Middlesex Homes with Historic Antique Style

Welcome to Middlesex County, Connecticut—a captivating blend of rich history and vibrant community life. Nestled along the picturesque Connecticut River, Middlesex County offers an enchanting mix of charming small towns, scenic landscapes, and a thriving arts scene. With its close proximity to major cities like Hartford and New Haven, residents enjoy the perfect balance of suburban tranquility and urban convenience.

One of the most alluring aspects of Middlesex County is its historic antique-style homes. These architectural treasures reflect the area’s rich heritage, showcasing exquisite craftsmanship and timeless designs that transport you back in time. From stately Colonial manors to quaint Victorian cottages, each home tells a story, offering a unique glimpse into the past. Imagine waking up in a beautifully restored 19th-century farmhouse, complete with original woodwork and vintage charm, or sipping coffee on the porch of a classic New England cape, surrounded by lush gardens.

Living in a historic home in Middlesex County means more than just owning a piece of history; it’s about being part of a community that values preservation and celebrates its roots. Explore the local farmer's markets, art galleries, and historic sites that contribute to the county's vibrant culture. Whether you’re seeking a peaceful retreat or an engaging community, Middlesex County’s historic homes provide a warm and inviting atmosphere for you and your family to thrive.

Discover the charm and character of Middlesex County—where history meets modern living, and every antique-style home is a gateway to a storied past. Come and experience the magic for yourself!

Newest Middlesex Homes with Historic Antique Style

$525,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$225,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24192834 MLS

Known as the historic Alice Manee House, this charming Colonial, built circa 1817 (town records list 1825), offers a unique opportunity in the heart of Moodus Village. Featuring 3 bedrooms, 1.5 baths, a wraparound porch, and a walk-up attic with excellent storage, this home offers character, history, and endless potential. Formerly home to a frame shop, the property offers flexibility for both residential and commercial use. The home is in need of cosmetic updates and TLC, being sold As Is. Conveniently located near shopping, dining, local amenities, state parks, and lakes.

17 Plains Rd, East Haddam

$499,900

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24192636 MLS

For more than 150 years, this magnificent Victorian has welcomed generations through its doors, and today it stands more beautiful than ever. Built in 1875, this timeless home celebrates the craftsmanship and character of a bygone era while offering the space, warmth, and flexibility for modern living. Gracefully set on 2.6 picturesque acres, it is more than a home-it's a legacy waiting for its next steward. From the welcoming wraparound porch to the original wood floors, intricate architectural details, soaring ceilings, and sun-filled living spaces, this exceptional home blends historic elegance with everyday comfort. Generously sized rooms provide flexibility for today's lifestyle, while the inviting sunroom with a wood stove is the perfect place to enjoy your morning coffee, unwind with a good book, or gather with family and friends throughout every season. Spacious bedrooms, including a peaceful primary retreat with a charming sitting area, provide comfort and privacy. Thoughtful modern improvements complement the home's timeless appeal. Owned solar panels significantly reduce electric costs, making year-round heating and air conditioning surprisingly efficient. It is a rare opportunity to enjoy the beauty and craftsmanship of an 1875 Victorian without sacrificing the comfort, efficiency, and convenience today's homeowners appreciate.

330 Candlewood Hill Rd, Haddam

$550,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192604 MLS

Step into the perfect blend of timeless New England charm and modern convenience in this beautifully maintained circa-1869 Colonial, ideally located in the heart of East Hampton. Offering over 2,275 square feet of living space, this 4-bedroom, 2.5-bath home showcases the character of a bygone era while featuring numerous thoughtful updates throughout. The custom kitchen is equipped with stainless steel appliances, corian countertops, and ample cabinetry, creating a functional space for everyday living and entertaining. Wide-plank hardwood floors, updated bathrooms, and a flexible floor plan provide warmth and versatility. Major improvements include a high-efficiency natural gas boiler with on-demand hot water, updated electrical service, newer windows, and newer roof, providing peace of mind for years to come. Outside, enjoy a level yard with detached garage and off-street parking. Conveniently situated within a very short distance to the Air Line State Park Trail, local shops, restaurants, schools, the town beach, and all that East Hampton's vibrant village center has to offer. Rich in history, thoughtfully updated, and ideally located, this is a wonderful opportunity to own a home that truly offers the best of old-world character and modern comfort.

