The 10-bedroom residence at 10024 Enchanted Oak Drive sits in Carolwood Reserve, a seven-home enclave inside Golden Oak, the gated residential community at Walt Disney World Resort, and it closed $800,000 above its final asking price of $17,900,000 β one of five reported sales across the metro that combined for $34.41 million.
The week’s closings span Orlando, Winter Park, Sorrento and Windermere, ranging from a lakefront house on the Winter Park Chain of Lakes to a 143-acre estate surrounded by state forest, a custom build in Lake Nona Golf & Country Club and a golf-course home in the guard-gated Keene’s Pointe community.
No. 1 — $18,700,000 · 10024 Enchanted Oak Drive, Orlando, Florida
The Golden Oak estate closed on September 1, 2026, and ranked No. 1 in RealtyWire’s weekly Top 5 for the Orlando metro area. Built in 2013, the house carries a reported 11,524 square feet, with 14 full bathrooms and two half baths among its 10 bedrooms, two of which are private guest suites.
The main room rises through two-story ceilings, and the kitchen is flanked by a walk-in pantry and a butler’s pantry that connects it to the dining room. A home office with built-ins, a bunkroom and a playroom fill out the floor plan.
Out back, the homesite overlooks the community golf course and a golf-course pond, with a pool and spa joined by a second pool shaped like Mickey Mouse’s head, an outdoor kitchen, a gas fireplace and a firepit area positioned for watching the Magic Kingdom fireworks visible from the property each evening. A four-car garage completes the house. Golden Oak residents have access to Summerhouse, the community’s private clubhouse, along with Club Life member services, park transportation and theme-park events, and the Four Seasons Resort Orlando and its 18-hole Tranquilo golf course sit within the community as well.
The property previously changed hands for $1,249,900 in 2011, before the current residence was completed in 2013.
Karen Balcerak of Golden Oak Realty represented the listing side of the $18.70 million Enchanted Oak Drive sale, and Greg Foxx, also of Golden Oak Realty, represented the buyer.
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No. 2 — $5,410,000 · 2025 Summerland Avenue, Winter Park, Florida
At No. 2, a five-bedroom house at 2025 Summerland Avenue in Winter Park sold for $5.41 million on September 2, 2026. The 1972 home fronts Lake Maitland, the largest lake on the Winter Park Chain of Lakes, in the city’s Green Oaks neighborhood, and carries a reported 4,432 square feet.
The kitchen is positioned to overlook the water, and expansive windows frame lake views throughout the house. The primary suite takes in panoramic views of its own and anchors one wing of a split floor plan alongside two bedrooms; the opposite wing holds two more bedrooms and a bonus room.
The lakefront setting puts boating, waterskiing, paddleboarding and fishing on the Chain of Lakes at the back door, and the house is minutes from the shops and restaurants of Park Avenue and from Rollins College. The property previously changed hands for $1,950,000 in 2018.
Alison Mosley of Premier Sotheby’s Intl. Realty was the listing agent.
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No. 3 — $3,600,000 · 32839 Webbs Way, Sorrento, Florida
No. 3 sits far from the metro’s suburban grid: a 143-acre estate at 32839 Webbs Way in Sorrento, surrounded by more than 50,000 acres of state forest, closed September 3, 2026, for $3.6 million.
The 1995 main residence offers five bedrooms, three full baths and two half baths in a reported 4,201 square feet, along with a safe room built with reinforced concrete walls, a fireplace anchoring the central living room and a three-car garage fitted with a Tesla universal charging station.
The acreage supports a full equestrian operation: a barn with two air-conditioned tack rooms and two wash racks, an Olympic-size dressage arena, a lighted riding arena and a round pen, tied together by more than five miles of trails. More than 30 acres have been cleared for pasture and recreation, roughly 80 wooded acres south of the house hold a secluded campsite, three ponds dot the grounds, and a backup generator system with a 550-gallon diesel tank can power the entire home.
The estate went under contract 28 days after the current listing date.
Lori Baker of Premier Sothebys Int’l Realty was the listing agent. Adolfo Pereira, III of Margaux Realty Inc represented the buyer.
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No. 4 — $3,400,000 · 8569 Lake Nona Shore Drive, Orlando, Florida
At No. 4, a custom house at 8569 Lake Nona Shore Drive in Orlando’s Lake Nona Estates sold for $3.4 million, closing September 3, 2026. DeVoe Custom Homes built the five-bedroom residence in 2017 inside Lake Nona Golf & Country Club, near the club’s member amenities and lake access, with five full baths, two half baths and a reported 5,259 square feet.
The family room rises under high ceilings trimmed with millwork, and 10-foot sliding glass doors frame the saltwater pool and the pond beyond. A chef’s kitchen conceals a hidden walk-in pantry, and the first floor adds a dedicated office, a second en-suite bedroom, a concealed walk-in wine cellar and an air-conditioned indoor-outdoor Florida room. Upstairs, three more en-suite bedrooms include a hidden fifth bedroom reached through a secret bookcase door, and Control4 automation runs the house.
Outside, the pool is joined by a spa and an outdoor grill, while an oversized three-car garage and a separate golf-cart garage handle the vehicles. The closing placed No. 4 on RealtyWire’s Top 5 list for the Orlando area this week.
Amanda Hoppenjans and Cathy Williams of Lake Nona Realty LLC were the listing agents. Heidi Bedell of Bedell Homes LLC represented the buyer.
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No. 5 — $3,300,000 · 6857 Valhalla Way, Windermere, Florida
The week’s fifth-ranked sale closed August 31, 2026, in Windermere, where 6857 Valhalla Way brought $3.3 million. Builder Rick Watson completed the house in 2006 on the 17th fairway of the Jack Nicklaus-designed Golden Bear Club course, inside the 24-hour guard-gated Keene’s Pointe community.
The five-bedroom house counts five full baths, two half baths and a reported 7,153 square feet, with the primary suite on the first floor. That suite opens to the lanai and includes two walk-in closets with custom organization systems, a stone-top jetted tub, a travertine wrap-around walk-in shower and separate vanities. An office with a coffered ceiling and built-ins, a gourmet kitchen with Wolf appliances, a home theater, a game room with a wet bar and a whole-house integrated sound system round out the interior.
The lanai carries a summer kitchen, covered seating, a gas fireplace and a pool and spa, and the property adds a stone-paver driveway, an oversized three-car garage and five air-conditioning units with an upgraded filtration system. The house previously changed hands for $2,500,000 in 2022.
Mely Carrero of Empire Network Realty was the listing agent.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, September 6, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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