Middlesex County Homes for Sale

Middlesex County Homes for Sale

Welcome to Middlesex County, Connecticut—an enchanting blend of natural beauty, rich history, and vibrant community life. Nestled along the scenic Connecticut River, Middlesex County offers residents a unique lifestyle characterized by charming small towns, bustling urban centers, and breathtaking landscapes. With its picturesque parks, historic sites, and a plethora of recreational opportunities, this county is the perfect place to call home.

Middlesex County is known for its diverse neighborhoods, each with its own distinct charm. From the quaint streets of Essex to the lively atmosphere of Middletown, there’s something for everyone. Whether you prefer the serene waterfront views or the energy of a thriving downtown area, you’ll find a home that suits your lifestyle perfectly.

For those considering a move, there are a variety of homes for sale in Middlesex County. From cozy single-family homes and charming historic properties to modern condos and spacious townhouses, the real estate market here caters to a wide range of tastes and budgets. Many properties boast stunning views, expansive yards, and easy access to local amenities, making it an ideal location for families, professionals, and retirees alike.

Middlesex County is also home to excellent schools, vibrant arts and culture scenes, and a multitude of dining options that celebrate local flavors. With a strong sense of community and an abundance of outdoor activities—like hiking, boating, and fishing—Middlesex County offers a lifestyle that is both fulfilling and enjoyable.

Explore the homes for sale in this captivating county, and discover the perfect place to create lasting memories. Your dream home awaits in Middlesex County, CT!

Newest Middlesex County Homes for Sale

404 Newfield St, Middletown
$450,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
206 W Elm St, Deep River
$358,900
2 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24217309 MLS
Brimming with quintessential New England charm, this cozy yet surprisingly versatile Cape Cod offers a unique blend of character, privacy, and natural beauty. Conveniently located near downtown Deep River, neighboring shoreline communities, and local beaches, the property also offers nearby access to state forest trails leading toward Pine Ledge. Originally built in 1950 and relocated to its current setting during the construction of Route 9 in the 1960s, this distinctive home has a history as interesting as its surroundings. Nestled along a lightly wooded hillside on approximately three-quarters of an acre, the home features two bedrooms, a full bathroom with radiant floor heating, a kitchen, dining area, inviting living room with a wood-burning fireplace, and an additional half bath. A bonus space on the main level showcases sweeping views of Pratt Read Reservoir and the surrounding woodlands, offering a peaceful place to enjoy the beauty of New England's changing seasons. The outdoor spaces are equally distinctive, with a secure poultry enclosure, fish pond, play structure, and open lawn area. An upper-level driveway provides access to a secluded picnic area and a second storage shed. Ample parking is available at the main level, while a separate private driveway below the home leads to an enclosed single-car garage, workspace, storage and interior staircase to the main floor of the home.

206 W Elm St, Deep River
9 Magnolia Pl, Middletown
$285,000
4 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 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 Pl, Middletown
45 Pent Rd, Durham
$649,000
3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24216140 MLS
Car collectors, contractors, landscapers take notice! If you've been searching for a property that offers both a comfortable home and space for your business, vehicles, equipment, this one checks all the boxes. This well-maintained home has many updates recently and is ready for its new owner. Step on to the welcoming front porch and a new front door opens to your new home. Entry foyer opens to spacious living room. Bright sunny and newly remodeled kitchen feature white shaker style cabinetry, quartz counter tops, a breakfast bar, and a dining area that flows seamlessly into the family room ideal for easy living and entertaining. The family room is highlighted by a cathedral ceiling and floor-to-ceiling brick fireplace, chimney is currently in need of repair for use, and sliders to a deck and backyard. Main level laundry room with cabinets and counter, add some shelving to create a walk-in pantry. Upstairs, you will find 3 bedrooms and 2 full baths, a primary bedroom with private bath, walk-in closet and an additional closet. 2 bedrooms with ample closet space and plenty of natural light. A Full basement providing storage and the option to finish. A newer heating system supplies radiant heat on the main level and baseboard on the upper level. 2 car attached garage access from the home, and 2 additional garage buildings, one 40x40 w/ 18ft ceilings. 16ft door, and Atlas 10,000 lb extra height capacity lift and infrared tube heating runs off propane. See additional remarks.

