Homes for Sale near Middlesex Middle School

Welcome to this classic center hall Colonial, perfectly situated on one of the most sought-after streets in town-renowned for its strong sense of community, annual block parties, and walkability to Holmes Elementary School. Just two doors down from the Middlesex Club, this home blends timeless charm with modern updates and outstanding potential. The renovated kitchen opens to an oversized family

Amy Barsanti William Pitt Sotheby's Int'l

Located on a peaceful cul-de-sac yet just minutes from town, the train, and top-rated schools, this stunning home offers the perfect balance of tranquility and convenience. Inside, you'll find high ceilings, beautiful moldings, custom built-ins, and an open floor plan designed for modern living. The large, renovated kitchen is a true centerpiece, featuring high-end finishes and generous space for

Stephanie Slatkow Compass Connecticut, LLC

This beautifully updated four-bedroom, four-and-a-half-bath home sits on the picturesque seven-acre Mather Pond-often compared to Thoreau's Walden Pond-offering a rare blend of tranquility and modern comfort. Thoughtfully renovated by its designer owner, the residence features a versatile layout with custom built-ins, generous storage, and a brand-new gourmet kitchen. Light-filled living spaces

Keiley Fuller Compass Connecticut, LLC

Exceptional NEW CONSTRUCTION - Walk to Town - Experience refined luxury living in this custom-built home by V&A Construction Inc., a respected local builder highly regarded for exceptional craftsmanship, meticulous attention to detail and upscale finishes. Set near Great Island and Pear Tree Point Beach, this home offers the best of coastal living with the ease of everyday convenience, just a

Katherine Kuras BHHS Darien/New Canaan

Perched high above the Goodwives River, this stunning Mid-Century Modern home offers sophisticated living in an extraordinary natural setting. Walls of floor-to-ceiling glass invite the outdoors in, seamlessly blending interior spaces with the serene beauty of the 1.8-acre private landscape. Reimagined by renowned architectural firm Joeb Moore + Partners, highlights include a dramatic

Carolyn Brook William Pitt Sotheby's Int'l

Nestled on a quiet cul-de-sac in the Boulder Ridge Association, 11 Old Oak Road is a timeless 5-bedroom, 5.5-bathroom colonial that offers the perfect blend of classic elegance and modern comfort. Step inside and you'll be greeted by spacious, sun-filled rooms that make this home ideal for both everyday living and elegant entertaining. The formal dining room, living room, sitting room, study, and

Kristin Nemec William Pitt Sotheby's Int'l

This classic Colonial has character, charm and generous space. The formal Living Room has a fireplace and adjoins the Music Room. The spacious Dining Room has a fireplace bordered by Dutch tiles and features a custom "River" mural. The kitchen has a bright copper exhaust hood, gas stove and opens to the family room with cathedral ceiling, skylights, fireplace and French Doors to the terrace. The

Suzanne Okie Brown Harris Stevens

This charming 5-bedroom Cape Cod home, originally built in 1941 and extensively renovated, expanded and rebuilt in 2015, is the perfect blend of classic elegance and modern comfort. Nestled in a highly sought-after neighborhood, the property offers spacious living with timeless details throughout. From the moment you step inside, you're greeted by beautiful hardwood floors, crown molding, and

Catherine Russell Brown Harris Stevens

Spectacular, luxury new construction nestled in one of Darien's most lovely neighborhoods. Thoughtfully designed and impeccably crafted, this home combines timeless sophistication with modern comforts. A dramatic double-height paneled foyer welcomes you inside, leading to a soaring vaulted ceilinged living room, which is anchored by a refined shiplapped gas fireplace. The space opens seamlessly

Alison Hanson Compass Connecticut, LLC

If prime location and exceptional craftsmanship are what you've been looking for, look no further than 10 Cross Road. Designed and built in 2006 by Louise Brooks & Artisan Builders, this exquisite custom built home is situated on an artistically landscaped knoll in the private Tokeneke Association. Extensive woodwork & moldings, 10 foot & cathedral ceilings, and recent exterior improvements,

