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$174,499
2 Beds ⋅ 2 Baths ⋅ 24195105 MLS ⋅ Hamlin Court BLDG.
Welcome to Hamilton Court! This beautifully remodeled 2 bedroom, 1.5 bath townhouse offers stylish updates, low-maintenance living, and an unbeatable location just one block from Wesleyan University. Renovated within the last year, this move-in-ready home features a remodeled kitchen with updated appliances, renovated bathrooms, new flooring, brand-new carpeting, freshly painted walls and trim, and modern finishes throughout. The bright and inviting main level offers an open layout with a spacious living room flowing into the dining area and kitchen, creating the perfect space for everyday living and entertaining. A convenient half bath and private front terrace add to the home's appeal. Upstairs, you'll find two generously sized bedrooms, including a primary suite with a walk-in closet and en-suite bathroom. An in-unit washer and dryer provide added convenience. Enjoy one assigned parking space and a prime location within walking distance to downtown Middletown, Middlesex Hospital, restaurants, shopping, parks, and entertainment, with easy access to major commuter routes. Whether you're looking for a primary residence or an investment opportunity near Wesleyan University, this turnkey townhouse is one you won't want to miss. Property is being sold AS IS, WHERE IS.

201 College St Unit 22, 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
$257,000
2 Beds ⋅ 2 Baths ⋅ 24192644 MLS ⋅ Newfield Commons BLDG.
spacious 2-bed townhouse in a quiet complex near shopping, coffee, restaurants and the high school. You'll enjoy a peaceful spot to sip your coffee on the upgraded trex deck & with a view of the woods. Heat pump is under 10yrs, CAIR, Low HOA cost includes trash and snow removal. super spacious primary suite and bath with double sinks. Finish the basement for even more space. This is the perfect place to start out. Some upgrades will make this home shine, but well-loved for years. Visitor parking is a plus too!

675 Newfield St Unit 9, Middletown
$180,000
3 Beds ⋅ 2 Baths ⋅ 24194531 MLS ⋅ Beacon Hill Towne Homes BLDG.
Investment Opportunity! This spacious condo is being sold as-is and offers excellent potential for investors or buyers looking to build sweat equity. The unit features gleaming hardwood floors throughout, a partially finished basement offering additional living or storage space, and a finished attic that adds even more usable square footage. A convenient 1.5 bath layout rounds out the floor plan. Enjoy community amenities including access to a sparkling in-ground pool. Conveniently located near I-91 and Route 9, offering easy access for commuters. With its combination of extra finished space, low-maintenance hardwood flooring, and community amenities, this unit presents a strong opportunity for value-add renovation or rental income. Sold as-is.

106 Rising Trail Dr Unit 106, 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
$539,999
3 Beds ⋅ 3 Baths ⋅ 24191099 MLS
Welcome to this beautifully updated 3-bedroom Contemporary- ranch style home, privately set on a lush .92-acre lot. A charming wraparound covered porch creates an inviting first impression and a wonderful place to relax. Inside, vaulted ceilings, abundant natural light, fresh paint and new luxury vinyl flooring enhance more than 1,600 square feet of above-grade living space, with an additional 800+ square feet on the lower level. The home offers 2 full and 1 half baths, including a primary bathroom upgraded in 2022. More than $70,000 in recent improvements include a new upper-level balcony, siding, refinished deck, Driveway, new appliances and a washing machine installed in 2025. Additional updates include a 30-year architectural roof installed in 2004, replacement shingles adjacent to the rear balcony in 2026, a new central-air condenser installed in 2016 and two 100-amp electrical panels, including one installed in 2018. The versatile lower level features a heated family room with a fireplace, a new sliding door and existing plumbing, creating exciting possibilities for an en-suite guest area, potential in-law, home office, studio or salon. Buyers should perform their own diligence regarding any intended use and applicable municipal requirements and approvals. The outdoor space has been beautifully refreshed with more than $5,000 in new landscaping and a brand-new saltwater above-ground pool installed just three weeks ago...

