Homes for Sale near Middlesex Middle School

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  /40

  $4,888,000

  • 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
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• 

  

  

  /40

  $2,750,000 Open Sat 2PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 4,376 Sq Ft

  50 Mansfield Ave, Darien, CT 06820

  Experience the best of Darien in this extraordinary in-town retreat - a rare blend of luxury, lifestyle, and location. Steps from top-rated schools, Metro North, shops, and dining, this home is a true sanctuary with every modern amenity. Beyond the gracious front entry, discover light-filled spaces designed for effortless entertaining: an elegant living room with fireplace, an inspiring

  Genevieve Schettino Compass Connecticut, LLC

  50 Mansfield Ave, Darien, CT 06820
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  /39

  $2,895,000 Open Sun 2PM - 4PM

  • 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
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  /40

  $4,025,000

  • 5 Beds
  • 6 Baths
  • 5,338 Sq Ft

  2 Tanglewood Trail, Darien, CT 06820

  Welcome to this beautifully renovated custom-designed home, perfectly situated steps from town and train for ultimate convenience. Nestled on a quiet Darien cul-de-sac, this light-filled, modern retreat blends timeless design with thoughtful updates throughout. Renovated in 2022-2023, the home features 9.5 ft ceilings, new hardwood floors, custom lighting, and a stunning chef's kitchen with

  Genevieve Schettino Compass Connecticut, LLC

  2 Tanglewood Trail, Darien, CT 06820
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  /40

  $2,600,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,787 Sq Ft

  13 Outlook Dr, Darien, CT 06820

  Move right into this completely renovated home on a sought-after street in the Hindley School district. The kitchen and bathrooms have all been thoughtfully remodeled for today's lifestyle while preserving the charm and integrity of this classic Tudor. With a sunny open kitchen-family room, separate vaulted ceiling office/sunroom, and living and dining rooms, the spacious floor plan allows for

  Carolyn Brook William Pitt Sotheby's Int'l

  13 Outlook Dr, Darien, CT 06820
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  /40

  $3,450,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 5,265 Sq Ft

  2 Dogwood Ln, Darien, CT 06820

  Welcome to 2 Dogwood Lane, a stunning home nestled in the prestigious Tokeneke Association. This elegant home offers the perfect blend of modern luxury and timeless design, with an expansive 5,265 square feet of living space on a beautifully landscaped 1.5 acre lot. Step inside to discover a tastefully renovated interior featuring high ceilings, tons of light and spacious living areas. The home

  Keiley Fuller Compass Connecticut, LLC

  2 Dogwood Ln, Darien, CT 06820
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  /40

  $3,000,000

  • 5 Beds
  • 6 Baths
  • 7,446 Sq Ft

  32 Old Oak Rd, Darien, CT 06820

  32 Old Oak Road is a stunning 6,000 square foot, turn-key home featuring 5 bedrooms and 4.5 bathrooms located on a quiet cul-de-sac within the coveted Boulder Ridge Association. From the moment you step inside, the high ceilings, custom finishes, and abundant natural light reflect the comforts and elegance of modern living. The main level includes: formal living and dining rooms, family room with

  Kristin Nemec William Pitt Sotheby's Int'l

  32 Old Oak Rd, Darien, CT 06820
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  /39

  $3,995,000

  • 5 Beds
  • 5.5 Baths
  • 5,328 Sq Ft

  84 Nearwater Ln, Darien, CT 06820

  Nestled on Nearwater Lane just moments from the beach, this beautifully renovated 5-bedroom/5 and a half bath home offers the perfect blend of luxury, comfort, and functionality. Step inside to discover a thoughtfully designed floor plan that flows effortlessly from room to room. The heart of the home is the stunning, fully renovated kitchen-complete with top-of-the-line appliances, sleek

  Janine Tienken Houlihan Lawrence

  84 Nearwater Ln, Darien, CT 06820
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  /38

  $5,295,000

  • 5 Beds
  • 7 Baths
  • 6,242 Sq Ft

  48 Dorchester Rd, Darien, CT 06820

  Welcome to the epitome of sophisticated elegance at 48 Dorchester Road. As you ascend the graceful driveway, the declaration "I've arrived" is truly realized in this grand estate where the grandeur of Versailles meets the charm of Darien. This unique residence is replete with architectural surprises, including a hidden main staircase which gracefully leads to an enchanting interior balcony

  Maggie Marchesi Compass Connecticut, LLC

  48 Dorchester Rd, Darien, CT 06820
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  /40

  $3,250,000

  • 5 Beds
  • 6 Baths
  • 4,358 Sq Ft

  12 Driftway Ln, Darien, CT 06820

  Welcome to your dream home! Nestled on a picturesque street, this stunning 5 bedroom colonial boasts incredible curb appeal that will captivate you from the moment you arrive. As you step inside, you'll be greeted by an inviting flow that seamlessly connects the spacious living area, all bathed in natural light thanks to the abundance of windows and elegant french doors. Picture yourself

