Middletown CT Just Listed Real Estate, Homes, Condos for Sale

Beautiful Colonial tucked away on a quiet cul-de-sac offering comfort, space, and modern updates. The inviting living room features a large picture window and cozy wood-burning fireplace, creating the perfect gathering space. Updated kitchen includes granite countertops, with plenty of cabinet space, and easy access to the deck - ideal for cookouts and outdoor entertainment. The main level also offers a formal dining room and convenient half bath. With 1 yr old HVAC (heating and cooling) on 1st floor. Upstairs, the spacious primary bedroom includes a walk-in closet. There are two add. bedrooms and an updated full bath. The finished basement provides additional living space perfect for a home office, gym, or add. room. Energy-efficient 2-year-old solar panels, newer roof and boiler helps keep utility costs down. Conveniently located near the HOA common area with a playground, basketball court, and picnic area for additional outdoor enjoyment. Complete with a one-car garage. Perfect alternative to condo living. House to be sold AS IS.

19 Kent Ct, Middletown

$375,000

3 Beds ⋅ 3 Baths ⋅ 24175825 MLS

Built in 2010 and meticulously maintained, this Cape-style home offers the perfect blend of comfort, flexibility, and peace of mind. From the moment you arrive, you'll appreciate that everything has already been done for you - simply move in and enjoy. Inside, hardwood floors flow throughout the main level, where the versatile layout is designed to fit a variety of lifestyles. The spacious main-floor primary suite features a full bath, walk-in closet. There is convenient first-floor laundry and a half bath as well. Upstairs, you'll find 2 more bedrooms, one so large it could easily serve as an additional primary suite. Another full bath as well! The oversized eat-in kitchen offers abundant space for cooking, entertaining, and gathering around a large table. Sliders lead directly to the back deck - the perfect spot for grilling and outdoor dining all summer long. Major updates provide added value and confidence, including all new appliances in 2024, CAIR installed in 2020, and a natural gas furnace that has been serviced annually. Even better, the seller will purchase the solar panels at closing, allowing the new owner to enjoy the benefits of owned solar energy and lower utility costs from day one. Attached one car garage is a plus. Nicely sized side yard that's easy to enjoy without overwhelming maintenance. This is the kind of home buyers wait for, well cared for and truly move in ready. Subject to sellers finding suitable housing, actively looking! Excuse the boxes!

72 Durant Ter, 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

$389,900

3 Beds ⋅ 2 Baths ⋅ 24175189 MLS

PRICE REDUCED FOR QUICK SALE! Welcome home to this beautifully renovated 3-bedroom, 2-bathroom raised ranch in Wesleyan Hills, where all the major work is already done for you. This move-in ready home features a brand new roof and new efficient boiler, giving you years of worry-free ownership and energy savings. The heart of the home is a stunning new kitchen with crisp white shaker cabinets, quartz countertops, and modern finishes that's perfect for everyday living and entertaining. Both full bathrooms have been completely updated with contemporary tile, vanities, and fixtures. The raised ranch layout offers bright main-level living space plus flexible finished lower-level space ideal for a family room, home office, or guest suite. Conveniently located on Long Hill Rd with easy access to Route 9, schools, and Middletown's shops and dining, this home delivers the perfect blend of comfort, style, and location. With all the big-ticket items checked off the list, all you need to do is unpack.

492 Long Hill Rd, Middletown

$589,000

3 Beds ⋅ 2 Baths ⋅ 24176671 MLS

Get ready to fall in love with this beautiful newer construction ranch that perfectly blends modern style with easy, carefree living! Bright, open, and filled with natural light, this home welcomes you with gorgeous hardwood floors throughout and an open floor plan made for everyday living and entertaining alike. The stylish kitchen is truly the heart of the home, featuring granite countertops, stainless steel appliances, and plenty of room for gathering with family and friends. The spacious primary suite is your own private escape, complete with a full bath and plenty of room to relax and recharge. Two additional oversized bedrooms and a second full bathroom offer space for everyone, whether you need guest rooms, a home office, or playroom. Main floor laundry and direct access to the attached garage make life easy and convenient. Need more space? The full walkout basement is bursting with potential and ready to become the ultimate family room, home gym or game room! Outside, the back deck is the perfect spot to sip your morning coffee while taking in stunning mountain views and spectacular sunrise skies. Add in the peace of mind of a home completed in 2020 with a full house generator, central ac, natural gas fuel, and you've found a home that checks every box - and then some!

