30

Homes for Sale near Darien High School

Section Image Section Image
  • /40

    $1,750,000 Open Sun 1PM - 3PM

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

    47 Hollow Tree Ridge Rd, Darien, CT 06820

    PRICE ADJUSTMENT. 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 those seeking rental income. Historic Charm, Modern Comfort: *

    Agent Photo

    Karen Finn

    Gatehouse Realty Inc

    (475) 325-5924

    47 Hollow Tree Ridge Rd, Darien, CT 06820
  • /2

    $1,410,000 Open House 9/13

    • 4 Beds
    • 3 Baths
    • 2,552 Sq Ft

    17 Lynn Ct, Darien, CT 06820

    This is the one you've been waiting for! Spacious 4 BR, 3 BA home in coveted, friendly neighborhood conveniently located within walking distance to Holmes School. Recent 2-story addition includes dreamy new primary suite with 12' ceiling, large new primary bath with jacuzzi tub, walk-in closet, upper-level laundry and walk-up attic-one of TWO attics! Three more bedrooms and two full baths, formal

    Agent Photo

    Karen Finn

    Gatehouse Realty Inc

    (203) 780-0811

    17 Lynn Ct, 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
  • /37

    $2,695,000

    • 5 Beds
    • 4.5 Baths
    • 3,400 Sq Ft

    46 Sunswyck Rd, Darien, CT 06820

    Nestled within the highly sought-after Delafield Island Association, 46 Sunswyck Road is a distinguished brick estate set on 1.3 acres of impeccably landscaped grounds. Manicured lawns, a variety of plants, and mature trees create a serene, park-like setting that enhances the home's timeless architecture. This stately 5-bedroom residence blends classic elegance with modern upgrades. Inside, a

    Nellie Snell William Raveis Real Estate

    46 Sunswyck Rd, Darien, CT 06820
  • /29

    $2,350,000

    • 5 Beds
    • 4 Baths
    • 3,897 Sq Ft

    76 Deepwood Rd, Darien, CT 06820

    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

    76 Deepwood 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
  • /40

    $2,895,000

    • 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
  • /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
  • /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
  • /33

    $2,185,000

    • 4 Beds
    • 2.5 Baths
    • 3,209 Sq Ft

    8 Leeds Ln, Darien, CT 06820

    Welcome to 8 Leeds Lane, one of just six homes on a private cul-de-sac in Darien. This meticulously maintained Colonial is move-in ready and offers the perfect blend of elegance, functionality, and comfort. Step inside to find sun-filled rooms, soaring ceilings, and generous open spaces ideal for today's lifestyle. Thoughtfully updated within the past decade and in amazing condition, the home has

    Tamara Hanford Hughes Compass Connecticut, LLC

    8 Leeds Ln, Darien, CT 06820
  • /40

    $6,795,000

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

    10 Cross Rd, Darien, CT 06820

    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

    10 Cross Rd, Darien, CT 06820
  • /31

    $1,895,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 2,568 Sq Ft

    3 Devon Rd, Darien, CT 06820

    Welcome to 3 Devon Road, - a modern gem on a tree-lined street in a desirable neighborhood. This stunning 2017 custom built pristine home offers plenty of thoughtfully designed space featuring a flexible floor plan for today's lifestyle! This custom home features an open-concept main level with a contemporary gourmet kitchen equipped with sleek white cabinetry and high-end appliances, perfect for

    Keiley Fuller Compass Connecticut, LLC

    3 Devon Rd, Darien, CT 06820
  • /38

    $775,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 1 Bath
    • 724 Sq Ft

    41 Wakemore St, Darien, CT 06820

    Opportunity knocks in Darien, CT! Located on a private road, across from Kensett (Luxury townhouse complex), this oversized level 0.49-acre corner lot offers endless potential. The existing 724 sq ft cottage can be expanded, renovated, or replaced-ideal for end-users or investors. Bonus outbuilding with second story loft ideal for a home office or studio. Fix & flip, build new, or customize your

    Fiona Porter Keller Williams Realty

    41 Wakemore St, Darien, CT 06820
  • /24

    $1,425,000

    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    223 Middlesex Rd, Darien, CT 06820

    223 Middlesex Road is a picture-perfect, early 1900's Colonial in the heart of Darien, Connecticut. Upon entering this charming home, you'll be embraced by a delightful blend of classic elegance and contemporary comfort. The main level features a welcoming living/family room complete with a cozy fireplace, creating the perfect setting for evenings of relaxation. The kitchen is a culinary haven

