Weston Homes with Weston Middle school

Welcome to Weston, Connecticut – a charming and picturesque town nestled in the heart of Fairfield County. Known for its stunning landscapes, tight-knit community, and top-tier educational institutions, Weston offers a perfect blend of suburban tranquility and vibrant living.

With a population that appreciates the finer things in life, Weston is characterized by its lush greenery, scenic parks, and beautiful homes that reflect the town’s rich history and commitment to quality living. The town's commitment to preserving its natural beauty is evident in its numerous trails and open spaces, making it a haven for outdoor enthusiasts and families alike.

One of the standout features of Weston is its highly acclaimed school system, particularly the Weston Middle School, which is renowned for its academic excellence and nurturing environment. Families looking to settle in this idyllic town will find an array of beautiful homes conveniently located within the school district, ensuring that children have access to top-tier education just a stone's throw away from their front door.

Weston’s real estate market offers a diverse selection of properties, from charming colonial homes to modern estates, catering to a variety of tastes and budgets. The community is vibrant, with local shops, dining, and recreational activities that foster a strong sense of belonging.

Whether you’re drawn to Weston for its exceptional schools, serene surroundings, or the welcoming atmosphere, this town has something for everyone. Explore the homes in Weston and discover the perfect place to create lasting memories in a community that truly feels like home.

Newest Weston Homes with Weston Middle school

$1,799,000

4 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 24183665 MLS

Embrace the ultimate country club lifestyle at this stunning two-acre estate, where privacy and recreation meet in perfect harmony. The grounds are rich with amenities, including a sparkling Gunite pool and spa, a private tennis court, and a separate sport court. The thoughtfully designed pool house elevates every gathering with its summer kitchen, changing room, half bath, and refreshing outdoor shower. Perched above the detached garage, you'll find a quiet retreat with a half bath - the perfect set up for a professional home office, a dedicated creative studio, or a home gym. The main residence is a sun-drenched contemporary, offering three finished levels of effortless living. Soaring ceilings and well-placed skylights create an airy atmosphere, while hardwood floors anchor the intuitive floor plan. All four bedrooms are tucked away on the upper level. The walkout lower level adds even more versatility, ready to serve as a media room, play room and/or a fitness hub to suit your needs. All this just minutes from Weston's top-rated schools, the town center, the Merritt Parkway, and neighboring Westport. Whether you're lounging poolside, perfecting your serve, or simply savoring the serenity of this incredible property, every day here feels like a getaway.

7 White Oak Ln, Weston

$1,000,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188955 MLS

Welcome to this spacious 4-bedroom, 3-bath Colonial offering 2,700+ square feet of versatile living space in Lower Weston. Set on 2.3 private wooded acres, the home features a flexible floor plan with generous living areas, a finished lower level, and a bright four-season room that provides additional year-round living space. The main level has the convenience of first-floor laundry along with an additional room and full bath, creating an ideal setup for guests, or a home office, while the finished lower level adds even more flexibility for a den or entertaining. Enjoy the best of Weston living with award-winning schools, and convenient access to major commuting routes. Here's your opportunity to create your dream home in one of Fairfield County's most desirable communities.

103 Steep Hill Rd, Weston

$1,065,258

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191063 MLS

"A rare retreat where nature, comfort, and craftsmanship come together in perfect harmony." Enter through electronic gates,experience quiet & calm & feel as though you've stepped into another world. This charming 2-bedroom,2-bath cottage welcomes you w/warmth, character & timeless appeal. Inside,you'll discover the results of thoughtful renovations & meticulous upgrades completed over the years. Aside from the main house--2 additional structures. Each room & outbuilding possess its own distinctive charm & function. Above the garage, a versatile 624+/- sq.ft. studio loft offers the perfect setting for either home/office/gym/studio or recreation room & is complete w/sauna,gas fireplace & abundant storage. The detached 204+/- sq.ft. studio office showcases soaring vaulted ceilings w/cedar & hemlock beams,rich pine floors,gas fireplace, baseboard heating & wrap around wood deck w/built-in seating-- overlooking a tranquil pond. The sun-filled kitchen features premium new appliances, custom cabinetry & new tile heated floors. The primary suite offers vaulted ceilings,revamped walk-in closet & private deck complete w/hot tub. The spacious primary bath is a spa-like retreat. Both rooms have access & views to the spacious backyard. Set on nearly 2 acres of beautifully landscaped grounds. Privately tucked away off Georgetown Road &bordering the protected open space of the Honey Hill Preserve. More than a home-it's a lifestyle.

