Homes for Sale near Middlesex Middle School

Originally the sole residence on Wildcat Road, this distinguished 1925 stone manor blends timeless architectural elegance with a commanding setting. Located within Darien's coveted Delafield Island private association, the property is approached by a sweeping circular drive and surrounded by mature landscaping offering a rare sense of privacy, grandeur, and permanence, just minutes from downtown

Janine Tienken Houlihan Lawrence

New construction from foundation up and ready for 2026! On a coveted Darien cul-de-sac, this modern colonial boasts 6500sf of elegance and comfort. Step through the welcoming foyer, complete with a coat room and powder room, and into a spacious, light-flooded living room, perfect for gatherings that stretch into the evening. The custom kitchen is a true centerpiece, with a grand stone island,

Serena Richards Brown Harris Stevens

Set on one of Darien's most sought-after, multi-million dollar cul-de-sacs, this sprawling wood and brick ranch offers exceptional scale and endless potential for the discerning buyer, renovator, or builder. Positioned on a remarkably private 2.5 acre lot, abutting another 10+ acres of protected wetlands, the setting affords unmatched peace, natural beauty, and exclusivity. The interior boasts a

Ingrid Hess Compass Connecticut, LLC

Introducing One Sedgwick Lofts - a Boutique Collection of thoughtfully designed, one-of-a-kind condominium residences offering a fresh and refined approach to low-maintenance luxury living in the heart of Darien. Blending modern design with timeless sophistication, these residences are crafted for today's discerning buyer seeking both style and simplicity. Open-concept layouts, soaring ceilings,

Kathryn Bates Compass Connecticut, LLC

A rare opportunity to live, earn, or invest, all in one property! Stylishly renovated main residence paired with a fully renovated one bedroom cottage, creating a rare opportunity for supplemental income, multigenerational living, or a private home office. Both residences are currently leased below market rents, offering immediate upside for future income potential. Each home has been updated to

Shannon Drury Berkshire Hathaway NE Prop.

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering one acre of east facing views that can be enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored

Shelly Tretter Lynch Compass Connecticut, LLC

This Dockside home is a short paddle away from Five Mile River. Quietly iconic. Effortlessly cool. Live large without living complicated. This is the rare waterfront home that offers the lifestyle of a grand estate with the ease of a true lock-and-leave retreat. Set on just over an acre in the private Tokeneke Association it's designed for living well not maintaining endlessly. There are four

Stacy Book William Raveis Real Estate

Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the

Ashley Dineen Compass Connecticut, LLC

Nestled on a quiet cul-de-sac in a convenient Darien location, this beautifully renovated and expanded Nantucket-style Cape offers timeless charm and exceptional functionality. Set on .46 landscaped acres, the light-filled home features an open-concept kitchen with updated appliances, gas fireplace, and spacious dining area flowing seamlessly into sun-filled living spaces and multiple stone

Robin Halsey Compass Connecticut, LLC

Home with seasonal water views of Holly Pond. Present use: Boarding House. Sold "As Is".

Angela Abate William Raveis Real Estate

Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and

Keiley Fuller Compass Connecticut, LLC

Welcome to this beautifully renovated two-bedroom condo in one of Darien's most convenient locations. Just steps from Goodwives shopping center, the Metro-North train station, and the vibrant energy of downtown Darien, this home offers the perfect blend of modern comfort and walkable lifestyle. Pass through the private gate and be greeted by a serene personal courtyard and garden. A sliding glass

Nellie Snell William Raveis Real Estate

Exceptional new construction estate by K&C Builders Inc., set on over 2.5 private acres on coveted Brookside Road. Offering approximately 11,000 SF across four finished levels, this stunning residence features 6 bedrooms, 8 full baths, and 1 half bath. Designed for elegant entertaining and everyday living, the home showcases a spectacular great room, gourmet chef's kitchen, private study,

Sylwia Kozlowski William Raveis Real Estate

105 Rose Lane blends classic charm with modern updates in a welcoming Darien neighborhood. This sun-filled 4-bedroom, 2-bath home features an open-concept first floor, an updated kitchen, and beautifully renovated bathrooms for a move-in ready experience. An additional living space offers flexibility for relaxing or entertaining, while the fantastic front porch is perfect for enjoying morning

Genevieve Schettino Compass Connecticut, LLC

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned

Shelly Tretter Lynch Compass Connecticut, LLC

Tucked in the Delafield Island Association and moments from the beach, town, train, & schools, this custom built 5-bedroom residence offers an ideal blend of timeless elegance & modern comfort. Thoughtfully designed with soaring ceilings, an open floor plan & sun-filled interiors, nearly every main living space enjoys beautiful views of the pool & private backyard. A dramatic two-story foyer

Cheryl Williams Brown Harris Stevens

Welcome to 20 Locust Hill Road, a stunning in-town, new construction opportunity in Darien, CT. This now completed modern colonial/farmhouse-style home, constructed by an experienced builder renowned for high-end residential properties throughout Fairfield County, offers 5 bedrooms, 4.5 bathrooms, and an expansive 4,897 square feet of living space. Situated on a generous .50 acre in-town lot,

Robert Marchesi Compass Connecticut, LLC

Spacious Colonial in the sought-after Hindley Elementary School district! Offering over 2500sf on the main and upper levels, this 5-bedroom, 3 full and 1 half bath home is designed for comfortable everyday living and entertaining. The oversized primary suite is complemented by generous living spaces, while 500sf finished lower level with wet bar provides an ideal recreation room, media room, home

Fay Goebert William Raveis Real Estate

A rare opportunity to own a new construction home with Deeded Beach Rights on coveted Nearwater Lane in one of Darien's most desirable coastal neighborhoods. A seamless blend of sophisticated design, modern comfort, and coastal living. Moments from Weed Beach, downtown Darien, commuter rail service, and a Blue Ribbon elementary school. Designed for everyday living and entertaining, the home

Michael Ferraro Compass Connecticut, LLC

Welcome to 36 Richmond Drive! Tucked into a great Darien neighborhood, this three-bedroom, two-bath ranch is close to everything, bike to Cherry Lawn Park, walk to local shops and restaurants, or hop on the train in minutes. The home sits on a level, corner lot of over half an acre, with stone patios, a built-in grill, and plenty of yard space for play and entertaining. Inside, you'll find a

Nancy Peter Houlihan Lawrence

Set on 2.19 private acres in a prime Darien location, 222 Brookside Road offers exceptional space, privacy, and opportunity just minutes from town and Cherry Lawn Park. With more than 7,000 square feet above grade, plus an additional 3,000 square feet on the lower level, this expansive 4-bedroom, 5.5-bath residence provides an incredible canvas to create a home tailored to your vision. Generously

Amanda Spatola Houlihan Lawrence

Exceptional NEW CONSTRUCTION - Walk to Town - Experience a thoughtfully designed home by V&A Construction, a highly regarded local builder known for exceptional craftsmanship. Just a short walk to town, shops, restaurants and the train, the location is as convenient as it is desirable. The home features handcrafted cabinetry and millwork, wide-plank white oak floors and high ceilings throughout.

Katherine Kuras BHHS Darien/New Canaan

Designed by custom home builder Vita Design, this exciting newly constructed modern residence is a refined architectural statement that balances scale and light, capturing direct 5 Mile River views and a connection to its natural surroundings. Finished across four levels, the home features dramatic 10- and 16-foot ceilings and a main level wrapped in floor-to-ceiling European-style windows

Nellie Snell William Raveis Real Estate