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

Open house November 2nd 5pm-6pm Welcome to 9 Burr Avenue! This charming Colonial offers 3 bedrooms, 1 full bathroom, and 1,344 square feet of living space per public records. The home features a recently remodeled kitchen, updated within the past year, along with a finished walk-up attic that provides versatile additional space, ideal for a home office, hobby room, or bonus area. Additional improvements include a newer hot water heater, approximately one year old. Outside, enjoy a fully fenced backyard offering privacy and plenty of room for entertaining, outdoor gathering, or simply relaxing. This home is ready for its new owners! Property is being sold AS-IS

9 Burr Ave, Middletown

$410,000

4 Beds ⋅ 2 Baths ⋅ 24216990 MLS

Welcome to 1511 Country Club Road, a remarkably versatile property offering 4-bedroom functionality situated on an expansive 1.25-acre parcel on a peaceful, non-through street. A charming entry introduces the main Cape, which features two comfortable bedrooms, a full bath, and an upper loft ready to serve as a home office, recreation room, or potential third bedroom. Seamlessly connected yet private, the dedicated in-law/secondary living quarters boast their own bedroom and an additional loft space currently utilized as a primary suite-ideal for multi-generational living, extended guests, or a dedicated private wing. Peace of mind comes built-in with a brand-new septic system. Outside, the sprawling acre-and-a-quarter grounds provide mature greenery, a fenced-in play/pet area, and boundless room for entertaining, gardening, or outdoor expansion. A rare combination of privacy, acreage, and adaptable living space.

1511 Country Club Rd, Middletown

$345,000

3 Beds ⋅ 2 Baths ⋅ 24216264 MLS

Do you love downtown Middletown, but want to live in a quieter area? 360 Chauncey Road is the answer you're looking for! Enjoy what Middletown has to offer while being tucked away in a quiet area. This property offers 3-4 bedrooms, two full bathrooms, hardwood floors, harvey windows and a yard to enjoy. Throughout the home you'll find pockets of character that make it unique; the wood paneling on the ceilings, the bathroom trim, or the covered porch paired with a charming blue door. The eat-in kitchen has plenty of counter and cabinet space, all your needed appliances, and access to the brand new deck. The main floor bedroom is accompanied with a full bath and another potential bedroom, study, rec room, or dining room. Upstairs are the two spacious bedrooms with another full bath and crawl space storage. In the basement you'll find a ton of storage and future expandable space. Enjoy dedicated laundry space & shelving with access to outside. Outside, the back deck overlooks the level yard with plenty of tree cover for the Summer months and offering beautiful views in the Fall. Come check out 360 Chauncey Road and then head downtown to enjoy some of the incredible restaurants and shops Middletown has to offer, or hit the nearby hiking trails at Millers Pond or Crystal Lake! Updates include Brand new 2026 deck, 2021 plastic septic tank, 2022 well pump, 2026 well tank & water softener, 2019 roof, and AO Smith 2021 water heater. Take advantage of this well maintained home!

360 Chauncey Rd, Middletown

$399,000

2 Beds ⋅ 1 Baths ⋅ 24217601 MLS

Antique 2-Bedroom Cape with Country Charm, 15+ Acres of Land and Endless Potential! Looking for a home with character, charm, over 15 acres of land, and the opportunity to make it your own? This quaint antique 2-bedroom Cape is nestled in a peaceful country setting, with beautiful views from the front porch and backyard that truly make this property special! This antique home received a new roof in the Spring, but it needs your vision and creativity to make the space your own while exploring its potential. The first floor includes an eat-in- kitchen, a laundry room, a full bathroom, and a bonus room. Upstairs, you'll find two bedrooms and a storage area. The bonus on the main level that could serve as a 1st floor bedroom, office or a library, or simply be considered flex space? Enjoy a peaceful country setting while remaining conveniently close to Route 9, Middlesex Health, Middlesex Community College, Wesleyan University, shopping, and the restaurants and amenities of downtown Middletown. If you're looking for an antique home with character and the opportunity to add your personal touch, this could be the one for you!

368 Bow Ln, Middletown

38 Trolley Crossing Ln Unit 38, Middletown

$148,000

1 Beds ⋅ 1 Baths ⋅ 24217926 MLS ⋅ Trolley Crossing BLDG.

Welcome home to this beautifully updated, first-floor, one-bedroom condo offering the perfect blend of comfort, convenience, and privacy! Featuring a spacious, open feel and a newer kitchen, this move-in-ready home has been tastefully renovated throughout. Enjoy the ease of one-level living with no stairs to navigate. Step outside to your screened-in back porch, the perfect spot to relax and unwind while enjoying the peaceful, secluded surroundings. Additional highlights include natural gas heat and AC with access to the community pool, ideal for those warm summer days. Centrally located in Middletown, with convenient access to shopping, dining, highways, and everyday amenities, yet tucked away in a private, tranquil setting. A wonderful opportunity for easy, low-maintenance living in a great location. Don't miss this one!

38 Trolley Crossing Ln Unit 38, Middletown

270 Burgundy Hill Ln Unit 270, Middletown

$139,900

1 Beds ⋅ 1 Baths ⋅ 24217655 MLS ⋅ Peppermill Village BLDG.

Investment Opportunity: Updated and leased condo in a quiet end building, conveniently located near 91 and RT 9. This top floor unit has two floors, with 1 bedroom, living/dining, and kitchen on the main floor, plus a spiral staircase to a bonus loft space with tons of windows and natural light. Soaring cathedral ceiling in the living area, plus a sliding door to rear balcony make this an easy unit to keep leased! New LVP flooring throughout, freshly painted, with all new appliances.

270 Burgundy Hill Ln Unit 270, Middletown

$340,000

4 Beds ⋅ 1 Baths ⋅ 24203998 MLS

Set on approximately 5.2 acres in Middletown, this historic 4-bedroom home offers a unique opportunity to enjoy space, privacy, and the character of an older property. Built in 1760, the home offers approximately 1,680 square feet of living space and plenty of room to explore the possibilities. The expansive parcel provides a peaceful setting with ample outdoor space for gardening, recreation, entertaining, or simply enjoying the privacy of your own property. Inside, the home offers four bedrooms and one full bath, providing a flexible layout with plenty of potential to make the space your own. The generous acreage creates opportunities for those looking for more land while still being conveniently located in Middletown. Whether you're looking for a property with history, land, or the opportunity to bring your own vision to life, 150 Millbrook Road is worth a look. Come see the property and discover its potential for yourself.

