N/A Homes with Middlesex Middle school

Welcome to the charming community of Darien, Connecticut, where picturesque landscapes meet a vibrant suburban lifestyle. Nestled in Fairfield County, Darien is celebrated for its top-notch schools, including the highly regarded Middlesex Middle School. This school is a cornerstone of the community, known for its dedicated educators and a diverse array of extracurricular activities that foster both academic and personal growth.

Darien boasts a rich tapestry of neighborhoods, each offering a unique blend of character and charm. From stunning waterfront properties along the Long Island Sound to cozy family homes in tree-lined streets, there’s something for everyone. The town’s commitment to maintaining green spaces and parks makes it an ideal place for families, providing ample opportunities for outdoor activities and community gatherings.

Residents of Darien enjoy a seamless blend of suburban tranquility and urban convenience. With easy access to the Metro-North train station, commuting to New York City is a breeze, making it a perfect location for professionals seeking a peaceful retreat after a busy workday. The town also offers a range of boutique shops, delightful restaurants, and cultural attractions, ensuring that there’s always something to explore.

Living in Darien means becoming part of a close-knit community that values education, family, and a high quality of life. If you’re looking for a place to call home, where exceptional schools like Middlesex Middle School are just a stone's throw away, Darien awaits with open arms. Discover the perfect blend of luxury, comfort, and community in this idyllic Connecticut town!

Newest N/A Homes with Middlesex Middle school

$1,600,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193539 MLS

105 Rose Lane blends classic charm with modern updates in a welcoming Darien neighborhood. This sun-filled 4-bedroom, 2-bath home features an open-concept first floor, an updated kitchen, and beautifully renovated bathrooms for a move-in ready experience. An additional living space offers flexibility for relaxing or entertaining, while the fantastic front porch is perfect for enjoying morning coffee or evening unwinding. Tucked on a quiet private road, the home offers a sense of privacy with a friendly, community feel. A finished basement provides space for a playroom, gym, or home office. Conveniently located just half a mile from the elementary school and close to Darien Commons for dining and shopping, with the train less than a mile away for an easy commute.

105 Rose Ln, Darien

$1,695,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192928 MLS

HIGHEST AND BEST BY 7/27 AT 5PM. UPDATED TAX CARD .. 2745 SQFT! Beautifully sited on a professionally landscaped corner lot, this turnkey home offers the perfect blend of comfort, flexibility, and convenience. The thoughtfully designed floor plan features four bedrooms and three updated full baths, including two spacious bedrooms and a renovated bath on the main level, plus two additional bedrooms upstairs with a large shared bath and a convenient second-floor laundry room. The exceptional fully permitted finished lower level expands the living space with a spa-inspired bath featuring heated floors, plus flexible areas for a home office, gym, playroom, media room, abundant storage, and a second laundry with oversized smart washer and dryer. Outside, mature landscaping, privacy fencing, irrigation, and a custom stone seating area create a private backyard retreat. Spend summer evenings gathered around the fire pit as professionally designed landscape lighting casts a warm glow across the property, creating the perfect setting for entertaining or unwinding at the end of the day. Extensively updated with a Navien tankless gas heating and hot water system, dual-zone central air, spray foam insulation, whole-house water softener and drinking water filtration systems, and updated mechanicals throughout. An attached two-car garage, natural gas, public water, and public sewer complete the package. Just moments from downtown Darien, the train, parks, shopping, and restaurants.

105 Holmes Ave, Darien

$1,395,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24129833 MLS

Welcome to 36 Richmond Drive! Tucked into a great Darien neighborhood, this three-bedroom, two-bath ranch is close to everything, bike to Cherry Lawn Park, walk to local shops and restaurants, or hop on the train in minutes. The home sits on a level, corner lot of over half an acre, with stone patios, a built-in grill, and plenty of yard space for play and entertaining. Inside, you'll find a lower level that's perfect for hanging out, with a playroom, bar, and a cozy wood-burning stove. Whether you're ready to update and make it your own, or you're looking for a project with great potential, this home is a terrific opportunity. All in the award-winning Ox Ridge Blue Ribbon School district!