1512 Country Club Rd, Middletown
$239,900
2 Beds ⋅ 2 Baths ⋅ 24193840 MLS ⋅ Cedar Ridge BLDG.
This lovely move in ready unit, is set within a peaceful and quiet complex. On the main level you with find a large living room, dining room combination, 1/2 bath, pretty kitchen with plenty of cabinets, and a brand new refrigerator and oven hood. Also, the door off the kitchen will lead you right out onto your pretty deck for some relaxation time and grilling. Upstairs you will find the primary and 2nd bedrooms, along with a spacious full bath. There are pull down stairs, as well as an attic fan. The basement is large and ready for your special touches to create a workout room, office, or whatever may be suitable for you. Located close to highway access, both route 17 as well as Routh 9, Middlesex Community College, plenty of restaurants, shopping, banking, and just about anything else that you may need. C'mon and make your appointment today, as this very clean unit will surely not last long. Lucky will be the new owner for this truly great unit!

10 Countryside Ln Unit 5, Middletown
$677,000
4 Beds ⋅ 3 Baths ⋅ 24193869 MLS
Welcome to this beautifully maintained 4+-bedroom, 2.5-bath Colonial conveniently located in the heart of Middletown. Freshly painted and move-in ready, this home offers the rare combination of generous living space, flexible room options, entertaining areas, and valuable recent updates-including a new roof in 2025. The spacious eat-in kitchen features a center island and bright breakfast nook with skylight, opening directly into a welcoming great room with a fireplace and built-in sound system. It's an ideal layout for both everyday living and entertaining. But the feature you'll want to see is the approximately 500-square-foot first-floor fifth bedroom/media room. With a projector and surround sound already in place, it's perfect for movie nights, watching the big game, or hosting friends. Because of its size and location, it can easily be transformed into a first-floor primary suite, guest suite, home office, gym, playroom, or recreation space. Upstairs, four generously sized bedrooms provide plenty of room for family, guests, or dedicated work-from-home space. A separate living room and formal dining room offer even more flexibility for entertaining.

166 Mccormick Ln, Middletown
$194,999
2 Beds ⋅ 2 Baths ⋅ 24193843 MLS ⋅ Hamlin Court BLDG.
This freshly painted townhouse-style condo offers 2 bedrooms, 1.5 bathrooms, newer windows, updated appliances, newer flooring throughout, and an open-concept layout. The main level features a spacious living room that flows into the dining area and kitchen, along with access to a private terrace. The kitchen includes tile flooring, a mosaic tile backsplash, and appliances replaced within the past three years. Upstairs are two bedrooms with spacious closets, a full bathroom, and convenient in-unit laundry with a new washer and dryer. Previously rented for $1,900 per month, this investor-friendly unit offers strong income potential. Additional features include a dedicated storage unit, one assigned parking space, and visitor parking. Ideally located within walking distance of Downtown Middletown, Wesleyan University, and Middlesex Hospital, with easy access to restaurants, shopping, and major commuter routes.

201 College St Unit 20, 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
$229,900
3 Beds ⋅ 1 Baths ⋅ 24192281 MLS
Welcome to 21 Inverness Ln. Make this spacious 3 bedroom your new home. This home is nestled in the sought-after Highland Lake Community. The home features an open floor plan with generous sized rooms. Upon entering, you'll be met with an updated kitchen and a comfortable dining area. The adjacent family room features laminate flooring and sliders to a private fenced in patio complete with a pergola to shield you from the sun on scorching hot summer days. The upstairs features 3 spacious bedrooms, updated full bathroom, laundry nook and an area for den, office or media play. The 2-car garage also has an additional storage area off the back. You can enjoy single family home living without the extensive yard work. This home is waiting for your next summer party. Highest and best Sunday, 7/26 by 5:00 PM.

21 Inverness Ln, Middletown
$759,000
3 Beds ⋅ 3 Baths ⋅ 24189442 MLS
Welcome to South Farms, where "staycation" is a way of life. This custom-built home is made for lazy mornings on the wraparound porch and sunny afternoons by the pool - all behind a brand-new full privacy fence with an acre of land. The grounds bloom spring through fall, and a charming chicken coop with its own shed adds hobby-farm charm. Inside, an open-concept layout shines with soaring cathedral ceilings, skylights, and a dramatic floor-to-ceiling fireplace. The kitchen boasts new appliances and flows into a breakfast bar and dining area made for gathering. A flexible downstairs den works as a fourth bedroom, playroom, office, or media room. Spacious full sized unfinished basement perfect for pool table and endless storage. The main floor primary bedroom suite offers a fully renovated bathroom and French doors leading to your own backyard oasis. A heated in-ground pool, lush plantings, and a footbridge over a koi pond to a pool house complete with a half bath! Upstairs, a sunny loft overlooks the living room; two bedrooms feature built-in window seats, and a huge room ready for anything; gym, playroom, extra bedroom; you name it. City sewer means no septic to worry about. Homes like this don't come around often. Come make it yours.