124 Main St, East Hampton

$775,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192511 MLS

A rare opportunity to own TWO single-family adjacent homes in the heart of East Hampton! Rich in history and thoughtfully updated, the main residence at 124 Main Street beautifully blends timeless architectural character with the comfort and convenience of modern living. Historic details, classic craftsmanship, and tasteful updates create a home that is both elegant and inviting. A first-floor bedroom and full bath provide the option for a desirable primary bedroom suite or flexible living arrangement to accommodate a variety of lifestyles. Situated toward the rear of the property, 126 Main Street is a second single-family residence offering exceptional versatility. While it could benefit from some updating, it presents endless possibilities as an in-law home, income-producing rental, private guest house, home office, studio, or space for entertaining family and friends. Whether you're looking for multi-generational living, rental income, or simply the flexibility of owning two homes on one parcel, this unique property offers endless potential in a desirable location close to East Hampton's charming downtown, Lake Pocotopaug, restaurants, shopping, and local amenities. A truly one-of-a-kind opportunity!

126 Main St, East Hampton

$3,595,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24190330 MLS

Steeped in history and prominently positioned in the heart of Essex Village, the distinguished "Frederick Scholes House" (circa 1890) offers a rare opportunity to own a landmark waterfront estate. Cherished by its current owners for 49 years and nestled on a quiet lane along picturesque Middle Cove, just off the Connecticut River, this property seamlessly blends timeless character with refined living. Set on a .45 private lot, this meticulously maintained antique residence spans approximately 3,769 square feet and captures serene water views from its beautifully landscaped grounds. Despite its central village location, just moments to shops, dining, and marinas, the home offers an exceptional sense of privacy and tranquility. Rich in architectural charm, the home features soaring ceilings, expansive windows, and elegant, light-filled interiors that reflect generations of thoughtful stewardship. Once known as one of the village's grand homes, its legacy continues today as a warm and inviting retreat with sophisticated style and historic integrity. Designed for both everyday living and entertaining, the property includes a spacious three-car garage and generous living areas that honor its past while accommodating modern lifestyles. The grounds unfold toward the water, offering a peaceful backdrop and a true connection to Essex's coastal beauty. This Historic Essex Village waterfront home is a rare offering where heritage, location, and lifestyle converge.

10 Scholes Ln, Essex

$399,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24179607 MLS

Move right into this Deep River home just moments from the Connecticut River and the charming village and town center. Since purchasing the property, the current owner has completed numerous valuable improvements, including a brand-new roof, new furnace, new oil tank, a tastefully remodeled kitchen, and an updated full bathroom. The main level offers inviting living spaces that blend character and functionality. The living room on first floor is presently used as a bedroom. The laundry is conveniently located off the eat in kitchen and there is a large pantry for storage. The finished upper-level features hardwood floors and provides exceptional flexible living space, while also offering exciting potential for future expansion to create additional bedrooms, a spacious primary suite, home office, or craft room. Additional highlights include updated 200-amp electrical service, and the home is generator-ready, providing added convenience and peace of mind. With public water and public sewer, the property offers both ease of maintenance and flexibility for future growth. Ideally located just minutes from downtown Deep River, you'll enjoy easy access to local restaurants, unique shops, marinas, parks, and the scenic Connecticut River. Whether you're searching for your first home, looking to downsize, or seeking a property with room to grow, this well-maintained home offers the perfect blend of thoughtful updates, future possibilities, and a highly desirable location.

79 River St, Deep River

$895,000

3 Baths ⋅ ACTIVE Status ⋅ 24185656 MLS

A rare and unparalleled opportunity to acquire an iconic c.1900 property set atop a gentle rise at the head of Main Street in historic Essex Village. This substantial, professionally maintained building is comprised of two legal condominium units, and offers unmatched flexibility with its APPROVED MIXED RETAIL/OFFICE/RESIDENTIAL USE status. Potential to create your own custom Essex village pied-a-terre with an income-producing component, or to convert this current office building into your full-time Essex home. Solid and well maintained, the building is currently divided into two condominium units. Unit 'A' consists of 1,200 SF on the first floor. Unit 'B' comprises 1,977 SF on the second level and 1,083 SF on the third level. Features include first class mechanical systems, kitchen, and a spacious second level room overlooking Main and Pratt Street with glimpses of the CT river. A terrace and private rear yard are accessed from the second level. The location is spectacular. Enjoy a commanding presence, and commanding views, of the heart of Essex village. Adjacent to shops, restaurants, yacht clubs, marinas, and artist galleries.