36 Richmond Dr, Darien

$2,695,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24190949 MLS

Set on one of Darien's most sought-after, multi-million dollar cul-de-sacs, this sprawling wood and brick ranch offers exceptional scale and endless potential for the discerning buyer, renovator, or builder. Positioned on a remarkably private 2.5 acre lot, abutting another 10+ acres of protected wetlands, the setting affords unmatched peace, natural beauty, and exclusivity. The interior boasts a versatile layout. The back of the home features expansive walls of glass, with a fully enclosed glass terrace, which creates a seamless visual connection to the serene, wooded surroundings. Highlights include 3 generously sized bedrooms, 3.5 baths, a sauna, a spacious living room anchored by a beautiful stone fireplace, a formal dining room, and a large eat-in kitchen, with a large breakfast area. Designed with an indoor-outdoor flow in mind, the substantial multi-purpose room anchoring one end of the house, can be used according to any family's needs: a playroom, family room, studio, in-law suite. With its sliding doors that open to the flagstone terrace and the private free-form pool, it shows the flexibility of the design. Whether remodeling, renovating, expanding, or building new, this is a special one-of-a-kind opportunity to create your dream in your new home. Agents please check confidential remarks.

18 Linda Ln, Darien

$3,950,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$1,249,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24185967 MLS ⋅ Sedgwick Village At Darien BLDG.

Welcome to this beautifully renovated two-bedroom condo in one of Darien's most convenient locations. Just steps from Goodwives shopping center, the Metro-North train station, and the vibrant energy of downtown Darien, this home offers the perfect blend of modern comfort and walkable lifestyle. Pass through the private gate and be greeted by a serene personal courtyard and garden. A sliding glass door from the living area provides seamless access to this peaceful outdoor retreat-ideal for morning coffee, evening relaxation, or entertaining. The open-concept main level features a bright, updated kitchen that flows effortlessly into the dining and living areas. A cozy fireplace anchors the living room, creating a warm and inviting space for gatherings or quiet nights in. Upstairs, the primary suite impresses with dramatic vaulted ceilings and an enviable en-suite bathroom. Soak in the large soaking tub or enjoy the separate shower after a long day. A second en-suite bedroom and laundry is also located on this level. This turnkey condo is move-in ready with thoughtful updates throughout. Whether you're looking for an easy commute to New York City, a low-maintenance home base near shops and restaurants, or simply a stylish retreat in the heart of Darien, 4 Sedgwick Village Lane delivers

4 Sedgwick Village Ln Unit 4, Darien

$1,475,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24184745 MLS

The one you've been waiting for! Rarely does a home offer the character of an established neighborhood with the quality and convenience of essentially brand-new construction. Completely renovated from top to bottom, this turnkey 3-bedroom, 2.5-bath home is perfect as a starter home, condo alternative, or right-sizing opportunity. Every detail from the designer kitchen and luxurious baths to the roof, windows, siding, and major mechanical systems has been replaced or upgraded, creating a home designed for effortless living. The inviting open floor plan seamlessly blends comfort and functionality. The professionally landscaped grounds and an oversized entertaining deck provide the perfect backdrop for summer gatherings, outdoor dining, and everyday enjoyment. Just moments from Darien's award-winning schools, Metro-North, Rowayton Village, Five Mile River, beaches, shops, and restaurants, this home is perfectly positioned to enjoy an effortless coastal lifestyle. Simply unpack and enjoy summer just minutes from the water.

7 Raymond Hts, Darien

$3,850,000

6 Beds ⋅ 7 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24181525 MLS

Set on 2.9 private acres in one of Darien's most coveted locations, this exceptional 1937 residence seamlessly blends timeless architectural character with modern luxury. Encompassing approximately 5,700 square feet, the home offers six bedrooms, six full baths, and beautifully proportioned living spaces designed for both everyday living and elegant entertaining. A gracious foyer introduces sun-filled interiors featuring refined millwork, hardwood floors, and an effortless flow throughout. The thoughtfully designed floor plan includes formal and informal gathering spaces, a spacious chef's kitchen, and multiple rooms that overlook the property's picturesque grounds. Upstairs, the generous primary suite is complemented by well-appointed secondary bedrooms and baths, providing comfort and privacy for family and guests alike. Surrounded by mature landscaping and expansive lawns, the property offers a rare combination of estate-like privacy and convenience to town, train, schools, and beaches