150 Millbrook Rd, Middletown

$275,000

3 Beds ⋅ 2 Baths ⋅ 24209665 MLS ⋅ Ridgely Condo Iii BLDG.

A great opportunity to own an end-unit townhouse in Middletown's Wesleyan Hills community! This 3-bedroom home offers 1,360 square feet of living space and a layout that lends itself to a variety of possibilities. The living room serves as the heart of the home, with a wood-burning fireplace that adds warmth and character. The adjoining space offers flexibility for a dining area, while the eat-in kitchen provides plenty of room for meal preparation and casual dining around the center island or kitchen table. Upstairs, three bedrooms offer comfortable accommodations and the opportunity to create spaces tailored to your needs. The primary bedroom features direct access to the full bathroom. A full basement with laundry adds valuable storage and extra flex space that could host a home gym or additional living or storage space. Central air provides added comfort throughout the warmer months. Set in a convenient Middletown location, this home is close to Wesleyan University, downtown shops and restaurants, and major commuter routes. Whether you're looking for your first home, a place to downsize, or an opportunity to add your personal touch, this end-unit townhouse is full of potential and ready for its next owner!

732 Long Hill Rd Unit 732, Middletown

$450,000

3 Beds ⋅ 3 Baths ⋅ 24217472 MLS

One level living with room for expansion in this spacious ranch. Three bedrooms and 3 full baths with and oversize mudroom between the house and garage give you lots of options. Oversized 2 car garage gives you plenty of room for storage in the event you may want to finish off the lower level of this home. Completely remodeled home allows you peace of mind knowing all you have to do is move in. New Windows, new roof, new gutters, new flooring in kitchen and living room and remaining floors refinished The kitchen offers lots of countertop space, cabinets, quartz countertops, island, stainless steel appliances and room for the dining table. Recessed lighting and tile back splash finish off the detail. All three bedrooms are roomy and the master bedroom offers a fully renovated master bath with tiled walk in shower. Keep the open fireplace or add a pellet or wood stove to give you that New England feel while keeping the chill off. The basement would make for great additional living space as there is already a full bath there. New Bilco door and steps to basement. Updated mechanicals including new gas boiler, city water and sewer will give you peace of mind. New roof, windows and fresh paint throughout. There is a shared driveway however there is room from survey (in photos) that was done to have a private driveway. Located near the heart of Middletown, with so many options when it comes to dining, shopping or entertainment.

404 Newfield St, Middletown

$285,000

4 Beds ⋅ 1 Baths ⋅ 24217261 MLS

Welcome to 9 Magnolia Place, a charming and well-maintained Middletown home offering an impressive list of thoughtful updates inside and out. Tucked along a quiet dead end, this 4-bedroom home combines character, comfort and many of the major improvements buyers appreciate. Recent updates include new kitchen cabinetry, new quartz countertops, sink and faucet, a metal range hood, and fresh interior paint throughout nearly every room, both hallways and the upper staircase. Approximately a year and a half ago, the first 10 feet of the exterior sewer line were replaced, another valuable improvement to the property. Additional improvements over the years include newer vinyl siding with insulation, energy-efficient double-pane replacement windows, a designer front entry door and surrounding structure, added attic/crawl-space and ceiling insulation, and an updated large shower/bath with generous built-in shelving. The home is equipped with an oil-fired Crown heating system, an above-ground oil tank, a newer A.O. Smith water heater and solar panels. The roof features high-performance asphalt shingles, reported by the seller to carry a 50-year rating and designed for winds up to 130 mph, along with updated gutters. Outside, enjoy a partially fenced backyard, storage shed and a wonderful covered rear deck overlooking the yard-a comfortable spot for morning coffee, outdoor dining or simply relaxing. A full unfinished basement with hatchway access provides additional storage

9 Magnolia Ave, Middletown

$549,900

2 Beds ⋅ 3 Baths ⋅ 24217347 MLS

Your Next Chapter Starts at 2 Sonoma Lane! Looking for low-maintenance living without sacrificing space, style, or flexibility? Welcome to Sonoma Woods, one of Middletown's sought-after 55+ communities! This beautifully maintained detached home offers approximately 1,903 sq. ft., 2 bedrooms, 2.5 baths, and a layout full of surprises! Step inside to soaring cathedral ceilings, hardwood floors, and a spacious living room with a cozy gas fireplace. The inviting kitchen features granite countertops, abundant cabinetry, and a breakfast nook, while the dining area opens to a private deck, perfect for morning coffee or entertaining. The main-level primary suite offers a walk-in closet and full bath with double vanities and a tiled shower. First-floor laundry adds everyday convenience. Upstairs, discover a second bedroom, full bath, bonus room, and loft offering incredible flexibility. But here's the fun part! Behind charming bookshelf barn doors awaits a hidden retreat that's anything but ordinary! Create your own private speakeasy-inspired lounge, movie hideaway, reading sanctuary, or creative studio. The possibilities are limited only by your imagination! A full basement offers exceptional storage, while the attached two-car garage adds convenience. Enjoy central air, a community clubhouse, and more time for the things you love. Less upkeep, more freedom, and a secret space all your own. Welcome home to 2 Sonoma Lane!

2 Sonoma Ln Unit 2, Middletown

212 Carriage Crossing Ln Unit 212, Middletown

$248,500

2 Beds ⋅ 2 Baths ⋅ 24209475 MLS ⋅ Carriage Crossing BLDG.

Rear first floor 2 bed/2 full bath unit at Carriage Crossing. It features the complex's trademark vaulted ceilings and wall of windows, with comfortable open plan of living room with fireplace, kitchen, and dining area. Enjoy in-unit laundry, central heat and air, and two private outdoor spaces. An active lifestyle is easy with outdoor pool, spa and exercise facilities, and tennis court, in this walkable neighborhood. Pet friendly and investors welcome. Conveniently located near shopping, dining, and commuter routes.

