Middlesex County Real Estate

Welcome to Middlesex County, Connecticut! Nestled in the heart of the state, Middlesex County offers a perfect blend of small-town charm and modern convenience. With a rich history dating back to the 17th century, this county is brimming with character and a strong sense of community.

Middlesex County is known for its picturesque landscapes, including the stunning Connecticut River that winds its way through the region. Residents and visitors alike can enjoy a variety of outdoor activities, from hiking and biking along scenic trails to boating and fishing on the river.

The county is home to several vibrant towns, each with its own unique appeal. Middletown, the largest city in the county, boasts a thriving arts and culture scene, with galleries, theaters, and live music venues. Portland, known as the "town that built the state," is steeped in history and offers a glimpse into Connecticut's industrial past.

Families are drawn to Middlesex County for its top-notch schools, safe neighborhoods, and abundance of parks and recreational facilities. Whether you're looking for a historic home with classic New England charm or a modern property with all the latest amenities, Middlesex County has something to offer everyone.

Come discover the beauty and warmth of Middlesex County, where small-town living meets big-city convenience. Find your perfect home in this welcoming community and start living the Connecticut dream!

Newest Listings in Middlesex County

$850,000

3 Beds ⋅ 4 Baths ⋅ 24192283 MLS

Contemporary 3-bedroom, 2 full bath, 2 half bath home offering exceptional flexibility, character, and entertaining space. The open-concept main level features vaulted ceilings, dramatic architectural lines, and seamless flow between the kitchen, dining, and living areas. A striking firebox anchors the living room, while the four-season sunroom opens through French doors to a private tiered deck complete with a custom stone fireplace-perfect for outdoor gatherings year-round. The second floor offers two bedrooms plus a spacious primary suite with cathedral ceilings and a truly one-of-a-kind spa bath inspired by a traditional retreat, featuring custom tilework and natural stone accents for a serene, luxurious experience. The finished lower level includes a recreation room and custom-designed bar, creating the ideal space for entertaining. A two-car garage is complemented by a third attached bay leading to a professional woodworking shop with French door access to the beautifully landscaped backyard. Set on picturesque grounds with a gentle stream along the eastern boundary, the property also features mature fruit trees and a productive vegetable garden. Whether you're an entertainer, hobbyist, home-based business owner, or seeking potential in-law living space, this unique property offers endless possibilities and versatile living in a truly special setting.

170 Bushy Hill Rd, Deep River

$425,000

5 Beds ⋅ 2 Baths ⋅ 24194376 MLS

Come see this beautiful lakefront property with endless possibilities! This raised ranch offers a spacious and versatile layout, beginning with an open-concept kitchen, dining, and living area that's perfect for everyday living and entertaining. Just off the kitchen, you'll find a stunning sunroom with breathtaking views overlooking Lochwood Lake. Down the hall are three bedrooms and a full bathroom. The finished lower level offers excellent potential for an in-law suite, complete with two additional bedrooms, a full bathroom, an eat-in kitchen, and a spacious family room. Step outside and enjoy the peaceful backyard that backs directly to the lake. Whether you love canoeing, fishing, swimming, or simply relaxing by the water, this property offers the perfect setting to enjoy it all. Additional features include a two-car garage, city water, and a generous .66-acre lot. Don't miss this unique opportunity to own a waterfront home-schedule your showing today!

166 Glenwood Rd, Clinton

$180,000

3 Beds ⋅ 2 Baths ⋅ 24194531 MLS ⋅ Beacon Hill Towne Homes BLDG.

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

106 Rising Trail Dr Unit 106, Middletown

$484,900

4 Beds ⋅ 2 Baths ⋅ 24190416 MLS

A perfect home! A perfect neighborhood! This move-in-ready 4 Bedroom, 2 Bath Cape offers 1,892 sq ft of living space, a 1-car garage, and amazing deck and backyard. The sun-filled Living Room features a beautiful fireplace, crown molding, recessed lighting, large picture window, and flows seamlessly into the remodeled Kitchen. The Kitchen boasts granite countertops, a peninsula w/seating for 4, and new stainless steel appliances. Completely open to the Kitchen, the bright Dining Room showcases a vaulted ceiling, sliders to the deck and daylight from 3 sides. The first floor also offers 2 spacious Bedrooms and a beautifully renovated Full Bath with a granite vanity and luxury vinyl flooring. Upstairs you'll find 2 additional generous Bedrooms, including the Master Bedroom Suite w/walk-in closet and full Bath. The finished lower level adds a 400 sq. ft. Family Room w/newer carpeting and updates, providing endless possibilities for recreation, work, or hobbies. Step outside to the captivating 20'x12' composite deck overlooking the level, outstanding backyard for entertaining/games. Home boasts Cent/Air, refin'd hardwd floors thru-out first floor (2025), 200-amp electrical service & updated electrical wiring, and city water/sewer. Updates: First-floor interior paint (2026), new A/C condenser & air handler coils (2025), newer Bilco doors, and 6-foot vinyl privacy fence (2016). Walking distance to Cromwell Middle School & Watrous Park. Strategically priced: This could be your home!

