Middlesex Homes with Other Style

Welcome to Middlesex County, Connecticut, a hidden gem that perfectly marries natural beauty with vibrant community living. Nestled along the picturesque Connecticut River, this region boasts a rich tapestry of history, culture, and recreation, making it an ideal destination for homebuyers seeking both tranquility and convenience.

Middlesex County is renowned for its charming towns, each with its unique character. From the bustling streets of Middletown, home to Wesleyan University and an array of eclectic shops and restaurants, to the serene coastal beauty of Old Saybrook, there's something for everyone. The county's diverse landscape offers stunning views, with lush parks, scenic riverside trails, and beautiful beaches, perfect for outdoor enthusiasts and families alike.

When it comes to real estate, Middlesex County presents a delightful array of homes with various architectural styles. Whether you’re drawn to historic colonial homes that whisper stories of the past or modern designs that embrace contemporary living, you’ll find it all here. Many properties feature spacious yards, inviting porches, and proximity to local amenities, ensuring that you can enjoy the best of both worlds—peaceful suburban life and easy access to urban conveniences.

As you explore the housing market, you'll discover that Middlesex County is not just about the homes; it's about the lifestyle. With a strong sense of community, excellent schools, and a commitment to preserving the environment, this county offers a quality of life that is hard to beat. Come and experience the charm of Middlesex County, where your dream home awaits amidst a backdrop of stunning landscapes and warm, welcoming neighborhoods.

Newest Middlesex Homes with Other Style

$450,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205103 MLS ⋅ Island View Community BLDG.

Enjoy refreshments on the deck and a boat ride to boot while taking in beautiful views of the community's private beach, docks, gazebo and Lake Pocotopaug! Located within an intimate, self-managed lakefront community of just 19 seasonal and year-round homes, this spacious two-bedroom, two-bath condominium offers 1,152 square feet of comfortable living space and a generous awning-covered deck. With only a limited number of year-round residences, this shared community setting offers a distinctive alternative to the expense and responsibility often associated with owning a traditional standalone waterfront home. Whether you're searching for a year-round residence or a weekend retreat, this special property invites you to enjoy swimming, boating and relaxing by the lake-even taking your boat to a nearby lakeside restaurant-all while remaining conveniently close to East Hampton's shops, restaurants and other amenities. The spacious upper level is currently configured as one bedroom with a private bath and offers flexibility for a possible additional bedroom, office or playroom, subject to town and association approvals.

1 Day Point Rd Unit 19, East Hampton

$895,000

9 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24203866 MLS

A rare investment opportunity in the Moodus section of East Haddam. Two apartment buildings on one .88 acre lot, well maintained with updated mechanicals. These buildings must be sold together, the lot cannot be subdivided. A 1900 5 unit Victorian (1 bd/1 bth units) and a 1860 2 family duplex with a 2 bedroom unit on each floor. Plenty of parking for tenants. Leases inplace for all units except one freshly updated 2 bd unit, ready for owner occupancy should you choose. Basements include new Oil tanks, new boilers, updated electrical, updated plumbing, coin laundry. Large level back yard. Close to Rt 9 & Rt 2 for easy commuting. Property is shown by appointment only.

23 Plains Rd, East Haddam

$289,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200726 MLS

A Unique opportunity, 2 Homes on 1 Lot. Plus a barn/garage. First Home has 2 bedrooms and is 1,061 sqft. Second Home has one bedroom and is 350 sqft. Separate town water and sewer to each home. Ready for your updating! Electric 100 AMPS each.

1721 Winter Ave, Deep River

$2,749,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24196837 MLS

Wake up to spectacular waterfront views of the Connecticut shoreline from this beautifully designed 4,381 sq.ft, 4 bedroom, 4 bath residence, where luxury, comfort, and effortless coastal living come together. Designed for a low-maintenance waterfront lifestyle, the home features vinyl siding, Ipe and azek decking, automated storm shutters, reinforced seawall with steel bulkheads, and owned solar panels. Three spacious levels, connected by an elevator and grand staircase, showcase sun drenched natural light, sweeping water views, and seamless indoor-outdoor living. The gourmet kitchen features a large island, built-in appliances, wine chiller, and white cabinetry with glass accents, opening through a generous butler's pantry to the formal dining room, and to a sun-filled breakfast area and adjoining sunroom. The grand living room is anchored by a stone fireplace, with sliders opening to an expansive waterfront deck. A full bath and outdoor shower complete the main level. Upstairs, the luxurious primary suite offers a gas fireplace, private sunroom and deck, two walk-in closets, and a spa-inspired bath with jetted tub, oversized walk-in shower, heated towel bars, and radiant-heated floors. An additional bedroom with wraparound deck, full bath, a laundry room, and a versatile bonus space ideal for a fitness studio, recreation room, or lounge complete the second level. The third floor offers two additional bedrooms, a full bath, sunroom, and private deck.