212 Carriage Crossing Ln Unit 212, Middletown

$375,000

2 Beds ⋅ 1 Baths ⋅ 24217229 MLS

Charming ranch sitting on a corner lot in a pretty cul-de-sac neighborhood! Hardwood floors, central a/c and a finished basement! The living room with hardwood floors leads to the dining room and kitchen with new flooring and dishwasher. Two bedrooms with hardwood floors and a full bath finishes the main level. Downstairs is large den with new carpeting and a dry bar, perfect for entertaining! The one car attached garage is spacious and offers more storage! The deck overlooks the pretty lot that boarders a babbling brook (no flood insurance required). Roof and central air are approximately 10 years old. Come enjoy one-level living just minutes from bustling downtown with numerous restaurant, shops and activities! Welcome Home!

5 Castanea Ct, Middletown

$889,900

3 Baths ⋅ 24215163 MLS

Excellent Mixed-Use Investment Opportunity in Middletown! Prime location on busy Newfield Street (Route 3) with excellent visibility and road exposure! This 4,336 sq. ft. mixed-use property is being sold with two parcels totaling approximately 1.20 acres (0.43 acres and 0.77 acres). The building features three ground-level commercial units-two combined and occupied by one tenant, plus one vacant unit offering rental or business potential. The second floor includes an occupied residential apartment. Existing long-term leases provide investment appeal and potential steady rental income. Ideal for investors or owner-users seeking a versatile income-producing property in a convenient location near major routes and businesses.

970 Newfield St, Middletown

$425,000

3 Beds ⋅ 2 Baths ⋅ 24216846 MLS

Don't miss this pristine and charming Gambrel Colonial on a perfect level half acre, offering a quiet setting, gorgeous views, generous outdoor living spaces, and tasteful renovations in every room. Infused with beautiful natural light, this right-sized home offers 1718 sf with loads of windows (11 have been replaced by this owner), 3 bedrooms, and 2 bathrooms. The main floor space takes full advantage of its front-to-back design with two living/family rooms anchored by a central combined kitchen and dining room. The kitchen was renovated in 2026 with new LifeProof flooring, solid surface counters, subway tile backsplash, paint, and lighting. With separate coffee bar area and pantry and cool exposed brick, the kitchen offers great storage and is large enough for a long dining table, and can accommodate an island too! The family room features a wood-burning fireplace for cozy nights. The second floor offers a full bathroom and 3 generously sized bedrooms and spacious hallway, all updated with paint and featuring new flooring. The large remodeled full bath (2024) features marble tile tub surround and gorgeous hexagonal floor tile. More to love: half bath (remodeled 2023); new A/C (2023); new paver patio, garage doors, and shed (2021); new siding (2020); full basement; underground pet fence; and generator-ready.

400 Coleman Rd, Middletown

$474,900

3 Beds ⋅ 3 Baths ⋅ 24215505 MLS

Welcome to 126 Rolling Green in Middletown! This spacious Ranch-style home combines comfortable one-level living with versatile additional space and an inviting setting in a fantastic neighborhood. The main level features three bedrooms, two full baths and a convenient laundry room, offering an easy and functional layout for everyday living. Step inside to discover abundant natural light and a formal dining room with vaulted ceilings and an elegant Palladian-style window. The spacious eat-in kitchen offers extensive cabinetry, recessed lighting, and a large pantry, opening to a versatile adjoining room with vaulted ceilings, a wine rack, and beverage refrigerator - perfect for entertaining or everyday relaxation. The living room features a natural gas fireplace, creating a warm and welcoming gathering space. The primary bedroom offers a large walk-in closet and an en-suite bathroom with a stand-up shower and Jacuzzi-style tub. Two additional bedrooms and two full bathrooms complete the main-level living space.

126 Rolling Grn, Middletown

$370,000

3 Beds ⋅ 2 Baths ⋅ 24216927 MLS

Welcome to 55 Berkeley Road, a charming New England Cape nestled on a quiet, low-traffic street in Middletown. Offering 3 bedrooms, 1.5 baths, and approximately 1,386 square feet of living space, this inviting home blends classic character with modern updates and a versatile floor plan. The living room features a cozy fireplace, while the formal dining room provides an ideal setting for everyday meals and entertaining. The beautifully updated kitchen boasts quartz countertops, a farmhouse sink, and a subway tile backsplash, combining style and functionality. A main-level bedroom offers added convenience and flexibility, while the partially finished lower level features a spacious family room with a second fireplace that is perfect for recreation, entertaining, or relaxing. Outside, the .32-acre lot provides plenty of room for gardening, outdoor gatherings, and recreation. A detached one-car garage and ample off-street parking add to the home's appeal. Additional highlights include public water and sewer and a convenient location just minutes from Wesleyan University, downtown Middletown's vibrant shops and restaurants, and Route 9. With its timeless Cape Cod charm, thoughtful updates, and desirable location, 55 Berkeley Road is ready to welcome you home!

55 Berkeley Rd, Middletown

$275,000

3 Beds ⋅ 3 Baths ⋅ 24216918 MLS

Welcome home to this charming contemporary styled home featuring 3 bedrooms, 1 full and 2 half bathrooms, 2 car garage and 1196 square feet of living space! The main level features an updated kitchen with granite counters, tiled flooring and backsplash! The open concept is great for entertaining! On the upper level, you will find the laundry room, a full bathroom, 3 bedrooms and another half bathroom in the master! Newer roof and replacement windows! Schedule your showing today!

12 Woodlot Ln, Middletown

$250,000

2 Beds ⋅ 2 Baths ⋅ 24215771 MLS ⋅ Forest Glen BLDG.

Lovely first-floor, end-unit condo with zero steps for easy entry! This surprisingly spacious home has an open-concept design, offering a roomy heart-of-the-house while keeping the bedrooms nicely separated. Step into the dining and family room, featuring a cozy fireplace and a slider to the patio with a private, locked storage closet. Down the hall at the back, you'll find a large primary suite with a walk-in closet, en suite bath, and a window seat with storage. There's also a large second bedroom, a hallway/guest bath, and a laundry room. Bedrooms are carpeted wall-to-wall, while the rest of the space has rich vinyl plank flooring. Updates include kitchen appliances (2018), hot water heater (2018), primary bath with walk-in shower (2018), washer/dryer (2021), brand-new windows and slider (2025/2026), and dishwasher (2026). Well maintained and full of upgrades-New windows and sliding glass door is WOW! Move in and enjoy easy living! One assigned parking space plus plenty of visitor spots.

