Homes for Sale near Darien High School

• 

  

  

  /40

  $1,800,000 Open Thu 10AM - 12PM

  • 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

  

  Karen Finn

  Gatehouse Realty Inc

  (475) 325-5924

  47 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  

  

  /40

  $4,888,000 Open Sat 1PM - 3PM

  • 6 Beds
  • 7 Baths
  • 8,972 Sq Ft

  276 Mansfield Ave, Darien, CT 06820

  Introducing "Les Pierres Dorees", a unique European-style Chateau boasting 6 bedrooms and 6 bathrooms. This magnificent home is constructed with hand-selected stones from the Champlain Valley and is situated on a 1.3-acre property overlooking the signature 12th hole of the Darien Country Club. Step inside through the authentic wrought iron door and be greeted by a breathtaking entry foyer

  

  Federico Martinez

  Keller Williams Prestige Prop.

  (475) 258-8937

  276 Mansfield Ave, Darien, CT 06820
• 

  

  

  /38

  $2,995,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 6 Baths
  • 5,348 Sq Ft

  4 Echo Dr, Darien, CT 06820

  Welcome home to this fabulous like new construction home on a sought after street in Darien. Incredible updates and high end finishes will blow you away including light fixtures and window treatments throughout. Opportunity awaits to live in this amazing 5348 SF center hall colonial with gorgeous Wagner pool! Flow is everything here at 4 Echo Drive. Sun drenched rooms flow into the next with

  Keiley Fuller Compass Connecticut, LLC

  4 Echo Dr, Darien, CT 06820
• 

  

  

  /39

  $2,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,976 Sq Ft

  19 Stephanie Ln, Darien, CT 06820

  Welcome to this classic 4-bedroom Colonial set on a level 2-acre property in a prime cul-de-sac location within the coveted Ox Ridge School district. Beautifully updated throughout, this home features a stunning gourmet kitchen with top-of-the-line appliances and timeless finishes. The spacious layout includes a finished lower level with a playroom and gym-ideal for today's lifestyle.A new patio

  Janine Tienken Houlihan Lawrence

  19 Stephanie Ln, Darien, CT 06820
• 

  

  

  /37

  $2,950,000

  • 4 Beds
  • 3.5 Baths
  • 3,417 Sq Ft

  9 Sunset Rd, Darien, CT 06820

  An Exceptional Offering in the Heart of Darien. A unique opportunity not to be missed, this gracious four-bedroom Dutch Colonial masterfully blends timeless 1930s charm with modern sophistication. Nestled on one of Darien's most sought-after in-town streets-known for its deep-rooted traditions and close-knit community-this exceptional home is set on a lush, level, one-acre lot in a coveted

  Amy Barsanti William Pitt Sotheby's Int'l

  9 Sunset Rd, Darien, CT 06820
• 

  

  /37

  $2,695,000

  • 4 Beds
  • 4.5 Baths
  • 4,103 Sq Ft

  5 Dorr Rd, Darien, CT 06820

  Tucked away on a quiet cul-de-sac in the highly coveted Allwood Neighborhood, this charming 5-bedroom home is set on a beautifully maintained 1.61-acre property and offers over 4,000 sq ft of thoughtfully designed living space. Classic yet comfortably casual, the home features high ceilings and generous living areas throughout. The welcoming foyer opens to a step-down living room with vaulted

  Carla Kupiec William Raveis Real Estate

  5 Dorr Rd, Darien, CT 06820
• 

  

  /40

  $3,795,000

  • 5 Beds
  • 4.5 Baths
  • 5,475 Sq Ft

  16 Morley Ln, Darien, CT 06820

  Tucked away at the end of a private cul-de-sac in Darien's highly coveted Delafield Island, this custom 5BR, 4.5BA Colonial offers 5,475 sq. ft. of luxury living on over one acre. Built by a renowned high-end homebuilder, this home combines in-town convenience with the privacy of a resort-style backyard featuring a heated free-form infinity saltwater pool, spa, waterfall, and freestanding stone

