Middletown CT Historical Real Estate, Homes for Sale

3 Beds ⋅ 2 Baths ⋅ 24194943 MLS

Move right in! 34 Franklin Street is a well-cared-for Middletown split-level offering 3 bedrooms, 1 fully renovated bath, and 966 sq ft of comfortable living. Highlights include hardwood flooring, an eat-in kitchen with sliders to a huge covered deck, and a spa-style bathroom with a walk-in shower, built-in seat, and skylight. Outside, enjoy a private, fenced 0.16-acre yard with mature trees and a storage shed - plenty of room to garden, play, or entertain. Forced-air heat, central air, and durable vinyl siding keep maintenance simple. Zoned for Farm Hill Elementary (0.5 mi) and Woodrow Wilson Middle School, with quick access to downtown Middletown and major routes. Priced to move and ready for its next owner - schedule a showing today.

34 Franklin 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

$352,500

4 Beds ⋅ 2 Baths ⋅ 24194795 MLS

Turnkey investment opportunity! Well-maintained two-family with both units fully rented, providing immediate rental income. Each unit offers 2 bedrooms, separate utilities, natural gas heat, and spacious layouts. Level lot with ample off-street parking in a highly convenient location near Middlesex Hospital, Wesleyan University, downtown Middletown's restaurants and shopping, and major highways including Routes 9, 17, and I-91. A great addition to any investment portfolio!

20 Cooley Ave, 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

$425,000

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

$334,500

3 Beds ⋅ 1 Baths ⋅ 24194926 MLS

Welcome to 67 Butternut, a charming home that offers comfort, character, and convenience. The main level features a bright, open kitchen with stainless steel appliances that flows seamlessly into the inviting living room, creating the perfect space for everyday living and entertaining. Beautiful hardwood floors extend throughout the home, adding warmth and timeless appeal. Upstairs, you'll find the comfortable bedrooms and a full bathroom. Ideally located just minutes from grocery stores, parks, shopping, dining, and major conveniences, this home combines charm with an unbeatable location.

67 Butternut St, 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

$365,000

2 Beds ⋅ 2 Baths ⋅ 24191334 MLS

***Highest and Best by Monday July 27th at 50pm***Turnkey two-family investment opportunity on a quiet residential street in Middletown. Built in 1900 and offering 1,654 sq. ft. across two self-contained units, this property brings in reliable rental income with minimal upkeep thanks to durable vinyl siding and an architectural shingle roof. Combined the units offer 2 bedrooms and 2 full baths, plus additional flex space in each unit ideal for a home office or storage. The upstairs unit's primary bedroom includes its own walk-in closet, and each unit has private laundry hookups - a major draw for tenants. Recent updates include new luxury vinyl plank flooring and a modern kitchen island in one unit, while the other retains warm hardwood floors and classic charm. Large double-hung windows keep every room bright. Each unit enjoys its own private deck, and parking accommodates up to 4-6 vehicles across two parking areas. The 0.19-acre lot also includes a shared, fenced backyard.

200 E Ridge Rd, Middletown

$425,000

3 Beds ⋅ 3 Baths ⋅ 24192475 MLS

HIGHEST AND BEST by 5pm Friday July24th. Seller reserves the right to accept an offer at any time prior to the deadline. Nestled near the end of a quiet dead-end road, this beautifully maintained 3-bedroom ranch offers peaceful country living with picturesque pasture views. Stunning perennial gardens, designed by a master gardener, provide exceptional curb appeal and seasonal color. Hardwood floors run through the bedrooms, hallway, and formal dining room. The inviting living room features a wood-burning fireplace and bay window overlooking the front gardens, while the dining room's picture window captures the scenic farmland beyond. The primary suite includes a private full bath. A spacious family room with sliders opens to a bright sunroom and deck, creating the perfect space to relax or entertain while enjoying the tranquil backyard. First-floor laundry, an attached two-car garage, solar panels, and a whole-house generator add comfort and convenience. The walk-out lower level features a second fireplace with a wood stove, dry bar, workshop, pool table, secure safe, abundant storage, and unfinished space for future expansion. A wonderful opportunity to enjoy one-level living in a beautiful country setting.