30 Inwood Rd, Darien

$1,999,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24181698 MLS

Perfectly positioned just steps from downtown Darien, the train station, schools, and the vibrant new Corbin District, this beautifully updated Colonial offers the ideal blend of convenience, charm, and move-in-ready living. Freshly painted throughout with newly refinished hardwood floors, this 5-bedroom, 3.5-bath home features generous living spaces including a formal living room, dining room, family room, rec room, and an open kitchen designed for both everyday living and entertaining. Set on .70 acres, the backyard is a true surprise, featuring an expansive multi-level deck ideal for outdoor dining, entertaining, and relaxing. Beyond the property lies an additional 1.19 acres of protected open space, creating a beautiful natural backdrop and an unexpected sense of space. Timeless curb appeal, abundant living space, and an unbeatable in-town location make this a truly exceptional opportunity. Walk to downtown Darien, the train station, schools, restaurants, and the vibrant new Corbin District while enjoying all the comfort and flexibility of a move-in-ready home.

93 West Ave, Darien

$5,997,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24179917 MLS

Designed by custom home builder Vita Design, this exciting newly constructed modern residence is a refined architectural statement that balances scale and light, capturing direct 5 Mile River views and a connection to its natural surroundings. Finished across four levels, the home features dramatic 10- and 16-foot ceilings and a main level wrapped in floor-to-ceiling European-style windows filling the interior with natural light, creating seamless indoor-outdoor living. All living spaces are designed for flexibility and function. The kitchen showcases an oversized center island, Leicht mahogany cabinetry, Miele appliances, huge pantry and spacious dining area overlooking the river. The primary suite offers a private retreat with balcony, water views, lux bath and generous closets. All other bedrooms feature en-suite baths with high-end, individual finishes. Lower-level and third-floor bedrooms provide privacy and adaptable use. Outdoor living centers around the covered wrap around patio and heated pool with retractable cover, enhancing the home's resort-like feel. Additional amenities include home automation, mudroom, laundry room, and a fully finished lower level with large recreation / home gym space. An oversized three-car garage completes the home. Minutes to world class Darien, Rowayton, Long Island Sound, and easy access to New York City & New Haven by train or car. Coastal CT at its very best!

14 Five Mile River Rd, Darien

$1,195,000

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24177739 MLS ⋅ One Sedgewick Lofts BLDG.

Introducing One Sedgwick Lofts - a Boutique Collection of thoughtfully designed, one-of-a-kind condominium residences offering a fresh and refined approach to low-maintenance luxury living in the heart of Darien. Blending modern design with timeless sophistication, these residences are crafted for today's discerning buyer seeking both style and simplicity. Open-concept layouts, soaring ceilings, expansive windows, and abundant natural light create an airy, loft-inspired feel unlike anything else on the market. High-end finishes and curated details elevate every space, from sleek designer kitchens with premium appliances to spa-inspired baths and versatile living areas designed for effortless entertaining and everyday comfort. A signature feature of each home is the spacious covered terrace complete with a gas fireplace - creating a seamless indoor-outdoor living experience and a private retreat designed for year-round enjoyment. Perfectly suited for those looking to right-size without compromise, One Sedgwick Lofts offers a rare opportunity to enjoy new construction in one of Fairfield County's most desirable communities. Ideally located moments from Darien's vibrant town center, residents enjoy easy access to the train, restaurants, boutiques, and everyday conveniences - delivering the ultimate walkable lifestyle rarely found in Darien. Blending the energy of urban living with the relaxed elegance of coastal Connecticut. Estimated completion date December 2026.

1 Sedgwick Ave Unit 2-06, Darien

$1,695,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24176255 MLS

Nestled on a quiet cul-de-sac in a convenient Darien location, this beautifully renovated and expanded Nantucket-style Cape offers timeless charm and exceptional functionality. Set on .46 landscaped acres, the light-filled home features an open-concept kitchen with updated appliances, gas fireplace, and spacious dining area flowing seamlessly into sun-filled living spaces and multiple stone patios designed for effortless indoor-outdoor entertaining. Thoughtfully designed for today's lifestyle, the home includes two potential primary suites, flexible living and work spaces, a spacious walk-out lower level, oversized two-car garage, and beautifully landscaped yard. Ideally located close to schools, town, train, and beaches, this special property combines warmth, character, and modern convenience.

28 East Ln, Darien

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.