Kathryn DeSalvo Compass Connecticut, LLC

World class one of a kind newly constructed modern masterpiece designed by award winning architect Vita Design with stunning unobstructed water views from every room in the house. This custom coastal build sets luxury to the highest level. The home features tall ceilings with an abundance of open space filled with natural light coming in through the floor to ceiling oversized European style

Jennifer DaSilva Mixer William Raveis Real Estate

LOCATION! LOCATION! LOCATION! Renovated, Bright, Hardwood floors, Central AC, Mint condition &,4Bedrooms,2.5 Bath on.21 Acres in the prime area of DARIEN. Units are side by side. 3Bedrooms, Living room with fireplace, Full Bath & Kitchen with dining area on one side. Other side has 1bedroom, Full bath & combo of kit & living room. Separate heat. Close to I-95. Walking distance to train station,

Meera Banta BHGRE Shore & Country

Experience the perfect blend of luxury and convenience in this beautifully appointed townhouse offering resort-like amenities and effortless, low-maintenance living. The open and airy layout showcases high-end finishes throughout, with an elevator providing easy access to all three levels. The location is ideal being on quiet cul de sac with private backyard. The current owners have added

Pam Pokorny Compass Connecticut, LLC

Tucked at the end of a quiet cul-de-sac, 20 Seagate Road is a rare find in one of Darien's most sought-after waterfront neighborhoods. With direct water views and a private dock, this property has a lot to offer. The backyard is the real standout - a large pool surrounded by mature trees and open lawn, all overlooking Holly Pond and the Long Island Sound. It's the kind of space that's perfect for

Janine Tienken Houlihan Lawrence

Sun-drenched and brimming with character, this home resides on a quiet, sought-after street in the heart of Darien. A welcoming front porch sets the tone, inviting you into a home that blends timeless charm with modern sophistication. Inside, an expansive living room flows seamlessly into the dining room, enhanced by classic pocket doors, while the modern kitchen opens to a spacious new

Nellie Snell William Raveis Real Estate

Welcome to Middlesex Commons-Darien's most coveted condominium community! This stunning upper level (2nd floor) unit offers the perfect blend of luxury, comfort, & convenience. From gleaming hardwood floors to a beautifully updated kitchen & sparkling baths, every detail has been thoughtfully curated. Step out onto your private deck and take in the impeccably landscaped grounds. Inside, you'll

Catherine Richardson William Pitt Sotheby's Int'l

Wonderful opportunity in one of Darien's most sought after neighborhoods; 4,000+ sqft of custom, renovated space that is truly in move-in condition. Designed by a renowned local architect, the home has charm, sophistication with a light filled open floor plan well suited for entertaining. Beautifully sited on .68 acres with mature trees and lush landscaping, there is ample room to expand and add

Stephan Von Jena William Pitt Sotheby's Int'l

This newly re-built 4-bedroom, 3-bath Colonial offers 2400 sq feet of finely crafted living space on a level .25-acre lot. Set on the corner of Anthony Lane and a cul-de-sac, the property pairs neighborhood charm with privacy. Enjoy the outdoors in a newly fenced yard with professional landscaping and a full irrigation system. Inside, the open layout is defined by natural light and superior

Hillary Miller Houlihan Lawrence

Incredible value in one of Darien's most-loved neighborhoods! 4 bedrooms, 3 full bathrooms with 2,707 square feet of space. Walk to Holmes School, Middlesex Middle School, Darien High School and Noroton Heights train and shopping. Improvements include: fully fenced backyard, new gas range, new dishwasher, refinished hardwood floors and kitchen cabinets, new driveway with Belgium blocks and curb,

Sara Hesli Houlihan Lawrence

25 Tokeneke Trail - Where the Sky meets the Sea. Wake up to breathtaking sunrises, spend afternoons on the water, and end each day with sunset views from your private terrace. 25 Tokeneke Trail isn't just a home-it's a lifestyle. Perfectly perched above the shoreline and not in a flood zone, this stunning waterfront retreat offers direct access to the water with its own private beach, dock and