131 Georgetown Rd, Weston

$1,369,900

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24191446 MLS

Thoughtfully sited high above Aspetuck Country Club's picturesque 16th fairway, this 5-bedroom, 4-bath residence offering over 5,300+ square feet was curated from the ground up to celebrate its extraordinary setting. Walls of glass, soaring vaulted ceilings, skylights, and multiple decks were thoughtfully designed to capture the ever-changing play of natural light-from the first rays of sunrise to the soft glow of moonrise-while framing breathtaking panoramic vistas that extend well beyond the fairway. Here, the eye is drawn to long-distance views that seem to stretch for miles, creating a living backdrop that transforms beautifully with every season. At the heart of the home, the centrally located eat-in kitchen opens to a spacious great room, creating an inviting gathering space for family and friends. Enjoy entertaining from expansive decks, where indoor & outdoor living blend seamlessly. However, the one-of-a-kind private indoor pool pavilion-an extraordinary year-round retreat for swimming, entertaining, recreation, fitness, and relaxation that sets this property apart from virtually any other in the area. 2-striking granite fireplaces add warmth & architectural character to the gracious living and dining spaces. All 5bd's are conveniently located on the main level, including the spacious primary suite with a balcony and a retro-inspired bath featuring a sunken soaking tub & separate shower +4 additional bd's of which have private balconies with stunning views!

4 Aspetuck Hill Ln, Weston

$1,035,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24115297 MLS

Welcome to 49 Blue Spruce Circle, a sun-drenched contemporary colonial nestled on two picturesque acres of mature trees and vibrant flowering plants. Boasting 3,297 square feet of versatile living space, this 4-bedroom, 3.1-bath home features a unique, airy layout designed to maximize natural light at every turn. The heart of the home centers around an inviting, open floor plan that flows effortlessly to the expansive back deck-perfect for indoor-outdoor entertaining or enjoying peaceful woodland views. Relax on the sweet front porch, or retreat to the upper level, where you will find the private primary suite complete with a full bath and walk-in closet. Directly adjacent to the primary is a fantastic, light-filled studio loft, offering a creative sanctuary for an art studio, home office, or additional recreation space. Additional features include a fully finished 1,430sf walk-out basement providing endless possibilities for recreation, along with convenient interior access to the 2-car garage. While being Sold AS-IS, this exceptional 2 acre property with a fully fenced backyard represents an incredible opportunity to bring your personal touch and updates to a truly special Weston retreat.

49 Blue Spruce Cir, Weston

$899,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24186968 MLS

Nestled on 2.25 breathtaking hilltop acres, this is one of Lower Weston's beautiful building sites. Set in a picturesque, level meadow w/ mature trees, the property offers exceptional privacy on a coveted cul-de-sac just south of Weston Center, near the Historical Society, & minutes from the Merritt Parkway. Whether you choose to renovate the existing home or create the custom estate you've always envisioned, the possibilities are endless. The existing residence offers 5 beds, 4 baths, & timeless features including original oak hardwood floors. The spacious layout includes a living room w/ fireplace, formal dining room, kitchen, and a family room with a second fireplace and radiant heated floors. The primary suite features a private entrance & deck, while a second-floor laundry room adds everyday convenience. A versatile 5th bedroom on the main level includes a kitchenette & full bath, making it ideal as a guest suite, in-law apartment, home office, or pool changing room. Additional highlights include a welcoming front foyer with heated slate flooring, a full dry basement with laundry sink, two separate attics, & a heated 21/2-car garage complete with sink, work area, radiant heat, & generator hookup. Outside, a secluded 20' x 40' in-ground pool enjoys a sunny, private setting & offers the opportunity to be restored to its former glory. An extraordinary opportunity to own one of Lower Weston's premier properties & create your dream home in an idyllic setting. Sold As-Is

18 Briar Oak Dr, Weston

$1,299,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190123 MLS

Nestled at the end of a quiet cul-de-sac on two picturesque acres, this extraordinary five-bedroom, three full bath residence offers a rare combination of timeless elegance and peaceful seclusion. Overlooking a gently flowing brook, the property is surrounded by natural beauty, creating a private retreat just minutes from the vibrant shops, acclaimed restaurants, beaches, and Metro-North train station in neighboring Westport. Designed for both everyday living and effortless entertaining, the home features two luxurious primary suites, including one on the main level and a second upstairs with its own private balcony overlooking the tranquil landscape. The sleek kitchen is beautifully appointed with new countertops, while the bathrooms offer sophisticated, contemporary finishes. Brand-new Andersen windows throughout bathe the home in natural light while enhancing comfort and efficiency. Offering an exceptional balance of privacy, convenience, and refined living, this is a rare opportunity to own a truly special home in sought-after Weston.

21 Deepwood Rd, Weston

$1,349,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24188962 MLS

Reintroduced & Reimagined! This stylish Contemporary High Ranch at the end of a serene cul-de-sac, has been renovated by Nova Design Build of NYC. Vaulted ceilings and a wall of windows bathe the home with natural light, creating a modern aesthetic with MidCentury warmth. Newly renovated kitchen with skylights, dining area and a double sided woodburning fireplace in the living room. The expansive open floorplan has a living room & dining room which gaze upon an oversized deck & private backyard. Spoil yourself in a Primary suite which features a vaulted ceiling and brand new spa bath (2026). Three additional renovated bathrooms, new roof (2026), solid custom 7.5ft doors, and custom closets elevate the home throughout. Abundant in flexibility, thanks to four bedrooms on the main level plus two more on the lower level. Lower level includes family room with fireplace, gym/5th bedroom, office/6th bedroom, renovated bath, recreation space, and updated laundry and mudroom. Enjoy a bucolic lifestyle at a home that abuts Aspetuck Land Trust for privacy and nature access.

