32

Homes for Sale near Darien High School

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  • /40

    $1,800,000

    • 6 Beds
    • 5 Baths
    • 3,461 Sq Ft

    47 Hollow Tree Ridge Rd, Darien, CT 06820

    A Rare Darien Gem and opportunity to own this historic Federal Colonial 2-family home, one of Darien's few multi-family properties. Spanning over 3,460 SF on .47 acres, this turn-key furnished residence blends timeless elegance with modern versatility, ideal for investors, families, multi-generational households, or young couples seeking rental income. Historic Charm, Modern Comfort: * Two

    Agent Photo

    Karen Finn

    Gatehouse Realty Inc

    (475) 325-5924

    47 Hollow Tree Ridge Rd, Darien, CT 06820
  • /12

    $3,499,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 6,444 Sq Ft

    20 Locust Hill Rd, Darien, CT 06820

    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

    Agent Photo

    Robert Marchesi

    Compass Connecticut, LLC

    (475) 253-5609

    20 Locust Hill Rd, Darien, CT 06820
  • /40

    $3,095,000

    • 6 Beds
    • 6 Baths
    • 4,848 Sq Ft

    9 Point o Woods Rd S, Darien, CT 06820

    Charming Cape with Guest Cottage & Pool in Coveted Ox Ridge District Tucked away on a peaceful cul-de-sac in the highly sought-after Ox Ridge School district, this enchanting 4-bedroom Cape style home offers timeless charm, exceptional privacy, and flexible living options. A breezeway connects the main residence to a delightful 2-bedroom cottage-perfect for guests, in-laws, or a private home

    Margot Klingman Houlihan Lawrence

    9 Point o Woods Rd S, Darien, CT 06820
  • /40

    $3,495,000

    • 5 Beds
    • 6 Baths
    • 6,069 Sq Ft

    74 Brookside Rd, Darien, CT 06820

    Built in 2016 this turnkey home combines classic charm with modern convenience all just steps from downtown Darien, Cherry Lawn Park, train and shops. The beautifully landscaped yard and welcoming exterior radiate warmth and character. Step onto the front porch and through the front door into a bright and gracious entryway leading to the formal living and dining rooms and private office. As you

    Kristin Nemec William Pitt Sotheby's Int'l

    74 Brookside Rd, Darien, CT 06820
  • /40

    $4,675,000

    • 6 Beds
    • 8 Baths
    • 6,762 Sq Ft

    66 Stanton Rd, Darien, CT 06820

    Welcome to 66 Stanton Rd! Yes, that fabulous home with the beautiful VT slate roof! Sitting proudly atop 1.34 manicured acres, this handsome 1938 clapboard clad colonial demands to be noticed. This house underwent a major renovation and expansion that was completed in 2009. Entertaining spaces abound both formal and casual, perfect for hosting both gatherings intimate and large in scale. Step

    Nancy Peter Houlihan Lawrence

    66 Stanton Rd, Darien, CT 06820
  • /40

    $3,050,000

    • 4 Beds
    • 4.5 Baths
    • 4,643 Sq Ft

    44 Scofield Farms, Darien, CT 06820

    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

    44 Scofield Farms, Darien, CT 06820
  • /16

    $4,700,000 New Construction

    • 6 Beds
    • 7 Baths
    • 8,500 Sq Ft

    1 Pratt Island, Darien, CT 06820

    Proposed site plan and new construction drawings by Hatley Homes Design. Are you looking for a private, waterfront haven to build your dream home? Look no further than 1 Pratt Island. This 1 acre property is at the end of a private association with sunrise and sunset views. The lot comes with easements to a deep water dock and an incredible sandy beach steps away. With gorgeous mature trees, this

    Keiley Fuller Compass Connecticut, LLC

    1 Pratt Island, Darien, CT 06820
  • /2

    $4,900,000 New Construction

    • 5 Beds
    • 8 Baths
    • 6,535 Sq Ft

    20 Marianne Rd, Darien, CT 06820

    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

    20 Marianne Rd, Darien, CT 06820
  • /21

    $6,600,077

    • 6 Beds
    • 7.5 Baths
    • 7,580 Sq Ft

    14 5 Mile River Rd, Darien, CT 06820

    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

    14 5 Mile River Rd, Darien, CT 06820
  • /36

    $1,325,000

    • 3 Beds
    • 2 Baths
    • 2,343 Sq Ft

    33 Ridgeley St, Darien, CT 06820

    Welcome Home to this Storybook Cape Cod style set beneath a Picturesque Magnolia Tree. This 3 bedroom two full bath house offers the perfect blend of character, comfort and convenience. Inside you'll find beachy floors and freshly painted walls that give the home a light, breezy feel. The thoughtfully designed layout is ideal for a family including an expansive finished basement with fireplace