  Carla Kupiec William Raveis Real Estate

  16 Morley Ln, Darien, CT 06820
• 

  

  /33

  $2,400,000

  • 4 Beds
  • 3.5 Baths
  • 3,678 Sq Ft

  2 Knollwood Ln, Darien, CT 06820

  Welcome to this inviting four-bedroom home perfectly situated on one of Darien's most coveted in-town streets, renowned for its strong sense of community and vibrant neighborhood gatherings. Just steps from Royle Elementary School and a short walk to town, train, and schools, this property offers the ultimate in convenience and lifestyle. At the heart of the home is a spacious eat-in gourmet

  Amy Barsanti William Pitt Sotheby's Int'l

  2 Knollwood Ln, Darien, CT 06820
• 

  

  /39

  $3,695,000

  • 5 Beds
  • 6 Baths
  • 4,295 Sq Ft

  162 Leroy Ave, Darien, CT 06820

  This stunning 5-bedroom, center hall colonial, built in 2013, seamlessly blends timeless architecture with modern luxury. Ideally situated on a level 1-acre lot in a prime location close to town and the Darien train station, this home offers the perfect balance of convenience and comfort. Inside, you'll find a thoughtfully designed open floor plan featuring a spacious family room with soaring

  Stephanie Slatkow Houlihan Lawrence

  162 Leroy Ave, Darien, CT 06820
• 

  

  /36

  $3,150,000

  • 5 Beds
  • 4.5 Baths
  • 6,860 Sq Ft

  326 Hollow Tree Ridge Rd, Darien, CT 06820

  Welcome to 324 Hollow Tree Ridge Road! Setback from the street on a generous 1.6+ acres this house has everything you need including a beautiful inground swimming pool. Convenient to everything, DHS is right around the corner, MMS down the street, a short distance to town and the train, you are truly at the center of it all! Offering 5 bedrooms, 4 1/2 baths and a combined 6900 ft.2 of living

  Nancy Peter Houlihan Lawrence

  326 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  

  /33

  $4,195,000

  • 5 Beds
  • 3.5 Baths
  • 4,932 Sq Ft

  39 Deepwood Rd, Darien, CT 06820

  Set in one of Darien's most desirable neighborhoods, this impeccably renovated home blends timeless charm with modern luxury- all within walking distance to schools, the train station, and the shops and restaurants of Noroton Commons. The location simply can't be beat. Sitting on nearly one flat acre, the stunning and ultra-private backyard feels like your own secluded retreat. Mature landscaping

  Amanda Spatola Houlihan Lawrence

  39 Deepwood Rd, Darien, CT 06820
• 

  

  /39

  $2,495,000

  • 5 Beds
  • 4 Baths
  • 3,618 Sq Ft

  24 Sunswyck Rd, Darien, CT 06820

  Charming Shingled Colonial nestled in the heart of coveted Delafield Island, this beautifully updated home offers the perfect blend of classic charm and modern luxury. Ideally located just a short walk to the beach and a scenic bike ride to town, train or Great Island, this home combines convenience with coastal tranquility. Thoughtfully designed for both comfort and entertaining, the home

  Janine Tienken Houlihan Lawrence

  24 Sunswyck Rd, Darien, CT 06820
• 

  

  /38

  $4,395,000

  • 5 Beds
  • 4.5 Baths
  • 3,919 Sq Ft

  3 Edgehill Dr, Darien, CT 06820

  Experience the perfect blend of charm and sophistication in this beautifully updated Nantucket-style Colonial, located within the Tokeneke Association. Originally built in 1921, this home has been thoughtfully expanded and renovated, preserving its classic architecture while introducing contemporary comfort and style. Perched on a naturally elevated lot, the home enjoys sweeping views of Scott's

  Ashley Dineen Compass Connecticut, LLC

  3 Edgehill Dr, Darien, CT 06820
• 

  

