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Weston

A One-of-a-Kind Connecticut Estate: "Chestnut Farm" Having changed hands just three times in over two centuries, Chestnut Farm is not just a home-it's a legacy waiting to continue. Discover the rare opportunity to own this breathtaking estate, where timeless charm and modern refinement make every day extraordinary. Step into the unparalleled charm of Chestnut Farm, a Circa 1830s Federal Colonial masterpiece that seamlessly marries historic elegance with modern luxury. Once owned by Samuel Banks, this one-of-a-kind estate has been masterfully reimagined and completely modernized in 2013 to create a retreat where every day feels like a vacation. From the moment you enter the inviting entryway, you're embraced by a sense of history and hospitality. The heart of the home-a kitchen-great-room with oyster-quartz countertops, iridescent tilework, stainless steel appliances, and a vintage pub-style bar-combines style and functionality, making it perfect for entertaining or unwinding. The media area, framed by exposed beams and a stately stone fireplace, flows effortlessly to a newly built sprawling TimberTech deck and charming stone terraces. The estate offers four fireplaces, a tranquil study-bedroom, and formal living and dining rooms designed for gatherings of any scale. The luxurious primary bedroom boasts 15-foot rustic tray ceilings, a spa-inspired bath, and vintage touches that echo timeless elegance.

$3,900,000 Coming Soon

227 Lyons Plain Road Weston, Connecticut

5 Beds 5 Baths 4,595 SqFt 7.05 Acres

Once in a while, a property emerges that transcends expectations - perfectly sited and timelessly designed. Welcome to 50 Kettle Creek Rd, a masterpiece of modern sophistication nestled on the toniest road in one of America's best towns. Ideally located close to town, schools, and the Merritt Parkway, this estate offers a rare combination of convenience and tranquility.This 6-bedroom home boasts a transitional style that seamlessly blends classic elements with contemporary design. Luxurious amenities abound, from the 3-car garage with 13' ceilings for car lifts to the custom kitchen equipped with top-of-the-line Thermador appliances and dual refrigerators. Gas fireplaces adorn both the family room and primary suite, creating warm and inviting spaces to gather and unwind. Step outside to discover an oasis of relaxation, featuring an inviting 18'x40' pool with a heater and auto cover, surrounded by lush landscaping and serene views of the sprawling 2.85-acre property. Once a cherished farmstead owned by a revered figure in town, 50 Kettle Creek pays homage to its heritage with an exterior reminiscent of the historic barn that once graced the land. With five of the six bedrooms situated on the second floor, including a flex-in-law suite and a secondary primary suite/guest room, this home offers ample space and flexibility for modern living. The finished basement provides an additional 2,200 square feet of living space, perfect for recreation or entertainment.

$3,540,000 Active

50 Kettle Creek Road Weston, Connecticut

6 Beds 9 Baths 1,427 SqFt 2.85 Acres

A breathtaking approach off a quiet cul- de-sac leads to 3.2 private acres at 16 Equestrian Trail. Extensively renovated in 2024, this home is a blend of luxury technology and energy efficiency. Enter the two-story foyer open to elegant formal & informal spaces flooded with natural light. The casual area includes a huge new chef's kitchen & dining area with an oversized island uncompromising bultler's pantry and family room with stone fireplace. The primary suite is a luxury statement with vaulted ceiling, sunlit sitting room, private office and large walk-in closets. The lavish bath features modern finishes, soaking tub, twin vanities, steam shower and warm floor. A 900 square foot bonus room with full bath inspires guests, working at home, creative pursuits or oversized gym. The stunning grounds feature a circular drive, bluestone patios, wisteria pergola, & specimen plantings overlooking a tranquil spring fed pond. Only 7 minutes from Weston's esteemed schools, this home offers privacy just 75 minutes to Manhattan. A technology forward property with 25 KW propane generator, 13 tons of HVAC, IAQ system, commercial Wi-Fi, hardwired fire and burglar system, independent temp controls for every bedroom, Caseta programmable lighting, & 30 Zone sprinkler, all smart app controlled. Amenities include large mudroom, 8-foot doors, oak floors, radiant heat, electric pet fence, tons of storage, 4 ensuite beds, vaulted ceilings, oversized 3 car garage, foam insulation and much much more