    Kathryn Bates Compass Connecticut, LLC

    33 Ridgeley St, Darien, CT 06820
  • /27

    $940,000 Open Sat 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,278 Sq Ft

    10 Pine Brook Ln, Darien, CT 06820

    Sophisticated two-bedroom, two full bathroom townhouse walkable to town and train. Cathedral ceilings, light-filled and completely renovated. Enter through the attached one car garage with epoxy floor or foyer with herringbone brick, shiplap wall and built-in bench. Sunny kitchen with Calcutta gold quartz counters, dual side-by-side refrigerators, and abundant storage opens to the living room

    Sara Hesli Houlihan Lawrence

    10 Pine Brook Ln, Darien, CT 06820
  • /36

    $1,999,999

    • 6 Beds
    • 5.5 Baths
    • 3,266 Sq Ft

    254 West Ave, Darien, CT 06820

    Located in the highly sought-after Noroton Heights neighborhood of Darien, this move-in-ready 6 bedroom with 5.5 bath residence offers the perfect blend of convenience and flexibility. Just steps from the vibrant new Darien Commons, residents will enjoy easy access to shopping, dining, school, health club, Metro-North for commuters & major highways, making this an ideal location for today's

    AnneMarie Rayhill Houlihan Lawrence

    254 West Ave, Darien, CT 06820
  • /29

    $2,300,000

    • 4 Beds
    • 4 Baths
    • 3,637 Sq Ft

    2 Mccrea Ln, Darien, CT 06820

    Minutes to the beach, train, Tokeneke School, and both downtown Darien and Noroton Heights, 2 McCrea Lane sits on a cul-de-sac close to everything. Sun-filled two-story foyer, high ceilings and traditional layout. Updated kitchen with quartz counters, large center island, pantry, and sliders with private deck - the perfect spot for the grill and morning coffee. Family room with custom built ins,

    Sara Hesli Houlihan Lawrence

    2 Mccrea Ln, Darien, CT 06820
  • /3

    $1,895,000

    • 4 Beds
    • 4.5 Baths
    • 3,436 Sq Ft

    178 Christie Hill Rd, Darien, CT 06820

    This is an extraordinary opportunity to build new home in a top Darien location. literally minutes to all schools k-12 ,Noroton Heights station and the all new Darien Commons with multiple restaurants and shopping. Level 2.86 acres. Plenty of room for pool, pool house or sports court. House offered as is. New survey available shortly.

    Douglas Milne Houlihan Lawrence

    178 Christie Hill Rd, Darien, CT 06820
  • /25

    $725,000 Open Sun 12PM - 2PM

    • 1 Bed
    • 1.5 Baths
    • 900 Sq Ft

    51 Hale Ln Unit 51, Darien, CT 06820

    Welcome to Middlesex Commons-Darien's most coveted condominium community! This stunning 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-your own tranquil escape. Inside, you'll

    Catherine Richardson William Pitt Sotheby's Int'l

    51 Hale Ln Unit 51, Darien, CT 06820
  • /34

    $1,795,000

    • 4 Beds
    • 2.5 Baths
    • 3,630 Sq Ft

    489 Hoyt St, Darien, CT 06820

    Welcome home to your quintessential New England Farmhouse, where you can enjoy stunning sunsets from the comfort of your covered front porch. Step into a welcoming center hall Colonial featuring a formal living room & elegant dining room complete with a butler's pantry & wet bar. The eat-in kitchen boasts granite countertops, stainless steel appliances, and an open sightline to the inviting

    Kim Tromba Keller Williams Realty

    489 Hoyt St, Darien, CT 06820
  • /37

    $1,850,000

    • 4 Beds
    • 3.5 Baths
    • 3,511 Sq Ft

    28 Great Hill Rd, Darien, CT 06820

    Discover a special opportunity to own this sun-filled, spacious cape on a cul-de-sac close to downtown Darien, Rowayton, and a short walk to Tokeneke school. Set on a generous half-acre lot in a quiet neighborhood, this beautifully refreshed home offers 4 spacious bedrooms and 3.5 bathrooms across 3,511 SF of living space. Culinary enthusiasts will love the newly renovated European-style kitchen