167 Shore Rd, Clinton

$269,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24196275 MLS ⋅ Parker House BLDG.

Step into a piece of history with all the comforts of modern living! Located in a beautifully renovated factory building that was thoughtfully converted to condominiums in 1987, this distinctive residence is part of a property listed on the National Register of Historic Places. Rich in character and architectural charm with exposed beams, wood ceiling and brick walls, this meticulously maintained condo offers a unique lifestyle in one of the area's most desirable locations. Enjoy the convenience of being just a short walk to vibrant downtown Middletown, where you'll find exceptional restaurants, boutique shopping, entertainment, Wesleyan University, and Middlesex Hospital. Inside, you'll appreciate the many recent updates, including a beautifully remodeled kitchen, with stainless steel appliances that are only four years old. Gleaming hardwood floors in the living and dining room. Major mechanicals have already been taken care of, with the central air conditioning system, furnace, and water heater all replaced just two years ago, providing comfort and peace of mind for years to come. Whether you're looking for a primary residence or a weekend retreat, this one-of-a-kind home combines historic character, modern amenities, and an unbeatable walkable location. Don't miss your opportunity to own a truly special property.

234 S Main St Unit 203, Middletown

$339,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24195937 MLS

Beautiful Home walking distance to CT River. Fully renovated in 2025

7 Oakum Dock Rd, East Hampton

$479,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24195197 MLS

Welcome to your new home! A neutral kitchen with split face natural stone backsplash, Corian counters, cherry finish cabinets breakfast nook with wainscoting and decorative chair rail throughout for that customized look along with a great window layout that streams in natural light. The floor plan flows nicely as you make your way from dining room to the comfort of your living room with custom shadow boxing wall accents, ceiling fan, sliders looking out at the deck and best of all the gas log fireplace to take the chill off those early fall evenings. Your guests will enjoy the privacy of a first-floor bedroom tucked away with walk in closet and bathroom amenities across the hall. With two full bathrooms, you'll notice the first-floor bathroom is uniquely complimented with a colorful stained-glass window. Making your way upstairs, you'll appreciate the beauty of the Brazilian teak hardwood floors throughout bedrooms and hallway. The convenience of second floor laundry with tile floor makes laundry clean-up a breeze. Enter the spacious primary bedroom that overlooks your inground pool then make your way to the primary bathroom that is well appointed with jacuzzi tub, walk-in shower with newly installed glass enclosure and double vanity. Tiled throughout. The final bedroom on the second floor has ample space with walk-in closet and can easily double as a home office. Outdoor shed makes lawn maintenance equipment and tool storage easy.

149 Liberty St, Clinton

$2,400,000

8 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24195471 MLS

Three direct beachfront cottages located right on the sand of Long Island Sound in Clinton, Connecticut offer a rare turnkey coastal investment opportunity. The property included two well-appointed 2-bedroom cottages and one spacious 4-bedroom cottage. All fully furnished and recently updated for modern comfort. Each cottage provides unobstructed waterfront views, immediate beach access and the charm of classic shoreline living. With a strong and proven rental history, this unique package is ideal for investors or buyers seeking a move in ready. income producing beachfront retreat along the Connecticut shoreline.

127 Shore Rd, Clinton

$1,400,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24194154 MLS

A Home Like No Other on the Connecticut River. Some homes are built others evolve into something extraordinary. An original agricultural silo has been thoughtfully transformed into one of the most distinctive waterfront homes. Rich in character makes it impossible to duplicate, this exceptional property blends history, creativity & breathtaking riverfront living. The original silo remains a remarkable historical centerpiece of the home, preserving the property's unique character & architectural story. The circular kitchen within the silo flows into a spectacular living & dining area where graceful curved walls create an inviting & unforgettable gathering space. A spiral staircase winds upward through the silo, leading to a cozy sitting room, a full bath, and a unique third-floor bedroom offering sweeping views of. Thoughtful additions have expanded the living space to include an additional kitchen, 2bedrooms, 2nd floor & the flexibility today's buyers appreciate. An oversized garage provides exceptional versatility, offering ample room for vehicles, storage, workshop or hobbies. Above the garage, a spacious finished studio. This is more than a waterfront home-it is a conversation piece, a distinctive architectural treasure, & a rare opportunity to own a property that simply cannot be replicated. For those seeking something beyond the ordinary, enjoy an unforgettable combination of character, river views, versatile living space & timeless New England charm.