85 Ten Acre Rd, Middletown

$370,000

3 Beds ⋅ 2 Baths ⋅ 24190857 MLS

Beautifully maintained ranch offering the perfect blend of comfort, style, and functionality! This move-in-ready home features 3 spacious bedrooms and 2 full bathrooms, including a generous primary suite with a private en-suite bath. The bright and inviting living spaces are ideal for both everyday living and entertaining. A true highlight of the home is the stunning full-glass sunroom overlooking the expansive backyard, creating the perfect space to enjoy your morning coffee, unwind after a long day, or host family and friends year-round. An attached one-car garage and enclosed patio provide additional flexible space for entertaining, hobbies, or relaxing in every season. Conveniently located with central air conditioning and a thoughtfully designed layout, this home offers comfort, versatility, and pride of ownership throughout. Whether you're a first-time homebuyer, looking to downsize, or searching for your next home, this exceptional property is ready to welcome its new owners. Don't miss this incredible opportunity-schedule your private showing today!

417 Mile Ln, 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

$365,000

3 Beds ⋅ 2 Baths ⋅ 24187059 MLS

Tucked at the quiet end of a cul-de-sac on a level half-acre, this move-in ready split level delivers the one thing that's hard to find: it's already done. Extensively remodeled in 2018, the home blends timeless finishes with the kind of major updates buyers hope for but rarely get. A bright kitchen with granite counters and stainless appliances opens to warm, refined living space, where hardwood floors carry through and the baths have been tastefully reworked. The improvements extend well beyond the cosmetic, reaching the roof, siding, and windows along with the doors, garage, and central air. Three comfortable bedrooms rest upstairs, while a flexible finished lower level offers space for a variety of uses, and mud room space with easy walk-out access to the attached garage. Out back, the porch and hot tub wait for slower evenings. Nothing left here but to move in and enjoy.

24 Annette Pl, Middletown

$359,000

3 Beds ⋅ 2 Baths ⋅ 24190638 MLS

Welcome to 116 Schuyler Ave! This home is conveniently located on a dead end close to Middletown's shopping and restaurant district, highways, parks and more. This 3 bedroom home was built in 1890 and carries a lot of colonial charm like the incredible hardwood floors throughout, a fully finished attic, and built-in cabinets. The Main level has a full bathroom with a walk-in shower, living room, formal dining room, an eat-in kitchen, sunroom featuring 180 degree windows and French doors, and a mudroom located on the back of the home. The Upper Level has three bedrooms, and a full bath. The master bedroom has been opened up into a fourth bedroom to create a versatile primary space. Access to the third floor is a pull-down ladder in bedroom #2 and includes two finished rooms, floor to ceiling wood paneling, and built-in storage. The basement is fitted with a French drain, a new electric hot water heater, and storage space. *Primary bedroom not pictured

116 Schuyler Ave, Middletown

$349,900

4 Beds ⋅ 2 Baths ⋅ 24189620 MLS

Bring your growing family to this spacious colonial! 4 bedrooms with two on first floor. 2 full baths. Eat in kitchen. Living room with fireplace. Spacious room at top of staircase can potentially be 5th bedroom! Hardwood floors thru-out. Walk out basement to level yard. Deck. Whether you are a car enthusiast or need a lot of storage space, you will love the oversized detached 2 car heated garage with steel beam and loft area. Solar panels...see attachment

125 Stevens Ln, Middletown

$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

$480,000

3 Beds ⋅ 3 Baths ⋅ 24188018 MLS

Nestled in the highly desirable South Farms neighborhood, this well-maintained home is filled with quality features and timeless appeal. Car enthusiasts and hobbyists will appreciate the impressive 4-car garage, offering exceptional space for vehicles, storage, or the perfect workshop. The spacious eat-in kitchen features granite countertops, abundant cabinetry, and generous workspace for cooking and entertaining. Throughout the home, you'll find an abundance of closet space in each of the 3 bedrooms. Hardwood floors lie beneath the carpeting, offering the opportunity to restore their original beauty. The expansive finished basement, complete with a full bath, additional laundry room, and cozy gas fireplace, provides the perfect setting for entertaining, relaxing, or creating the ultimate recreation space. The sunroom off the kitchen can also be used for a home office. A second gas fireplace in the living room adds warmth and charm, making this home inviting in every season. Step outside to enjoy the deck, complete with a retractable awning for shade on sunny days. Additional highlights include a full-house generator, walk-up attic, central A/C, laundry on the main floor and exceptional storage space throughout the home. Take advantage of all that Middletown has to offer with its many restaurants, cultural centers, and shopping. Close to I-91 and Rt 9. This home presents an exceptional opportunity for its next owner. Don't miss your chance to make it yours!