26 Hill Farm Rd, Weston

$1,100,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24189056 MLS

The Weston Cottage-where timeless charm, remarkable history, and tranquil riverfront living come together. Nestled along the river on the coveted Weston/Westport border, this beautifully updated 3-bedroom, 2.5 bath home offers a rare opportunity to own a piece of Connecticut history. Famously known as the retreat of legendary actress Bette Davis, the cottage became the setting for the true story that inspired the hit play Me and Jezebel, after Davis unexpectedly stayed for 32 unforgettable days. Today, this captivating home blends historic character with modern comfort. The renovated kitchen features a Wolf range, Bosch column refrigerator, and inviting marble fireplace, while all three bathrooms have been tastefully updated. Fresh interior and exterior paint, new lighting, and custom built-ins completed in 2025 enhance the home's move-in-ready appeal. Wake to the soothing sounds of the river, enjoy peaceful outdoor living, and experience the privacy and beauty of this exceptional setting just minutes from the shopping, dining, beaches, and train station in Westport. Whether you're searching for a full-time residence or a weekend escape, The Weston Cottage offers an extraordinary lifestyle in one of Fairfield County's most desirable locations.

78 River Rd, Weston

$2,200,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24187814 MLS

Bring your vision to life in the heart of Weston with this rare opportunity to collaborate with a premier local builder. Sited on a sprawling, private 2.1-acre lot, this sophisticated new construction offers 4,500 square feet of meticulously designed living space, including a finished 900-square-foot lower level. The heart of the home is an expansive chef's kitchen that flows seamlessly into the dining room and a sun-drenched living area. Large windows frame picturesque views of the lush, private acreage, creating a stunning backdrop for daily life. The main floor also features a thoughtful guest suite with a full bath, perfect for visitors or a quiet home office. Upstairs, the primary suite serves as a true sanctuary, complemented by three additional well-appointed bedrooms. With five bedrooms and five bathrooms in total, the layout provides exceptional space and privacy. Outside, the three-car garage and vast backyard provide plenty of room for a custom pool or outdoor oasis. The property and septic are specifically designed to accommodate an ADU if desired, offering incredible flexibility. Because construction is in the early stages, you can step in now to select finishes and personalize the aesthetic. Looking for just the land? The lot is also available to purchase separately (see MLS#24180742). Move into a home uniquely yours, set against a backdrop of natural beauty.

96 Georgetown Rd, Weston

$1,599,000

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24178099 MLS

This architecturally distinctive mid-century modern Deck House offers a rare lifestyle retreat on two serene acres in Lower Weston. Designed to embrace its surroundings, the home features signature walls of glass, warm wood ceilings, and an open-flow layout that creates a seamless connection between the indoors and the natural beauty outside. The main residence makes an unforgettable impression with expansive windows framing sweeping lawn views and stunning western sunsets. At the heart of the home, a renovated kitchen with a large island flows into the dining and living areas, anchored by two wood-burning fireplaces. With four bedrooms and 3 full baths, the layout provides exceptional flexibility, including a dedicated home office and additional flex space perfect for a fitness studio or creative retreat. The primary suite continues the aesthetic with oversized windows overlooking the private grounds. The property transforms into a private resort with an expansive wrap-around deck and a spectacular 40x20 heated gunite pool. A private tennis court adds to the recreational appeal. Enhancing the compound is a separate guest cottage featuring a great room with cathedral ceilings, a kitchenette, a gas fireplace, and two bedrooms. Thoughtfully maintained with a newer roof, whole-house generator, and EV charger, this architectural gem is located minutes from Weston Center and Westport.

9 Fall Ridge Rd, Weston

$1,750,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24181401 MLS

Tucked away on a coveted lower Weston cul-de-sac, this beautifully renovated colonial offers the rare combination of privacy, style, and resort-inspired living. Thoughtfully updated by the current owner, the home is truly turnkey and ready for its next chapter. Sun-filled interiors showcase sophisticated finishes and an effortless flow for both everyday living and entertaining. The renovated kitchen, appointed with stone countertops and premium appliances, opens to a bright sunroom overlooking the property. A dramatic family room with soaring cathedral ceilings, fireplace, and wet bar serves as the heart of the home, while walls of windows fill the space with natural light. The luxurious primary suite is a true retreat, featuring a cathedral ceiling, dual walk-in closets, and a spa-like marble bath. Additional bedrooms are generously sized, and the finished lower level offers exceptional flexibility with a guest bedroom, full bath, and direct access to the outdoor entertaining areas. Outside, the property unfolds into a private oasis anchored by a gunite pool and expansive grounds. A former Har-Tru tennis court remains on the property, presenting an opportunity for restoration or reimagining to suit your lifestyle. Beautifully sited in one of Weston's most sought-after neighborhoods, this special offering is just minutes from award-winning schools, downtown Westport, Metro North, shopping, dining, and beaches.

32 Silver Ridge Cmn, Weston

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