Nellie Snell William Raveis Real Estate

In one of Darien's most convenient locations, this move-in-ready home is just a short distance to Noroton Train Station, Corbin District, Darien Commons, and nationally recognized Darien Library. The renovated kitchen features new cabinetry, quartz countertops and high-end vinyl floors. A new full bath with step-in shower, quartz counters, and a new washer/dryer sits off the hallway. The first

Kim Petre William Raveis Real Estate

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

Introducing one of Tokeneke's most iconic waterfront estates-available for the first time in 50 years. This rare and storied compound is set on 2.4 acres of exquisitely landscaped grounds with 180 feet of private shoreline along Long Island Sound. It offers an unrivaled blend of historic charm, timeless elegance, and breathtaking coastal beauty. A sweeping two-story paneled foyer leads to a

Douglas Milne Houlihan Lawrence

Freshly priced to sell, this Darien home offers timeless style and comfort in one of the area's most desirable neighborhoods. With a charming brook alongside the property, enjoy added privacy and no neighbor on that side. It is your own peaceful retreat at a new, incredible value. With its exciting new price, there has never been a better time to make your move. This classic 1927 colonial-style

Jennifer Baukol Coldwell Banker Realty

Charming 3-bedroom Darien colonial on quiet cul-de-sac offers 2,064 sf of beautifully appointed living space on a lush 0.52-acre parcel with large rear private patio with a low maintenance setting with tasteful landscaping. Inside the home flows effortlessly, with a spacious living room featuring hardwood floors and a cozy fireplace. The heart of the home - an open kitchen with center island that

Paul Incerto William Raveis Real Estate

Set on a full acre in one of Darien's most sought-after neighborhoods, this property presents a rare and versatile opportunity for visionary buyers. Whether you choose to undertake a renovation-reviving the charm of mid-century modern design-or build a custom new construction estate from the ground up, the potential here is extraordinary. Surrounded by multi-million dollar homes, this centrally

Carolyn Brook William Pitt Sotheby's Int'l

Back on the Market after improvements! Gorgeous Nantucket-Style Retreat with Spacious Layout & Private Backyard Set behind stately stone pillars, this stunning Nantucket shingle-style home, fully renovated in 2011, offers timeless curb appeal and modern comforts throughout. With 4 bedrooms, 3 full baths, and thoughtfully updated newer construction, this home is designed for today's lifestyle. The

Kathryn Bates Compass Connecticut, LLC

Stunning, fully updated 4-bedroom Colonial in highly sought-after Noroton Heights. Featuring an ideal first-floor primary suite for convenience and privacy. Enjoy a spacious, level backyard perfect for outdoor entertaining or play. This home is in move-in condition with modern finishes throughout, located close to all area amenities-shopping, dining, top-rated schools, parks, and beaches. Superb

Tara Travers Century 21 AllPoints Realty

Nestled at the end of a serene cul-de-sac is a 4-acre sanctuary where luxury and enchantment intertwine. Designed for the ultimate entertainer, the heated pool, complete with a swim-up bar, invites endless summer soirees under the stars, while the adjacent outdoor kitchen transforms every gathering into a culinary spectacle. A full tennis court and full basketball court promises spirited matches

Melissa Engel Douglas Elliman of Connecticut

HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom,

Leslie McElwreath Sotheby's International Realty

HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom,

Leslie McElwreath Sotheby's International Realty

Blending refined elegance with complete privacy, this 9.5-acre estate is a true sanctuary for those seeking a sophisticated lifestyle. At the end of a Bradford Pear-lined gravel drive, the compound features a 10,000 sq. ft. main house, pool and pool house, two-bedroom guest cottage, and a breathtaking field house by architect Louise Brooks. The main home marries historic charm with sleek, modern

Ashley Dineen Compass Connecticut, LLC

Dreaming of customizing your new home? Nestled on a private and flat 1.2 acres on a desirable Darien cul-du-sac, this modern-colonial stunner will feature a custom kitchen with breakfast room that opens to a sizable deck overlooking the private yard and flows into a huge great room with gas fireplace. An oversized living room is perfect for entertaining, while the first floor bedroom/office

Serena Richards Brown Harris Stevens