779 Ridge Rd, Middletown

$319,900

2 Beds ⋅ 3 Baths ⋅ 24189364 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

$1,299,000

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

$475,000

3 Beds ⋅ 2 Baths ⋅ 24188822 MLS

Some homes are built to impress. Others are built to be lived in. This extraordinary farmhouse does both. A charming covered front porch, framed by mature perennial gardens that bloom with the seasons, welcomes you home. It's the kind of place where evenings are best spent watching breathtaking sunsets as the sounds of nature replace the noise of the day. Inside, rustic charm blends seamlessly with modern design. Exposed beams, leathered granite countertops, and a stunning tile backsplash create a kitchen that is as beautiful as it is functional. Tucked behind the home, a detached viewing deck overlooks the neighboring tree farm, offering a peaceful retreat immersed in nature. Whether you're enjoying your morning coffee while listening to birdsong or simply taking in the ever-changing landscape, this setting provides a sense of tranquility that's hard to find. As evening falls, gather beneath the pergola around the fire pit, where laughter lingers and every night feels like a getaway. The primary bedroom offers its own private sanctuary with fireplace and private balcony overlooking the peaceful surroundings. This is more than a beautifully designed farmhouse-it's a home that celebrates simple pleasures, timeless craftsmanship, and a connection to nature. **HIGHEST AND BEST DUE 07/13 7PM**

364 Coleman Rd, Middletown

$284,500

2 Beds ⋅ 1 Baths ⋅ 24189063 MLS

Welcome home to this well-maintained 2-bedroom, 1-bath ranch offering easy one-level living and the perfect condo alternative. The inviting floor plan features a spacious living room, formal dining room, and an updated kitchen complete with stainless steel appliances. Beautiful hardwood flooring flows throughout much of the home, while recent updates, including a newer furnace, new hot water heater, and newer roof, provide added peace of mind. Relax with your morning coffee or unwind in the three-season porch overlooking the level, private backyard-ideal for gardening, entertaining, or simply enjoying the outdoors. Additional features include a one-car detached garage and a sought-after South Farms location close to shopping, dining, parks, and major commuter routes. Don't miss this wonderful opportunity to own a move-in-ready home in a desirable neighborhood!

4 Crown St, Middletown

$369,900

3 Beds ⋅ 2 Baths ⋅ 24189064 MLS

*HIGHEST AND BEST OFFER DEADLINE - TUESDAY, JULY 14th AT 12:00pm ET* Welcome home to 193 Ridge Rd, a 3-bedroom, 2-full-bath gem, lovingly updated but full of warmth and charm. Step onto the large front porch and you'll feel it - this one's different. The updated kitchen shines with granite counters, soft-close cabinetry, and a generous pantry, ready for morning coffee or holiday hosting. The dining and living rooms stretch out with beautifully refinished hardwood floors (2024), and a gas heating stove in the dining room adds cozy, supplemental warmth. One full bath per floor keeps mornings easy, including an updated upstairs bath with fresh carpeting and a custom stair runner. Downstairs, a finished bonus room offers flexible living space - perfect for a media room, office, or playroom. Outside, unwind on the low-maintenance Trex deck with vinyl railings, take a dip in the above-ground pool, or let kids and pets roam the fenced-in backyard. Major updates done: new roof (2023), replaced water service line (2021), and fresh interior paint throughout - move-in ready. Come see why 193 Ridge Rd feels less like a house and more like home.