16 Raymond Pl, Cromwell

$395,000

3 Beds ⋅ 3 Baths ⋅ 24194117 MLS

Welcome home to this charming property located at the end of a peaceful cul-de-sac. This residence features three bedrooms, including a primary bedroom with an ensuite full bathroom. There are two updated full bathrooms in total, along with a convenient half bath. As you enter, you'll notice the gleaming hardwood floors that flow throughout the main living areas. The kitchen is thoughtfully designed with granite countertops, maple wood cabinets, and stainless steel appliances, offering a great setup for everyday cooking. The dining area seamlessly connects to the cozy living space, which features a gas fireplace and a mini-split system, providing an additional heating and cooling option for year-round comfort. From the dining area, sliding doors open to a patio with Trex decking, complete with a retractable awning, perfect for providing shade when needed and easily rolled back for sunny days. The two-car garage provides direct access to a finished basement area that includes a half bathroom and laundry facilities, enhancing the home's functionality. Energy-efficient solar panels ensure excellent coverage, leading to no current electric bill. Step outside to discover a private walking path accessible right from your backyard. This home is fully move-in ready, waiting for you to create lasting memories.

3 Yellow Pine Cir, Middletown

$539,999

3 Beds ⋅ 3 Baths ⋅ 24191099 MLS

Welcome to this beautifully updated 3-bedroom Contemporary retreat, perfectly situated on a lush, private lot. A charming wraparound covered front porch welcomes you home and offers the perfect space to relax, unwind, or gather with family and friends. Inside, you'll find 1,604 square feet of thoughtfully designed living space featuring soaring vaulted ceilings, abundant natural light, beautiful wall-to-wall luxury vinyl plank (LVT) flooring, three bathrooms, and a spacious primary suite with an updated en-suite bathroom complete with a relaxing Jacuzzi tub. More than $60K in renovations have been completed within the past year, including a new roof, new siding, a new balcony, a freshly stained deck, and numerous additional updates, making this home truly move-in ready. The finished lower level expands your living space with a cozy family room centered around a fireplace. Adjacent to the family room is an unfinished area already equipped with plumbing, offering a true blank canvas for your vision. Whether you dream of a future kitchenette, home office, guest suite, multigenerational living space, or a potential in-law setup (subject to local approvals), the possibilities are endless.Step outside to your own backyard oasis. Surrounded by mature trees & lush greenery, the expansive deck, brand-new above-ground pool, and newly built balcony create a private, resort-like setting that's perfect for morning coffee, summer pool parties,or relaxing evenings under the stars...

1512 Country Club Rd, Middletown

$699,900

5 Beds ⋅ 4 Baths ⋅ 24193584 MLS

Updated Dutch Colonial with room for everyone and every activity. A total of five bedrooms, three on the second floor and two on the main floor. A den on the lower level has sliders that open to an oversized stone patio overlooking the yard and woods on this very private 2.4 acre lot. This home includes a remodeled cook's kitchen, updated baths and central air. In addition to the two car garage and driveway parking, there is an overflow parking area on the property for larger gatherings.

502 Rte 148th Rte, Killingworth

$389,900

3 Beds ⋅ 2 Baths ⋅ 24192182 MLS

Welcome to this well-maintained 3-bedroom, 2-bath ranch situated on just under an acre in a desirable East Hampton location. This move-in-ready home offers comfortable one-level living with hardwood floors and tile throughout, creating a warm and inviting atmosphere. The spacious backyard is designed for entertaining, featuring a patio and a custom outdoor bar and kitchen setup-perfect for hosting family and friends or enjoying summer evenings at home. Car enthusiasts, hobbyists, and those in need of extra space will appreciate the oversized detached two-car garage, complete with a semi-finished room above. Whether you're looking for additional storage, a private man cave, game room, home office, or creative studio, this versatile space offers endless possibilities. The partially finished basement provides even more flexible living space, ideal for a recreation room, home gym, or additional storage. The home also features a roof that is approximately five years old and solar panels to help improve energy efficiency and reduce utility costs. With its combination of indoor comfort, outdoor entertaining space, thoughtful updates, and versatile areas, this property is a wonderful place for your home. Schedule your private showing today!

