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

$589,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206098 MLS

A rare blend of history, privacy and natural beauty awaits at this exceptional Clinton residence, set on over two beautifully landscaped acres. Built in 1825 and thoughtfully renovated, this 1,902 square foot Colonial seamlessly combines historic character with modern comfort. Surrounded by extensive gardens, mature plantings, stone walls, open lawns and a nearby stream, the property offers a picturesque New England setting. A charming greenhouse, detached two-car garage, patios and a screened porch provide inviting spaces to enjoy the tranquil surroundings. Inside, timeless architectural details blend effortlessly with thoughtful updates. The custom Gedney kitchen serves as the heart of the home, multiple fireplaces and a classic beehive oven add warmth and character. Expansive windows fill the interior with natural light and frame beautiful views of the meticulously maintained grounds. Original features and wide-board hardwood floors reflect the home's rich heritage. The first floor primary bedroom offers convenience and privacy, while the living room and library provide comfortable gathering spaces. Three additional bedrooms are located on the upper level. Ideally located near Clinton's town center, restaurants, marinas, shopping and beaches, Chamard Vineyard, art galleries, dog park, Peters Memorial Woods with hiking trails, kayaking through local waterways this distinctive property offers the perfect balance of peaceful seclusion and coastal convenience.

130 Glenwood Rd, Clinton

$850,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204587 MLS

Welcome to 36 Waterside Lane, a unique historic home located steps from Clinton Town Beach. With its four bedrooms, six fireplaces, wide-plank floors, exposed beams, and original window sashes, this home exudes character throughout. The layout is generous and flexible - studios, libraries, guest quarters, laundry room, walk-in pantry, home offices - without losing the bones that make this place what it is. There is an unmistakable sense of craftsmanship here that no newly constructed residence can reproduce. A detached two-car garage equipped with built-in workbenches, pegboard walls, oversized shelving and 780sq feet of work area provides ample space for an artist's studio, pottery shed, craftsman workshop, or garage band. Additional storage space can be found in the full basement and walk-up attic. Set on .88 acres, professionally landscaped, with extensive stonework, a back patio and lined with mature trees offering shade, this is a rare find so close to everything. Walk to Clinton Town Beach or downtown that's alive with cafes, restaurants, shops, music and theater - a true New England maritime gem! A chance to own what can't be built new: authenticity, craftsmanship, and provenance, ready for its next chapter. Recent updates: new convection gas range with air-fry, new hood, new 50-year roof, full interior/exterior repaint, 100+ panes of glass replaced, original sashes restored, new bulkhead and basement windows.

36 Waterside Ln, Clinton

$749,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24196454 MLS

Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.

19 High St, Middlefield

$650,000

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

$1,055,000

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

$1,550,000

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

$340,000

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24096243 MLS

** A Unique Opportunity at 30 Chestnut Hill Road, Killingworth** Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of transformation. Exterior work-including masonry, roof detailing, windows, and finish-is underway. Current renovation plans envision a spacious 3-bedroom, 2.5-bath layout featuring a dedicated office, library, and over 3,000 square feet of living space. When completed, the home-along with a barn/garage addition and refreshed landscaping-is projected to be valued between $800,000 and $925,000. An optional larger barn built on the existing foundation at the rear of the property could add approximately $248,000 in additional value. The seller is now seeking a new steward for this exceptional property. There's also the option to retain the current owner as architect and contractor to help bring the vision to life. This is a rare chance to be part of a meaningful restoration-combining history, craftsmanship, and future potential.

30 Chestnut Hill Rd, Killingworth

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