    Maureen DeBoisbriand Compass Connecticut, LLC

    28 Great Hill Rd, Darien, CT 06820
  • /32

    $1,395,000

    • 4 Beds
    • 2.5 Baths
    • 2,659 Sq Ft

    14 Maple St, Darien, CT 06820

    SELLERS REPLACING ROOF. Will be completed by Brown Roofing by end of July. Well maintained colonial in prime location walking distance to Noroton Heights train station and Darien Commons. Backyard is an oasis including a deck with hot tub overlooking level yard that backs up to Baker Park. Same owners for 36 years! Thoughtfully updated throughout the years with central air, laundry on main level,

    Abigail Forbes Realty ONE Group Connect

    14 Maple St, Darien, CT 06820
  • /33

    $2,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,591 Sq Ft

    109 West Ave, Darien, CT 06820

    A short and sweet stroll to Darien's vibrant downtown, convenient to train for a jaunt to the city, this stunning 2014 colonial reflects the architectural and cosmetic aesthetic of today's discerning eye. A gorgeous approach and fabulous curb appeal, the stone stairs to the front entry welcome you to a gracious foyer. Boasting a kitchen for a chef to admire. The stone kitchen counters and

    Susan Vanech Compass Connecticut, LLC

    109 West Ave, Darien, CT 06820
  • /27

    $1,250,000

    • 4 Beds
    • 3 Baths
    • 2,251 Sq Ft

    475 Hoyt St, Darien, CT 06820

    ** Please submit offers by 5pm 7/1/25** Opportunity knocks near the greens! This 4 Bedroom, 3 full bath ranch home, nestled just steps from a private golf course, offers incredible potential in a highly desirable location. Set on a scenic, wooded lot with handsome, mature landscaping and an in-ground pool, the property is bursting with character and ready for its next chapter, offering ample

    Mary Kate Klemish-Boehm Brown Harris Stevens

    475 Hoyt St, Darien, CT 06820
  • /37

    $8,795,000

    • 5 Beds
    • 7 Baths
    • 6,108 Sq Ft

    25 Tokeneke Trail, Darien, CT 06820

    Welcome to 25 Tokeneke Trail, an exceptional waterfront residence in the private Tokeneke Association. Perfectly positioned to capture panoramic water views from nearly every room and not in a flood zone, this home blends coastal charm with the finest in modern living. The property offers direct water access via a dock. Mooring available with approved Town application, and permitting for a deeper

    Breda Casey Brown Harris Stevens

    25 Tokeneke Trail, Darien, CT 06820
  • /38

    $6,795,000

    • 5 Beds
    • 8 Baths
    • 6,959 Sq Ft

    10 Cross Rd, Darien, CT 06820

    With timeless appeal, this quintessential New England stone & shingle style colonial offers finely crafted architectural details with thoughtful design and exceptional quality. Designed and built in 2006 by Louise Brooks & Artisan Builders, this exquisite home is situated on a beautifully landscaped hillside knoll in the private Tokeneke Association. With four levels of living the list of first

    Kathryn DeSalvo Compass Connecticut, LLC

    10 Cross Rd, Darien, CT 06820
  • /21

    $2,325,000

    • 3 Beds
    • 2 Baths
    • 2,220 Sq Ft

    23 Beach Dr, Darien, CT 06820

    Ideally located in the heart of the sought-after Noroton Manor Association and within the coveted Hindley Blue Ribbon school district, this delightful three-bedroom, two-bath home offers the perfect blend of charm and convenience. Enjoy exclusive access to a private beach and tennis courts, all within a welcoming, close-knit community. Inside, you'll find a spacious eat-in kitchen with an island,

    Janine Tienken Houlihan Lawrence

    23 Beach Dr, Darien, CT 06820
  • /24

    $1,238,000

    • 3 Beds
    • 3 Baths
    • 1,636 Sq Ft

    128 West Ave, Darien, CT 06820

    The home you've been waiting for! Move-in ready and minutes to Darien train station, downtown, Noroton Heights, multiple parks, and the town's pristine beaches. Beautifully updated with an open floor plan, the bright and spacious living room flows seamlessly into the renovated kitchen with a large center island. The adjoining dining area opens directly to the outdoor living space. The main level

