3‑Acre Weston Retreat w/ Pool & Basketball Court

The space

ABOUT THIS SPACE Private 3-acre retreat featuring a heated seasonal pool, full basketball court, gas fire pit, and expansive wooded grounds. The dramatic double-height great room showcases soaring windows that bring the outdoors inside, while curated African artwork adds warmth and character throughout. Enjoy privacy, nature, and easy access to Compo Beach, Devil's Den, charming New England towns, and NYC. Maximum 8 registered guests. Strictly no parties. Please review photos to check if the house is suitable for your family/group. Children need to be supervised as there are a lot of open stairs. THE SPACE Welcome to a peaceful escape set on more than 3 wooded acres in the heart of Fairfield County. Designed for families and friends seeking space, privacy, and a connection to nature, the home combines resort-style amenities with the warmth and character of a thoughtfully maintained family residence. At the center of the home is a dramatic double-height great room where exceptionally large windows bring the outdoors inside, filling the space with natural light and showcasing the changing beauty of the surrounding woods throughout the year. Throughout the home, guests will find a thoughtfully curated collection of African artwork collected over many years, reflecting the family's travels and giving the property a distinctive sense of place. 🏡 INSIDE THE HOME A bright, open layout designed for comfort, connection, and relaxation: Double-height living room with soaring windows and wooded views Open-concept chef's kitchen with premium appliances, island seating, and large dining table Comfortable gathering spaces ideal for movie nights, reading, conversation, or board games Four well-appointed bedrooms with quality linens and ample storage 3.5 bathrooms stocked with towels and essential toiletries Fast Wi-Fi and a dedicated workspace for remote work In-unit washer and dryer HDTV with smart streaming access and a Sonos sound system — guests are welcome to log into their own streaming accounts during their stay 🌲 OUTDOOR LIVING A private, nature-filled setting designed for both recreation and relaxation: Seasonal private pool (typically late May through mid-September) Optional pool heat available by advance request for an additional fee Full basketball court tucked among the trees Fire pit with seating for evening gatherings Spacious deck with outdoor dining, lounge seating, sun loungers, and BBQ grill Expansive lawn and wooded surroundings Private driveway with parking for up to 4 vehicles The property is intentionally maintained to preserve the beauty of its natural surroundings. 🏖️ 🏃 ⛷️ NEARBY Minutes from Devil's Den Preserve, roughly 15 minutes from Compo Beach and the Connecticut shoreline, and within easy reach of charming New England villages, local farms, restaurants, art museums, and the Maritime Aquarium. Whether you're after outdoor adventure, family activities, or a restorative escape, the area offers something memorable in every season. GUEST ACCESS Guests enjoy exclusive, private access to the entire home and all advertised amenities, including the four bedrooms, 3.5 bathrooms, double-height living room, dining area, fully equipped kitchen, outdoor deck, fire pit, basketball court, expansive backyard, and seasonal pool. Self check-in is available via a keypad at the main entrance, so your group can arrive on your own schedule. There is driveway parking for up to four vehicles. Any locked areas are for owner storage only. Otherwise, the home is entirely yours. OTHER THINGS TO NOTE Arrival and departure Check-in after 4:00 pm; check-out by 10:00 am. We are unable to accommodate early check-in, but please inquire about late checkout. Your group Maximum 8 registered guests — the home suits families or up to four couples. Only registered guests may be on the property; visitors, gatherings, celebrations, and events are not permitted. Quiet hours begin at 10:00 pm to preserve the peaceful character of the neighborhood. Children of all ages are welcome, but the home is not child-proofed. Open staircases, unfenced decks, a pool, and a fire pit all require active adult supervision at all times. The home also has multiple staircases and changes in level between floors, so please review the photos to confirm it's a good fit for everyone in your group. The pool The pool is seasonal, typically open Memorial Day through September 15. We can sometimes open up to two weeks early or extend two weeks late depending on weather and maintenance — please confirm before booking, as shoulder-season availability isn't guaranteed. Pool heating is available for $100 per day to offset propane costs, and must be requested in advance. When conditions permit, we target roughly 82°F. Because heating an outdoor pool in cold weather uses a great deal of energy, heat is generally unavailable when daytime temperatures stay below about 65°F. Outside the core season, cooler nights mean additional heating charges may apply and swimming comfort can't be guaranteed. Caring for the home Please leave furniture, artwork, and decorative and outdoor furnishings where you find them. If anything is moved during your stay, we ask that it be returned to its original spot before checkout. No smoking inside the home. Security Exterior cameras monitor entrances and outdoor areas only. There are no cameras inside the home or in any private guest space.