45 Pent Rd, Durham
73 Chapman Beach Rd, Westbrook
$1,375,000
4 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24165902 MLS
Own a piece of the Connecticut Shoreline lifestyle with this exceptional dual-cottage property in the sought-after Chapman Beach community! Just a short stroll to the sand with deeded private beach rights, this rare offering features two completely renovated, year-round single-family homes on one lot. This distinctive coastal property offers the perfect combination of seaside living, flexibility, and established rental income potential. The charming 824 sq. ft. guest cottage is a proven 5-star Airbnb with an established rental history and Summer 2027 reservations already secured, which must be honored by the buyer. Rental income details are available upon request. Also offering a history of academic rentals, this turnkey cottage features two bedrooms, one full bath, an updated kitchen with granite countertops, and an inviting open floor plan. A private yard and outdoor shower enhance the coastal experience, while a separate septic system, and utility meters provide added independence. New roof (2025). The fully renovated 1,100 sq. ft. main home is equally appealing, featuring two bedrooms, one full bath, an open floor plan, a new kitchen with quartz countertops and stainless steel appliances, a spacious living room with propane fireplace, and a dining area. A beautiful new 20' x 16' custom patio creates the perfect setting for outdoor entertainment. 2025 vapor barrier and blown in attic insulation ensure year round comfort.

73 Chapman Beach Rd, Westbrook
2 Sonoma Ln Unit 2, Middletown
$549,900
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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
2 Hawk Brk, Old Saybrook
$900,000
3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24215827 MLS
Very private location yet close to major commuter routes, this wonderfully maintained Colonial has large living spaces inside & out! Entry foyer w/2 oversized closets, tile flr and access to huge 2 car garage. The 1st flr features a huge eat-in kitchen w/rich cherry cabinetry, center island w/downdraft range, tile & hdwd floors, spacious pantry closet & access to the 16.5x24 back deck perfect for relaxing & dining. The formal DR is perfect for that special meal and the formal living rm has a cozy wood burning brick fireplace & hearth-both rooms have gleaming hardwood flrs. The 19.5x24 ft family room is a breathtaking space featuring soaring vaulted ceiling, hdwood flrs w/walnut inlay, oversized Palladian window & rear bay window. A full bath rounds out flr 1. The 2nd flr features a Master Suite comprised of huge BR, laundry room, full bath w/soaking tub and bidet, dressing area w/ample closets & spacious sitting rm. The remainder of the 2nd flr features 2 more well-proportioned BRs accompanied by a full bath w/tub-shower combo & tile flr. There is a full walkout basement w/partially finished 19.5x25 room w/French doors leading directly to the backyard. There is also an enormous walk up attic with soaring ceilings that will hold all your treasures or could be finished for even more living space. Oil hot water heat & a 2 zone central air conditioning system will keep you comfy all year. There is a Central Vac & whole house generator so you always have peace of mind. Come see

2 Hawk Brk, Old Saybrook
14 Cinnamon Rdg, Old Saybrook
$625,000
3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24217273 MLS
Available to be shown 10/31 --- NEW LISTING in beautiful Cinnamon Ridge! This absolutely charming cape on picturesque 1+/- acre lot has undergone several wonderful transformations with fresh paint, newer windows, Buderus boiler, newer water heater, newer floors and carpets, along with stunning kitchen and baths with gorgeous cabinetry, granite countertops, stainless steel appliances including a beverage/wine refrigerator. The entry foyer is bright with full-lite front door and skylights, coat closet and new half bath; the front to back family room has a fireplace for cozy fall-time fires and french door to large 40x14 deck; both the dining room (also with french door to deck) and the living room have beautiful hardwood floors. On the second floor is the Primary bedroom complete with it's new personal bath; two additional bedrooms plus the main bath also newly remodeled. Beautiful drive along Cinnamon Ridge with trees laden with fall leaves ... Don't miss this once-in-while opportunity to be in one of Old Saybrook's prime locations - off country roads yet close to all that Old Saybrook has to offer -- town parks, beaches, quaint Main Street, The Kate theater, restaurants, shopping, train station etc.

