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

$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

Privately set on over three picturesque acres in Deep River, 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

$215,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24190159 MLS ⋅ The Moorings Ii BLDG.

WOW! Location, location-minutes to Town Beach or town center! This 2nd floor, ranch style condo features beautiful hardwood floors through out. Updated eat in kitchen with stone counter, tile backsplash, stainless steel appliances & pantry. Spacious living room, 2 nice sized bedrooms with double closets, and a renovated tile bath with tub/shower complete this charming coastal home. Private storage is available in the basement along with card-op laundry. Off street parking and a private beach path make this a seamless getaway, centrally located, minutes to town, train station, and so much more. Easy living on the shore awaits!

24 College St Unit 6, Clinton

$1,100,000

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

$419,000

9 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24190092 MLS

Exceptional mixed-use investment opportunity convenient to downtown Middletown! This property features 2 commercial units and 3 residential units, offering a balanced blend of commercial and residential income that makes it an ideal addition to any investor's portfolio. Both commercial spaces are currently vacant, making this an excellent opportunity for someone who wants to open their own business on the ground floor while collecting steady rental income from the apartments upstairs. The commercial spaces enjoy excellent street frontage and high visibility along busy East Main Street, providing strong exposure for retail, office, or service-oriented businesses-with one of the commercial units already featuring a dedicated kitchen. The 3 residential units offer versatile 1, 2, and 3 bedroom layouts, each featuring 1 full bathroom. These units offer strong rental appeal in a highly desirable location. Situated within walking distance to restaurants, shopping, entertainment, public transportation, and local amenities, this property benefits from Middletown's vibrant atmosphere. Whether you're looking to expand your investment portfolio, generate multiple income streams, or establish your business while collecting residential rental income, this versatile property offers outstanding potential. Convenient access to Route 9, I-91, Wesleyan University, and surrounding communities. Make an appointment today to view this property!

71 E Main St, Middletown

$1,150,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24062033 MLS

A remarkable blend of architecture, nature, and modern comfort, this modernist custom home offers a living experience unlike any other. Nestled within a private and serene setting, the property is surrounded by natural beauty, where meandering streams feed a tranquil pond that spills into a cascading waterfall before winding through the marshlands toward the Connecticut River. The setting is both peaceful and inspiring, with gorgeous water views enhancing the landscape. The approach to the home is an experience. A charming, covered bridge connects the detached two-car garage to the main residence, crossing over the stream and pond below. The property reflects thoughtful design and a deep connection to its natural surroundings. Extensively renovated over the years, the home combines artistic character with modern efficiency. Recent updates include a brand-new Viessmann boiler, freshly painted exterior, newly paved driveway completed in 2024, new IPE upper deck, and a septic system replacement in 2010. Radiant heated floors provide year-round comfort, while the beautifully renovated kitchen and baths showcase quality craftsmanship and timeless design. The sun-filled main level offers an open and inviting floor plan ideal for both everyday living and entertainment. The dining area, with its wall of windows, provides stunning year-round river views. The primary suite serves as a private retreat with a stunning spa-inspired bathroom featuring distinctive fixtures & finishes.

112 River Rd, Essex

$2,850,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24177108 MLS

Experience beachfront living at its finest in this exquisitely designed coastal oasis offering over 2,900 square feet of refined luxury. Thoughtfully crafted to maximize breathtaking ocean views, this stunning residence seamlessly blends elegant design with relaxed waterfront living. The gourmet kitchen is a chef's dream, featuring premium Bertazzoni appliances, granite countertops, and a spacious butler's pantry perfect for effortless entertaining. Sun-filled living spaces capture panoramic water views and create an inviting atmosphere throughout the home. Retreat to the spectacular primary suite complete with a luxurious ensuite bath featuring a steam shower, bidet, and spa-like finishes designed for ultimate comfort and relaxation. Step outside to an exceptional outdoor entertainment area where you can host guests, dine al fresco, or simply unwind while enjoying the sights and sounds of the shoreline. This remarkable beachfront property offers the perfect blend of sophistication, comfort, and coastal elegance.

