Homes for Sale near Darien High School

Newly rebuilt to perfection in 2019 this 4 bed, 3.1 bath Colonial offers the ideal blend of luxury, comfort, and convenience. Just 2 blocks to Noroton Heights train station, Darien Commons, and Heights Crossing, the home provides easy access to shopping, dining, schools, and commuting. Perfect for both everyday living and entertaining, the open floor plan boasts 9+ft ceilings and gleaming

Gaynor Brennan BHHS Darien/New Canaan

28 Shields Road offers the lifestyle today's buyers seek-refined design, effortless flow, and spaces equally suited for relaxed evenings or lively gatherings. Set along one of Darien's most desirable streets, this six-bedroom residence spans four finished levels, filled with natural light, crisp architectural lines, and thoughtfully updated interiors that feel both current and timeless. The

Deirdre McGovern Compass Connecticut, LLC

Perfectly positioned in one of Darien's most coveted neighborhoods, 8 Sunset Road is the home you've been waiting for. This elegantly updated Colonial seamlessly blends timeless architecture with the ease of modern living. Spanning over 4,800 square feet, this five-bedroom, four-and-a-half-bath residence offers an exceptional floor plan suited for both entertaining and everyday comfort. The

Katharine Gray Bunoski Compass Connecticut, LLC

Introducing 13 Sunswyck Rd, a distinguished custom residence set within Darien's prestigious Delafield Island. Completed in 2020, this architecturally refined home offers a seamless balance of modern sophistication and timeless design, with an emphasis on light, scale, and craftsmanship. Offering 5 bedrooms (with a possible 6th in the unfinished attic), 4 full and 2 half baths, 2 office spaces

Cheryl Williams Brown Harris Stevens

Nestled on one of Noroton Heights' most sought-after streets, this sun-drenched coastal charmer seamlessly blends classic appeal with thoughtful modern updates. With newly renovated bathrooms, a new deck, and beautifully refinished hardwood floors, this home captures the essence of Darien living with an enviable walk-to-everything location. The fully fenced, level backyard has been lovingly

Victoria Banks William Raveis Real Estate

Nestled in one of Darien's most cherished neighborhoods, this charming Cape Cod home offers the perfect blend of comfort, convenience, & community. Situated on .21 acres, this 4-bedroom, 2 full-bath residence is filled with warmth, character, & endless potential. The main level features a spacious living and dining area, ideal for both everyday living & entertaining, anchored by a cozy

Cristina Veeder Compass Connecticut, LLC

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

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

Tucked away on a quiet cul-de-sac setting just off a private road, 201 Middlesex Road offers a rare combination of turnkey luxury, convenience, and timeless family living in one of Darien's most sought-after neighborhoods. Extensively renovated and beautifully maintained, this 4-bedroom home is ideally located close to town, Metro North, shopping, parks, and Darien's award-winning schools,

Meg Schwanhausser 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 guest retreat. Both residences are currently leased below current market, offering immediate upside for future income potential. Each home has been updated

Shannon Drury Berkshire Hathaway NE Prop.

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

**Best and final offers provided to seller agent by Wed (6/3/26) at 5pm. Seller will have a decision by Noon on Thursday.** Move right into this beautifully updated Darien home offering an exceptional blend of modern luxury, open-concept living, and commuter convenience. Designed for both effortless entertaining and comfortable everyday living, the sun-filled interior features soaring ceilings,

Ben Fitts Coldwell Banker Realty

Come see this charming, move-in-ready home in pristine condition! Featuring 3 bedrooms and 2 full baths, this inviting residence offers a completely fenced, private backyard perfect for relaxing, entertaining, or gardening. Ideally located just steps from the train station and the vibrant shops and restaurants of Noroton Heights, convenience is at your doorstep. Inside, you'll find eight

Maggie Marchesi Compass Connecticut, LLC

Built by an award-winning builder and thoughtfully updated throughout, this exceptional home offers timeless design, quality craftsmanship, and a highly desirable location close to town, shopping, and everyday conveniences. A welcoming open floor plan features elegant living and dining spaces, a private home office, and a gourmet kitchen that seamlessly flows into the sun-filled family room with

Robin Halsey Compass Connecticut, LLC

You don't arrive here by accident. You arrive because something in you was looking for this. It begins quietly, panoramic views 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

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

Peace, Privacy, and Timeless Elegance in Darien Discover the perfect antidote to busy life in this beautifully refreshed, custom-built colonial. Lovingly maintained by its original owners, 107 Raymond Street offers an idyllic blend of quiet sophistication and spacious comfort. Step into a grand two-story foyer with herringbone oak floors, leading to formal spaces rich in architectural

Melissa Engel Douglas Elliman of Connecticut

Step into timeless elegance at 150 Holmes Avenue in Darien. This sunlit Victorian home effortlessly blends classic charm with modern convenience, offering a warm and inviting space for living, entertaining, and making memories. With 4 spacious bedrooms and 2 full baths, there's plenty of room to grow, host, or simply enjoy the good life. Inside, high ceilings and an abundance of natural light

Keiley Fuller Compass Connecticut, LLC

Waterviews!! Welcome to 8 Seagate Road, a rare opportunity to live in one of Darien's most sought after waterfront communities! Enjoy views of Holly Pond from this custom-built home, offering a terrific layout. The large living room offers built-in cabinetry, a cozy fireplace & leads to the formal dining room, both with beautiful water views! The bright kitchen is nicely sized, with quartz

Kevin Quick William Pitt Sotheby's Int'l

Welcome to 85 Hecker Avenue, a stunning custom rebuild in the heart of Darien's coveted Noroton neighborhood, where modern luxury meets everyday convenience. Thoughtfully designed with 4 spacious bedrooms and 5 full bathrooms, this turnkey home features an open-concept floor plan centered around a beautifully appointed kitchen and inviting living spaces, along with a dedicated home office for

Michael Spindler Real Broker CT

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

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

Escape to your own private waterfront sanctuary at this hidden gem on Holly Pond, where relaxing on a back porch with a gentle breeze as the sun sinks into the water is your daily reality. Seamlessly designed for effortless entertaining and coastal living, the main level features a formal dining room and a fully renovated chef's kitchen (2021). The spacious living room, anchored by a cozy

Kristin Nemec William Pitt Sotheby's Int'l

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

Welcome to 20 Locust Hill Road, a stunning in-town, new construction opportunity in Darien, CT. This 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, this home

Robert Marchesi Compass Connecticut, LLC

Storybook Cape nestled in one of Darien's most sought-after in-town neighborhoods. From the moment you step through the front door, this home captivates with its warmth, charm, and thoughtfully updated interiors. The heart of the home is the beautifully renovated kitchen featuring new gourmet appliances, Quartz countertops, and an open flow into the dramatic family room with soaring ceilings,

Janine Tienken 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

Step into a truly special offering- a stately New England home, thoughtfully RENOVATED and completely MOVE-IN READY. Conveniently located close to the train, elementary school, downtown shopping/dining, and parks. Situated on over half an acre this home also enjoys access to a private Cul de sac ideal for bike rides and walks, creating a true neighborhood feel. As you enter the home, you are

Allison Santopietro William Raveis Real Estate

(Don't miss the spectacular waterfront video). On the water in the private Tokeneke Association, Short Rocks Manor is poised at the very tip of Arrowhead Way, high above Scotts Cove and Long Island Sound. This breathtaking, updated 1925 English-style stone manor sits on 2.11 private acres of sweeping lawns and gardens down to the water. The 5,823 square feet of exquisite craftmanship houses five

Becky Munro 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

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

Jennifer DaSilva Mixer William Raveis Real Estate