Darien, CT Homes for Sale with Acreage

Exquisitely renovated center hall colonial set on two perfectly manicured acres at end of quiet, private cul-de-sac, offering exceptional space & timeless appeal for both everyday living & entertaining. Renovated in 2023 by ERI Building & Design, this stunning six-bedroom home with private office, four full & two half baths showcases impeccable craftsmanship & sophisticated design throughout.

Deborah Hidy Houlihan Lawrence

You don't arrive here by accident. You arrive because something in you was looking for this. It begins quietly, a glimpse of water, a sense that the noise of everything else has begun to fall away. Nestled within Tokeneke along the Five Mile River, the house is not just seen, but felt, like a song you've loved forever. Reimagined, redefined, and brought into its full expression by Brinley

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

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

This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately

Robin Stineman William Pitt Sotheby's Int'l

Privately set within Darien's coveted Tokeneke neighborhood, 45 Old Farm is a remarkable custom estate by award-winning builder Oliver Wilson. A tree-lined drive framed by natural stone pillars sets the tone for this exceptional property. Inside, every room is thoughtfully composed with striking sight lines and abundant natural light. The chef's kitchen is a true centerpiece, anchored by a

Amanda Spatola Houlihan Lawrence

Just in time for summer-this exceptional property offers the ultimate in luxury living and outdoor enjoyment. Imagine relaxing poolside by your new heated pool and spa, surrounded by beautifully landscaped grounds and sweeping views of the golf course. Inside, the home is equally impressive. The expansive primary suite is a true retreat, featuring a private sitting room that opens onto a deck

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

A truly exceptional offering! This beautifully expanded Colonial sits on a rare, level acre in one of Darien's most coveted neighborhoods. The property sets itself apart with sweeping, flat grounds, professionally landscaped to create both privacy and an elegant sense of openness. Inside, the home is designed for refined living and effortless entertaining. A gracious living room with a wood

Serena Richards Brown Harris Stevens

This stunning custom-built home, completed in 2005, showcases exceptional craftsmanship and timeless design throughout. Rich millwork, refined architectural details, and high-end finishes create an elegant yet inviting atmosphere across every level. Ideally situated in a quiet, sought-after location, the home offers the perfect balance of privacy and convenience, just moments from town,

Janine Tienken Houlihan Lawrence

Beautifully sited expanded cape on open level 1.5 acres renovated by Fox Hill Builders. This open-concept home features 4 bedrooms, 4 and 1/2 baths, and sun-filled, spacious rooms built for easy living and entertaining. The kitchen offers stainless steel appliances, custom cabinetry, a large center island, and granite countertops. The family room, open to the kitchen with New England colonial

Lynne Somerville 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

This charming and updated colonial home, steeped in gracious style and beautiful natural light, is a great place for entertaining. It's set on a gorgeous professionally landscaped flat acre+ with heated pool and is located on one of Darien's most desirable in-town streets. A spacious living room with fireplace flows into a generous formal dining room and sunroom, both of which have wall-to-wall

Melinda Beardsley Brown Harris Stevens

Set along a picturesque stretch in one of Darien's most sought-after neighborhoods, 234 Brookside Road offers a rare blend of timeless architecture, privacy, and modern comfort. Surrounded by mature trees and beautifully landscaped grounds, this exceptional property provides a serene, retreat-like setting just minutes from town, top-rated schools, and the coastline. This HOBI award-winning

Kristin Nemec William Pitt Sotheby's Int'l

Come see this freshly transformed home on a gorgeous, flat 2.64 acre lot in the heart of Darien. Rooted in history and alive w/possibility, this freshly renewed and effortlessly inviting, 3,411 sf residence welcomes w/antique wide plank floors whispering the past, while a bright, open flow draws you into the present. The formal dining room sets the stage for memorable evenings, while an expansive

Serena Richards Brown Harris Stevens