650 Ridgewood Rd, 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

$559,900

3 Beds ⋅ 3 Baths ⋅ 24175571 MLS

Welcome to a lifestyle that blends neighborhood charm with everyday convenience in one of Middletown's most connected and vibrant locations. Nestled within a planned community, this completely updated 3-bedroom, 2.5-bath home offers the perfect balance of comfortable living, modern style, and easy access to everything the area has to offer. From the moment you step inside, you'll appreciate that everything has already been done - simply move in and enjoy. The fully remodeled kitchen serves as the heart of the home with crisp cabinetry, beautiful quartz countertops, stainless appliances, an oversized island for gathering, and finishes that blend timeless design with everyday function. Hardwood floors and inviting living spaces create warmth and flexibility throughout, while the thoughtful layout offers room to entertain, work from home, or simply relax and unwind. Upstairs, the spacious primary suite provides a peaceful retreat complete with a beautifully remodeled bathroom designed with comfort and style in mind. Additional bedrooms offer flexibility for guests, hobbies, office space, or changing lifestyle needs. Major updates throughout the home provide peace of mind, including a roof only 4 years old, allowing the next owner to enjoy a truly turnkey experience. Outside your door, enjoy the feeling of a true neighborhood community while being just minutes from Middletown's thriving downtown filled with local restaurants, coffee shops, arts, live music, Wesleyan

265 Briarwood Ln, Middletown

$950,000

24174532 MLS

This property abuts 35 acres of mixed conservation land and offers views of the Connecticut River and two nearby state parks, ensuring the scenery will remain protected and undeveloped. The spectacular, lightly wooded parcel is the result of combining three approved lots within the River Park Subdivision to create one exceptional private homesite with breathtaking river views. Underground electrical is already in place-just bring your plans. The property is easily accessible via approved private roads maintained by an association, with a properly constructed 18-foot wide gravel Scovill Road.

Scovill Rd, 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

$163,000

1 Beds ⋅ 2 Baths ⋅ 24174644 MLS ⋅ River's Edge BLDG.

Premium Connecticut River views from this 9th floor, almost end unit on the bridge side. This beautiful unit is in move in condition. It includes a newly renovated kitchen, 1.5 updated bathrooms, freshly painted, and new flooring throughout. The laundry is conveniently located in the unit and there are plenty of closets in this well laid out condo. The building has a comcrete wall construction which ensures peace and quiet in your unit. The building has a secure entry, and is well maintained with an unbeatable location, a short walk to Middlertowns vibrant downtown and the Wesleyan University campus. The condo is close to ourdoor activities, including hiking, biking, kayaking and the Ct. River and shoreline. The HOA includes heat, air conditioning, a spacious gym and heated pool, and community room for social activities along with water/sewer, hot water, trash, landscape/snow removal and professional property management. Elevators and HVAC systems have been updated recently. The unit comes with private storage and assigned parking! Near to Rt 9 - and I-91- 20 min. to Hartford, 30 min. to New Haven. Come see this beautiful unit today!

111 Dekoven Dr Unit 908, 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

$324,900

3 Beds ⋅ 2 Baths ⋅ 24173942 MLS

** OFFER DEADLINE: MONDAY 5/18 - 6PM ** Spacious and thoughtfully expanded, this ranch-style home offers nearly 1,500 square feet of comfortable living space on the main level in a quiet neighborhood just minutes from downtown Middletown. Featuring a brand new central air system (2026), newer windows, new porch, and a freshly updated deck, this home is packed with value and versatility. Step inside to find a bright and inviting living room with hardwood flooring and a large bay window that fills the space with natural light. The eat-in kitchen offers newer stainless steel appliances, ample cabinet space, and easy access to the back deck - perfect for entertaining or relaxing outdoors. Down the hall, you'll find a massive office, playroom (or 4th bedroom!), convenient main-level laundry, and a spacious full bathroom with tile flooring. A 2006 addition significantly expanded the home, creating two generously sized guest bedrooms and a large primary ensuite complete with high ceilings, abundant natural light, and a bright full bathroom for added comfort and convenience. The finished lower level provides even more living space with a spacious recreation area, additional storage, workshop space, and access to the oversized two-car garage. Outside, enjoy a fully fenced backyard ideal for pets, play, or gardening. A rare combination of space, updates, and location - this Middletown gem is ready to welcome its next owner!