  Pam Pokorny Houlihan Lawrence

  12 Driftway Ln, Darien, CT 06820
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  /36

  $3,495,000 Open Sun 1PM - 4PM

  • 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
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  /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
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  /36

  $2,095,000

  • 4 Beds
  • 2.5 Baths
  • 2,762 Sq Ft

  4 Duffys Ln, Darien, CT 06820

  Welcome to your new home! This fully renovated 4-bedroom, 2.5-bath beauty is tucked away on a quiet cul-de-sac, just over a mile from the beach in a top-rated, award-winning school district. Inside, you'll love the bright, open layout, updated kitchen, and modern finishes throughout. There's plenty of space to relax, entertain, and make memories. The bedrooms are spacious and comfortable,

  Stephanie Slatkow Houlihan Lawrence

  4 Duffys Ln, Darien, CT 06820
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  /32

  $1,325,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  39 Dubois St, Darien, CT 06820

  Move right into this beautifully renovated three-bedroom Colonial nestled in sought-after neighborhood. Conveniently located near Hindley School, trains, beaches and town amenities. This well-maintained home features a sun-filled living room with fireplace which opens to a stunning kitchen and dining area perfect for entertaining. Sunroom offers additional space ideal for an office, playroom or

  Deborah Hidy Houlihan Lawrence

  39 Dubois St, Darien, CT 06820
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  /40

  $950,000 Open Sun 1PM - 3PM

  • 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
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  /21

  $685,000 Open Sun 1PM - 3PM

  • 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
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  /30

  $2,449,000 Open Sat 12PM - 3PM

  • 5 Beds
  • 3 Baths
  • 3,947 Sq Ft

  23 Miles Rd, Darien, CT 06820

  Welcome to 23 Miles Drive, a beautifully rebuilt 5-bedroom, 3-bath home offering nearly 4,000 sq ft of move-in ready living space in one of Darien's most desirable neighborhoods. Completely rebuilt down to the foundation in 2007, this home features a bright white eat-in kitchen that opens to a spacious family room and a private deck and patio overlooking a professionally landscaped, level

  John Schiaroli Coldwell Banker Realty

  23 Miles Rd, Darien, CT 06820
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  /31

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

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

  1745 Post Rd, Darien, CT 06820

  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 with a wood

  Kathryn Bates Compass Connecticut, LLC

  1745 Post Rd, Darien, CT 06820
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  /40

  $2,495,000 Open Sun 1PM - 3PM

  • 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
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  /25

  $1,200,000 Open Sun 12PM - 4PM

  • 2 Beds
  • 1.5 Baths
  • 1,428 Sq Ft

  36 Park Place, Darien, CT 06820

  Welcome to this charming 3-bedroom, 1.5-bath home nestled in a quiet, well-established neighborhood and sitting on a level corner lot. As you enter this classic Cape, the welcoming layout of the main level immediately makes you feel at home. This well-loved family home has been occupied by the same family for over 70 years. It is now ready for a new family to personalize and make your own. The

  Valerie Applebaum Berkshire Hathaway NE Prop.

  36 Park Place, Darien, CT 06820
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  /29

  $1,599,000

  • 4 Beds
  • 4 Baths
  • 2,633 Sq Ft

  4 Kelsey St, Darien, CT 06820

  A Commuter's Delight! Beginning from the lower level & up, this terrific new listing is as close to brand new as you can get! The unique floor plan offers great flexibility w/open entertaining space on the main level in addition to a bonus den/office/potential 5th BR & full bathroom. The 2nd floor delivers a stylish Primary bedroom suite w/plentiful closet space & a luxurious en-suite bathroom.

  Carlalisa Giansanti Outlook Realty

  4 Kelsey St, Darien, CT 06820
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  /37

  $1,375,000 Open Sat 12PM - 2PM

  • 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
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  /38

  $1,099,000

  • 5 Beds
  • 3 Baths
  • 1,954 Sq Ft

  2715 Post Rd, Darien, CT 06820

  Darien CT!!! Location, Location, Location! Super Spacious 4+ Bedroom, 3+ Bath Home in Prime Darien-Stamford Location! Welcome to this light-filled, beautifully aportioned home offering the best of both worlds-highly sought-after Darien schools with the vibrant lifestyle of Stamford, CT! Enjoy easy access to Cove Island Park, Stamford dining and entertainment, and the Darien YMCA with pool and

  Fiona Porter Keller Williams Realty

  2715 Post Rd, Darien, CT 06820
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  /38

  $1,750,000

  • 4 Beds
  • 3 Baths
  • 3,045 Sq Ft

  24 Laforge Rd, Darien, CT 06820

  Step right into this inviting 3-4 bedroom home, ideally situated in a desirable, quiet neighborhood just minutes from all the conveniences of town. The open kitchen flows seamlessly into the family room, which leads out to a spacious deck overlooking a private backyard-perfect for relaxing or entertaining. The primary bedroom features built-in storage to keep everything neatly organized, while a