Guest access

Guests enjoy exclusive, private access to the entire home and all advertised amenities, including the four bedrooms, three-and-a-half bathrooms, dramatic double-height living room, dining area, fully equipped kitchen, outdoor deck, fire pit, basketball court, expansive backyard, and seasonal pool. Self check-in is available via a keypad at the main entrance, allowing your group to arrive conveniently on your own schedule. There is driveway parking for up to four vehicles. To ensure smooth operations and maintain the home, some spaces are secured and reserved for owner or housekeeping use. These areas are not part of the guest accommodations and remain inaccessible during your stay. Guests will have full access to all living spaces, bedrooms, bathrooms, and amenities featured.

Other details

Perhaps you are planning a trip to see the foliage. Perhaps there is a wedding or a celebration nearby, and you have discovered what locals already know — that there are few hotels in this part of Connecticut, and none quite like a house of one's own. Perhaps you are a group of old friends in search of a quiet place to gather, to make new memories and revisit the old ones. Or perhaps it is simply Wednesday afternoon, the week has revealed itself to be a long one, and you would like to leave New York for the weekend. Some places announce themselves. White Oak Estate prefers to be discovered. The house sits at the end of a long driveway on more than three wooded acres in Weston, Connecticut — a town that has chosen, quite deliberately, to remain what so much of this region once was: two-acre zoning, no strip of storefronts, and more preserved forest than nearly any community within an hour of New York City. What that means for a guest is simple. You wake to birdsong. You swim in a pool with not a single other house in sight. And yet you are twenty minutes from some of the best dining in New England, and just over an hour from Grand Central. Every season makes its own argument here. In summer, it's the pool glittering in the sun, the light falling through the trees, and the green grown so lush that the property becomes its own private world. In autumn, the woods turn kaleidoscopic, and the leaves come down to blanket the lawn in gold, copper, and crimson. In winter, the bare trees stand like etchings beyond the great room's tall windows, and we find ourselves hoping for snow, which turns the woods overnight into perfect stillness. And in spring, we simply watch everything come back to life — the first green haze in the branches, the birdsong returning across the road at the September Lane Bird Sanctuary. The House Four bedrooms and three and a half baths, on more than three wooded acres — room enough for three generations or a gathering of friends, with privacy enough that no one ever feels crowded. The heart of the home is the great room: soaring ceilings and walls of glass we deliberately left uncovered, so that nothing stands between you and the trees. The kitchen, anchored by a Sub-Zero refrigerator and fed by filtered well water, is made for slow breakfasts and ambitious dinners alike. Outside, the heated pool waits in its clearing of green, a basketball court stands ready for the competitive, and the entire property — house, grounds, and woods — is exclusively yours for the length of your stay. The Sound Less than twenty minutes from the house lies Long Island Sound — and if you know it only by reputation, its beaches may surprise you. The Sound is sheltered water, not open ocean: calm, warm by mid-summer, and forgiving, which makes its beaches ideal for small children, paddleboards, kayaks, and long unhurried swims. Compo Beach in Westport offers a wide crescent of sand, gentle surf, and one of the loveliest sunset views in Connecticut; Sherwood Island State Park, just beside it, adds boardwalk strolls, picnic groves, and quieter stretches of shore. Kayakers can put in at the Saugatuck River boat launch on Elaine Road in Westport, or arrange rentals and a guided paddle in season; sailing and boating are close at hand along the river as well. Horse Country Drive half an hour north or west and the landscape opens into genuine horse country — stone walls, white fences, and farms that have been working land for three centuries. If you love to ride, trail rides can be arranged nearby, and the equestrian towns of northern Westchester make for some of the most beautiful drives in the region. Few places let you swim in the Sound in the morning and watch show jumping in the afternoon; this one does. The Towns White Oak Estate sits at the quiet center of a constellation of towns, each with its own character. All distances are easy, scenic drives from the house. Georgetown, in Redding · 5 minutes Our nearest village, and quietly becoming one of Fairfield County's most exciting corners — a historic mill settlement at the crossroads of Weston, Redding, Ridgefield, and Wilton, with