38 Harris 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

$650,000

3 Baths ⋅ 24173282 MLS

Industrial condo unit 5 located at 362 Industrial Park Road in Middletown offering a total of 8545 square feet, including 5,000+ square feet of office space and 3,000+ square feet of warehouse space. The property features 15 private offices, three bathrooms, ADA accessibility, and 440 amp three phase power to support a wide range of operations. The warehouse area includes two loading docks for efficient distribution. Gas central heating and cooling serve the space. Situated within a well maintained industrial park with convenient access to I-91, this clean and move in ready property is zoned IT (Interstate Trade) and is available for both sale and lease.

362 Industrial Park Rd Unit 5, 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

$1,700,000

2 Baths ⋅ 24171508 MLS

942 Washington Street presents a prime commercial investment opportunity in the heart of Middletown's busiest retail corridor. Positioned on the heavily traveled Route 66, with an average daily traffic count of approximately 20,000 cars, this property offers exceptional visibility and exposure for investors and end users alike. Surrounded by national retailers including Wendy's, McDonald's, AutoZone, and Home Depot, the location benefits from strong neighboring businesses and consistent consumer traffic. This high-profile commercial property is ideal for retail, restaurant, or service uses, or for redevelopment, and represents a valuable addition to any investment portfolio. Washington Street remains one of Middletown's most active commercial corridors, offering convenient access, strong demographics, and long-term growth potential. Don't miss the chance to secure a property in one of the city's most sought-after business locations.

942 Washington St, Middletown

$749,900

9 Beds ⋅ 6 Baths ⋅ 24171799 MLS

Outstanding Mixed-Use Investment Opportunity at 227 East Main Street, Middletown, CT Now offered at a newly reduced price, 227 East Main Street presents an exceptional opportunity for investors or owner-occupants seeking strong income potential and long-term value. This well-maintained mixed-use property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bath, 1 half bath, bright living spaces, and eat-in kitchens-highly desirable layouts that help attract and retain tenants. A standout feature is that each unit includes its own private under-house garage with direct access, creating the convenience and feel of a single-family home. The property also offers ample off-street parking and a driveway behind the building, providing easy access and added convenience for residents and guests. Separate utilities, hardwood floors, abundant natural light, and additional basement storage further enhance the property's appeal and ease of management. Ideally located near downtown Middletown, shopping, dining, parks, major commuter routes, Wesleyan University, and Middlesex Health, this property benefits from strong rental demand and excellent accessibility. With its price improvement, desirable townhouse-style units, private garages, ample parking, and proven income-producing potential, 227 East Main Street is a compelling investment opportunity in the heart of Middletown. Agent owner related.

227 E Main St, Middletown

$285,000

2 Beds ⋅ 3 Baths ⋅ 24171013 MLS ⋅ Parker House BLDG.

Welcome to 234 S Main St, Unit 416. This spacious end-unit condo offers 2 bedrooms and 2.5 baths across approximately 1,450 sq ft with a bright, functional layout and great natural light. The unit features two balconies, newer windows throughout, central air, and forced air heating. One of the only units in the building with a Gas Fireplace as well. A covered garage parking space is included for added convenience. All assessments have been paid off, making this an easy, move-in ready option. The association allows rentals, offering flexibility for owners-but with a home like this, why rent when you can own? Located just minutes from downtown Middletown, Route 9, Middlesex Hospital, Wesleyan University, and local favorites like Neil's Donuts, this property offers simple, comfortable living in a highly convenient location. Pets allowed.

