Darien Real Estate

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Newest Listings in Darien

$1,750,000

4 Beds ⋅ 3 Baths ⋅ 24199724 MLS

Set on a flat property with flexible living spaces and a wonderful Noroton Heights location just 0.6 miles from the train, 2 Fairfield Avenue offers an inviting blend of comfort, character, and convenience. The open kitchen is at the heart of the home, with a separate living room, family/TV room, playroom or home office, and convenient first-floor powder room. French doors between the kitchen/dining area and the living room with fireplace allow for more defined spaces when desired. A first-floor ensuite bedroom can serve as a primary suite, guest room, or fourth bedroom, while three additional bedrooms and a spacious full bath are upstairs. The partially finished lower level offers space for a workout area, playroom or additional family room, spacious laundry, and plenty of storage. The flat property offers generous outdoor space, from a bluestone terrace off the family room to a large lawn with a storage shed, framed by mature shade trees and privacy hedges. Improvements include a redesigned and waterproofed basement with new flooring and enclosed sump pump system, new kitchen appliances, updated trim, crown molding and baseboards, an expanded smart-home system, and landscaping. Ideally located near the Noroton Heights train station, Heights Commons, beaches, parks, playgrounds, Little League fields, shopping, and dining.

2 Fairfield Ave, Darien

$1,299,000

3 Beds ⋅ 2 Baths ⋅ 24200714 MLS

Own two fully renovated residences on one Darien property, offering the flexibility to live, earn, invest, or create a combination that works for you. 53 Maple Street pairs a beautifully renovated main residence with a separate, fully renovated one bedroom cottage, creating an income producing property unlike most offerings in Darien. Imagine living in the main home while rental income from the cottage helps offset your monthly expenses, or maintaining both residences as an investment with two established income streams. The property also offers exceptional flexibility for guests, a private home office, or changing needs over time. Both residences have been renovated for comfortable, easy living, with updated interiors and distinct living spaces that provide privacy and independence. The main residence is currently leased at $4,050 per month and the cottage at $3,500 per month, with both rents below current market potential. For buyers searching for a Darien CT home with rental income, a two residence property, or a long term real estate investment, 53 Maple Street presents a compelling opportunity: two renovated homes, two potential income streams, and the freedom to decide how the property works for you.

53 Maple St, Darien

$7,500,000

5 Beds ⋅ 8 Baths ⋅ 24200463 MLS

Built in 2023 and stunningly refreshed in 2026, this five-bedroom, eight-bath home is set on two landscaped acres framed by handmade stone walls. Soaring 9' to 12' ceilings, oversized simulated divided light windows and Pella doors enhance the light-filled interiors. The open living and breakfast areas center around a spectacular eat-in chef's kitchen with high end appliances and a waterfall-edge marble island and a formal dining room with butler's pantry. A double-height vaulted great room features a wood-burning fireplace, wet bar and French doors out to the Gunite pool with auto cover. The first floor also offers an office with powder room, a sunroom/pool cabana room and en-suite bedroom with exterior entrance. Upstairs, a luxurious primary suite includes a cathedral ceiling, balcony, four closets and spa bath with dual showers, plus three additional en-suite bedrooms with walk-in closets, a homework room, sitting area and a playroom / game room. The beautifully finished lower level is complete with a theater, a bar, a mirrored gym, full bath, a sauna and a steam room. 3 car oversized garage. Generator. This stunning build by Ritzzo Development has everything!