  /40

  $2,465,000

  • 6 Beds
  • 3.5 Baths
  • 4,799 Sq Ft

  177 Old Kings Hwy N, Darien, CT 06820

  Old-World Charm Meets Modern Living. Step into a special place where timeless character blends seamlessly with contemporary comforts. Renovated and expanded in 2009, this spacious home features a generous open floor plan ideal for both intimate gatherings and large celebrations. At the heart of the home is a chef's kitchen, complete with a large professional range, dual sinks, and separate

  Julie Hancock Houlihan Lawrence

  177 Old Kings Hwy N, Darien, CT 06820
• 

  

  /36

  $3,495,000

  • 6 Beds
  • 9 Baths
  • 6,233 Sq Ft

  6 Bouton Ln, Darien, CT 06820

  Welcome to 6 Bouton Lane - a beautifully designed Colonial offering six bedrooms in a prime location. Step into the grand three-story foyer, where elegant millwork and a sweeping staircase set the tone for this timeless home. Gorgeous skylights and expansive windows flood the interiors with natural light, enhancing the home's airy, welcoming ambiance. Both the formal living room and expansive

  Janine Tienken Houlihan Lawrence

  6 Bouton Ln, Darien, CT 06820
• 

  

  /39

  $2,895,000

  • 5 Beds
  • 3.5 Baths
  • 4,020 Sq Ft

  4 Rabbit Ln, Darien, CT 06820

  This contemporary Colonial, crafted by Alfieri Enterprises and thoughtfully reimagined in 2025 by Gill & Gill Architects, blends timeless charm with modern sophistication. Nestled on a sought-after cul-de-sac convenient to downtown Darien, this nearly 4,000SF home offers 5 bedrooms, 3.5 bathrooms-perfectly designed for both everyday living and elegant entertaining. The main level boasts open

  Becky Munro Brown Harris Stevens

  4 Rabbit Ln, Darien, CT 06820
• 

  /2

  $2,795,000 Coming Soon

  • 6 Beds
  • 7 Baths
  • 6,058 Sq Ft

  202 Mansfield Ave, Darien, CT 06820

  Dive into luxury at 202 Mansfield Avenue, Darien, CT! This 6-bedroom, 5.2 bath beauty boasts 6,058 sq. ft. of pure elegance on over an acre with a heated pool. This home is perfect for living the Darien dream. Don't miss out on this Connecticut treasure!

  Lindsay Sheehy Compass Connecticut, LLC

  202 Mansfield Ave, Darien, CT 06820
• 

  

  /35

  $1,495,000

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft

  10 Fairfield Ave, Darien, CT 06820

  Charming Colonial in Prime Location: Welcome to this beautifully maintained 3-bedroom, 2.1-bath Colonial, perfectly situated in one of the area's most desirable neighborhoods-just moments from schools, train, and town. Offering a seamless floor plan ideal for both everyday living and entertaining, this home features a thoughtfully renovated gourmet kitchen with a center island, premium finishes,

  Janine Tienken Houlihan Lawrence

  10 Fairfield Ave, Darien, CT 06820
• 

  

  /39

  $1,799,000

  • 5 Beds
  • 3.5 Baths
  • 3,108 Sq Ft

  154 Holmes Ave, Darien, CT 06820

  Welcome to 154 Holmes Avenue! Only the second owner since 1920 this charming colonial is all about blending classic vibes with modern comfort. With 5 bedrooms, 3.5 bathrooms, and 3108 square feet, there's plenty of space for everyone to spread out and relax. Step inside to the inviting foyer which opens up to an oversized living room with fireplace, formal dining room and the gorgeous freshly

  Keiley Fuller Compass Connecticut, LLC

  154 Holmes Ave, Darien, CT 06820
• 

  

  /40

  $7,295,000

  • 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
• 

  

  /38

  $1,799,000

  • 4 Beds
  • 2.5 Baths
  • 2,337 Sq Ft

  16 Dubois St, Darien, CT 06820

  Welcome home to 16 Dubois! This lovely Cape exudes charm and character throughout. Bright filled rooms with special built-ins, newer kitchen and baths, hardwood floors, wood burning fireplace, freshly painted interior and a 4th bedroom added and expanded guest bathroom, all of this on a highly desirable street. The exterior boasts an attached two car garage, cedar shingles, copper gutters and a