    Jennifer Leahy Compass Connecticut, LLC

    128 West Ave, Darien, CT 06820
  • /40

    $1,375,000

    • 5 Beds
    • 3.5 Baths
    • 3,327 Sq Ft

    64 Old Kings Hwy S, Darien, CT 06820

    Own a piece of history with the Quintard-Frost House, a stunning antique Dutch Colonial home built in 1715 that seamlessly blends historic charm with modern comfort. This 5-bedroom, 3.5-bathroom residence showcases timeless craftsmanship, including original wide-plank floors, exposed beams, and period details throughout. At the heart of the home is a true antique bar with fireplace, a rare and

    Seema Dohil Brown Harris Stevens

    64 Old Kings Hwy S, Darien, CT 06820
  • /38

    $29,500,000

    • 6 Beds
    • 7.5 Baths
    • 8,684 Sq Ft

    0 Hay Island Unit 24078034, Darien, CT 06820

    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

    0 Hay Island Unit 24078034, Darien, CT 06820
  • /41

    $29,500,000

    • 6 Beds
    • 8 Baths
    • 8,684 Sq Ft

    157 Long Neck Point Rd, Darien, CT 06820

    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

    157 Long Neck Point Rd, Darien, CT 06820
  • /12

    $4,700,000

    • Land
    • 1.00 Acre
    • $4,700,000 per Acre

    1 Pratt Island, Darien, CT 06820

    Are you looking for a private, waterfront haven to build your dream home? Look no further than 1 Pratt Island. This 1 acre property is at the end of a private association with sunrise and sunset views. The lot comes with easements to a deep water dock and an incredible sandy beach steps away. With gorgeous mature trees, this property overlooks Darien Harbor in one direction and Stamford's Shippan

    Keiley Fuller Compass Connecticut, LLC

    1 Pratt Island, Darien, CT 06820
  • /38

    $17,000,000

    • 6 Beds
    • 9 Baths
    • 10,197 Sq Ft

    865 Hollow Tree Ridge Rd, Darien, CT 06820

    Combining refined elegance with complete privacy, this 9.5-acre estate is the quintessential sanctuary for those seeking an elevated, sophisticated lifestyle in a tranquil and secluded setting. Situated at the end of a gravel drive lined with Bradford Pear trees, the compound features a 10,000-square-foot main house, a luxurious pool and pool house, a charming two-bedroom guest cottage, and an

    Ashley Dineen Compass Connecticut, LLC

    865 Hollow Tree Ridge Rd, Darien, CT 06820
  • /3

    $4,000,000

    • Land
    • 1.00 Acre
    • $4,000,000 per Acre

    74 Long Neck Point Rd, Darien, CT 06820

    This is a rare opportunity to build the home of your dreams on Long Neck Point - one of the most sought after and picturesque communities on the Eastern Seaboard! As part of a 4 unit subdivision, you will have shared use of two boat docks and Long Island Sound access! Your newly constructed home will enjoy amazing views to Gorham's Pond and Long Island Sound. Walk or bike to Pear Tree Point or

    Jon Magnotta Outlook Realty

    74 Long Neck Point Rd, Darien, CT 06820
  • /11

    $4,500,000

    • Land
    • 1.24 Acres
    • $3,629,032 per Acre

    92 Pear Tree Point Rd, Darien, CT 06820

    This is a rare opportunity to build the home of your dreams on Long Neck Point - one of the most sought after and picturesque communities on the Eastern Seaboard! As part of a 4 unit subdivision, you will have shared use of two boat docks and Long Island Sound access! Your newly constructed home will enjoy amazing views to Gorham's Pond and Long Island Sound. Walk or bike to Pear Tree Point or

    Jon Magnotta Outlook Realty

    92 Pear Tree Point Rd, Darien, CT 06820
  • /11

    $4,500,000

    • Land
    • 1.14 Acres
    • $3,947,368 per Acre

    88 Pear Tree Point Rd, Darien, CT 06820

    This is a rare opportunity to build the home of your dreams on Long Neck Point - one of the most sought after and picturesque communities on the Eastern Seaboard! As part of a 4 unit subdivision, you will have shared use of two boat docks and Long Island Sound access! Your newly constructed home will enjoy amazing views to Gorham's Pond and Long Island Sound. Walk or bike to Pear Tree Point or

    Jon Magnotta Outlook Realty

    88 Pear Tree Point Rd, Darien, CT 06820
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