1270 Saybrook Rd, Haddam

$1,065,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24192002 MLS

Essex Village is a short walk to this one-of-a-kind home, privately set on over three picturesque acres. Just moments from the Essex town line, this extraordinary custom home is the result of an exceptional architectural transformation, blending timeless New England character with thoughtful, high-end design. Enjoy a peaceful, private setting while being just minutes from the charming village centers of Deep River and Essex, with their acclaimed restaurants, boutique shops, marinas, yacht clubs, the Connecticut River Museum, and the historic Griswold Inn. A comprehensive redesign of the home's exterior was completed by renowned architect Christopher Arelt, featuring all-new windows, structural insulated panels for enhanced energy efficiency, cedar shingle siding, copper gutters, Azek trim, a 4-zone heating system, an expansive Ipe deck and stairs, a bluestone patio, and a private outdoor shower. A brand-new well, drilled in May, and a whole-house generator powered by a 500-gallon underground propane tank provide year-round comfort and peace of mind. The home's showpiece is the spectacular four-season sunroom. This breathtaking space features a coffered beadboard ceiling, rich Brazilian cherry flooring, walls of windows, a wood-burning stove, custom built-in seating, and French doors opening onto the expansive Ipe deck, creating an extraordinary setting for year-round living and entertaining.

106 Meadow Woods Rd, Deep River

$995,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191006 MLS

The best of both worlds-enjoy the tranquility of a peaceful setting while being just a short stroll to the beach. Beautifully updated and impeccably maintained, this year-round home offers the perfect blend of coastal charm and modern comfort. A welcoming front porch invites you inside where you'll find beautifully renovated kitchen and baths as well as quality finishes throughout. You'll love the four-season sunroom, with French doors and a wall of windows offering marsh views and spectacular sunsets year-round. Some recent updates include a newly added one-car garage, windows, siding, roof, rear deck, electrical panel, A/C, and sprinkler system. A deck off the living room and sunroom provides the perfect place to relax, entertain, or simply enjoy the peaceful surroundings. The full walkout lower level offers flexibility with an additional bedroom, family room, full bath and separate laundry room. Easy access to Beamon's Creek where you can launch a kayak and explore South Cove. The Knollwood Beach Association includes a private beach, clubhouse, tennis/pickleball, basketball court, a playground and the charm of a golf cart-friendly community. Low-maintenance and truly move-in ready, this exceptional shoreline home offers a lifestyle that's hard to beat.

65 Knollwood Dr, Old Saybrook

$749,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190498 MLS

Nestled in the heart of scenic Middlefield, this distinctive and beautifully maintained 4 bedroom 2.5 bathroom property offers a rare blend of classic New England character and modern flexibility. Inside on the first floor, an open-concept kitchen and dining area invite gathering and entertaining, seamlessly flowing into a sunroom-style flex space with room to grow-ideal for a home office, playroom, or reading nook. A separate living room, complete with a working fireplace, creates a cozy retreat for New England winters or days on the slopes of the nearby Powder Ridge Ski Resort. For the summer, step outside and you will find a stunning in-ground pool surrounded by a spacious brick patio, perfect for lounging and outdoor dining. An attached two-car garage adds everyday convenience and a second private driveway offers access to the rear of the property and the detached barn. The true gem is this fully renovated, detached barn-an inspired space with limitless potential. Featuring whitewashed wood walls and an airy farmhouse aesthetic, the barn offers a dramatic open-plan ground level and a second floor with three rooms and a bathroom. Off of the ground level, french doors lead to a private terrace shaded by mature grapevines, ideal for al fresco dining or sunset cocktails. Whether used as a luxurious art studio, at-home gym or work-from-home suite, this space delivers unmatched versatility with its own entrance and a beautiful walkway connection to the main home and pool.

88 Powder Hill Rd, Middlefield

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