234 S Main St Unit 416, Middletown

$479,900

3 Beds ⋅ 3 Baths ⋅ 24170759 MLS

Welcome to 25 Pleasant View Drive in the highly desirable Westfield section of Middletown. A completely updated home nestled on a quiet cul-de-sac, offering the perfect blend of comfort, style and functionality. This inviting property features large, sun filled rooms and beautiful hardwood floors throughout the main living areas, adding warmth and appeal. The spacious living room is highlighted by a cozy fireplace, creating the perfect setting for relaxing evenings at home. The updated kitchen offers modern finishes, plenty of cabinetry, and a layout ideal for both everyday living and entertaining. Downstairs, the fully finished basement expands your living space and includes a custom bar perfect for hosting gatherings, game nights, or creating your own private retreat. Step outside to enjoy the large yard, offering plenty of space for outdoor entertaining, gardening, or simply unwinding in your own private setting. A 2 car garage with ample storage. A truly move in ready home not to be missed. AGENT RELATED TO SELLER

25 Pleasant View Dr, Middletown

$125,000

24170659 MLS

Build your dream home on this 3.5 acre approved building lot bordering open space. Last lot on a private cul-de-sac! Beautiful, wooded country setting for a home, yet only 1 mile from Rt 9 and 10 minutes to Downtown Middletown! Enter the lot down a picturesque driveway though the woods to a clearing with old stone walls and natural rock outcroppings. The open space for the cul-de-sac borders this lot, offering more privacy. Well and septic are required, a perc test from years ago available upon request.

Mountain Laurel Drive, Middletown

$645,000

4 Beds ⋅ 2 Baths ⋅ 24162489 MLS

VERY unique property. Use to be a goat farm. Contains 6 outbuildings consisting of a 3 bay open shed - perfect for storing just about anything, a 3 story red bank barn this barn is huge 3 levels inside - would be perfect for car storage, boats, trailers, jet skiis anything you need covered - you rent it out for storage, a 1 car detached heated garage with an office and a furnace with a separate oil tank, a feed shed, a detached garage for the house and an outhouse. The home has 4 bedroom on the 2nd floor - one of the bedrooms would be perfect for an office as it has a lot of outlets, a walk up attic that is floored , a large updated bathroom on the 2nd floor, a cedar closet, and a very unique curved wall upstairs. The 1st floor has a front living room, a formal dining room, a laundry rm with a 1/2 bath/pantry, and a large updated kitchen. There are 2 fireplaces in the home - both of them have been closed up and are currently not working. Beautiful solid wood doors. There is a full basement. Front and back staircases. This home over the years has been lovingly updated. Included in the sale is a separate lot - map is in disclosures. Please do not drive onto property and walk around without an agent present. Shown by appointment only.

110 Freeman Rd, Middletown

$350,000

3 Beds ⋅ 2 Baths ⋅ 24169081 MLS

Looking for a charming home? This one is dying to meet you! Welcome to this character-filled Middletown home blending classic details with thoughtful updates. Freshly painted with original wood trim and refinished hardwood floors, it offers warmth and charm throughout. The kitchen features newer appliances, an antique sink, and great natural light with porch access. A dedicated laundry room includes updated washer, dryer, and utility sink. Upstairs offers three bedrooms, plus a full bath with a walk-in shower. The partially finished attic adds a full-size room, cedar closet, and extra storage. The primary bedroom features a private porch with views of the Arrigoni Bridge. Outside, enjoy established plantings, a detached two-car garage, walk-out basement, and three enclosed porches. Relax with sunset views from the front porch overlooking St. John's Cemetery.

38 Johnson St, Middletown

$1,500,000

1 Beds ⋅ 1 Baths ⋅ 24166400 MLS

Prime Mixed-Use Investment Opportunity - Downtown Middletown, CT. This asset currently produces 9.7 cap annually, features a total of 16 units, including 4 retail storefronts and 12 on1-bedroom residential apartments. The retail spaces are currently occupied by established neighborhood businesses, including a grocery store, Boost Mobile, a barber shop, and a convenience store-providing steady foot traffic and consistent rental income.The residential component consists of twelve 1-bedroom units, offering strong demand in this vibrant downtown location. The asset include: mostly of windows recently replaced, hardwired smoke detectors throughout, fire sprinkler system installed, tenants cover their own electric utilities. Well-maintained asset with value-add potential. Street parking is readily available, and tenants can get a residential permit for approximately $55/month for access to designated parking lots nearby. The asset is well located in downtown Middletown, the property benefits from high visibility, walkability, and proximity to restaurants, shopping and public transportation.