1 Forest Glen Cir Unit 6, Middletown

$419,900

3 Beds ⋅ 2 Baths ⋅ 24216288 MLS

This meticulously maintained raised ranch offers 2,712 square feet of total living space on a beautiful 0.41-acre lot. Vaulted ceilings with skylights enhance the living and dining rooms, while hardwood floors flow through both spaces and the eat-in kitchen. A wood-burning fireplace adds warmth and character to the living room. The up-dated kitchen features granite countertops and stainless steel appliances. Three bedrooms and two full baths include a primary bath with a shower. Six-panel raised doors add a classic touch throughout the home. The lower level provides additional living space with a wood-burning stove, a pine ceiling, and a separate laundry room. Central air conditioning, a newer roof, an attached two-car garage, and pull-down attic storage offer comfort and convenience. A stone walkway and beautiful backyard enhance the outdoor setting. Conveniently located near highways, this move-in-ready home is ready to welcome its next owners.

14 Cimarron Rd, Middletown

$235,000

2 Beds ⋅ 2 Baths ⋅ 24215455 MLS ⋅ Indian Hill BLDG.

Tremendous opportunity for an end unit townhome in a small, well managed complex just steps from Wesleyan University campus. Light and bright with a generous sized kitchen open to the living space. Both bedrooms are on the upper level and share access to a Jack and Jill full bath. Laundry is on the upper level and there is a half bath on the main floor. Ground level has garage and basement with ample storage area. Enjoy low maintenance living with a reasonable HOA and easy access to all downtown Middletown has to offer.

111 Knowles Ave Unit 111, Middletown

$119,900

1 Beds ⋅ 1 Baths ⋅ 24215844 MLS ⋅ Peppermill Village BLDG.

This well-maintained, one-bedroom ranch-style end-unit condominium is located in the desirable Westlake area of Middletown. Whether you're looking for an affordable place to call home or a great rental investment, this property offers an excellent opportunity. The unit features carpeting and a sliding glass door off the dining area that leads to a private wood deck with an attached exterior storage closet. Conveniently located with easy access to Route 9 and I-91, and just minutes from Middlesex Health, shopping, restaurants, and fitness centers, this property offers both convenience and value. A rare opportunity at an affordable price!

27 Burgundy Hill Ln Unit 27, Middletown

$250,000

24209958 MLS

Great opportunity for builders and investors! This 0.35-acre vacant lot is conveniently located near Wesleyan University and Downtown Middletown, with easy access to Main Street, restaurants, and shopping. The City of Middletown's Land Use Department has confirmed that recent zoning changes allow for the potential development of up to 9 residential units, subject to city requirements and approvals. Other uses may also be permitted. Please see Additional Documents for more information on zoning and development possibilities.

180 Washington St, Middletown

$319,999

3 Beds ⋅ 2 Baths ⋅ 24215963 MLS

WELCOME HOME to 106 S. Front Street, Middletown! Conveniently located near town with easy access to Route 9, this inviting 3-bedroom, 2-bath home offers comfortable living, charming details, and move-in-ready appeal. Inside, beautiful hardwood floors and fresh paint create a bright, welcoming atmosphere. The cozy living room fireplace adds warmth and character, while the relaxing sun porch provides the perfect spot for morning coffee, quiet reading, or unwinding at the end of the day. Outside, the lovely backyard offers plenty of room to gather, entertain, and enjoy the crisp autumn air-with space to create your own fire pit area... With its comfortable layout, inviting outdoor space, and convenient location, this home is ready for its next chapter-and it may not be available for long. Convenient Location, close to shopping, downtown with wonderful restaurants and Route 9 and the hospital easy commute. Don't miss the opportunity to make 106 S. Front Street yours! Schedule your private viewing and start imagining life in your new home today!

106 S Front St, Middletown

$279,000

3 Beds ⋅ 2 Baths ⋅ 24215577 MLS ⋅ Ridgely Condo I BLDG.

**End unit? Yes, please!** More windows, more natural light, and a little extra breathing room! Welcome to 854 Long Hill Road, a spacious 3-bedroom townhouse in Middletown's desirable Wesleyan Hills-Ridgely One community. With 1,360 square feet of living space, this home has plenty of personality and room to make it your own. The generously sized living room features a wood-burning fireplace, built-in shelving, a charming bay window, and extra windows that let the sunshine in. There's even room for a dining area, because dinner deserves more than the coffee table! The oversized eat-in kitchen offers plenty of cabinet and counter space, plus sliders leading to a private deck, perfect for morning coffee, outdoor dining, or simply enjoying a little fresh air. A convenient half bath rounds out the main level. Upstairs, you'll find three comfortable bedrooms, including a spacious primary with a cozy window seat and direct access to the full bathroom. The two additional bedrooms offer flexibility for guests, a home office, or a creative space. One even has built-in bookshelves, ready for your favorite reads or collections! Need storage? The full basement has you covered, with laundry, plenty of room for life's extras. Central air and assigned parking add everyday convenience. Tucked into Wesleyan Hills community, you're just minutes from downtown Middletown, Wesleyan University, restaurants, shopping, and major commuting routes. A little charm, a lot of space, and an end-unit!

854 Long Hill Rd Unit 854, Middletown

$220,000

2 Beds ⋅ 1 Baths ⋅ 24215423 MLS ⋅ Quail Run Village BLDG.

Two-bedroom, one full bathroom at Quail Run Village with basement Garage. This townhouse features an open floorplan which includes the kitchen with all stainless-steel appliances, dining area and living room. there is a slider to the deck from the kitchen. the 2ND floor has a primary bedroom with double closets. a guest bedroom/office. this unit includes an oversized basement garage with laundry area. There is a inground pool for summer enjoyment. the location offers quick access to route 9 and I-91, close to shopping, dining, downtown Middletown and Middlesex Hospital.