193 Ridge Rd, Middletown

$437,900

3 Beds ⋅ 2 Baths ⋅ 24188898 MLS

Rarely does a home blend historic character, creative energy & walkable in-town living so effortlessly. Nestled on a beautifully landscaped corner lot just moments from Wesleyan University, vibrant downtown Middletown & the Connecticut River waterfront, this thoughtfully updated early-1900s home offers warmth, flexibility & timeless appeal. Featuring 3 bedrooms, 2 full baths & a versatile third-floor studio, the flexible layout is ideal for an artist's retreat, home office, guest suite or creative sanctuary. Original character shines throughout with exposed brick, custom built-ins & abundant natural light. The updated kitchen features a Viking 6-burner range & opens seamlessly to the living & dining areas, creating an inviting space for everyday living & entertaining. Significant updates include newer windows, roof & a tankless hot water heater, while the classic brownstone foundation reflects the home's enduring craftsmanship. Outside, enjoy the charm of your own private city homestead with mature perennial gardens, window boxes, a fenced corner lot, dedicated garden beds, a welcoming back porch & even a chicken coop. A detached garage with bonus studio space offers endless possibilities for hobbies, a workshop or additional workspace. Just a short stroll to downtown restaurants, shops, local schools, parks & the riverfront, this exceptional property offers the perfect balance of historic charm, modern comfort & an unbeatable in-town lifestyle.

598 High St, Middletown

$399,900

3 Beds ⋅ 1 Baths ⋅ 24188777 MLS

Welcome home to this beautifully remodeled brick ranch, perfectly situated in a highly desirable neighborhood. This move-in-ready home offers three spacious bedrooms and two full bathrooms, combining classic charm with modern updates throughout. Step inside to find a welcoming living room featuring one of two cozy fireplaces, creating the perfect space for relaxing or entertaining. The thoughtfully designed layout also includes a dining room, a beautiful kitchen with brand-new stainless steel appliances, stunning granite countertops, and plenty of cabinet space. A convenient mudroom adds extra functionality for everyday living. Major updates provide peace of mind, including a brand-new roof, new windows, and a newer furnace. Every detail has been carefully updated, making this home truly turnkey. Whether you're enjoying quiet evenings by the fireplace or hosting family and friends, this beautifully renovated home offers comfort, style, and convenience in one of the area's most sought-after neighborhoods. Don't miss your opportunity to make this exceptional property your new home!

347 Farm Hill Rd, 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

$349,900

3 Beds ⋅ 2 Baths ⋅ 24183637 MLS

This lovely contemporary offers 3 bedrooms with hardwood flooring, 1-1/2 baths with a beautiful fenced in back yard. Your lover level includes a recreation room, a half bath and an additional bedroom. There is an oil-fired stove in lower level for energy extra savings. The lower level could be a potential in-law or guest area. Come see this soon because it will not last.

66 East St, Middletown

$90,000

5 Beds ⋅ 3 Baths ⋅ 24182301 MLS

Opportunity awaits at this 2-family residential property in a convenient Middletown location. The existing structure has sustained fire damage and is being offered strictly as-is. Ideal for investors, contractors, or buyers seeking a renovation or redevelopment project. Situated on a level lot with access to public water and public sewer. Close to shopping, dining, parks, and commuter routes. A unique chance to restore, reimagine, or rebuild subject to municipal approvals.

18 Portland St, Middletown

$319,000

3 Beds ⋅ 1 Baths ⋅ 24185726 MLS

Welcome home to this charming Cape Cod, lovingly maintained by the same family for more than 60 years. This is the kind of home that buyers rarely come across, filled with character, original charm, and a level of care that is evident from the moment you step inside. Many original features have been beautifully preserved throughout the years, including the original front door and a remarkable mid-century kitchen complete with the original 1957 sink, cabinetry, and stove, all still in excellent working condition. The flexible floor plan offers 3-4 bedrooms, including two rooms on the main level that can be used as bedrooms, a den, home office, or guest space. Two additional bedrooms are located upstairs. Hardwood floors run throughout much of the home, with hardwood also located underneath most of the carpeting. Central AC for summer comfort. The full walkout basement features full-size windows and direct access to a patio, providing excellent potential for future finished living space. Outside, you'll find a level, cleared backyard with plenty of room for gardening, entertaining, recreation, or simply enjoying the outdoors. Located on a quiet street and just minutes from the outstanding restaurants, shopping, parks, and amenities that make Middletown such a desirable place to call home, this special property is ready to welcome its next owners.