  Cheryl Williams Brown Harris Stevens

  16 Dubois St, Darien, CT 06820
• 

  

  /32

  $1,125,000

  • 3 Beds
  • 2 Baths
  • 1,838 Sq Ft

  9 Glenwood Dr, Darien, CT 06820

  A serene water garden below a magnificent dogwood tree is one of the many highlights of this charming residence nestled in a tranquil Darien neighborhood that delivers beauty, comfort and convenience. This delightful home offers three bedrooms and two full bathrooms, spread across a generous 1,838 sq feet of well-designed living space. Step inside to discover a remodeled island kitchen,

  Robert Marchesi Compass Connecticut, LLC

  9 Glenwood Dr, Darien, CT 06820
• 

  

  /36

  $1,399,000

  • 4 Beds
  • 2.5 Baths
  • 2,869 Sq Ft

  108 Colony Rd, Darien, CT 06820

  Exciting opportunity to live on Colony Road, one of the most coveted neighborhoods in Darien, known for its warmth, character and community feel! Lovingly cared for by the same family for the past 50+ years, this cherished 4/5 bedroom, 2 1/2 bath Colonial home is ready for its next owner to reinvent and make it their own, and offers a formal living room with fireplace and picture window, a dining

  Meredith Derosa William Pitt Sotheby's Int'l

  108 Colony Rd, Darien, CT 06820
• 

  

  /19

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  30 Cherry St, Darien, CT 06820

  Discover this beautifully renovated, energy-efficient, 3-bedroom home in Darien. Nestled in a peaceful cul-de-sac, this turn-key property features a flat, fenced-in backyard, perfect for relaxation or play. Enjoy the convenience of being within close proximity to Norton Heights Train Station, Darien Commons, and downtown Darien's vibrant restaurants and shops. Inside, the modern, open floor plan

  Katherine Sparkman William Raveis Real Estate

  30 Cherry St, Darien, CT 06820
• 

  

  /21

  $2,195,000

  • 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
• 

  

  /17

  $1,395,000

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

  128 West Ave, Darien, CT 06820

  Move-in ready and ideally located moments to all the best Darien has to offer! Welcome to 128 West Avenue - a beautifully updated home with an open-concept layout designed for modern living. The bright and spacious living room flows effortlessly into the renovated kitchen featuring a large center island, and 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
• 

  

  /37

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  365 West Ave, Darien, CT 06820

  Discover the epitome of modern living at 365 West Avenue. This one-of-a-kind residence boasts a contemporary and stylish aesthetic, highlighted by unique materials and finishes with a distinct Danish flair. This home is thoughtfully designed to blend comfort with sophistication. Step inside to find a fully renovated kitchen featuring a Viking gas range & hood, and a breakfast bar with room for 3

  Maggie Marchesi Compass Connecticut, LLC

  365 West Ave, Darien, CT 06820
• 

  

  /40

  $950,000

  • 5 Beds
  • 2 Baths
  • 2,352 Sq Ft

  65 Maple St, Darien, CT 06820

  Charming Cape Cod Home in Prime Noroton neighborhood Location! Welcome to this light-filled 4-5 bedroom, 2-bath Cape Cod home, boasting a flowing floor plan with dual front and back staircases. The updated open kitchen/family room shines with marble counters, beadboard wainscoting, and a cozy breakfast bar - perfect for gatherings. The first floor features a spacious guest room with a walk-in

  Eileen Murphy William Pitt Sotheby's Int'l

  65 Maple St, Darien, CT 06820
• 

  

  /21

  $685,000

  • 1 Bed
  • 1.5 Baths
  • 900 Sq Ft

  33 Hale Ln, Darien, CT 06820

  Enjoy easy, FIRST FLOOR living right in the heart of downtown Darien. Tucked into one of the most private corners of the complex, this home has been thoughtfully updated to blend style and function.The open floor plan includes a kitchen with dedicated dining area, a spacious living room with wood wood-burning fireplace, a covered balcony, and a primary suite with ample storage. The kitchen