  Julie Hancock Houlihan Lawrence

  24 Laforge Rd, Darien, CT 06820
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  /35

  $1,750,000

  • 4 Beds
  • 3 Baths
  • 2,521 Sq Ft

  7 Walmsley Rd, Darien, CT 06820

  Charming Renovated Colonial in Prime Darien Neighborhood Nestled in one of Darien's most sought-after neighborhoods, this beautifully renovated and expanded custom Colonial offers the perfect blend of classic charm and modern comfort. Thoughtfully updated in 2017 & 2023, this 4-bedroom, 3 full-bath home features sun-drenched living spaces and a versatile layout designed for today's lifestyle. At

  Janine Tienken Houlihan Lawrence

  7 Walmsley Rd, Darien, CT 06820
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  /35

  $1,895,000

  • 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
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  /35

  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,818 Sq Ft

  15 Cliff Ave, Darien, CT 06820

  This stunning, fully updated four-bedroom Colonial seamlessly blends modern luxury with timeless charm. The main level, with 9 ft ceilings, boasts multiple living spaces, including a formal living room with gas fireplace, a cozy family room with wood-burning fireplace, and a spacious dining room-perfect for entertaining. The eat-in kitchen features radiant heat flooring and ample

  Genevieve Schettino Compass Connecticut, LLC

  15 Cliff Ave, Darien, CT 06820
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  /15

  $950,000 Open Sun 1PM - 3PM

  • 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
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  /33

  $2,400,000

  • 5 Beds
  • 3.5 Baths
  • 3,638 Sq Ft

  24 Casement St, Darien, CT 06820

  Nestled in a close-knit neighborhood with front yard playdates and backyard barbecues, this 5 bedroom classic colonial, set on a flat .5 acre lot, is a perfect blend of tradition and modern comfort. Located just moments from Noroton Heights Train Station, the vibrant energy of Darien Commons, shopping, restaurants and local beaches, this home offers a rare combination of convenience and serene

  Genevieve Schettino Compass Connecticut, LLC

  24 Casement St, Darien, CT 06820
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  /16

  $999,000

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

  14 Sedgewick Village Ln, Darien, CT 06820

  Sun-filled oasis with ample privacy, yet still a convenient walk to Old Kings Market, town, train, and Tilley Pond Park. Well-maintained home with enclosed courtyard and garden area, perfect for outdoor entertaining. Eat-in kitchen, living/dining room with fireplace, 2 bedrooms with cathedral ceilings, 2.5 baths. Laundry on 2nd floor. Plenty of storage with two attics, hatch in unit and pull-down

  John Tibbets CT Waterfront Properties

  14 Sedgewick Village Ln, Darien, CT 06820
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  /33

  $989,000

  • 3 Beds
  • 2 Baths
  • 2,408 Sq Ft

  191 Hollow Tree Ridge Rd, Darien, CT 06820

  Well-loved family home, first time on the market in many years, and ready to make your own. 3 Bedrooms upstairs with a full bathroom. There is also a full bathroom on the main level with a possible 4 th bedroom /office/ Au-pair room/playroom. Large eat-in-kitchen with ample space for a center island. The finished basement is ideal for family gatherings, games, or a playroom. The driveway is

  Beverley Macgregor William Raveis Real Estate

  191 Hollow Tree Ridge Rd, Darien, CT 06820
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  /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
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  /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
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  /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
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  /40

  $14,900,000

  • 6 Beds
  • 10 Baths
  • 10,579 Sq Ft

  Unlisted Address

  Home by the Sea is set majestically behind stone pillars and gates on one of the largest Long Neck Point parcels, affording its residents 3.2 landscaped acres of privacy. As you enter, the peaceful setting of the secluded cove takes your breath away. There are wrap-around decks, velvet lawns, flowering gardens and water views for miles. Nature lovers will be in Heaven. The acclaimed architect

  Candace Blackwood BHHS Darien/New Canaan

  Unlisted Address
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  /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
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  /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
• 

  

  /40

  $6,250,000

  • 6 Beds
  • 8 Baths
  • 8,454 Sq Ft

  26 Peach Hill Rd, Darien, CT 06820

  This newly constructed Nantucket-Style Colonial, exudes timeless elegance. The 6 bedroom and 6.2 bathroom home is meticulously designed with high-end finishes and exquisite millwork throughout. An impressive 3-story foyer anchors the expansive main level as formal living and dining rooms seamlessly flow to the family room and gourmet kitchen. While French doors lead to a patio overlooking the

  Janine Tienken Houlihan Lawrence

  26 Peach Hill Rd, Darien, CT 06820
• 

  

  /38

  $6,900,000

  • 6 Beds
  • 7.5 Baths
  • 9,872 Sq Ft

  28-A Old Farm Rd, Darien, CT 06820

  Nestled within the prestigious Tokeneke Association, this exceptional modern farmhouse is a masterpiece of design, offering a luxurious lifestyle on a grand scale. Boasting 9872 square feet of exquisitely crafted living space, this architectural gem seamlessly combines the timeless charm of a farmhouse with the sophistication of modern luxury. Upon entering, you are greeted by an impressive foyer

  Keiley Fuller Compass Connecticut, LLC

  28-A Old Farm 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

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