, and two bedrooms. Step outside from the kitchen onto the Brand-new deck. An ideal spot for morning coffee or entertaining family and friends. A standing room attic primed for remodeling provides storage and offers excellent potential to be finished for additional living space, subject to local approvals. The low-maintenance yard is perfect for those seeking easy upkeep while still enjoying outdoor space. Situated on a quiet street, this home is conveniently located near a park, schools, shopping, restaurants, and major commuter routes. Don't miss this wonderful opportunity to own this 1776 square feet America's house. Has a lot of possibilities for a growing family.

70 Bielefield Rd, Middletown

$289,900
3 Beds 2 Baths 24199099 MLS
Welcome to 177 Front Street, a charming farmhouse-style home in Middletown's desirable Farm Hill District. This 3-bedroom, 1.5-bath home offers a functional layout with comfortable living space, a formal dining room, and plenty of natural light throughout. Recent updates include fresh interior paint, newer Stainless Steel appliances and countertops, and freshly painted wood cabinetry, giving the kitchen a clean, refreshed feel while maintaining the home's original character. Outside, enjoy the cedar front porch, a great spot to relax year-round, along with a rear deck overlooking the level backyard. This lovely home is located just minutes from downtown Middletown, shopping, restaurants, major highways, and everyday conveniences. A move-in-ready home with farmhouse charm, thoughtful updates, and a location that makes getting around easy.

177 Front St, Middletown

$369,900
4 Beds 1 Baths 24198560 MLS
Back on Market, and meant to be for You!! This adorable Cape boasts 4 bedrooms, an Open Layout, Fully Finished Basement, and an Enchanting private, flat fenced yard with a pool, Magnificent Weeping Willow tree, Firepit, and Gazebo. The Main level welcomes a friendly open layout connecting the open kitchen to the living room with cozy wood burning fireplace, Primary bedroom, Full bathroom, and another bedroom which can be used as an office if a 4th is not needed, as well as a laundry area quietly tucked away. Enter the Breezeway with dramatic wood vaulted ceiling, and french doors looking out to the patio and pool, which is currently being used as a Romantic Dining Room. Upstairs you will find two ample sized bedrooms. The Fully Finished basement offers more room for an In-Law possibility complete with kitchen and full bath. The oversized Tandem garage will hold 3 compact cars, or two large trucks and motorcycles, or hobbies. The roof is 5 years old, and the solar panels are owned and convey with the home at no additional cost to save you money on your electric bill. Located in a convenient location for commuting close to 91, route 9, close to shopping, restaurants, golf courses and more. Must Come see!!

171 Smith St, Middletown

$429,000
3 Beds 2 Baths 24196637 MLS
Welcome to 76 George St, Middletown! This 1,600 SF home offers 3 bedrooms, a spacious kitchen, and plenty of potential to make the property your own. The walk-out lower level features roughed-in plumbing, creating an exciting opportunity for additional living space, a recreation area, or a possible in-law apartment. Set on nearly one acre of land, the property offers additional road frontage on Boston Rd and the potential for an additional structure, subject to zoning and approvals. With generous land, flexible space, and multiple possibilities for future use, this property offers an excellent opportunity for homeowners, investors, or those looking to create additional living space. A lease-to-own option is also available. Don't miss this unique opportunity-bring your vision and explore the possibilities!

76 George St, Middletown

$450,000
2 Beds 2 Baths 24196263 MLS
Welcome to 1511 Country Club Rd, a charming 2-bedroom Cape with the posability of 5- bedrooms offering comfort, character, and exceptional versatility. This inviting home features a flexible layout with a private in-law suite or separate living space-perfect for multi-generational living, guests, a private home office or income possibility. Step outside to enjoy the expansive backyard, offering plenty of room for entertaining, gardening, or relaxing. A fenced-in area provides a safe and secure space for people or pets to play, while the rest of the large yard offers endless opportunities to enjoy the outdoors. Whether you're looking for your first home, room to grow, or a property with flexible living options, this charming Cape is a wonderful place to make your next home.

1511 Country Club Rd, Middletown

$699,000
4 Beds 3 Baths 24197740 MLS
Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.