cafés, boutiques, and walks along the Norwalk River. Nearly a dozen good places to eat and drink sit within five minutes of the house; you'll find them all in the dining chapter below. Wilton · 10 minutes Home to Weir Farm National Historical Park, the only national park site in Connecticut and one of very few in the country devoted to art — the summer home of the American Impressionist J. Alden Weir, where you can walk the same meadows he painted. Ambler Farm and the seasonal farmers' market round out a town that rewards a slow afternoon. Westport · 15 minutes The cultural and culinary anchor of the coast. Main Street offers genuinely good shopping; Compo Beach and Longshore bring the water close; the Levitt Pavilion stages free concerts on summer evenings beside the river; and the Westport Country Playhouse and MoCA Westport carry the town's long artistic tradition. The dining — from Felice and Maman to The Whelk and Hudson Malone — has become quietly remarkable, and gets its own chapter below. Norwalk · 15–20 minutes Casual, salty, and fun. South Norwalk — SoNo to everyone — has a working waterfront, the Maritime Aquarium, and an easy, unfussy restaurant scene built on the oysters the town has harvested for generations. Ridgefield · 20–25 minutes One of the prettiest Main Streets in New England, lined with antiques shops, galleries, and good restaurants. The Aldrich Contemporary Art Museum — founded by the collector and fashion designer Larry Aldrich in 1964, and one of the oldest contemporary art museums in the country — anchors the street; the Keeler Tavern, which took a British cannonball in 1777 and kept it in the wall, anchors the history. And The Ridgefield Playhouse brings nationally touring musicians, comedians, and speakers to an intimate hall — check the calendar for your dates, because there is almost always something worth seeing. Darien · 25 minutes A very handsome town center for a morning of wandering: the Darien Sport Shop, family-run for a century; Barrett Bookstore for a beautifully chosen shelf; the new Corbin District with its restaurants and shops; and coffee to fuel the browsing. Polished without being precious. New Canaan · 25 minutes Worth the trip for the Philip Johnson Glass House alone — the architect's transparent masterpiece on forty-nine pastoral acres, open seasonally for tours, with rotating art installations. Book ahead; it sells out. South Salem, New York · 25 minutes Winding roads, horse farms, reservoir views, and almost no commerce at all — which is exactly the point. This is a drive to take slowly, ideally with the windows down. Pound Ridge, New York · 30 minutes One of my favorite towns simply to wander. The little village holds boutiques and galleries; Ward Pound Ridge Reservation, Westchester's largest park, holds more than four thousand acres of trails; and The Inn at Pound Ridge by Jean-Georges makes a destination lunch of it all. North Salem, New York · 35 minutes True horse country. Old Salem Farm hosts world-class show jumping each spring; the Hammond Museum's Japanese stroll garden is a small marvel; and in autumn the orchards open for apple picking. Where to Eat These are not listings; they are the places we actually go. Drive times are from the house. Begin in Georgetown — staying local is one of the real pleasures of this property — and work outward as the mood takes you. Historic Georgetown, at Our Doorstep (2–5 minutes) The Given Inn · 3 min — our favorite morning stop: specialty coffee, flaky pastries, proper panini, flowers, artisan gifts, and vinyl records in a beautifully designed room — and if you'd like a pastry basket delivered to the house, just ask. Milestone · 3 min — one of our favorite neighborhood restaurants — elevated comfort food, excellent pizza, creative cocktails, and live music. Wire Mill Saloon & Barbecue · 3 min — rustic barbecue — smoked brisket, ribs, burgers — with craft beer, live music, and a great patio with fire pits. Rancho Alegre · 3 min — excellent Mexican food and margaritas. Weston & Redding Neighbors (5–10 minutes) The Chase Inn · 6 min — Weston's own — relaxed, family-friendly American fare with a true neighborhood feel, open until ten. The easiest way to spend an evening feeling like a local. Aranci 67 · 10 min — warm neighborhood Italian. Luca Wine Bar · 10 min — an intimate room for wine and small plates. Breakfast & Coffee Kneads Bakery & Café · 15 min · Westport — one of the area's best breakfasts — exceptional pastries, artisan breads, breakfast sandwiches, and excellent coffee. Perfect for a leisurely morning. The Given Inn · 3 min · Georgetown — see above — and forgive us for mentioning it twice; it earns it. Pizza Pizza Lyfe · 15 min · Westport — award-winning New York-style pies on naturally fermented sourdough crusts with fresh local ingredients — voted best pizza in Westport three years running, and excellent takeout after a day at the pool. Milestone · 3 min · Georgetown — the closest very good pizza to the house. Date Night Hudson Malone · 15 min · Westport — a stylish New York-inspired tavern — excellent steaks, fresh seafood, handcrafted cocktails, and brunch through dinner. Owner Doug made his name at P.J. Clarke’s, and it shows: Manhattan energy with the relaxed charm of coastal Connecticut. The Cottage · 15 min · Westport — one of the area's premier New American restaurants — seasonal, refined, and still approachable. OKO · 15 min · Westport — contemporary Japanese cuisine and sushi, beautifully presented. Kawa Ni · 15 min · Westport — creative Japanese small plates and sushi in a lively room. Rive Bistro · 15 min · Westport — a charming French bistro with lovely riverside dining. Tavern at GrayBarns · 18min · Norwalk — elegant American dining in a beautiful historic inn — ideal for celebrations or a memorable evening. Arts & Culture This corner of Connecticut has been an artists' colony, a writers' refuge, and a stage for longer than anyone alive can remember, and it shows. The Westport Country Playhouse has staged professional theater since 1931; MoCA Westport mounts contemporary exhibitions and performances; and the Levitt Pavilion gives free concerts beside the Saugatuck on summer evenings. In Ridgefield, the Aldrich Contemporary Art Museum shares Main Street with galleries and antiques; The Ridgefield Playhouse hosts national touring acts in an intimate hall. The Bruce Museum in Greenwich moves gracefully between fine art, history, and science — save time for the gift shop — and the Philip Johnson Glass House in New Canaan offers, in season, one of the great architectural pilgrimages in America. And Weir Farm, ten minutes away in Wilton, lets you stand in the landscapes the American Impressionists painted. Farms & Markets The Westport Farmers' Market — founded with the help of Paul Newman, a Westporter to the end — runs Thursdays with more than forty-five vendors: summers in the lot of the Westport Country Playhouse, winters at Gilbertie's Garden Center. New Pond Farm in Redding, minutes from the house, offers farm tours and seasonal family programs on a working dairy and maple-syrup farm. Silverman's Farm in Easton does the seasonal works — apples and pumpkins in the fall, Christmas trees in winter, berries in spring, vegetables all summer — with a country market and an animal farm that delights small children. And Ambler Farm in Wilton rounds out a landscape where agriculture never really left. For Families Traveling with children is easy here. The Maritime Aquarium in Norwalk — seven thousand animals in a newly renovated space; do not miss the seal feeding — delights every age, and Stepping Stones Children's Museum beside it is made for the very young. Earthplace in Westport pairs a small natural history museum with woodland trails and resident birds of prey. A little farther afield, the Bruce Museum in Greenwich bridges art and science gracefully; and Bridgeport offers both the Beardsley Zoo — Connecticut's only accredited zoo — and the Discovery Center and Planetarium for the space-minded. Add the animal farm at Silverman's, the hands-on programs at New Pond Farm, and the calm beaches of the Sound, and a week here works as well for a four-year-old as it does for the grandparents. A Week Here If you spent a week at White Oak Estate — in spring, summer, or fall — there is more than enough to feed your soul. Mornings on the trails at Devil's Den, the Nature Conservancy's largest preserve in Connecticut, or at Huntington State Park among Anna Hyatt Huntington's sculptures; afternoons at the beach or in the pool; a paddle on the Saugatuck; an evening concert at the Levitt or a show at the Playhouse; a slow Thursday at the farmers' market; a long lunch in Pound Ridge or the Litchfield Hills; and always, at the end of it, the drive back down the long driveway into the trees, where the house is waiting and no one can see you at all. Winter Winter here has its own rewards — the etched woods seen from the warmth of the great room, the hoped-for snow, Christmas trees cut at Silverman's. And the mountains are closer than you might think: Thunder Ridge, about forty-five minutes away, is perfect for an easy day on the slopes, and Mohawk Mountain — Connecticut's largest ski area, about an hour north in the Litchfield Hills — makes a fuller outing, with the larger resorts of the Berkshires and Catskills within reach beyond. We look forward to welcoming you. — Busi

Interaction with guests

You will have the entire property to yourselves and we will not share any part of the space with you. We respect your privacy and give you plenty of space, but we are available via the Airbnb app if you have any questions, need local recommendations, or require assistance at any point during your stay. If you have requested daily housekeeping, you can coordinate your preferred times with our housekeeper by text - the number is provided on arrival.