87 Lewis St, Middletown

$273,000

2 Beds ⋅ 1 Baths ⋅ 24186100 MLS

Welcome home to this lovingly maintained Cape Cod-style house with the convenience of one-floor living in the highly desireable South Farm neighborhood. This charming home features a spacious two-bedroom layout filled with natural sunlight throughout. The inviting eat-in kitchen is equipped with off-white cabinetry, stainless steel appliances, and a durable tiled floor, creating a bright and functional space for everyday living. The oversized primary bedroom features beautiful hardwood flooring and offers ample space for a combined bedroom and home office setup if desired. A welcoming living room with hardwood floors provides the perfect place to relax, while the second bedroom also showcases hardwood flooring. The full bathroom is tastefully appointed with a pedestal sink, tile flooring, and a shower/tub combination. Additional highlights include a walk-up attic accessible from the kitchen, and a walk-out basement with convenient interior/exterior access, both with ample storage. The lower level also includes a dedicated laundry room complete with washer and dryer. Outside, enjoy a spacious backyard ideal for outdoor relaxation, gardening, or entertaining. The easy-to-maintain yard is accented by beautiful perennial gardens that provide seasonal color and curb appeal. Nestled in a well-established and highly sought after neighborhood, 65 Deerfield Avenue offers the perfect balance of peaceful residential living and everyday convenience. Enjoy nearby parks, shopping

65 Deerfield Ave, Middletown

$330,000

2 Beds ⋅ 2 Baths ⋅ 24184837 MLS

Step into the charm of this vintage circa 1860 bungalow cottage, thoughtfully updated for today's lifestyle. Offering 1,157 square feet, this inviting home features 2 bedrooms and 2 full bathrooms, blending historic character with modern upgrades. Recent improvements include a newer roof, updated windows, high-efficiency gas heating system with indirect hot water, and fresh interior and exterior paint for a maintenance free home. The heart of the home is a renovated, spacious kitchen with center island and designer appliances. This area flows seamlessly into a dramatic two-story living room/ dining area with a Jotul woodstove and stunning cathedral ceiling. You also have a dedicated office space, a primary bedroom with a fully renovated full bath which creates a flexible and functional layout. The standout feature is the expansive LR addition, showcasing floor-to-ceiling windows that frame serene views of the backyard and provide access to a new open wraparound Trex deck-perfect for relaxing or entertaining. The 2nd level is an open and versatile space ideal for the second bedroom, guest retreat, or creative area, along with a newly renovated full bath and ample storage in place of a traditional attic. Outdoors, the property is truly special. A lovingly cultivated "secret garden" awaits, with an abundance of perennials, trees, shrubs, and flowering plants. Enjoy your privacy surrounded by mature native trees with closeness to Wesleyan, downtown Middletown and recreation.

36 Hunting Hill Ave, 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

$435,000

3 Beds ⋅ 2 Baths ⋅ 24182220 MLS

Don't miss this beautifully maintained split-level home featuring numerous upgrades and exceptional care throughout. Hardwood floors enhance the main living level, where the Living room, with a brick fireplace, opens to the Dining room, which is highlighted by attractive built-in bookshelves. The remodeled Kitchen offers granite countertops, stainless steel appliances, a pantry and ample cabinet space. The second level includes two spacious bedrooms, each with generous closet space and hardwood floors, and a fully renovated bathroom with a shower. The private third-level primary bedroom features abundant closet space, including a cedar-lined closet, and is complemented by a remodeled full bathroom with a tub. Both bathrooms have been tastefully updated. Additional storage is found throughout the home, including a walk-up floored attic. One level below the main living area are two garages separated by a laundry room with exterior access. Down a couple of steps is an unfinished basement offering excellent storage, along with a small finished office space. Outside, a covered porch overlooks the peaceful, fully fenced backyard, complete with a vegetable garden and storage shed. Central air conditioning and a standby Generac generator add comfort and convenience to this move-in ready home.