  Robin Halsey Compass Connecticut, LLC

  33 Hale Ln, Darien, CT 06820
• 

  

  /33

  $1,995,000

  • 4 Beds
  • 4.5 Baths
  • 3,540 Sq Ft

  1745 Post Rd, Darien, CT 06820

  FULLY AVAILABLE. Tucked Gracefully back from the road this Elegant 4 bedroom & 5 bath home is not to be missed! When you walk through the Oversized Doors into the Grand front hall with soaring ceilings you will fall in love with this beautiful home. Incredible 9 foot ceilings throughout. A formal living and dining room with custom millwork, coffered ceilings & french doors. Enjoy the family room

  Kathryn Bates Compass Connecticut, LLC

  1745 Post Rd, Darien, CT 06820
• 

  

  /40

  $2,395,000

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft

  112 Camp Ave, Darien, CT 06820

  Classic charm meets modern living in this updated colonial, set on over an acre with a stunning wood roof, stone walls, and a circular driveway. Entirely new second floor added. Now you have 4+ bedrooms, 4 full baths, and flexible living spaces on both floors, there's room for everyone plus exciting potential for future expansion.The main level features a spacious living/family room, private

  Holly Hurd Houlihan Lawrence

  112 Camp 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
• 

  

  /35

  $1,799,000

  • 4 Beds
  • 2.5 Baths
  • 2,301 Sq Ft

  221 Old Kings Hwy N, Darien, CT 06820

  Bursting with charm, this home has a rare blend of classic old-world character and modern updates and amenities. The thoughtfully designed chef's kitchen features a vaulted ceiling, custom moldings, and a center island, serving as the heart of the home. An open layout connects the kitchen, living spaces, and outdoor areas, making it ideal for both daily living and entertaining. French doors

  Zoe Hamann Compass Connecticut, LLC

  221 Old Kings Hwy N, Darien, CT 06820
• 

  

  /15

  $950,000

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  86 Hecker Ave, Darien, CT 06820

  CONVENIENCE PLUS... This 1950's cape has so much to offer and a great opportunity to join the Darien community.. Three bedrooms, one conveniently on the first floor, living room with fireplace, 2 full baths (one on each floor) and a usable lot with great parking. WALK to Noroton Heights train and Darien Commons with its great shops and restaurants, and to Baker Park with playground and baseball

  Mary Lopiano Brown Harris Stevens

  86 Hecker Ave, Darien, CT 06820
• 

  

  /17

  $1,150,000

  • 4 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  17 Silver Lakes Dr, Darien, CT 06820

  This is a one acre property on a lovely cul-de-sac walkable to Tokeneke Elementary School. There is a school crossing guard at the street's entrance for school days. Hardwood floors, with a deck off of the kitchen. Spacious 4 bedrooms with 2 and 1/2 baths. Attached 2 car garage. Wood burning fireplace. This has been a rental property for many years.There are no disclosures, therefore this

  Pam Roberts William Pitt Sotheby's Int'l

  17 Silver Lakes Dr, Darien, CT 06820
• 

  

  /38

  $35,000,000

  • 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

  $35,000,000

  • 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
• 

  

  /38

  $6,495,000

  • 6 Beds
  • 5.5 Baths
  • 6,586 Sq Ft

  31 Contentment Island Rd, Darien, CT 06820

  Premier Darien Waterfront Residence on Contentment Island Road, in the private Tokeneke Association! This exquisitely renovated estate seamlessly blends classic beauty with modern amenities, catering to the desires of today's discerning homebuyers. This property boasts abundant space, featuring direct water access complemented by a private dock and moorings, as well as a charming guest house,

  Patricia Schram William Pitt Sotheby's Int'l

  31 Contentment Island Rd, Darien, CT 06820
• 

  

  /20

  $6,670,000

  • 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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 2