161 Cynthia Ln Unit F7, Middletown

$549,900

2 Beds ⋅ 3 Baths ⋅ 24215482 MLS ⋅ Sonoma Woods BLDG.

Your Next Chapter Starts at 2 Sonoma Lane! Looking for low-maintenance living without sacrificing space, style, or flexibility? Welcome to Sonoma Woods, one of Middletown's sought-after 55+ communities! This beautifully maintained detached home offers approximately 1,903 sq. ft., 2 bedrooms, 2.5 baths, and a layout full of surprises! Step inside to soaring cathedral ceilings, hardwood floors, and a spacious living room with a cozy gas fireplace. The inviting kitchen features granite countertops, abundant cabinetry, and a breakfast nook, while the dining area opens to a private deck, perfect for morning coffee or entertaining. The main-level primary suite offers a walk-in closet and full bath with double vanities and a tiled shower. First-floor laundry adds everyday convenience. Upstairs, discover a second bedroom, full bath, bonus room, and loft offering incredible flexibility. But here's the fun part! Behind charming bookshelf barn doors awaits a hidden retreat that's anything but ordinary! Create your own private speakeasy-inspired lounge, movie hideaway, reading sanctuary, or creative studio. The possibilities are limited only by your imagination! A full basement offers exceptional storage, while the attached two-car garage adds convenience. Enjoy central air, a community clubhouse, and more time for the things you love. Less upkeep, more freedom, and a secret space all your own. Welcome home to 2 Sonoma Lane!

2 Sonoma Ln Unit 2, Middletown

$425,000

3 Beds ⋅ 3 Baths ⋅ 24215323 MLS

What a beautiful opportunity to own in Autumn Meadows, a 55+ community in bustling Middletown. Featuring hardwood floors throughout both the main level and the lower level in-law apartment, this property offers comfortable living, versatile space and a wonderful layout. The main level features two bedrooms and two full bathrooms, including a spacious primary suite complete with a full bath and walk-in closet. The large kitchen boasts stainless steel appliances and granite countertops, while the convenient main level laundry is tucked away in a hallway closet. Just off the living room, a newer deck overlooks open space, providing a lovely spot to relax and enjoy the outdoors. The lower level in-law apartment offers excellent additional living space, featuring one bedroom, kitchen, dining area and living room with cozy free standing gas fireplace. A deck off the lower level provides another outdoor retreat, making this space ideal for extended family or guests. With its inviting layout, beautiful hardwood floors, multiple outdoor living spaces and flexible in-law accomodations, this home offers a wonderful opportunity to enjoy easy living in a 55+ community.

32 Autumn Ln Unit 32, Middletown

$259,900

3 Beds ⋅ 1 Baths ⋅ 24214896 MLS

*Highest & best offers due Sunday Oct. 25 by 4pm* CUTE RANCH HOME IN A GREAT NEIGHBORHOOD! Large eat-in kitchen with plenty of cabinet & counter space and a new oven range (2026.) Nice sized living room and 3 bedrooms, all with hardwood floors! Get cozy in the partially finished lower level with a wood burning stove, newer faux wood laminate floor that ADDS APPROX 330SQFT of beautiful living space. From the deck, enjoy your view of a huge, level, open backyard. The property backs to Upper Mill Pond that the seller has done some fishing and stand-up paddleboarding from! 2 sheds offer great storage. There's a solar panel Power Purchase Agreement (PPA,) for $206/month to lower electricity costs. The panels were installed in 2023 along with a new 200amp electrical service. New hot water heater in February 2026. Seller also has chickens! You can take over their care and reap the benefits of fresh eggs, or seller will find them a new home, your choice. Close to shops, restaurants, donuts, highway access, Middlesex Hospital and all the amazing food on Main Street!

116 Dorothy Dr, Middletown

$469,000

3 Beds ⋅ 3 Baths ⋅ 24212932 MLS ⋅ Autumn Meadows BLDG.

Welcome to Autumn Meadows, where beautiful improvements and versatile living come together! This freestanding 3-bedroom, 3-full-bath home offers no shared walls, An inviting open floor plan creates a wonderful sense of space, while three main-level bedrooms, including the primary suite, provide the ease and convenience of one-level living. The updated kitchen features quartz countertops, a generous breakfast bar, newer stainless steel appliances and abundant cabinetry. Gleaming hardwood floors, crown molding and a handsome propane fireplace enhance the living and dining areas. Sliders from the living room open to a spacious TimberTech deck overlooking a picturesque natural meadow with seasonal birdlife. Remodeled bathrooms feature stylish vanities and beautiful quartz and tile showers. The finished lower level offers over 600 square feet of additional living space with heat, central air, a full bath and hookups for a potential kitchenette. Imagine a guest retreat, recreation room, home office or possible second primary suite! Approximately 1,000 square feet of unfinished basement provides generous workshop, mechanical and storage space. The attached finished two-car garage features epoxy flooring and access to the lower walkout level. A new central A/C system installed August 2026 adds peace of mind. Convenient to downtown Middletown, Wesleyan University, Middlesex Health and major commuting routes. A truly special place to call home!

38 Autumn Ln Unit 38, Middletown

$350,000

5 Beds ⋅ 3 Baths ⋅ 24215211 MLS

Excellent investment opportunity in Middletown! Conveniently located near downtown Middletown, Wesleyan University, and major commuter routes, this three-family property is ideal for both investors and owner-occupants. Featuring two 2-bedroom units, one 1-bedroom unit, and a detached garage, the property currently has two long-term tenants and one vacant apartment, offering the flexibility to move right in while collecting rental income or operate as a fully rented investment property. A great opportunity to add value and build long-term equity!

