Tokeneke, CT Homes for Sale with Acreage

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

Nestled on a gorgeous, professionally manicured acre in desirable West Norwalk, this lovely 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of elegance and modern efficiency. The main level boasts a fantastic open floor plan, featuring a gourmet eat-in-kitchen with granite countertops and stainless steel appliances. Entertain in the formal dining room or relax in the spacious sunken

Maria Formanek William Pitt Sotheby's Int'l

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

Completely reimagined and renovated inside and out in 2023, 31 Hancock Lane is a remarkable English stone country residence where timeless architecture meets sophisticated modern living. Privately positioned on 1.5 beautifully landscaped acres, the property captures the romance and enduring character of a classic country estate while offering the refinement, comfort, and craftsmanship of a

Kristin Nemec William Pitt Sotheby's Int'l

Classic charm, updated for today. This distinctive English cottage offers over 4,000 square feet of gracious living space, set on over one acre of expansive, level grounds on one of the largest lots on the street-in one of Darien's most sought-after locations. Inside, generously proportioned, light-filled rooms blend timeless architectural character with an easy, comfortable flow. Rich hardwood

Caroline Hanley Houlihan Lawrence

Opportunities like this are rare. Calf Pasture Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a blank canvas for imagination. Properties like this remain in the same hands for many decades and do not come up for sale often. Located approximately a half mile offshore, it is among the closest islands to the mainland and takes its

Andrew Whiteley Brown Harris Stevens

Privately set at the end of a quiet cul-de-sac, this classic Colonial offers exceptional privacy, beautifully proportioned living spaces and a one-of-a-kind detached barn on a level 2-acre lot. The 4-bedroom home features a warm, timeless floor plan designed for both everyday living and entertaining. An open foyer leads to an inviting living room with built-in bookshelves and window seating,

Robin Halsey 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 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

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

Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance. Designed by Hunt & Hunt Architects and completed in 1914

Leslie McElwreath Sotheby's International Realty

Situated on a charming cul-de-sac in one of Darien's most desirable coastal neighborhoods, 21 Harbor Road offers approximately 4,400 square feet of beautifully updated living space, with water views from most rooms and within walking distance of Great Island, Pear Tree Point Beach, and Weed Beach. Expertly expanded and renovated, this 5-bedroom, 3.5-bathroom 1960s Cape pairs classic New England

Amanda Spatola Houlihan Lawrence

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

A rare opportunity to live in the exclusive Wilson Point Association, this stately Georgian Colonial is privately sited on 1.4 acres with sweeping views of Long Island Sound. A true secluded oasis, the home features a sophisticated open floor plan, vaulted ceilings, light-filled rooms, and exceptional custom millwork and architectural details throughout. The luxurious primary suite offers a

Janine Tienken Houlihan Lawrence

Opportunities like this are exceedingly rare. Betts Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a canvas for imagination. Located approximately one mile offshore, the island is distinguished by its natural land bridge, which connects its two halves and creates a protected cove long favored by boaters. A small bungalow

Andrew Whiteley Brown Harris Stevens

Set behind stone walls on nearly 2 acres, this exceptional 5-bedroom home offers over 5,000 SF of refined living in a truly extraordinary setting. A dramatic 2-story foyer w/circular staircase and exquisite herringbone floors sets the tone for elegance throughout. Walls of windows fill the gracious interiors with natural light and frame manicured grounds and lush gardens. The formal living room,

Serena Richards Brown Harris Stevens

Welcome home to the Gold Coast of Norwalk. Location, space and timeless design come together in this stunning turn-key colonial with waterviews of Long Island Sound. Set on one acre in Norwalk's coveted Shorehaven neighborhood, it's just a short walk to Sandy Beach and the Sprite Island Yacht Club boat launch. Custom features and 10-foot ceilings elevate the main level and make it ideal for both

Darlene Letersky Coldwell Banker Realty

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

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

Nestled at the end of a long private drive south of the Merritt Parkway, this classic Colonial offers timeless character, generous living space, and a highly convenient location. Beautifully expanded and thoughtfully updated years ago, the home showcases exceptional craftsmanship, enduring quality, and solid construction described as having "great bones." The main level is rich with architectural

Lisa O'Rourke William Pitt Sotheby's Int'l

Set on a level one acre lot along a private road in desirable Newfield neighborhood, 3 Megan Lane pairs classic Colonial curb appeal with a spacious, modern interior designed for both everyday living and entertaining. The expansive main level features generously proportioned rooms, three fireplaces, formal living and dining rooms, and a flexible den or home office. At the heart of the home is the

Max Dober Keller Williams Prestige Prop.

Welcome home to effortless one-level living on a premier, lush one-acre lot in Darien. Available for the first time in 56 years, this beautifully maintained 4-bedroom, 2.5-bath ranch features a newer roof, windows, and driveway. The large classic footprint spans over 3000sf and allows for easy customization and personal upgrades to make this house your own. This sweet home is nestled in a

Michelle Donzeiser William Raveis Real Estate

A truly exceptional private estate, this country compound set on more than three private acres, blends timeless character, refined design, and modern luxury. Anchored by a beautifully preserved 1932 main residence and an extraordinary 2,300-square-foot poolside entertainment barn, the property is designed for both everyday living and effortless entertaining. The main residence offers five

Christine Saxe Compass Connecticut, LLC

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

Built in 2023 by noted developer Ritzzo Development and refreshed in 2026, this striking Contemporary offers 10K+ SF of elevated living on two manicured acres with a heated saltwater pool and built-in BBQ. Extensive updates -- new paint, refinished wide-plank white oak floors, new trim, updated AV, generator, and a fully reimagined lower level with media room, gym, sauna, and steam room -- make

Amanda Bates Houlihan Lawrence

Privately set on 2.15 beautifully landscaped, park-like acres just minutes from town, this exceptional six-bedroom residence offers a rare blend of timeless elegance, everyday comfort, and complete privacy. Thoughtfully designed for the way people truly live, the home is filled with light, gracious proportions, and inviting spaces that welcome both intimate gatherings and memorable celebrations.

Janine Tienken Houlihan Lawrence

PRISTINE & PERFECT!! Nestled on a charming cul-de-sac close to town, this lovely and meticulously maintained 4-bedroom home offers the perfect blend of comfort, style, and convenience. Set on a level acre in a picturesque setting, the home features a welcoming open floor plan with sun-filled living spaces that flow effortlessly, creating an inviting setting for both everyday living and

Bettina Hegel Brown Harris Stevens

1716 Shippan Avenue represents a rare opportunity to own a legacy estate on 1.01 acres in Stamford's sought-after Shippan neighborhood. This distinguished Tudor home is comprised of approximately 6,000 square feet of timeless architectural character, sophisticated modern updates, and a thoughtfully designed 2016 renovation by Granoff Architects. With 5 bedrooms, 3 full and 2 half baths, the home

Amanda Spatola Houlihan Lawrence