530 Main St, Middletown

$1,500,000

1 Baths ⋅ 24161724 MLS

Prime Mixed-Use Investment Opportunity - Downtown Middletown, CT. This asset currently produces 9.7 cap annually, features a total of 16 units, including 4 retail storefronts and 12 on1-bedroom residential apartments. The retail spaces are currently occupied by established neighborhood businesses, including a grocery store, Boost Mobile, a barber shop, and a convenience store-providing steady foot traffic and consistent rental income.The residential component consists of twelve 1-bedroom units, offering strong demand in this vibrant downtown location. The asset include: mostly of windows recently replaced, hardwired smoke detectors throughout, fire sprinkler system installed, tenants cover their own electric utilities. Well-maintained asset with value-add potential. Street parking is readily available, and tenants can get a residential permit for approximately $55/month for access to designated parking lots nearby. The asset is well located in downtown Middletown, the property benefits from high visibility, walkability, and proximity to restaurants, shopping and public transportation.

530 Main St, Middletown

$1,100,000

8 Beds ⋅ 4 Baths ⋅ 24163304 MLS

Exceptional Multi-Family Investment Opportunity in CT! Located in desirable Middletown, this unique property package offers two two-family homes-for a total of four income-producing units-along with a versatile 2,898 sq ft workshop and two additional vacant land parcels. Each residential building offers approximately 1,380 sq ft with new roofs, new windows, upgraded electrical, and modernized plumbing-providing peace of mind for years to come. All properties are connected to natural gas, adding efficiency and convenience. One unit has been fully renovated, supplies to renovate the other units are located in the workshop. The standout feature is the expansive heated workshop with electricity and plumbing already in place, opening the door to endless possibilities-ideal for contractors, hobbyists, storage, or potential additional income use. Set on a combined .25-acre lot, plus two separate parcels (.08 and .02 acres), this offering provides flexibility rarely found * Expand your portfolio with strong rental income potential * Build on the additional lot (buyer to do due diligence) * Or enjoy extra outdoor space as a private side yard. Whether you're an investor looking for solid cash flow or an owner-occupant seeking supplemental income, this property delivers versatility, updates, and long-term value in one compelling package.

Portland Street, Middletown

$1,100,000

1 Baths ⋅ 24164387 MLS

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

Portland Street, Middletown

$299,900

4 Beds ⋅ 1 Baths ⋅ 24163941 MLS

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

475 Ballfall Rd, Middletown

$209,900

3 Beds ⋅ 2 Baths ⋅ 24163396 MLS

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

103 Prospect St, Middletown

$499,900

3 Beds ⋅ 2 Baths ⋅ 24159101 MLS

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

Lot 4 Nathan Hale, Middletown

$499,900

3 Beds ⋅ 2 Baths ⋅ 24159033 MLS

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

Lot 3 Nathan Hale, Middletown

$299,609

4 Beds ⋅ 2 Baths ⋅ 24158805 MLS

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

34 Inverness Ln, Middletown

$1,695,000

1 Baths ⋅ 24157523 MLS

The perfectly situated and meticulously maintained medical/office campus at 51 & 57 South Main Street in Middletown is now being offered for sale. The properties will have 6,618sf available for occupancy at the time of sale leaving ample room for a new owner and their medical practice or an investor bringing a new tenant/tenants with them. The properties are located directly across the street from Middlesex Hospital offering healthcare providers the convenience of just a quick walk to and from their procedures. The shared 30+ car parking area was freshly paved and striped less than a year ago and there is no deferred maintenance to speak of. The lone tenant at the properties is on a triple net lease relieving ownership of a portion of the maintenance, property tax and insurance burden. Financials and interior photos are available upon request. -Location: The properties are located directly across from Middlesex Hospital's main campus -Well Maintained: The current owner operated his ENT practice here for decades and has taken meticulous care and great pride in the upkeep of the properties -Income: The lone medical tenant pays good rent on a landlord-friendly triple net lease -Convenience: The campus is located just off of CT Route 9 which connects to I-91, I-95 and I-84 -Value-Add: 1,772sf basement at 57 South Main can be converted to paid tenant storage or possibly addit

51-57 S Main St, Middletown

$270,000

3 Beds ⋅ 2 Baths ⋅ 24156410 MLS

Excellent opportunity in a quiet. Ideal for rental portfolio expansion, or owner-occupants looking to build equity. All offers welcome. Fast closing available. featuring a bright and inviting open floor plan on the first floor with updated flooring throughout where the spacious living room flows seamlessly into the Kitchen and dining room, ideal for both everyday living and entertaining. The first floor comes complete with a convenient full bath on the main level and new sliding doors in the dining room right out to the private backyard with updated deck and concrete work. Upstairs, you'll find three bedrooms filled with natural light with the primary bedroom upgraded with vaulted ceilings. Theres also a second full bath upstairs serving the upper level, providing comfort and functionality. This house is move in ready and even has a brand new roof!