236 Maple Shade Rd, Middletown
$399,900
3 Beds ⋅ 3 Baths ⋅ 24190665 MLS
Classic Colonial on a picture-perfect lot with sweeping pastoral views in one of Middletown's most scenic settings! This home offers solid bones, generous room sizes, and loads of potential for anyone ready to add their own touches. The sun-filled living room offers oversized windows and flows easily into the dining area, while the beamed family room delivers warmth and character with wood paneling and a brick fireplace. The eat-in kitchen features ample counter space, stainless appliances, and a picture window overlooking the private backyard. A main-level laundry room and half bath add everyday convenience. Upstairs you'll find three comfortable bedrooms, including a spacious primary suite with its own private bath and double closets, plus a second full bath off the hall. The finished lower level adds fantastic flexible space with a large recreation room and dry bar - perfect for movie nights, a home office, or gym. Step outside and this property truly shines: an expansive deck with covered gazebo overlooks a sprawling, level backyard bordered by mature trees and open field views - a wonderful setting for entertaining or simply unwinding at the end of the day. Additional highlights include a two-car garage, mini-split systems for efficient heating and cooling, and a peaceful country feel just minutes from shopping, schools, and Route 9. Opportunities to own this view, space, and charm don't come along often. Bring your vision and make it home!

9 Round Hill Rd, 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...SELLER WILL CREDIT $15,000 TOWARDS BALANCE OF SOLAR PANEL CONTRACT.

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
$220,000
24188906 MLS
An exceptional opportunity to acquire a well-established restaurant that has successfully served the Middletown community for 26 years. This turnkey operation is strategically positioned in a high-traffic corridor surrounded by schools, office parks, medical facilities, and densely populated residential neighborhoods, generating consistent customer traffic and strong year-round demand. The business benefits from an efficient operating model, a loyal repeat customer base, and a fully trained, long-tenured staff already in place. With decades of successful operation, the restaurant has earned a strong reputation within the community and offers a proven foundation for continued growth and profitability. Recent renovations and upgraded kitchen equipment enhance the property's appeal and operational efficiency. The business is designed for smooth day-to-day management with minimal owner oversight, making it an ideal opportunity for an owner-operator or an experienced restaurant group seeking to expand its portfolio. To ensure a seamless transition, the current owner will provide comprehensive training and support at no additional cost.

280 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
$215,000
2 Beds ⋅ 2 Baths ⋅ 24188722 MLS ⋅ Carriage Crossing BLDG.
Welcome home to this sought-after condo complex at Carriage Crossing, where you will find this two bedroom two full bath unit, with open concept space. The galley kitchen has pantry. Both bathrooms have granite countertops and soft close cabinetry. In unit washer and dryer. Living room has a cozy wood-burning fireplace. Primary bedroom has a walk-in closet, and both bedrooms have their own full baths, and offer plenty of room. Unit offers recently replaced washer/dryer, water heater and the microwave. HVAC replaced 4 years ago. Take advantage of the incredible amenities, including an inground pool, clubhouse, basketball court, fitness center, racquetball, and tennis courts, and clubhouse available for events. This association is Pet friendly (allowing up to two pets small dogs only and/or cats) Conveniently located near shopping, dining, major highways and downtown Middletown. Also located near major employers and Medical centers, including Middlesex Hospital, and easy commutes to Yale New Haven Hospital and Harford Hospital, and near Wesleyan University. Property is ideal for owner occupants or investors seeking low maintenance living in a well managed community.

93 Carriage Crossing Ln Unit 93, 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
$898,000
4 Beds ⋅ 5 Baths ⋅ 24187393 MLS
Lakeshore Realty is proud to present 49 Partridge Lane, a beautifully maintained home tucked away on a quiet cul-de-sac in one of Middletown's most desirable neighborhoods. Designed for both everyday living and entertaining, this exceptional home features a bright, open floor plan, spacious living areas, and a beautifully appointed kitchen complete with premium Viking stainless steel appliances, offering both luxury and performance for the home chef. One of the property's most unique features is its location abutting the Mt. Higby Reservoir, providing a peaceful natural backdrop, enhanced privacy, and picturesque views. Enjoy direct access to nature while relaxing in your private backyard, perfect for entertaining, gardening, or unwinding after a long day. Generously sized bedrooms, well-designed living spaces, and meticulous upkeep make this home truly move-in ready. Conveniently located just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, golf courses, and major highways, you'll enjoy the perfect combination of tranquility and accessibility. With high-end finishes, a sought-after location, and the rare benefit of bordering protected natural surroundings, 49 Partridge Lane offers an outstanding opportunity to own a home that blends comfort, quality, and lifestyle. Schedule your private showing today!

