Homes for Sale near Middlesex Middle School

Spectacular quintessential New England home in Darien has it all! Step into a world of refined elegance with this stately 8,000+SF Colonial masterpiece. Set back on nearly two acres of manicured grounds, boasting a custom 2021 Gunite pool, outdoor kitchen, new patio, huge backyard and firepit, this treasured residence is the ultimate venue for indoor & outdoor living and entertaining. The main

Gaynor Brennan BHHS Darien/New Canaan

New construction 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, Thermador appliances,

Serena Richards Brown Harris Stevens

Welcome to 167 Hollow Tree Ridge Road! A move-in ready home offering comfort, convenience, and future potential in one of Darien's most accessible locations. This well-maintained residence features three generously sized bedrooms and one full bathroom. The kitchen features rich cherry wood cabinetry, granite countertops, stainless steel dishwasher and refrigerator, and ample storage and prep

Derek Heering Houlihan Lawrence

Ideally situated between the coveted town centers of Darien and New Canaan, this exceptionally and recently completely redesigned colonial rests on 2.4 acres of pristine, park-like grounds. Enveloped by a perimeter of mature trees, a rare sense of serenity is felt upon arrival. Finished with an uncompromising attention to detail, a sophisticated design aesthetic and superior craftsmanship

Nellie Snell William Raveis Real Estate

Welcome to 66 Stanton Road. Set on 1.34 landscaped acres, this classic 1938 clapboard colonial blends architectural charm with thoughtful updates, including a full renovation and expansion completed in 2009. Designed for effortless living and entertaining, the home offers refined formal rooms and relaxed gathering spaces. A gracious foyer with sweeping curved staircase is flanked by sunlit living

Amanda Spatola Houlihan Lawrence

A Rare Opportunity to live on the Coveted Tilley Pond Park with Sweeping Park & Water views. Beautifully designed for effortless living & entertaining, offering a rare blend of natural beauty, walkability, & coastal town charm. On the Pond - where mornings begin with coffee, peaceful water views and evenings end with sunsets reflecting off the park. Stroll along an idyllic street to downtown

Kathryn Bates 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

Set on 7 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house delivers a one-of-a-kind recreational

Ashley Dineen Compass Connecticut, LLC

Welcome to 171 Raymond Street - a beautifully updated 3-bedroom home offering the perfect blend of comfort, style, and convenience. The main level features an open floor plan designed for modern living, seamlessly connecting the beautifully renovated kitchen, family room, and dining area. The kitchen is thoughtfully updated with quality finishes and flows effortlessly into the main living spaces,

Nellie Snell William Raveis Real Estate

Set on 9.4 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, a two-bedroom guest cottage, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house

Ashley Dineen Compass Connecticut, LLC

Location, location, location! Welcome to 3 Hickory Lane, where charm meets luxury in a priceless setting. Nestled in a sought-after neighborhood with quiet tree-lined lanes, this move-in ready home is walking distance to top-rated elementary, middle and high schools and Woodland Park, with easy train access for NYC commutes. This fully renovated and meticulously maintained home with 4 bedrooms, 4

Keiley Fuller Compass Connecticut, LLC

Welcome to 20 Locust Hill Road, a stunning new construction opportunity in the heart of 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

Welcome to the heart of Noroton Heights nestled on one of the most sought-after streets in Darien. This incredible neighborhood offers the perfect blend of community, convenience, & everyday amenities just moments from your door! Renovated in 2008 with a significant addition, this home combines timeless charm, curb appeal & plenty of room for any lifestyle. Inside, you'll find 5 beds/ 3.5 baths,

Breda Casey Houlihan Lawrence

Welcome to 2 Red Rose Circle - a bright and beautifully maintained Four bedroom, Two full one 1/2 bath Colonial nestled on a quiet cul-de-sac in one of Darien's most sought after neighborhoods. Set on a flat, sunny half acre, this move-in-ready home combines timeless style with comfortable, everyday living. Natural light fills the spacious rooms, creating a warm and welcoming atmosphere

Deirdre McGovern Compass Connecticut, LLC

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

Where timeless design meets coastal living, 23 Beach Road sets a new standard in Darien. This stunning new construction sits in one of Darien's most charming and sought-after neighborhoods, just minutes from Weed Beach (paddle, tennis, playgrounds, and calm open water) and a top-rated elementary school. Thoughtfully designed with function and flow in mind, 23 Beach blends enduring architecture

Amanda Spatola Houlihan Lawrence

This beautifully designed residence seamlessly blends timeless charm with modern sophistication, showcasing sun-drenched interiors, inviting fireplaces, and refined architectural details throughout. A secluded stone patio overlooks the sparkling in-ground gunite pool and pool house, all set within a serene, park-like landscape - an idyllic backdrop for both intimate gatherings and grand

Lori Printz Coldwell Banker Realty

Welcome to 473 Hollow Tree Ridge Road in Darien - a custom built, stone and shingle Colonial set on 1.3 professionally landscaped acres offering exceptional indoor and outdoor living. This 5-bedroom smart home blends timeless architecture with extensive upgrades and modern technology throughout. The resort-style backyard features a pool with spa, pool house with nano doors, outdoor shower, custom

Ellen Mccue Houlihan Lawrence

Classic Ranch on Expansive Park-Like Acre+ in one of Darien's Most Sought-after Neighborhoods. Nestled on a prime 1.08-acre property, this home offers the perfect backdrop for your dream lifestyle. The light-filled formal living room, highlighted by a wood-burning fireplace and custom built-ins, flows seamlessly into the inviting family room with rich wood paneling and a second wood-burning

Sara Littlefield BHHS Darien/New Canaan

Introducing an exceptional new-construction home set in a neighborhood, thoughtfully designed for today's lifestyle and sophisticated entertaining. This home offers five well-appointed bedrooms on a single level, four full baths, and two half baths. At the heart of the home is a sun-filled, open-concept kitchen featuring a generous center island, eat-in dining area, and expansive pantry,

Sheree Frank Houlihan Lawrence

Charming, renovated Noroton Heights colonial, with an easy walk to train, dining and shopping, awaits! Beautiful kitchen with breakfast nook, breakfast bar and large dining area opening to a large family room will please all cooks and allow for flexible use. Three bedrooms, renovated bathroom with double sinks, and a walk-up attic (lending itself to expansion possibilities) complete the second

Amanda Bryan Compass Connecticut, LLC

Located on a quiet cul-de-sac in Darien's sought-after Ox Ridge School district, this inviting 4 bedroom Cape offers timeless character, privacy, and versatile living. Sun-filled living spaces and a well-designed floor plan enhance everyday comfort while maintaining the home's character. The primary bedroom features a fireplace, creating a warm and inviting retreat, complemented by three

Ashley Dineen Compass Connecticut, LLC

In the heart of Darien, where history lingers and owls whisper through the trees, stands a timeless 1800s home at 561 Middlesex Road - a place where memory breathes and dreams take root. Set upon 2.6 serene and level acres, yet close to all amenities, this enchanting farmhouse rests within a world of quiet beauty, where a secret garden path winds softly beneath the shade, inviting you to wander,

Serena Richards Brown Harris Stevens