65 Prout Hill Rd, 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

$169,900

3 Beds ⋅ 1 Baths ⋅ 24183830 MLS

WELL MAINTAINED 3 BEDROOM, ONE BATH HOME WITH MANY RECENT UPDATES. FEATURES INCLUDE A LARGE EAT-IN KITCHEN, SPACIOUS LIVING ROOM. MAJOR IMPROVEMENTS INCLUDE A ROOF, CHIMNEY AND GUTTERS THAT ARE ONLY TWO YEARS OLD. ALONG WITH FURNACE AND OIL TANK THAT ARE JUST ONE YEAR OLD. MAIN SEWER REPLACED ONE YEAR AGO. A SOLID HOME THAT HAS BEEN CARED FOR OVER THE YEARS AND OFFERS AND EXCELLENT OPPORTUNITY FOR OWNER OCCUPANTS OR INVESTORS ALIKE. OWNER PREFERS TO SELL AS IS

7 Portland St, Middletown

$315,000

3 Beds ⋅ 1 Baths ⋅ 24183345 MLS

It has style, it has grace, it has a new roof (3 years old) - you will absolutely love this place!! THIS is the cape you've been waiting for! Ideal floorplan - the primary bedroom on the first floor faces the backyard; the relaxing living room has a wood burning fireplace; the renovated full bathroom has a bathtub; the beautifully modernized kitchen is fully applianced and the separate dining room has a pantry! The staircase to the additional renovated two bedrooms on the top level is elegantly tucked out of the way to not take away from the living room space. The It is warm, it is roomy ... don't sleep on it because you may be gloomy - missing out on this beauty!

175 Newfield 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

$497,900

4 Beds ⋅ 4 Baths ⋅ 24179489 MLS

Experience the perfect blend of historic charm and modern comfort in this exceptional Colonial home. From the moment you enter the spacious foyer, you'll be captivated by the craftsmanship, warmth, and timeless elegance that define this residence. The formal dining room, living room, and sunroom showcase remarkable original plaster crown molding, a rare architectural detail that highlights the home's rich character. The beautifully updated kitchen features soapstone countertops, stainless steel appliances, and a classic swinging door that opens to the dining room. Just beyond, a private balcony provides the perfect setting for morning coffee or evening relaxation. A stylishly renovated half bath is conveniently located near the rear entry. The inviting living room centers around a gas-insert fireplace accented by stunning Art Deco sconces, while the adjacent sunroom offers terracotta tile flooring and abundant natural light, creating an ideal retreat for reading, relaxing, or enjoying the changing seasons. The home features four bedrooms and three-and-a-half bathrooms. The spacious primary suite includes a beautifully appointed full bath with a large tiled shower. Two additional bedrooms share a charming period-inspired full bath complete with the original tub, sink, and elegant vintage fixtures. The finished walk-up attic serves as a generous fourth bedroom and includes additional flexible space ideal for a home office, hobby room, studio, or extra storage.

46 Bretton Rd, 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

$395,000

3 Beds ⋅ 2 Baths ⋅ 24178648 MLS

Completely renovated and a truly move-in ready Cape Cod style home. Major improvements include a new roof, new siding, new windows, a beautifully remodeled kitchen, remodeled bathrooms, and brand-new appliances, giving you peace of mind and low-maintenance living for years to come. Ideally located in the heart of Middletown, this inviting 3-bedroom, 2-bath home welcomes you with a warm living room centered around a classic fireplace. The stunning eat-in kitchen has been thoughtfully redesigned with stylish finishes. The main level features two comfortable bedrooms and a beautifully updated full bath. Upstairs, the spacious primary suite offers a private retreat complete with a dedicated office or sitting area, abundant built-in storage, and an updated full bath with a walk-in shower. Additional highlights include basement laundry, generous storage space, and a detached one-car garage with an attached storage shed for tools, outdoor equipment, and seasonal items. Step outside to enjoy the private patio, an ideal setting for morning coffee, outdoor dining, or relaxing at the end of the day. With all the major renovations already completed, this turnkey home is ready for you to move in and start enjoying it!