99 Shore Rd, Clinton

$1,600,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24178395 MLS

Perched over the CT River on one of the largest lots on Main, the David Watrous House offers water views from each room. This 1850 architectural treasure offers over 4,000 square feet of living space, plus an additional 1,500+ square foot walkout lower level. A detached oversized 3-bay post-and-beam carriage house offers exceptional workshop/studio space, stained glass windows and crowned by a copper cupola with antique weathervane. A side porch entry leads to chef's kitchen with handcrafted Vermont solid cherry cabinetry, granite countertops, stainless appliances, a tin ceiling and dramatic 10-foot island. Formal dining with antique chandelier and fireplace make for elevated home entertaining. The dramatic riverfront great room with wall-to-wall windows, a river-facing 2nd kitchen, fireplace, and expansive deck captures ever-changing water views. A den, living room, office with cherry built-ins, 10+ foot ceilings and full bath offer flexibility on 1st flr. Upstairs, restored original chestnut floors lead to multiple living spaces, full laundry, a 3rd kitchen and a primary suite with gas fireplace with marble en suite. Recent upgrades include new windows, patio, driveway, refreshed landscaping, Buderus furnace, upgraded 400-amp electrical, restored chimneys, whole-house generator, and updated roofing. Stone pathways lead to private riverside seating areas for amazing sunsets. Rare chance to claim a home of notable architectural significance with recognized press coverage.

77 Main St, East Haddam

$825,000

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24178835 MLS

Rare mixed-use investment opportunity located in the heart of desirable Deep River Village. Positioned directly on Main Street, this 5-unit asset offers a strong blend of residential and commercial income within one of the Connecticut shoreline region's most sought-after rental and retail markets. The property consists of 3 residential apartments and 2 commercial storefronts occupied by long-term local tenants, providing stable in-place cash flow with additional upside through lease-up and rent optimization. Deep River continues to experience strong demand driven by its walkable downtown, restaurant scene, boutique retail presence, and proximity to the Connecticut River and shoreline communities. The residential units offer continued rental growth potential in a market with historically limited housing inventory, while the commercial spaces benefit from Main Street visibility and an established small-business environment. The property presents a compelling opportunity for investors seeking a stabilized mixed-use asset with value-add characteristics in a highly desirable shoreline-adjacent location. Projected stabilized income supports significant upside from current operations through continued lease-up strategy and operational optimization. Additionally, recent zoning updates may allow for the addition of residential unit(s) on the 3rd floor, creating a unique future expansion opportunity.

163-165 Main St, Deep River

$3,777,111

27 Beds ⋅ 22 Baths ⋅ ACTIVE Status ⋅ 24173970 MLS

The Village at 82 Main is - a pristine 22-unit asset located in the true heart of one of Connecticut's most charming small towns! Positioned directly on Main Street in East Hampton, this beautifully renovated property offers 17 apartments and 5 storefronts, creating a stable, diversified income stream within an exceptional lake-community setting. The property has become a recognizable destination woven into the fabric of the community, home to local favorites like ECO Coffee House, Tiny Paws Dog Grooming, 9 Lives Barber Shop, and Executive RE. Each apartment features beautifully updated interiors with modern finishes throughout, including stylish kitchens with granite countertops, stainless steel appliances, upgraded flooring, and open living spaces that continue to attract strong tenant demand. Extensive property-wide improvements and meticulous ownership have created a true turnkey investment opportunity with exceptional pride of ownership throughout. The commercial storefronts benefit from excellent visibility and steady foot traffic surrounded by popular local restaurants, boutiques, cafes, and recreational amenities. Residents enjoy immediate access to Lake Pocotopaug and the Air Line State Park Trail, while ownership benefits from tenant-paid electric, owner-paid gas heat, ample off-street parking w/ EV chargers, and ancillary laundry income. 82 Main Street represents a rare opportunity to acquire one of the area's premier mixed-use investment properties!

82 Main St, East Hampton

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