$3,000,000 Active

16 Equestrian Trail Weston, Connecticut

5 Beds 7 Baths 3.2 Acres

This exquisite custom estate with pool site on 4.7+/- acres (poss./potential to divide) will take your breath away. Set atop one of the highest points in the area, this luxurious retreat blends modern luxury, convenience, privacy and treetop vistas into one irresistible package. Sited to capture the incomparable views, every room and multiple terraces have gorgeous panoramas, with a circulating waterfall to set the stage for the tranquility that awaits upon arrival. A seemingly endless list of amenities speak to a home that was constructed with no expense spared, everything from an elevator, natural gas utilities, 6 BRs with choice of main or upper level primary suites, incredible craftsmanship and highest-end materials. The stunning Great Room is at the heart of the home, with an impressive stone fpl, French doors to the terrace, adjacent wet bar/butler's pantry, incredible dining rm w/coffered ceil. The gourmet kitchen is a stunning showplace of sophisticated design and unparalleled quality w/ Sub Zero & wolf appls, marble counters, cathedral ceiling, skylights & three exposures capturing views. Two private offices for ultimate productivity. Each BR is accompanied by a luxe bath & fitted closets of outstanding quality. The finished, walk-out LL has an array of flex spaces and is an ideal future cabana for the pool site, or multi-generational suite w/full kitchen, fpl, BR, full bth, space for sauna & much more. 2 laundry rms, 3 car garage. Addl. space avail on 3rd flr.

$2,999,000 Active

29 Rogues Ridge Weston, Connecticut

6 Beds 7 Baths 4.7 Acres

Welcome home to 36 Kettle Creek Road, where effortless elegance redefines luxury living. This impressive modern farmhouse features 5 bedrooms, 5.5 bathrooms, with over 5800-sq.ft. that seamlessly blends contemporary aesthetics with timeless design elements. The architecture exudes a sumptuousness & slightly edgy approach across 3-levels, highlighted by walls of glass creating a design-forward synergy throughout. Upon entering, a striking glass foyer with on-trend staircase sets the tone, complemented by a sleek metal porch. The stunning great room is ideal for entertaining & study share a handsome 2-sided FP-boast lofty ceilings with 4.5-inch white oak floors, maximizing space & design impact. The gourmet kitchen, with large island, quartz counters, custom cabinetry & top-end appliances, flows harmoniously into the great room, connecting effortlessly to expansive upper & lower outdoor living spaces. Formal rooms seamlessly blend with casual areas bathed in natural light. Private spaces include a lavish primary suite with sitting room and luxurious spa-bath-sanctuary, along with 4-additional en-suite bedrooms. The lower level multi-use rec/room with potential pool cabana & kitchenette, gym and guest suite, is customizable to suit your needs, there is even room for a golf simulator! Nestled into an estate enclave in sought-after Lower Weston, moments to acclaimed schools, trains & just 55 min. to NYC! Experience the epitome of modern luxury living at 36 Kettle Creek Road.

$2,779,000 Under Contract – Continue to Show

36 Kettle Creek Road Weston, Connecticut

5 Beds 6 Baths 2.45 Acres

Nestled in the heart of Weston, this timeless country estate is accessed via a private driveway and set on 6.77 secluded acres. Originally built in 1969 and beautifully refurbished in 2017, the stone and wood-shingled main house is a remarkable blend of historic charm and modern luxury. The thoughtful floor plan features a western-facing formal living room w/ fireplace, the perfect spot for enjoying stunning sunsets. Entertaining is a delight in the elegant dining room with its own fireplace, which flows seamlessly into the expansive kitchen which boasts a Calacatta Barerra marble coffee bar, a large center island, high-end stainless steel Bosch appliances, and bay window with a dining area that overlooks the professionally landscaped backyard and patio. Outdoor living is enhanced by a sparkling in-ground fiberglass pool, a cabana, a cozy pergola, and fire pit. The family room, complete with large stone fireplace and built-in bookshelves, provides a warm and welcoming space to unwind. Upstairs, the tranquil primary suite offers a fireplace, sitting area, luxurious five-fixture bath, and a private deck for ultimate relaxation. Two add'l ensuite BRs complete this level. The third floor includes two more BRs and full bath. The property also features an updated 5-stall horse barn with loft, a versatile space that has hosted memorable celebrations and offers endless possibilities. A true masterpiece, this home is a timeless treasure designed to be cherished for generations.

$2,350,000 Active

15+19 Harvest Lane Weston, Connecticut

5 Beds 5 Baths 6.77 Acres

New Construction opportunity in lower Weston's premier location - at the top of Michaels Way and set close to Town center and schools. Beautiful level treed lot is idyllic setting for luxurious New 4500 sf quality Colonial from acclaimed builder. Optional third level opportunity for bedroom, bath and playroom.