20 Chimney Hill Rd, Middletown

$299,900
2 Beds 3 Baths 24197288 MLS
Welcome to 824 Randolph Rd, Middletown! You'll fall in love with this beautiful ranch offering the convenience of one-floor living, a two-car garage, and an inviting in-ground pool with patio that's perfect for relaxing or entertaining. Step inside to find a bright, spacious living room with a beautiful fireplace, an eat-in kitchen with stainless steel appliances, and a dining room featuring a cozy wood stove. Most of the interior has been freshly painted, giving the home a fresh, welcoming feel throughout. The home offers two full bathrooms, plus a convenient half bath located just off the primary suite and with easy access to the pool-perfect for guests while entertaining. The expansive basement offers endless possibilities for a home gym, office, media room, or additional living space. Complete with energy-efficient solar panels, this home truly has something for everyone!

824 Randolph Rd, Middletown

$289,900
2 Beds 1 Baths 24197062 MLS
Welcome home to this well-maintained ranch in Middletown! The spacious living room and dining area feature beautiful hardwood floors, creating a warm and inviting space for everyday living and entertaining. The kitchen offers newer stainless steel appliances and durable laminate flooring. In addition to two generously sized bedrooms, you'll find a versatile bonus room that's perfect for a home office, craft room, or flex space to fit your needs. Major updates include a new boiler and hot water heater installed in 2020, along with solar panels added in 2023 for increased energy efficiency. Step outside to enjoy the large, level backyard-ideal for gardening, play, entertaining, or simply relaxing. Conveniently located close to shopping, dining, parks, and major highways, this move-in-ready home is one you won't want to miss!

115 Markham St, Middletown

$425,000
4 Beds 2 Baths 24197069 MLS
Welcome to 104 Bell Street - a rare find on 2.6 private acres in the heart of Middletown. This 4-bedroom, 2 full bath home offers a truly unique setting where you drive down a long, secluded driveway and cross a bridge over Sawmill Brook to arrive at your own private oasis. Fully updated throughout, this home features a renovated kitchen, updated bathrooms, new flooring, new 200-amp electrical service, new AC unit and furnace, new oil tank, an updated well system, and a resurfaced bridge. The wooded, incredibly private lot offers endless potential - whether you envision expanded outdoor living, gardens, or simply the peace and quiet of your own retreat tucked away from the world. Despite the secluded feel, the property is easy to show and conveniently located with quick access to I-91, Wesleyan University, and downtown Middletown. With so much already done, this is a move-in ready home with room to dream on 2.6 acres. Buyer to verify flood zone designation and obtain flood insurance quotes prior to purchase. Agent/Owner.

104 Bell St, Middletown

$379,900
4 Beds 2 Baths 24196455 MLS
Welcome home to this charming Cape Cod-style house, offering 1,874 square feet of comfortable living space, plus an additional 150 square feet of finished space in the basement. This inviting four-bedroom, 2 full bath home is nestled in a wonderful neighborhood, combining timeless charm with everyday comfort. The updated kitchen is ready for cooking, gathering, and entertaining, while the spacious living room features a cozy fireplace-perfect for relaxing evenings at home. A one-car garage and an outdoor storage shed provide added convenience and plenty of room for tools, lawn equipment, or seasonal storage. Step outside to a spacious deck overlooking the backyard, creating a wonderful setting for morning coffee, outdoor dining, or simply enjoying the peaceful surroundings. The property also includes an above-ground pool that offers great potential and just needs a little TLC to be enjoyed again. The upper bathroom present an excellent opportunity to update and personalize the home to your own style, allowing you to add value while making the space uniquely yours. With its generous layout, desirable location, updated kitchen, classic Cape Cod character, and inviting outdoor living space, this home is ready to welcomes its next owners. VERY MOTIVATED SELLERS!

25 Morgan St, Middletown

$394,500
3 Beds 2 Baths 24195917 MLS
Welcome to 45 Annette Place! This beautifully maintained home is truly move-in ready and has so much to offer. The updated kitchen features granite countertops, stainless steel appliances, and recessed lighting, creating a bright and modern space. Hardwood floors flow throughout the living room and bedrooms, adding warmth and timeless appeal. The partially finished basement provides additional living space and is complete with a cozy pellet stove-perfect for relaxing year-round. Need room for vehicles, hobbies, or storage? The impressive 3-car garage offers endless possibilities. Outside, you'll be welcomed by beautifully landscaped grounds that add exceptional curb appeal and create a wonderful outdoor setting to enjoy. This is a home you'll be proud to own!