50 Garfield Ave, Middletown

$380,000

3 Beds ⋅ 2 Baths ⋅ 24174089 MLS

Charming Cape Cod-style home offering 3 bedrooms and 2 full bathrooms in a convenient location near major highways, shopping, dining, and local amenities. This well-maintained home features original hardwood floors throughout, a functional layout, and a spacious first-floor primary bedroom. Additional highlights include two laundry areas located on the main level and in the basement for added convenience, along with a versatile bonus room situated between the dining area and garage that can accommodate a variety of uses such as a home office, sitting room, or hobby space. Enjoy the beautiful yard, newer driveway, whole-house generator, leaf guard gutter protection system and solid craftsmanship through-out. With great bones and endless potential, this home presents a wonderful opportunity to make it your own. Don't miss the opportunity to own this charming home!

152 Middle St, Middletown

$315,000

5 Beds ⋅ 2 Baths ⋅ 24172630 MLS

* INVESTORS ONLY* FULLY rented, well-maintained and spacious two-family home, perfect for investors. Each unit offers 2-3 bedrooms, a full kitchen, living areas, and separate utilities. Features include updated front and back porch. Private backyard with entertainment and garden space. Full basement for plenty of storage. Updated water heaters for both units and main sewer were replaced less than 2 years. Conveniently located near schools, downtown restaurants and shopping. Close to public transportation. Great income potential! Price reflects needing new roof and minor repairs. Sold in As-Is condition. Agent/Owner

19 Portland St, Middletown

$679,900

24175820 MLS

Exceptional opportunity to own a beautifully maintained commercial property in one of Middletown's most desirable and visible locations. Currently operating as a professional attorney's office, this versatile building offers endless potential for professional, medical, office, boutique, or mixed-use possibilities. Perfectly positioned across from the historic town green and hospital, and just moments from downtown restaurants, shops, and major commuter routes, the location offers outstanding convenience and exposure. Blending timeless historic charm with modern updates, the property features an inviting entrance, impressive grand staircase, and a tastefully updated interior that preserves elements of the home's original character while incorporating modern finishes and functionality. Dedicated off-street parking, with charging for your EV, provides added convenience for clients and staff. The upper level offers exceptional flexibility with an updated full kitchen featuring quartz countertops, a luxurious full bath with a full tile shower, and two bedrooms. Ideal for an owner-occupant or live/work setup, you can simply walk downstairs to work each day. The sellers have also obtained city approval for a future rooftop expansion, creating the opportunity for an upscale rooftop terrace or executive entertaining space overlooking the downtown setting. A rare landmark-style property combining character, convenience, and future potential in an unbeatable location.

27 Pleasant St, Middletown

$224,900

3 Beds ⋅ 2 Baths ⋅ 24175733 MLS

Beautifully updated home tucked away on a quiet cul-de-sac offering the perfect blend of comfort, functionality & major recent improvements. The open floor plan creates a bright, inviting feel, complemented by hardwood floors throughout the main level. The kitchen was updated in 2022 with new cabinetry, quartz countertops & a clean modern look ideal for everyday living. The flexible layout includes a convenient first-floor bedroom, while upstairs offers two generously sized bedrooms. Both bathrooms were tastefully renovated in 2022. Additional updates completed in 2022 include the roof, gutters, siding, electrical panel, water heater & fresh interior paint throughout the entire home, providing peace of mind for years to come. Move-in ready with modern updates in a desirable cul-de-sac setting.

2 Hillside Ct, Middletown

$1,300,000

8 Baths ⋅ 24174579 MLS

Exceptional mixed-use investment opportunity in Middletown, with views of CT River and landmark Arrigoni Bridge. Offering strong in-place cash flow with immediate upside potential. Features six fully occupied residential apartments (2-1bds, 2-2bds, 2-3bds) plus two 1,600 square foot commercial garage/workshop spaces, creating strong stability. One commercial garage is currently leased, while the second vacant garage presents a compelling opportunity for an owner-user or investor seeking additional income. If you're a contractor, workshop operator, have storage needs, or small business owner, the vacant commercial space (currently listed for rent) allows a buyer to occupy the space while offsetting ownership costs through the residential income stream. The residential apartments have been updated over time, have newer boilers/water heaters and offer a strong unit mix of one-, two-, and three-bedroom layouts with broad tenant appeal. Property features off-street parking, and excellent access to Route 9, downtown Middletown, shopping, restaurants, and commuter routes. * 8 total income-producing spaces * 6 fully leased residential apartments * 2 commercial garage/workshop units * One leased commercial space + one vacant 1,600 SF commercial unit * Owner-user opportunity (act soon before rented) * Minutes from Route 9 * Walk to downtown and Wesleyan - This is a rare, stable cash flow, turnkey opportunity!!!! Property to be conveyed in as-is condition.