3 Essex Sq, Essex

$2,200,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24180698 MLS

A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Registery of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity with six fireplaces, original hardware, twelve-over-twelve windows, elegant period moldings, richly detailed mantels, and a commanding facade highlighted by Ionic columns, a Palladian window, fanlight entry, and granite foundation. A 19th-century carriage house on the property evokes the atmosphere of Warner's original gentleman-farmer estate. This historic landmark property sets the stage for unforgettable event possibilities on picturesque pastoral grounds. Revered by historians and preserved with exceptional care, this irreplaceable legacy property offers a rare opportunity to own one of Connecticut's most significant surviving Federal residences. Extensive original letters, bills, receipts, and construction records survived, documenting the artisans, materials, suppliers, and methods used to create this architectural masterpiece. Chester offer an abundance of amenities / local events, and borders the CT River.

47 E Kings Hwy, Chester

$1,095,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24182878 MLS

Welcome to 8 Meeting House Road, a secluded and serene retreat. This special property was the former Reverend John Marsh parsonage circa 1818. It has been privately owned for the last 41 years by the same family and is now ready for a new steward. This gracious historic home features a light-filled eat-in kitchen, a fabulous enclosed sunporch overlooking verdant views of the property, and multiple fireplaces. There are several multifunctional rooms including a library with built-in bookcases, a music room, and a generously sized great room with beamed cathedral ceilings. There are also five spacious bedrooms and 2.5 updated bathrooms. The property is set on over four acres with stone walls running throughout, and outbuildings, including a carriage house that has plenty of space for a workshop, a studio, or an office. Behind the carriage house you'll find a natural in-ground gunite pool in a lush private setting. This is a rare opportunity to own an intact historic property with this kind of heritage in the Connecticut River Valley.

8 Meeting House Rd, Haddam

$12,000,000

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24183764 MLS

A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a local treasure for generations. The improvements require significant modernization and renovation, presenting an ideal opportunity for someone seeking to preserve and enhance a historic property. Whether envisioned as a private estate, hospitality-related use, office, wellness concept, or other permitted use, the property offers exceptional potential for those with a vision for restoration and stewardship. Ideally situated on Boston Post Road with convenient access to Interstate 95, Route 9, shoreline beaches, marinas, shopping, and restaurants, the property benefits from excellent visibility and accessibility within one of Connecticut's most desirable shoreline communities. This offering is subject to the property's historic designation and must be purchased together with the adjoining Bushnell Farm land parcel (MLS #24183765). The combined offering presents a truly unique opportunity to preserve, restore, and shape the future of one of the Connecticut shoreline's most recognizable historic properties.

1445 Boston Post Rd, Old Saybrook

$1,199,999

9 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24179935 MLS

Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and carefully selected reproduction details creating warmth and authenticity. Multiple living and dining spaces unfold effortlessly, anchored by six fireplaces, including an impressive 12' natural stone Rumford. With seven spacious bedrooms-each with its own private bath-the home is uniquely suited for multi-generational living, hosting, or continued hospitality use. The third-floor suite offers a private retreat with a wood-burning fireplace, perfect for extended family or guests. A new kitchen addition further enhances flexibility, easily accommodating in-law living or private guest quarters. Curated perennial gardens, a white oak pergola, and a beautifully crafted stone terrace create a setting designed for gathering and relaxation. Enjoy evenings by the fire pit, surrounded by timeless landscape design. This property offers style, comfort and charm all amidst the local shops, restaurants, marinas, and nearby shoreline destinations-all within two hours of both NY and Boston. Previously, an Award-Winning Bed & Breakfast, and currently featuring two Airbnb guest suites with private access.

209 Main St, Deep River

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