    Kelly Connell Compass Connecticut, LLC

    223 Middlesex Rd, Darien, CT 06820
  • /39

    $1,250,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 1.5 Baths
    • 1,502 Sq Ft

    19 Park Ln, Darien, CT 06820

    Nestled on a private street in an excellent neighborhood, this pristine Colonial offers 3 bedrooms and 1.5 bathrooms on .18 acres close to schools, trains and town amenities. Hardwood floors flow throughout the home, complementing a generous living room and dining room-ideal for entertaining. A light-filled office provides versatile living space perfect for work, family room or play space.

    Deborah Hidy Houlihan Lawrence

    19 Park Ln, Darien, CT 06820
  • /32

    $695,000 Open Sun 1PM - 3PM

    • 1 Bed
    • 1.5 Baths
    • 900 Sq Ft

    39 Hale Ln Unit 39, Darien, CT 06820

    Just steps from everything Darien has to offer, Middlesex Commons makes living easy. This lovely, sunfilled condo features an updated kitchen, open floor plan living/dining space with a wood burning fireplace, powder room and a deck overlooking the beautiful landscaping. The spacious bedroom suite has a walk in closet, spa like bath and full size laundry. A detached one car garage completes the

    Kelly Kraus Houlihan Lawrence

    39 Hale Ln Unit 39, Darien, CT 06820
  • /20

    $905,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 1,290 Sq Ft

    17 Stanley Rd, Darien, CT 06820

    Lovely, move-in ready home convenient to schools, train and town. Two-bedroom, one bath charmer with a handful of recent improvements including complete bathroom remodel, re-stained hardwood floors, new Bradford & White hot water heater, GE dishwasher, LG washer and dryer and pergola with professional landscaping. Cozy living room with wood-burning fireplace and dining room with French doors

    Sara Hesli Houlihan Lawrence

    17 Stanley Rd, Darien, CT 06820
  • /24

    $975,000

    • 3 Beds
    • 1.5 Baths
    • 1,883 Sq Ft

    415 West Ave, Darien, CT 06820

    Welcome to the well maintained 415 West Ave. Character meets charm! A must see to get the full beauty. This classic 1927 colonial-style home occupies a lush 0.30acre lot, offering privacy and a beautiful outdoor setting. With 3 bedrooms and 1.5 baths across approximately 1,900 sqft, it features original character, including a wood-burning fireplace and a layout ripe for entertaining. Upstairs,

    Jennifer Baukol Coldwell Banker Realty

    415 West Ave, Darien, CT 06820
  • /36

    $1,800,000

    • 3 Beds
    • 2.5 Baths
    • 2,064 Sq Ft

    5 Wakeman Rd, Darien, CT 06820

    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

    5 Wakeman Rd, Darien, CT 06820
  • /39

    $1,649,000 Open Sun 1PM - 3PM

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

    489 Hoyt St, Darien, CT 06820

    **Watch video link below!** Charming New England Farmhouse with golf course views. Perfect for sunset enjoyments from the covered front porch. Inside, a welcoming Center Hall Colonial features a formal living room, elegant dining area with a butler's pantry and wet bar-great for entertaining. The eat-in kitchen offers granite countertops, stainless steel appliances, and an open view to the family

    Kim Tromba Keller Williams Realty

    489 Hoyt St, Darien, CT 06820
  • /39

    $1,395,000

    • 4 Beds
    • 3 Baths
    • 2,124 Sq Ft

    3 Turnabout Ln, Darien, CT 06820

    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

    3 Turnabout Ln, Darien, CT 06820
  • /39

    $10,895,000

    • 6 Beds
    • 4.5 Baths
    • 7,174 Sq Ft

    17 Contentment Island Rd, Darien, CT 06820

    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

    17 Contentment Island Rd, Darien, CT 06820
  • /25

    $695,000

    • 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. Inside, you'll love the open concept

    Catherine Richardson William Pitt Sotheby's Int'l

    51 Hale Ln Unit 51, 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

    $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
    • 7.5 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
  • /38

    $17,000,000

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

    865 Hollow Tree Ridge Rd, Darien, CT 06820

    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

    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
How to Buy a Home How to Finance a Home How to Sell a Home