45 Annette Pl, Middletown

$385,000
3 Beds 2 Baths 24193289 MLS
Welcome home to this beautifully remodeled 3 bedroom, 2 full bath home that's truly move in ready! Enjoy relaxing on the inviting front porch or entertaining in the fenced backyard. The updated kitchen features stainless steel appliances, plenty of cabinet and counter space, and room for meal preparation. The spacious living room offers a cozy fireplace and new flooring, creating a warm and inviting atmosphere. The finished lower level provides additional living space with two finished rooms, a full tiled bathroom, and a laundry area with washer and dryer. Perfect for a family room, home office, gym, playroom, or guest space. Recent updates include central air, windows, flooring, fenced backyard, along with many additional improvements. This home is conveniently located near shopping, restaurants and parks and offers the perfect combination of comfort, style, and convenience. Don't miss your opportunity to make this beautiful home yours!

49 George St, Middletown

$410,000
3 Beds 1 Baths 24195038 MLS
Welcome to this charming 3-bedroom, 1-bath ranch nestled on the highly sought-after Higby Road. Set on a generous half-acre lot, this home offers the perfect opportunity for first-time buyers, downsizers, or anyone looking to add their personal touch. Inside, you'll find comfortable one-level living with a functional layout, hardwood floors, and a cozy fireplace. Additional features include an attached garage, partially finished basement for extra living or storage space, and a peaceful backyard with plenty of room to relax or entertain. Conveniently located near shopping, dining, parks, and major commuter routes, this home combines a desirable location with endless potential. Don't miss your chance to make this Higby Road gem your own!

104 Higby Rd, Middletown

$395,000
3 Beds 3 Baths 24194117 MLS
Welcome home to this charming property located at the end of a peaceful cul-de-sac. This residence features three bedrooms, including a primary bedroom with an ensuite full bathroom. There are two updated full bathrooms in total, along with a convenient half bath. As you enter, you'll notice the gleaming hardwood floors that flow throughout the main living areas. The kitchen is thoughtfully designed with granite countertops, maple wood cabinets, and stainless steel appliances, offering a great setup for everyday cooking. The dining area seamlessly connects to the cozy living space, which features a gas fireplace and a mini-split system, providing an additional heating and cooling option for year-round comfort. From the dining area, sliding doors open to a patio with Trex decking, complete with a retractable awning, perfect for providing shade when needed and easily rolled back for sunny days. The two-car garage provides direct access to a finished basement area that includes a half bathroom and laundry facilities, enhancing the home's functionality. Energy-efficient solar panels ensure excellent coverage, leading to no current electric bill. Step outside to discover a private walking path accessible right from your backyard. This home is fully move-in ready, waiting for you to create lasting memories.

3 Yellow Pine Cir, Middletown

$269,000
3 Beds 2 Baths 24191998 MLS
Investors are you looking for a charming 2/3 bedroom, 1.5 bath Colonial that is located on a quiet street in a desirable neighborhood, offering convenient location just minutes from the shops, restaurants, Wesleyan University, hospitals, and major healthcare centers? This is an excellent choice for anyone seeking an easy commute and access to everyday amenities. Filled with warmth and character, this inviting home is ready for its next chapter. Whether you're a first-time homebuyer, looking to make it your forever home, or searching for a great investment opportunity, this property offers endless potential. Add your personal touch and some love to make this charming Colonial truly your own while creating lasting memories for years to come. City water and city sewer. Don't miss the opportunity to own a home in a convenient and quiet location. Schedule your showing today and discover all that 153 Eastern Drive has to offer!

153 Eastern Dr, 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

$1,000,000
24189275 MLS
Exceptional commercial opportunity in one of Middletown's busiest retail corridors. Situated on approximately 0.47 acres, this 5,115 SF commercial building offers outstanding visibility with average daily traffic counts of approximately 20,000 vehicles. Currently operating as an auto repair facility with five vehicle lifts, the property is well-suited for continued automotive use or redevelopment. Located in the desirable B-2 General Commercial Zone, this site offers tremendous flexibility for a variety of commercial uses, making it an excellent investment or development opportunity. Surrounded by established national and local businesses, the property benefits from strong exposure, convenient access to major roadways, and a thriving commercial environment. Whether you're looking to expand your existing business, invest in an income-producing property, or redevelop a prime commercial site, this is a rare opportunity to secure a highly visible location in one of Middletown's most sought-after business districts.

516 Washington St Unit 1, 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

$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

$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

$4,500,000
4 Baths 24182009 MLS
Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts.

423 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

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