$2,250,000 Under Contract

7 Hills End Lane Weston, Connecticut

5 Beds 6 Baths 2.18 Acres

This stunning Colonial, built in 2003, offers 4,427 square feet of understated elegance, situated on a desirable one-acre lot in Weston. The home features an open floor plan with sun-filled, airy rooms throughout. Exquisite architectural details include a double-sided river rock fireplace separating the living and family rooms, antique beams, and deep moldings, adding charm and sophistication. The renovated chef's kitchen is a highlight, boasting custom cabinetry, marble countertops, Wolf range, Subzero refrigerator, and a large radiant-heated marble island countertop. The spacious primary suite features an oversized, renovated bath with a free-standing tub, marble finishes, and luxurious fixtures. With 5 bedrooms, 3 full baths, 2 half baths, and an additional 2,000 sq. ft. of basement with high ceilings and a fireplace that could be finished if desired, this home provides ample space for living and entertaining. The level, fully fenced backyard with a stone patio, vegetable rock -walled garden, and river rock wall is pool-ready, and the property includes a whole-house generator for added convenience. Three car garage complete with newly epoxied flooring. Located on a quiet street with a circular drive in an ideal Weston location, this very special home is a must-see!

$2,199,000 Active

11 Glory Road Weston, Connecticut

5 Beds 5 Baths 4,427 SqFt 1 Acres

Gorgeous new construction located in one of Weston's most beautiful and highly desirable neighborhoods (Singing Oaks). The private and wooded 3.56 acre site is situated at the end of a sunny cul de sac and has room for a pool!. This stylish 5 BR, 4 bath, 2 half bath home has an open floor plan which gives it a bright and airy feel! Meticulously constructed with custom luxury finishes and superior craftsmanship. This home has a well thought out design with living spaces that are both classic and functional. Special features include: a gorgeous chefs kitchen with custom cabinets, a large center island, high end appliances & sliders which leads to a spacious composite deck; efficient propane furnaces; a two story foyer; glass stair railings; oak hardwood flooring throughout; a light and bright 2 story family room with a gas FP (opens to the kitchen); The main level includes a generous sized dining room, an amazing mudroom off the garage w/separate powder room, a formal living room & a first floor guest bedroom with an en-suite bath. The stunning primary bedroom suite features dual walk-in closets, a luxurious primary bath with a soaking tub and huge shower area. The second floor also has 3 additional bedrooms, 1 with an en-suite bath and the other two with a Jack & Jill bath. The walk-out lower level will have approx 2200 Sq' of finished space. Minutes from town Center, Blue Ribbon award winning schools, parks, shopping, restaurants and approximately 1 hour commute to NYC.

$1,990,000 Active

35 Hidden Spring Drive Weston, Connecticut

5 Beds 7 Baths 3.56 Acres

Seize the opportunity to own your dream home on one of lower Weston’s premier streets, minutes from award-winning schools, town, train and beach! This modern colonial farmhouse was designed by an acclaimed local builder/design team. Combining modern aesthetics with traditional details, the open floorplan includes a gourmet chef’s kitchen and elegant family room with a vaulted ceiling. Options for three separate home offices are located on the main level, off the second family room and on the third level. Upstairs, an exquisite primary suite is home to a spa bath and walk-in closet. Three additional bedrooms and two bathrooms complete the second level. An additional family room and fifth bedroom offer private spaces for an additional home office or guest suite. The third floor is home to a large playroom and additional full bath. Poised on two sylvan acres with an outdoor shower and room for a pool, you’ll love to relax on the front porch or entertain under the stars in your private country retreat.

$1,895,000 Under Contract

5 Kettle Creek Road Weston, Connecticut

5 Beds 6 Baths 2.26 Acres

Amazing opportunity to be the first developer in Weston’s newly created mixed-use district! This pioneering role gives one the creative freedom to establish a unique atmosphere for the Village District, setting the stage for future development and commercial growth. With a variety of commercial options allowable on the first level and apartments on the second level, these essential services will bring positive change and vibrance to the community!

$1,800,000 Under Contract – Continue to Show

176 Weston Road Weston, Connecticut

4 Beds 1 Baths 1,792 SqFt 2.07 Acres

Get ready to be enchanted by this elegant country estate once owned by the Vanderbilt family who named the property Daisyfields. Steeped in history, Andy Warhol was said to have painted illustrations for Amy Vanderbilt's cookbooks in the guest house at this magical property - and the paint is still visible on the guest house floor! The main house features a high-end kitchen that's a chef's dream with Wolf, Subzero and Miele appliances and custom features throughout. The lovely kitchen opens to a welcoming family room area and flows out to the terrace and private back property. The second level is comprised of a well-appointed primary suite, 3 additional bedrooms and a spacious hall bath. Front and back stairs add a further touch of elegance. A spacious 3-car garage also has a full second level perfect for storage now, or to be finished. Gleaming hardwood floors throughout. The guest house is sure to spark your imagination. With soaring ceilings and so much space, bring your vision to create a truly amazing secondary dwelling on the property. Featuring its own heating system, kitchen and bath - it's a unique opportunity to round out this magical countryside estate! The nearly 5 acres of property offer beautiful gardens, specimen trees and so much privacy with its adjacency to conservation land. Easy access to Aspetuck Country Club offers a fun and active lifestyle. 51 Valley Forge Road is the perfect weekend retreat or fulltime home.