6 Hillside Ct, Middletown

$829,000

6 Beds ⋅ 4 Baths ⋅ 24148860 MLS

Experience over 5,500 square feet of beautifully updated living space in this fully remodeled 6+ bedroom, 3.5-bath residence, perfectly situated on a quiet and expansive 8+ acre lot. Every detail has been thoughtfully upgraded, creating a truly move-in-ready home offering exceptional flexibility and design versatility. The expansive kitchen is the heart of the home, featuring elegant quartz countertops, stainless steel appliances, a double oven, and generous prep and storage space-ideal for both everyday living and entertaining. Large windows and glass doors throughout flood the interior with natural light, enhancing the open-concept layout and spacious living areas. Designed with flexibility in mind, the floor plan offers multiple configuration options, including potential for a private secondary living area-perfect for multi-generational living, guests, or home-based business needs. Interior highlights include: * Large loft with adjoining office space * Two fireplaces * Hardwood flooring * High-end luxury vinyl plank flooring in key living areas The primary suite provides a peaceful retreat, complete with a spacious 7x10 walk-in closet and a beautifully designed bath featuring dual vanities and a custom tile shower. Step outside to enjoy the large deck just off the kitchen and dining area-an ideal setting for relaxing evenings or hosting gatherings.

44 Chamberlain Hill Rd, Middletown

$249,609

3 Beds ⋅ 2 Baths ⋅ 24153719 MLS

146 Liberty Street, Middletown, CT offers a three bedroom, one and a half bath home renovated in 2023. The main level features a functional layout with updated finishes and timeless details, along with a mudroom and a three season porch. All bedrooms are located on the second floor, along with a full bath. Additional features include a detached two car garage. Property is being sold as a short sale as a result of known foundation issues. Sale subject to third party approval. Short sale process has begun.*

146 Liberty St, Middletown

$599,609

2 Baths ⋅ 24152111 MLS

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

609 Newfield St, Middletown

$100,000

24149149 MLS

This scenic and beautiful lot has a stream running through it. The location is spectacular on this very quiet street located minutes to interstate 91 makes travel super easy. No test have been done.

Bell St, Middletown

$350,000

24149097 MLS

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

Middle St, Middletown

$750,000

24149055 MLS

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

Middle St, Middletown

$649,900

2 Beds ⋅ 2 Baths ⋅ 24133669 MLS

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

145 Webster Ln Unit 2-41, Middletown

$975,000

10 Baths ⋅ 24133406 MLS

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

504 Main St, Middletown

$589,900

2 Beds ⋅ 2 Baths ⋅ 24123204 MLS

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

137 Webster Ln Unit 2-42, Middletown

$399,900

2 Baths ⋅ 24131954 MLS

Location, Location, Location! Nice 1482sf retail building in the heart of Main St. Middletown. High traffic area, property currently being used as smoke shop, but can fit many other retail needs. Building is Zoned B-1. Currently being leased until Nov.2026

346 Main St, Middletown

$217,500

3 Beds ⋅ 2 Baths ⋅ 24111633 MLS

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

36 Rising Trail Dr Unit 36, Middletown

$999,999

24130767 MLS

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

575 Main St Unit STE 2, Middletown

$935,000

24130959 MLS

PERMIT IN HAND READY TO BUILD!!! In the heart of Middletown and within walking distance to countless amenities 54 Washington Street offers both location and opportunity. Once home to the Italian American Club, the building carries a unique history and is now ready for its new vision. This spectacular building has received zoning approval to convert this once community/event space to residential units. Take advantage of the already in place engineered 18 unit build out plans with extra room for a super. The possibilities are endless. Not only does this building have engineered plans, but it is also stamped for electrical and plumbing. With all the major systems professionally designed, code compliant, and permit ready, this property allows seamless transition straight to the build phase. The opportunities are endless for the savvy investor looking to maximize value in a prime location. 18 parking spots town approved across the street next to police station

54 Washington St, Middletown

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