14 Cinnamon Rdg, Old Saybrook
56 Witch Hazel Dr, Deep River
$615,000
4 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24217205 MLS
Welcome to your peaceful retreat in desirable Witch Hazel estates! This 4 bedroom, 2.5 bathroom home sits on a quiet cul-de-sac and offers a peaceful and tranquil setting. Tastefully updated and beautifully maintained, this home is great for everything from relaxing with your morning coffee to strolling down the sleepy street to entertaining on your expansive deck overlooking your private backyard. Falls River Sanctuary is a stone's throw from your front yard, adding to the serene setting. Extensive updates include a new roof (2021), remodeled kitchen with quartz countertops, updated bathrooms, refinished hardwoods floors throughout the main level, newer covered deck, new bulkhead door, and landscaping.

56 Witch Hazel Dr, Deep River
26 Powerhouse Rd, East Haddam
$299,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215204 MLS
Step into timeless charm and craftsmanship in this distinctive home, where they truly don't make them like they used to! Wide decorative baseboards, classic doors, detailed trim, stained-glass windows, and a welcoming covered front porch showcase its character. The original stone fireplace feels straight out of a fairytale book, creating a warm and inviting focal point. The dining room features a built-in hutch and cabinetry, while hardwood floors run throughout, including beneath all carpeting. A versatile first-floor room offers a beautiful picture window and built-in window seat with storage, creating the perfect spot for reading or relaxing. The first floor also features a walk-in laundry room with the added convenience of a toilet, along with a kitchen located just off the driveway for easy access. Enjoy the outdoors from the covered front porch or back deck. Upstairs, the oversized primary bedroom boasts vaulted ceilings, three generous closets, abundant natural light, and hardwood flooring beneath the carpet. An adjoining bonus room, accessed through the remodeled full bath with tiled walls, offers flexible possibilities as a dressing room, reading nook, private retreat or third bedroom. Located just a stone's throw from the Salmon River, with seasonal glimpses of the water through the trees, this home blends timeless character, charm, and everyday convenience.

26 Powerhouse Rd, East Haddam
5 Castanea Ct, Middletown
$375,000
2 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24217229 MLS
Coming Soon! 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
44 Haddam Neck Rd, East Hampton
$359,999
3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24217011 MLS
Welcome to 44 Haddam Neck Road! This charming raised ranch offers 3 bedrooms, 2 full bathrooms, and 1 half bathroom, situated on approximately 0.78 acres in East Hampton. Inside, you'll find a warm and inviting atmosphere with beautiful hardwood floors, natural wood accents, and plenty of natural light throughout. The spacious living room features a brick fireplace, while the adjoining dining area provides a comfortable setting for everyday meals and gatherings. All three bedrooms offer generous space and comfortable layouts, with the primary bedroom featuring the added convenience of its own private en-suite bathroom. The finished lower level provides additional living space, complete with a family room, wood-burning stove, and built-in bar area, offering a great setting for entertaining or relaxing at home. A separate laundry room adds everyday convenience, while the attached two-car garage provides additional parking and storage. Outside, the elevated rear deck overlooks a spacious backyard surrounded by mature trees and established landscaping, offering plenty of room for outdoor activities, gardening, or simply enjoying the peaceful surroundings. Conveniently located near East Hampton's local shops, restaurants, parks, and recreational opportunities, 44 Haddam Neck Road offers a wonderful combination of indoor comfort, outdoor space, and classic New England charm.

44 Haddam Neck Rd, East Hampton
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!