460 Middlesex Rd, Darien

$1,299,000

3 Beds ⋅ 2 Baths ⋅ 24200711 MLS

53 Maple St, Darien

$3,950,000

5 Beds ⋅ 6 Baths ⋅ 24198712 MLS

Set behind stone walls on nearly 2 acres, this exceptional 5-bedroom home offers over 5,000 SF of refined living in a truly extraordinary setting. A dramatic 2-story foyer w/circular staircase and exquisite herringbone floors sets the tone for elegance throughout. Walls of windows fill the gracious interiors with natural light and frame manicured grounds and lush gardens. The formal living room, w/classic wood-burning fireplace, is complemented by a handsome library w/fireplace and wet bar, while an elegant dining room, detailed w/wainscoting and custom built-ins, sets the stage for memorable gatherings. At the heart of the home, a gourmet kitchen with custom cabinetry and oversized island flows into a sun-drenched family room w/fireplace and a wall of glass opening to the expansive terrace - perfect for indoor/outdoor entertaining. The luxurious primary suite features generous walk-in closets and spa-like bath with dual vanities, soaking tub and radiant-heated floors. Four additional bedrooms each enjoy private baths. A separate wing with bedroom, bath and playroom offers an ideal retreat for guests. Additional amenities include a private vaulted-ceiling office, first-floor gym, mudroom, laundry, two-car garage and generator. Beyond the interiors lies a secluded oasis: a level lawn, tranquil pond and fountain, charming footbridge, and secret garden, w/protected land-trust property beyond. A rare expression of privacy, beauty, space, and enduring distinction

700 Hollow Tree Ridge Rd, Darien

$4,750,000

4 Beds ⋅ 3 Baths ⋅ 24196499 MLS

Rare opportunity to experience waterfront living at its finest. Perfectly positioned on the picturesque Five Mile River with 240 feet of direct water frontage, this exceptional shingle-style residence offers panoramic water views, an all-tide dock, & direct access to Long Island Sound for boating, paddleboarding, kayaking, fishing, and waterfront entertaining. Designed to embrace its setting, the turnkey 4-bedroom, 3-bath home features a light-filled floor plan with vaulted ceilings, a chef's kitchen appointed with a new Sub-Zero refrigerator, Wolf oven, and gas cooktop, and seamless indoor-outdoor living extending to a private, enclosed waterfront yard, perfect for entertaining or enjoying sunrises over the harbor. Equipped with a full-house generator, underground irrigation, and abundant storage. Ideally located within walking distance of Rowayton Village, Metro-North, and the scenic roads of Tokeneke, this exceptional home offers the best of Fairfield County's coastal lifestyle. Spend your days enjoying Darien's beaches, charming cafes, boutique shops, and local restaurants, while taking advantage of a direct commute to Manhattan, less than an hour away. Combining an all-tide dock, expansive water frontage, and unparalleled access to both nature and amenities, this is a rare offering in one of Fairfield County's most coveted coastal communities. The listing agent can secure your private appointment. Available to move in immediately (before closing).

61 Five Mile River Rd, Darien

$1,419,000

3 Baths ⋅ 24196218 MLS

Rare opportunity for an investor or user! Two (2) buildings consisting of front building with two (2) residential units and rear building consisting of offices over warehouse (three storage bays) with separate overhead door access and an additional storage shed to the rear. Great for contractors or any small business requiring warehouse/storage or vehicle storage with income from residential units. Rear office and warehouse are vacant available for use. Potential for conversion of rear office to residential. Gross potential income based on market rents of $108,000. Expenses total approximately $20,000, which includes $9,100 real estate taxes and insurance at $4,500.Projected Net Income is $88,000.

676 Boston Post Rd, Darien

$3,900,000

5 Beds ⋅ 6 Baths ⋅ 24189523 MLS

Set on 2.19 private acres in a prime Darien location, 222 Brookside Road offers exceptional space, privacy, and opportunity just minutes from town and Cherry Lawn Park. With more than 7,000 square feet above grade, plus an additional 3,000 square feet on the lower level, this expansive 4-bedroom, 5.5-bath residence provides an incredible canvas to create a home tailored to your vision. Generously proportioned rooms and tall ceilings create a wonderful sense of scale throughout, while a flexible floor plan offers endless possibilities, including the potential for a first-floor in-law or guest suite. The exceptionally spacious lower level provides abundant room for entertaining, relaxing, and recreation. Outdoors, the expansive property is highlighted by a pool and well-appointed pool house featuring a full bath, laundry hookups, and full kitchen with a range and space for a refrigerator-creating a private setting for summer gatherings and relaxation. An attached four-car garage, plus an additional detached two-car garage, provides parking for six cars and even more flexibility. A rare opportunity to enjoy significant acreage, remarkable space, and endless potential in an incredibly convenient Darien location.