239 Pearl St, Middletown

$460,000

3 Beds ⋅ 1 Baths ⋅ 24214279 MLS

Step Back in Time - with Comfort and Charm! Built in 1881, this lovingly maintained antique home is filled with character, warmth, and timeless beauty. Nestled on 2.62 acres of peaceful, picturesque grounds, this special property offers a rare blend of history, privacy, and possibility. Step inside and discover 1,964 sq. ft. of inviting living space where the craftsmanship of a bygone era shines through. Rich woodwork, vintage hardware, charming built-ins, and delightful architectural details create an atmosphere that simply cannot be replicated in today's homes. Each room tells a story, offering warmth, character, and a sense of nostalgia. The partially finished attic offers exciting possibilities for expanded living space, a creative studio, or a home office, allowing the next owner to imagine what could be. Outside, enjoy the beauty of mature trees, picturesque surroundings, and plenty of room to roam. Whether relaxing in the peaceful setting, enjoying nature, or envisioning your own outdoor retreat, the possibilities are endless. A detached garage and charming garden shed complement this wonderful property. More than just a house, this is a home that has been cherished through the years and is ready for its next chapter. Warm, welcoming, and full of soul, it awaits someone who appreciates the beauty and individuality of an antique home. Come experience the magic of this 1881 gem.

1040 Washington St, Middletown

$365,000

3 Beds ⋅ 2 Baths ⋅ 24214326 MLS

Welcome to 14 Casper Avenue in Middletown! This multifamily property offers approximately 2,225 square feet of living space, featuring 3 bedrooms and 2 full bathrooms. The in-law unit above the garage generates a monthly rental income of $900. Built in 1967, the property presents an excellent opportunity for investors or owner-occupants seeking a property with income potential. The home features gas forced-air heating, a partially finished basement for additional usable space, and a cozy fireplace. An attached garage provides convenient parking, while the lot offers outdoor space to enjoy. Conveniently located near local schools, shopping, dining, and everyday amenities, with access to major routes and the many attractions Middletown has to offer. Explore the possibilities this property presents!

14 Casper Ave, Middletown

$525,000

4 Beds ⋅ 3 Baths ⋅ 24212608 MLS

Welcome to 37 Valley Drive! Offering over 2,400 square feet of living space, this spacious 4-bedroom, 2.5-bath home features a versatile floor plan, distinctive architectural details, and numerous recent improvements! The main level offers a generously sized kitchen opening to an impressive great room featuring soaring vaulted ceilings, skylights, and a cozy fireplace. A bright and inviting sunroom provides additional living space with vaulted ceilings, skylights, and newly installed flooring. You'll also find an expansive bonus room, currently enjoyed as a billiards room, featuring beautiful exposed beams and plenty of space for entertaining, recreation, a home theater, or additional gathering space. An additional bedroom and living area provide flexibility for guests, a home office, or a potential extended-family arrangement with some finishing touches. Upstairs, the primary bedroom features its own private full bathroom, while the additional bedrooms share a beautifully updated second full bathroom. Exposed beams in the bedrooms add warmth and architectural character throughout the upper level. Recent improvements include fresh interior paint and new flooring in the upstairs bedrooms. Additional highlights include a roof approximately 6 years old, a newer hot water heater approximately 3 years old, central air conditioning, and a whole-house generator for added peace of mind. Step outside onto the beautiful newly constructed deck, perfect for entertaining, dining, or

37 Valley Dr, Middletown

$499,000

3 Beds ⋅ 3 Baths ⋅ 24214047 MLS

Welcome to 12 Brookview Lane, located in Middletown's desirable Westfield neighborhood! This beautifully maintained 3 bedroom, 2.5 bathroom home offers a wonderful combination of space, style, and functionality. Step inside to discover inviting, spacious living areas accented by beautiful hardwood floors. The stylishly updated kitchen features an open layout that flows effortlessly into the surrounding living space, creating an ideal setting for both everyday living and entertaining. A generously sized bonus room offers endless possibilities, whether you envision a home office, playroom, media room, or additional gathering space. The partially finished basement provides even more flexible living space to suit your needs. With its thoughtful layout, tasteful updates, and versatile spaces, this home offers comfort and convenience in a fantastic Middletown location. Come see all that 12 Brookview Lane has to offer!

12 Brookview Ln, Middletown

$384,900

3 Beds ⋅ 2 Baths ⋅ 24214296 MLS

Discover the perfect blend of comfort, privacy, and convenience at 36 McDowell Road! This updated two car ranch is tucked away on a quiet cul-de-sac and features a flat, fully fenced in yard ready for you to enjoy your own private outdoor retreat. Inside, you'll find a remodeled kitchen with granite countertops, two renovated bathrooms, and refinished flooring. Additional updates include three new mini split AC and heating as well, new radiators, recessed lighting, newer windows, a brand new deck, and a new washer and dryer. The basement offers excellent potential for additional living space. Conveniently located near shopping centers, restaurants, and everyday essentials, this Middletown home is ready for its next owner!

36 Mcdowell Rd, Middletown

$549,900

5 Beds ⋅ 4 Baths ⋅ 24213729 MLS

Welcome to this beautiful 10-room home offering 3,316 square feet of living space, five bedrooms, three full bathrooms, and a half bath. Mature landscaping enhances the property's charm and creates an inviting setting. The spacious layout offers. Plenty of room for everyday living and entertaining with flexibility to suit your needs. The first-floor primary bedroom features a private full bathroom for convenient main level living. Three fireplaces add warmth and character, including one in the basement. Where you'll find a half bath. There is an outbuilding equipped with heat, air conditioning and sink provides additional space for hobbies, a workshop, or create a pursuit. With generous living space and distinctive features throughout, this lovely property is ready for its new owners to make it their own.

495 Ridge Rd, Middletown

$99,900

1 Baths ⋅ 24213621 MLS

A truly unique opportunity awaits you in this newly renovated 432-square-foot commercial/industrial building located in the north end of Middletown's industrial park. This versatile property features electric split-system heating and air conditioning, a flexible layout, 1/2 bath and convenient location with easy access to Rt #9 and downtown Middletown. The space offers multiple potential zoning uses and may be suitable for beauty salon, barber shop, hair salon, retail, professional offices, biotech-related operations, building trades, contractor services, specialty businesses, administrative offices, and other compatible commercial or industrial purposes. Its efficient size and price point makes it an excellent option for a start-up, owner-operated business, satellite office, service location, or expanding company seeking a professional and manageable workspace. The recently renovated interior provides a clean, updated setting that can be adapted for your customer service, office workstations, retail operations or light commercial use. Located within an established industrial park, the property offers practical access for customers, employees, vendors, and deliveries. The combination of flexible use potential, modern improvements, climate control, parking, and a convenient Middletown location makes this an attractive opportunity for a wide range of businesses.