49 Partridge Ln, Middletown
$1,295,000
4 Beds ⋅ 4 Baths ⋅ 24187574 MLS
Nestled on an extraordinary 39-acre estate with breathtaking panoramic views, this stunning custom log home offers the perfect blend of rustic elegance, modern comfort, and exceptional investment potential. Originally built in 2005 with an addition completed in 2014, the home features 4 bedrooms and 3 full bathrooms. The interior showcases soaring cathedral ceilings, beautiful tile flooring, ceiling fans throughout, and a dramatic two-sided fireplace that serves as a focal point for multiple living areas. German-engineered windows with roll shutters & premium German doors provide exceptional quality. Kitchen features new appliances & an open concept. 2 bedrooms with full bathrooms on the main level offer one-floor living options. The lower level includes 2 oversized garages providing abundant storage, workshop space, and room for recreational equipment. A wood/storage shed adds even more utility. This home is in pristine condition with brand new well, new water heater, and 2 central air units. The property consists of three separately deeded parcels presenting a rare opportunity for future investment, development, or resale. The land features rolling acreage, mature trees, open spaces, and a picturesque man-made pond. Whether you're seeking a private retreat, recreational haven, family compound, or property with investment upside, this one-of-a-kind estate delivers stunning natural beauty, exceptional craftsmanship, and limitless possibilities.

1409 Millbrook Rd, 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
$145,000
2 Beds ⋅ 1 Baths ⋅ 24182065 MLS ⋅ Sumnerbrook Mill BLDG.
Super investment or owner occupancy in this spacious 2 bedroom, 1 full bath condo that exudes charm and character in the old mill building. Located on the 3rd floor, this unit offers privacy and tranquility. The floor plan allows for a private dining experience, a well equipped kitchen, and parquet wood flooring throughout the living areas with fresh carpet to the bedroom level. The bedrooms are located on the upper level of this townhouse style unit and share a full bathroom. The windows let in nice natural light and the large window ledges provide great space for natural plantings to flourish.The mill building has a pond and running water with an area to enjoy the peaceful sights and sounds of nature. Take a look, whether as an investment or as a private residence, this could be a great opportunity!

1 Russell St Unit 22, Middletown
$229,900
2 Beds ⋅ 2 Baths ⋅ 24184158 MLS ⋅ River's Edge BLDG.
Come see this beautiful freshly painted two bedroom, 2 bath remodeled unit which has Corian countertops and white cabinetry for a bright and light kitchen. All kitchen appliances are stainless steel and the flooring is tile. Walk into the dining room/living room with tile flooring and overhead fan to the slider for some extra views of the CT. River! Both bedrooms have Bamboo wood flooring with large windows and closets. The washer and dryer are in the unit. The HOA covers heat, hot water, water and sewer, air conditioning, trash, heated indoor pool, fitness room, community room, plowing, renovated elevator and ground maintenance. The fob opens the pool, fitness, storage and community room to enter. Each unit has it's own storage in the basement of this complex. It's close to Middlesex Hospital, Wesleyan University, Tates (riverfront restaurant) and downtown Middletown with shops and restaurants.

111 Dekoven Dr Unit 609, 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
$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
$649,900
4 Beds ⋅ 4 Baths ⋅ 24183475 MLS
Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and solid wood doors throughout. The floor plan provides plenty of flexibility for everyday living, entertaining, working from home, or accommodating changing needs over time. The partially finished walkout lower level adds valuable bonus space and offers a variety of potential uses, including a recreation room, home office, gym, hobby area, or possible in-law setup. Direct access to the yard makes the space feel like a natural extension of the home. Conveniently located near Middletown's amenities while offering a quieter setting, this property provides space, functionality, and quality construction in a sought-after area of town. Estate sale subject to probate court approval.

76 Thimble Rock Rd, 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

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