222 Brookside Rd, Darien

$3,950,000

4 Beds ⋅ 4 Baths ⋅ 24186583 MLS

Originally the sole residence on Wildcat Road, this distinguished 1925 stone manor blends timeless architectural elegance with a commanding setting. Located within Darien's coveted Delafield Island private association, the property is approached by a sweeping circular drive and surrounded by mature landscaping offering a rare sense of privacy, grandeur, and permanence, just minutes from downtown Darien, the Metro-North train, beaches, and Great Island. Rich in character and craftsmanship, the residence showcases architectural details rarely found today, including soaring 12-foot ceilings, a dramatic circular staircase, five fireplaces, Juliet balconies, vintage servant bells, graceful arches, skylights, and a sun-filled glass solarium. Thoughtfully designed for both grand entertaining and comfortable everyday living, the spacious country kitchen opens to an expansive deck overlooking the surrounding natural landscape. Adding to the property's exceptional appeal, several acres of protected land trust border the rear of the home, preserving a tranquil backdrop and enhancing the estate-like setting. Whether hosting family gatherings, entertaining guests, or simply enjoying the peace and beauty of its surroundings, 15 Wildcat Road offers a unique opportunity to own one of Delafield Island's most distinctive and historic homes.

15 Wildcat Rd, Darien

$1,699,900

5 Beds ⋅ 4 Baths ⋅ 24184615 MLS

Spacious Colonial in the sought-after Hindley Elementary School district! Offering over 2500sf on the main and upper levels, this 5-bedroom, 3 full and 1 half bath home is designed for comfortable everyday living and entertaining. The oversized primary suite is complemented by generous living spaces, while 500sf finished lower level with wet bar provides an ideal recreation room, media room, home gym, or entertaining space. The eat-in kitchen opens to a large deck overlooking a private, fully fenced backyard-perfect for outdoor dining, children, pets, and summer gatherings. Enjoy the convenience of sidewalks leading to Darien's train station, downtown shops, restaurants, parks, beaches, and the Darien YMCA with beach view just across the street, offering competitive swimming and outstanding gymnastic programs, nursery school and activities for all ages. Public transportation is nearby, and quick access to I-95 makes commuting a breeze. Move right in and experience the exceptional convenience and lifestyle that Darien has to offer.

2435 Boston Post Rd, Darien

$12,995,000

5 Beds ⋅ 8 Baths ⋅ 24187039 MLS

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering one acre of east facing views that can be enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored this cherished home with the renowned builders, Significant Homes and interior designer, Cindy Rinfret, Rinfret LLC. The architectural integrity has been preserved with comfort and quality for today's lifestyle. A world-class property.

209-209 Long Neck Point Rd, Darien

$5,999,000

4 Beds ⋅ 6 Baths ⋅ 24164271 MLS

A rare opportunity to own a new construction home with Deeded Beach Rights on coveted Nearwater Lane in one of Darien's most desirable coastal neighborhoods. A seamless blend of sophisticated design, modern comfort, and coastal living. Moments from Weed Beach, downtown Darien, commuter rail service, and a Blue Ribbon elementary school. Designed for everyday living and entertaining, the home features soaring 10-12-foot ceilings, open-concept floor plan, and abundant natural light. Andersen A-Series windows, glass railings, refined finishes create bright, elegant living spaces. The bluestone patio provides an inviting outdoor retreat.The flexible layout includes four ensuite bedrooms, a luxurious primary suite featuring a spacious walk-in closet, spa-inspired bath, and private balcony with water views. A first-floor bedroom with private access and a finished lower level with a separate entrance offer versatility for guests, extended family, or a home office.At the heart of the home, a chef's kitchen is anchored by an oversized quartz island and appointed with Sub-Zero, Wolf, Cove, and Kohler fixtures. Additional highlights include second-floor laundry, a detached garage, pre-wired audio and security systems, underground utilities, whole-house generator connection, and modern mechanical systems.An exceptional opportunity to enjoy the convenience of new construction in one of Darien's premier locations. Deeded Noroton Bay Beach rights; buyers to verify.

142 Nearwater Ln, Darien

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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