82 N Main St, Middletown

$589,000

2 Beds ⋅ 3 Baths ⋅ 24210931 MLS

Homes in Sonoma Woods don't come available often, and Unit 35 offers one of the largest models in this sought-after 55+ Middletown community. With 2 bedrooms, 2.5 baths, walkout basement with an exercise or craft room, and nearly 2,000 sq ft of living space, this home delivers the ease of condo living without giving up the space you want. The comfortable main level features a fireplace and a heated sunroom overlooking the back of the property, creating additional year-round living space and leading directly onto the deck for relaxing or entertaining. The full walkout basement offers more than 1,000 sq ft, with a portion already finished for even more usable space while still providing plenty of room for storage, hobbies, a workshop or future possibilities. An attached garage, natural gas heat and central air add everyday convenience. Built in 2005, this spacious unit offers a great opportunity for buyers looking to right-size without feeling like they have to squeeze into their next home. With limited turnover in Sonoma Woods, opportunities like this can be hard to find. If you've been waiting for a home in this community, could Unit 35 be the one worth making a move for?

35 Sonoma Ln Unit 35, Middletown

$424,900

3 Beds ⋅ 2 Baths ⋅ 24213654 MLS

Lovingly updated and maintained one floor living featuring a roomy eat in kitchen, living room with fireplace. A large primary bedroom with French doors to the deck, provides a large walk in closet an en suite bath with walk in shower and jet tub. The floors throughout the principal rooms of the home are hardwood with the exception of the kitchen and baths with tile flooring. There are two other bedrooms and a family bath also with a walk in shower. The current owners added a one car detached garage, installed a new oil tank and added a very useful workbench in the basement section where double doors allow for entry of their sit down mower. There is a nest system to make off site adjustments to heat and A/C and exterior cameras that are not currently connected to police, fire departments but could be. The deck is two tiered, has a gazebo and is the perfect spot for friends and families to gather. The rear yard is fully fenced for those who have pets that can enjoy a protected outdoor area. Please allow at least 2-3 hours notice to show.

526 Westfield St, Middletown

$584,900

2 Beds ⋅ 2 Baths ⋅ 24213623 MLS

A rare opportunity to own a beautifully appointed, original-owner ranch, just 12 years young! Set on a cul-de-sac with a private backyard, this 1,822-square-foot home offers the ease of one-level living with two bedrooms, a dedicated office, and two full baths. An inviting entry foyer, with a tray ceiling, welcomes you into an open floor plan enhanced by hardwood floors throughout, crown molding, and recessed lighting. The sunroom provides a delightful place to relax, with an atrium door opening to the deck for easy indoor-outdoor enjoyment. The spacious primary bedroom features a generous walk-in closet, while natural gas heating and cooking add everyday convenience. An enormous basement offers exciting potential for future expansion, and a two-car garage completes this appealing home. A seldom-available ranch combining comfort, thoughtful details, and room to grow!

19 Sonoma Ln Unit 19, Middletown

$349,900

4 Beds ⋅ 3 Baths ⋅ 24213576 MLS

Welcome to this spacious Colonial-style home offering over 2,500 square feet of living space. Featuring 4 bedrooms, central air conditioning, a generously sized kitchen with an eat-in area, and a separate dining area, this home offers plenty of room for comfortable living and entertaining. Originally designed as a side-by-side property, the home has been converted into a single-family residence, offering a unique layout with ample space and possibilities. Conveniently located near major highways, restaurants, shopping, and other local amenities, this property combines space, convenience, and opportunity. Don't miss the chance to make this home your own!

477 Hunting Hill Ave, Middletown

$349,900

3 Beds ⋅ 2 Baths ⋅ 24213449 MLS

Welcome to 217 Ridge Road! Nestled in Middletown's desirable South Farms neighborhood, this charming 1913 Colonial seamlessly blends historic character with modern conveniences. An inviting covered front porch sets the tone for the warmth and charm found throughout. Step inside to discover beautiful hardwood floors, a spacious living room with a gas fireplace, and a formal dining room featuring timeless built-ins. The kitchen offers a center island and flows into a convenient laundry area, half bath, and mudroom with access to the backyard deck. Upstairs, you'll find three comfortable bedrooms and a full bath, while the finished walk-up attic provides an additional 291 square feet of versatile space, perfect for a home office, playroom, or creative retreat. A partially finished basement offers even more possibilities. Enjoy peace of mind with numerous improvements including a newer furnace, oil tank, vinyl siding, windows, and energy-efficient mini-split systems providing supplemental heating and cooling. Outside the level lot offers plenty of room for outdoor entertaining, gardening, or simply relaxing. Conveniently located near shopping, restaurants, parks, and downtown Middletown, this home offers the perfect combination of character, comfort, and convenience. Schedule your private showing today!

217 Ridge Rd, Middletown

$274,900

4 Beds ⋅ 2 Baths ⋅ 24213164 MLS

*Highest & best offers due by Tuesday 10/20 at 5 PM* Downtown convenience, classic character, and two-family potential come together at 219 Pearl Street! Wesleyan University is just a few blocks away, and Main Street's restaurants, shops, and local favorites are within walking distance! Russell Library, parks, public transportation, and convenient access to Route 9 add to the appeal. Two apartments on separate floors offer flexibility for investors or owner-occupants looking to offset housing costs with rental income. Both kitchens feature quartz countertops, with stainless steel appliances and a stackable washer/dryer in the first-floor unit. Wood flooring and generous windows bring warmth and natural light, while the second-floor screened-in porch offers a place to relax. A HUGE walk-up attic is a standout feature, offering abundant storage and exciting finishing potential for a buyer with the right vision. The sewer line was relined in 2021, a major infrastructure improvement! The paved driveway provides plenty of off-street parking, and the level rear yard adds outdoor space to enjoy. An unfinished basement, public water and sewer, natural gas, and a Navien tankless water heater installed in 2020 round out the features. Whether you're looking to house hack, generate rental income, or explore the home's untapped potential, this downtown two-family deserves a look. Make it yours today, this one won't last!

