Imagine stepping into a world where history whispers through every wall, yet modern luxury awaits at every turn. Nestled in Connecticut’s most enchanting locales, from Mystic’s waterfront to Litchfield County’s sprawling estates, these five remarkable properties—priced between $1,999,000 and $2,280,000—offer a rare blend of historic charm and contemporary sophistication. Whether it’s breathtaking river views, preserved architectural gems, or vast acreages steeped in heritage, each home promises a lifestyle woven into the fabric of New England’s scenic beauty and cultural richness. Discover retreats that aren’t just places to live, but stories to tell.
40 Holmes Street | $2,280,000


Jason Pollard

Jason Pollard
Rising above the vibrant heart of Mystic’s historic district, this captivating 3-bedroom, 2.5-bath residence offers an elevated perspective with stunning water views from every window. Overlooking the scenic Mystic River, the home provides direct water access through a private mooring, ideal for boating enthusiasts eager to explore the waterways. Positioned between the renowned Mystic Seaport and the iconic Mystic River bascule drawbridge, this well-maintained property places you at the center of a dynamic riverfront community. Step outside and stroll to an array of charming shops, acclaimed restaurants, and engaging entertainment options. Blending historic allure with modern convenience, the location caters to those seeking both tranquility and an active lifestyle. Embrace the rich culture and timeless beauty of New England coastal living in a home that effortlessly balances serenity with the pulse of downtown Mystic.
- Price:
- $2,280,000
- Size:
- 2,402 sq ft
- Contact:
- Jason Pollard, Randall, Realtors-Christie’s, 860.287.1976
Historic Luxury Country Estate | $2,200,000


Sharon Wyant Mcguire

Sharon Wyant Mcguire
Set against the serene backdrop of Litchfield County’s waterfront, this expansive 22.9-acre estate seamlessly marries historic allure with contemporary sophistication. Original wide-board floors and five cozy fireplaces evoke timeless charm, while a newly added 1,500-square-foot primary suite offers modern indulgence with heated floors, a luxurious bath, and a fully equipped lower-level gym. The heart of the home, a gourmet kitchen, boasts updated appliances and a stylish coffee bar, complemented by renovated bathrooms throughout. Outside, meticulously landscaped grounds feature a stone patio, greenhouse, and basketball court, with a whole-house generator ensuring peace of mind. A renovated party barn provides extraordinary versatility, housing 10-car storage with a professional lift, vibrant entertaining spaces like a rec room and axe-throwing area, and a complete guest apartment. Nearby, hiking, skiing, serene lakes, and a rich local culture await exploration.
- Price:
- $2,200,000
- Size:
- 3,971 sq ft
- Contact:
- Sharon Wyant Mcguire, William Pitt Sotheby’s International Realty, 203.417.2925
Located In The Heart Of Essex Village | $2,195,000


Listing agents: Kyle Hinding & Kyle Hinding

Listing agents: Kyle Hinding & Kyle Hinding
Set against the serene backdrop of a waterfront haven, the Simeon Post House, circa 1818, stands as a timeless treasure in historic Essex Village. This iconic residence welcomes with an inviting front porch, setting the tone for the architectural elegance within. A gracious entry ushers you into beautifully proportioned rooms that harmonize with the natural surroundings, from the front parlor flowing into a cozy family room with a gas-burning fireplace to the striking river stone floor that adds warmth. French doors reveal a formal dining room, ideal for cherished gatherings, while the chef’s kitchen, boasting a Wolf six-burner gas range, offers a casual dining nook for everyday ease. Upstairs, the primary suite provides a tranquil escape with dual walk-in closets and a private bath, accompanied by three additional bedrooms. Outside, a sprawling bluestone terrace overlooks park-like grounds, perfect for entertaining, with a charming post-and-beam carriage barn adding versatile space for guests or a studio.
- Price:
- $2,195,000
- Size:
- 3,724 sq ft
- Contact:
- Kyle Hinding & Kyle Hinding, Coldwell Banker Realty, 860.857.4219 , 860.391.1701
65 Wildbrook Lane | $1,999,900


Listing agents: Amanda Martin & Nina Fee

Listing agents: Amanda Martin & Nina Fee
Set against the serene backdrop of a waterfront haven, this extraordinary estate in Eliot, Maine, marries the timeless charm of a New England farmhouse with the sophistication of a custom-built retreat. Spanning 9.6 tranquil acres, the property promises rare privacy while remaining just minutes from Kittery Foreside, downtown Portsmouth, and York beaches. The main residence captivates with a wraparound porch, solid maple flooring, quartz counters, and a primary suite featuring Italian marble. A private au pair suite and a brand-new 2024 two-bedroom accessory dwelling unit above a heated three-car garage offer versatile living options for guests or family. Modern comforts abound with central air, a whole-house generator, and a finished basement boasting a gym and home theater. Perfect for those seeking space and style, this turnkey compound provides an idyllic escape near vibrant coastal communities.
- Price:
- $1,999,900
- Size:
- 5,960 sq ft
- Contact:
- Amanda Martin & Nina Fee, KW Coastal and Lakes & Mountains Realty, 603.610.8500 , 603.610.8500
241 Wallace Rd | $1,999,000


Marianna Vis

Marianna Vis
Set against the serene backdrop of rolling countryside, this iconic landmark estate redefines rural luxury with its modern farmhouse design, meticulously crafted in 2014. Spanning an impressive layout, the home offers seven spacious bedrooms and seven bathrooms, thoughtfully arranged to accommodate multi-generational living with ease. Its flexible floorplan adapts to diverse family needs, while a sprawling entertaining deck invites gatherings under open skies, perfect for creating cherished memories. A standout feature, the Carriage House, boasts radiant floor heating and space for over six vehicles, catering to car enthusiasts with style. Additionally, it includes two well-designed in-law apartments, ensuring privacy and comfort for extended family. This estate seamlessly blends functionality with elegance, offering a tranquil retreat where every detail enhances a harmonious lifestyle amidst the beauty of nature.
- Price:
- $1,999,000
- Size:
- 9,113 sq ft
- Contact:
- Marianna Vis, Four Seasons Sotheby’s International Realty, 603.413.7600