$1,689,000 Under Contract

51 Valley Forge Road Weston, Connecticut

4 Beds 3 Baths 4.19 Acres

Nestled in the verdant hills of Weston bordering Aspetuck Land Trust acreage, this 1940's charmer was reimagined by way of Provence, and the owners' extensive European travel. Oak hardwood flooring, romantic archways, vintage architectural details and custom French doors/windows transport you to the south of France. The home's highlight is a gorgeous country kitchen (Thermador, Bosch, SubZero, LG appliances) and a great room that boasts 9 ft ceilings, exposed beams and a Rumford fireplace. The elegant living room with built-in bookcases, original fireplace, and reading alcove leads to an outdoor pea gravel terrace beneath a leafy, grape arbor. An unexpected Yves Klein Blue dining room, and a wonderful library/office tempt guests to wait for the bar to run out! Spacious primary suite has a fireplace, sitting area and sweeping views of the property. Three additional bedrooms and two full bathrooms round out the second floor. Finished basement space with a full bath is above ground and currently being used for guests. And there is a wine cellar for those 58 degree needs! The privacy is captivating; a sun-drenched stone patio makes entertaining or peaceful reflection effortless. The fieldstone fireplace, outdoor kitchen with Viking gas grill, wood-fired pizza oven and refrigerator will encourage you to entertain friends and family. Boules you ask... the owners say Petanque, but the court is here along with a mature landscape, meandering stone walls and boxwood parterre gardens

$1,675,000 Active

1 Katydid Lane Weston, Connecticut

4 Beds 5 Baths 2.95 Acres

Welcome to this Colonial revival home in a highly sought-after neighborhood in Lower Weston. This exquisite home is designed for stylish entertaining both indoors and out, w/spaces that cater to every need. At the heart of the home is the sun-drenched kitchen, featuring with quartz countertops, a six-burner dual fuel Thermador range w/griddle, beverage drawers & an expansive dining area.The center island , w/granite countertops and seating opens seamlessly to the great room, making it the perfect hub for gatherings. Step out to the charming screened porch, where you can enjoy serene views & ample space for dining and relaxation. The porch overlooks the stunning Glengate salt water pool & spa, a stone terrace w/fire pit & enchanting gardens, creating a private oasis perfect for both intimate & large celebrations. The main level is also ideal for entertaining w/ spacious DR/LR. This elegant residence boasts 4 beds, 4.5 baths + incredible flex space for a potential au pair/in-law separate living suites. The spacious primary suite features a large WIC, fpl, radiant flrs, jacuzzi tub. Secondary beds have oversized or WIC. This level is completed by laundry, and adaptable spaces that could serve as playroom, office/homework space & au pair suite. Expansive LL includes dedicated gym/playroom. This home masterfully combines timeless charm w/ modern amenities, offering a luxurious, comfortable and private retreat to enjoy all year long!

$1,649,000 Under Contract

34 Pheasant Hill Road Weston, Connecticut

4 Beds 5 Baths 2 Acres

At the end of a cul-de-sac on a private road, you will find 12 Winslow Rd! Situated on 3 acres in Lower Weston, offering both serenity and a convenient location. This home has been masterfully reconstructed with the perfect blend of contemporary and traditional design elements, spanning over 3,700 sf with 4 bedrooms and 4.5 baths. Upon entering, the foyer showcases an open concept design with natural light encompassing every room. The main level boasts a dramatic family room featuring vaulted ceilings, fireplace set on a Roman Clay background and slider doors leading to an extended deck. A spacious modern eat- in kitchen with quartz counters and vast waterfall island opens to both the dining and living room with a second fireplace, creating the optimal space for hosting. Just down the hall from the kitchen, you will find an expansive office that is perfect for the" work from home" setup. Upstairs, the primary suite boats a stone fireplace, a spa like bathroom, sitting area and 2 walk in closets. Three additional bedrooms and 2 baths complete this floor, including an "ensuite." The walk-out lower level is the perfect flex or recreational space featuring an additional 750sf+ of finished space with sliders leading to a patio. Enjoy breathtaking sunset views and tranquility from this sprawling property and outdoor living space, featuring a large deck spanning across the back of the home, patio and masonry. This is truly a must-see property!

$1,598,000 Active

12 Winslow Road Weston, Connecticut

4 Beds 5 Baths 3.09 Acres

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