219 Pearl St, Middletown

$269,900

2 Beds ⋅ 3 Baths ⋅ 24212348 MLS ⋅ Camden Pines BLDG.

Move right in! This spacious and well-maintained 2-bedroom, 2 1/2-bath condo in Camden Pines offers comfortable living with plenty of space to spread out. The main level features a large living room that flows into the dining area and kitchen, creating a welcoming layout for everyday living and entertaining. Step out onto the deck off the living room and enjoy peaceful views overlooking the woods and surrounding nature. Upstairs, you'll find two generously sized bedrooms, each with its own private full bathroom. The finished basement provides additional living space and flexibility for a home office, recreation room, gym, or storage. An attached garage adds convenience, especially during the colder months. Enjoy being within walking distance of many everyday amenities, while also having easy access to major highways for commuting and travel. Visitor parking is just steps away, making it convenient for guests. One dog or one cat is permitted. Clean, comfortable, and very well maintained, this Camden Pines unit is ready for its next owner to move right in and enjoy!

565 Newfield St Unit 29, Middletown

$999,999

24212681 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 2, Middletown

$440,000

3 Beds ⋅ 2 Baths ⋅ 24212850 MLS

Welcome to 43 Jefferson Ave, Middletown! This charming 3-bedroom brick ranch offers comfort, space, and convenience in an established neighborhood. The spacious living room features beautiful hardwood floors and a cozy fireplace. The generously sized kitchen and dining area offer ample cabinetry, a center island, and direct access to the rear deck. All three bedrooms are conveniently located on the main level with hardwood flooring and plenty of natural light. The finished lower level adds valuable living space with a recreation/family room and second fireplace, half bath, laundry area, workshop, and storage-perfect for a home office, gym, entertainment area, or hobbies. Outside, enjoy the spacious rear deck, private driveway, detached one-car garage with additional storage space, and well-maintained yard. A newer roof adds peace of mind, while the classic brick exterior provides timeless curb appeal. Conveniently located near shopping, restaurants, schools, parks, downtown Middletown, and major commuting routes. With its easy one-level living, flexible lower-level space, garage, deck, newer roof, and desirable location, 43 Jefferson Ave is ready for its next owner. Schedule your private showing today!

43 Jefferson Ave, Middletown

$415,000

3 Beds ⋅ 2 Baths ⋅ 24212078 MLS

Beautiful views, abundant natural light, and distinctive architectural details define 972 Ridgewood Road. This three-bedroom, one-and-a-half-bath ranch pairs hardwood floors throughout the main living areas with a kitchen renovated in 2018, featuring granite countertops, custom storage drawers, and updated appliances. The adjoining dining room centers on a wood-burning fireplace, while two sets of French doors open to a striking living/sitting room with cathedral ceilings, an inviting setting for entertaining, a library, or a private office. The mostly finished walkout lower level, finished in 2020, offers additional living space, a half bath, laundry, and separate utility and storage areas. A three-car garage accommodates vehicles and hobbies, while the generous yard invites gardening, gathering, and enjoying the views. Thoughtful improvements include double-hung replacement windows (2019), picture windows and solar installation (2020), a UV water filter (2021), and a well expansion tank (2020). A roof and electrical panel replaced in 2017, plus a septic tank and leaching field installed in 2016, round out the updates. Enjoy Middletown's Main Street dining and shopping and the trails and waterfalls of Wadsworth Falls State Park. Schedule your showing to experience this home's memorable blend of character, light, and views.

972 Ridgewood Rd, Middletown

$249,900

3 Beds ⋅ 2 Baths ⋅ 24212253 MLS ⋅ Quail Run Village BLDG.

End-unit townhouse at Quail Run Village with a private entrance, an under-house garage, and a back deck that looks out over woods. A foyer entry leads upstairs to the main living level, where the kitchen, dining area, and living room connect through an open arched layout. The kitchen has granite counters, stainless steel appliances, tile backsplash, and a built-in pantry closet. Sliders from the living room open to the deck, a quiet spot for morning coffee or evenings outside with a backyard full of mature trees. A half bath is conveniently located on this level. Upstairs are three bedrooms and a full bath. The large primary has a ceiling fan and generous natural light. The lower level has a flexible bonus room with recessed lighting, perfect for a home office, gym, or hobby space. A laundry and utility area is next to it, with a washer and dryer included, and the attached one-car garage has an automatic opener. As a Quail Run resident, you can enjoy the community's in-ground pool. The monthly HOA fee covers grounds maintenance, snow removal, trash pickup, and pool service. The location offers quick access to Route 9 and I-91 and is close to shopping, dining, Wesleyan University, and Middlesex Hospital.

161 Cynthia Ln Unit C6, Middletown

27 Rising Trail Court, Unit 27, Middletown

$199,900

3 Beds ⋅ 2 Baths ⋅ 24212390 MLS ⋅ Beacon Hill Towne Homes BLDG.

Welcome to 27 Rising Trail Court, a spacious 3-bedroom, 1.5-bath townhouse-style condo offering three levels of living space, a two-car carport, and a desirable end-unit location! Step inside to an open-concept main level featuring luxury vinyl flooring throughout, where the recently updated kitchen overlooks the dining area and sunken living room. The kitchen features granite countertops, stainless steel appliances, recessed lighting, and plenty of workspace, with a convenient half bathroom nearby. Just beyond, the sunken living room is filled with natural light from sliding glass doors that lead directly to your private back deck. Upstairs, the second floor offers two generously sized bedrooms with wall-to-wall carpeting, a dedicated laundry area, and a remodeled full bathroom featuring tile flooring, a tiled tub/shower surround, and an updated vanity. Continue to the third floor where you'll find an additional bedroom along with a large unfinished storage area offering excellent potential for additional usable space. Additional highlights include a brand-new water heater installed earlier this year, two-car covered parking, pool access, and an end-unit location situated beside the community swing set. The association also allows one dog or one cat, making this a great option for pet owners. Offered at $199,900, this is a fantastic opportunity to make the move from renting to homeownership!

27 Rising Trail Court, Unit 27, Middletown

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