13 Portland St, Middletown

$399,000

2 Baths ⋅ 24173252 MLS

Commercial property located just off Main Street in a visible area with nearby restaurants, retail, and mixed use activity. B-1 zoning offers a variety of potential uses including retail, office, bakery, coffee shop, barbershop, commercial kitchen, community space, bar/brewery, or other business opportunities. Property was previously used as a bar/restaurant. Convenient location with close proximity to downtown amenities while situated on a quieter side street. Features open space, two bathrooms, and an oversized 800 sq ft garage/storage area in the rear of the property. Some photos include virtual staging or conceptual renderings to show potential layout and use ideas for the space. Buyer to perform all due diligence with the town regarding zoning, permitted uses, approvals, and any intended future use of the property.

73 Ferry St, Middletown

$259,000

3 Beds ⋅ 1 Baths ⋅ 24172327 MLS

Move right into this centrally located Middletown home! This 3 bedroom, 1 full bath home offers comfort, many updates, and timeless character in the heart of Middletown. Inside, you'll find a spacious living room perfect for entertaining lots of family and friends, along with touches of classic 1900s charm including a beautiful wood staircase and original railing details that add warmth and character throughout the home. The fully-fenced backyard is a perfect space for summer barbeques, relaxing, and keeping your pets safe with easy access to the detached 1-car garage. Updates include 1 year old windows with a transferable 25-year warranty, a 1 year old oil tank, a 3 year old furnace, and a 3 year old fence, offering peace of mind for years to come. Rough plumbing started for a second bath in the basement. Enjoy an unbeatable location just a 5 minute walk to the Connecticut River, Harbor Park, and vibrant downtown Middletown, known for it's bustling dining scene, local shops, parades, and community events on the Green. Close walk to Middlesex Hospital and not far from Wesleyan University. Commuters will appreciate convenient access to Rte 9 along with multiple nearby highways. A wonderful opportunity to own in a great town!

3 Flower St, Middletown

$300,000

3 Beds ⋅ 2 Baths ⋅ 24173819 MLS

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.

118 Grove St, Middletown

$2,249,500

21 Baths ⋅ 24165225 MLS

Investors dream - fully leased with value add potential! 18-unit corner brick building located on Main Street in the heart of Downtown Middletown, steps from gourmet restaurants and boutiques. Originally built in 1850, this 11,232 SQ FT building consists of 17 residential units and one ground level retail space. The retail space is leased to a mobile carrier/retailer through 2028 with annual rent escalation, allowing the new owner to focus on executing on the business plan for the 17 residential units. The building features four rare 2 beds, 2 bath units, seven 1-bedroom units, and six studio apartments. The building is currently fully leased, giving the new Owner an opportunity to capture the incredible rent upside over time while collecting rent income. The building has all separate gas boilers, huge unfinished basement and shared electricity. The units feature great layouts with nice natural light, high ceilings and large bedrooms with good closet space. The current owner has recently replaced some of the units windows, appliances and carpeting. Easy access to route 9 and a short drive/walk to Wesleyan University. This corner brick building is located near the beautiful, historic town center with over 7 walkable blocks of different restaurants and shops, featuring dozens of choices of dining, art, music, entertainment and unique finds. Neighborhood attractions include: Perkatory Coffee Roasters; Eli Cannons Tap Room; The Whey Station; Luce. Become part of this exciting tow

668 Main St, Middletown

$339,900

4 Beds ⋅ 2 Baths ⋅ 24172703 MLS

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

37-39 Hotchkiss St, Middletown

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