46 Champion Hill Rd, East Hampton

$525,000

3 Beds ⋅ 2 Baths ⋅ 24194369 MLS

One of a kind, period home of historical significance in the heart of Higganum. Formerly a general store, this home exudes charm and whimsy. Lovingly restored by a family and then maintained by a notable antique dealer, this home has been in the same family for two generations. The interior remains period correct with useful and necessary updates like newer windows, kitchen and baths. The original stone fireplace is large and impressive. The living room wraps around it with ease. Unique to this home is a large dining room which can seat 6 or more. Laundry, full bath and one bedroom can all be found on the first floor. The second floor has a versatile landing currently used as an office, full bath and two additional bedrooms, including a large primary overlooking the private backyard. The lower level includes a finished large living room, walk out patio, work room and another fireplace. A post and beam barn (newer than the house) is magnificent with three bays, a work room and full second floor as well as running water and electricity! Follow the cobblestone driveway and then keep going into the woods to find a swimmable spring-fed pond and summer sleeping cabin! This house must be toured to be understood and to understand the opportunity here is to fall in love with all it has to offer.

369 Saybrook Rd, Haddam

$239,900

2 Beds ⋅ 2 Baths ⋅ 24193840 MLS ⋅ Cedar Ridge BLDG.

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

10 Countryside Ln Unit 5, Middletown

$749,000

3 Beds ⋅ 2 Baths ⋅ 24193856 MLS

Welcome to your private waterfront sanctuary retreat! This Contemporary Ranch is situated on Trout Brook and Johnson Pond, and is tucked away on a peaceful cul-de-sac. It's the perfect place for entertaining and rest & relaxation in & out. Step inside to a popular open-concept layout. The living, dining, and kitchen areas soar with cathedral ceilings and walls of windows framing breathtaking views of the beautiful 2 acres. A double-sided brick fireplace anchors the space, perfect for cozy gatherings or holiday feasts. The bright kitchen offers an abundance of natural light as well as recessed lighting. Large island and breakfast bar. The private bedroom wing features a primary suite with three closets and a spa-like bath with a walk-in shower. Two additional bedrooms and a full bath complete the while the first-floor laundry and an oversized two-car garage add effortless convenience. A generous sized basement offers room for storage, a workshop, or a home gym. Outside, the wrap-around deck invites summer barbecues; the fire pit with built-in seating promises cool evening s'mores and winter cuddles. Easy-care gardens and a level lawn - ideal for yard games and lively get-togethers - complete this mesmerizing retreat. A large, fenced flat area is just perfect for pets. This property checks off many boxes for everyone - with one-level living at its best on a gorgeous parcel filled with wildlife and amazing vistas. It makes every day feel like you are on vacation.

147 Johnson Pond Ln, Westbrook

$499,900

3 Beds ⋅ 2 Baths ⋅ 24194133 MLS

302 Hidden Lake Road offers the perfect blend of timeless New England charm, modern comfort, and exceptional outdoor living on a beautiful 2-acre lot in the highly sought-after Haddam-Killingworth School District. This classic Dutch Colonial showcases its signature gambrel roof, wide-plank pine flooring throughout the first floor, exposed post-and-beam details, and a cozy fireplace that creates a warm and inviting atmosphere. Thoughtful updates include efficient zoned mini-split heating and cooling, a whole-house generator ready to be connected, and a spacious composite deck overlooking the private backyard. The walk-out lower level with sliders provides flexible living space ideal for a family room, home office, gym, or recreation area. A large, detached garage offers exceptional versatility for multiple vehicles, hobbies, a workshop, recreational equipment, or additional storage. Enjoy the best of Connecticut's "big enough, small town" lifestyle with nearby Cockaponset State Forest, Higganum Reservoir, Haddam Meadows State Park, the Connecticut River, hiking, biking, kayaking, boating, and fishing, along with local favorites including the Goodspeed Opera House, Chester, Essex, Lavender Pond Farm, farmers markets, and charming restaurants and shops throughout the Connecticut River Valley.

302 Hidden Lake Rd, Haddam

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