The five highest-priced home sales reported in the Orlando metro area for the week ending October 18, 2026, came to a combined $16.537 million. The sales were spread across five communities, from Lake Mary in Seminole County to Winter Park, Windermere, Oakland and Orlando in Orange County.
All five are two-story single-family homes, and two of them are new construction, including one that has yet to be built. The oldest went up in 1988.
No. 1 — $3,900,000 · 1795 W Lake Mary Boulevard, Lake Mary, Florida
Behind a custom gate on the shore of Lake Mary, the top sale of the week is a Mediterranean estate built in 2012 on 4.70 acres. It sold for $3.9 million. A circular drive with a fountain leads to a porte cochere, and inside, a two-story foyer opens onto arches, columns, detailed millwork and travertine floors set with stone medallions. Hardwood floors run through the bedrooms.
The home has seven bedrooms, 13 bathrooms (11 full and two half baths) and 8,319 square feet of living space, along with an elevator and a six-car garage. Those are the largest figures among the five sales on each count, and its lot is the largest as well. The family room has a gas fireplace and looks out over the lake. The kitchen has solid wood cabinets, stone counters, a Viking Professional rangetop, a pair of Sub-Zero refrigerators and a butler’s pantry. There are two primary suites, and one of them has a dressing room fitted out like a small boutique, with a center island, floor-to-ceiling cabinetry and clerestory windows. Two custom aquariums are built into the home.
Much of the estate sits apart from the main residence. A detached guest building has a two-bedroom, two-bath residence on its upper floor and about 3,654 square feet below for executive offices, conference and gathering rooms and a fitness room. A separate garden apartment adds another place for family or guests to stay. Outside are an infinity-edge pool and spa, travertine terraces, a covered summer kitchen and a gazebo by the lake, as well as a covered dock with a boat lift and a boat garage.
The property last sold for $1.24 million in 2009, before the current home was built.
Jessica Estrada of KELLER WILLIAMS ADVANTAGE III was the listing agent, and Eddie Lopez of EXP REALTY LLC represented the buyer in the highest-priced sale of the week.
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No. 2 — $3,550,000 · 1150 Via Salerno, Winter Park, Florida
In the Vias neighborhood of Winter Park, a newly completed Mediterranean-minimalist home sold for $3.55 million. Steve and Jodie Konold of Scout & Co. conceived, developed and designed the home, and architect Cynde Norris worked with them on its terraced front walk. Antique French gates open from that walk into an entry garden of native plants, and a glass foyer with a woven rattan chandelier, sourced in London, leads to a sculptural staircase.
The great room has tall ceilings, a custom plaster fireplace and walls of glass doors and windows. Floors are micro-crete on the main level and wide-plank European oak upstairs. In the kitchen, a Thermador dual-fuel range sits under a matching plaster hood, and the large island is topped in honed black quartzite, the same stone used for a floating trough sink in the mezzanine powder room. Antique doors open into the main-floor primary suite, which has a light-filled gallery looking out to the rear courtyard and pool. Each guest bedroom has its own bath, and a rooftop terrace is reached from the second-floor hallway.
The home has four bedrooms, six bathrooms (five full and one half bath) and 3,826 square feet, the smallest living area of the five, on a 9,145-square-foot lot, also the smallest in the group. Outdoor living takes up much of the lot: a heated saltwater pool, two garden courtyards, an outdoor kitchen and a gravel courtyard screened by mature bamboo. A detached casita with a full bath opens to the pool courtyard through accordion glass doors on two sides. The two-car garage is on the lower level.
The property last sold for $700,000 in 2021, before the current home was built. Padgett McCormick of KELLY PRICE & COMPANY LLC was the listing agent, and Alison Mosley of PREMIER SOTHEBY’S INTL. REALTY represented the buyer.
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No. 3 — $3,337,000 · 9648 Mccormick Place, Windermere, Florida
Overlooking the second fairway on Isleworth’s front nine, with Lake Chase beyond, this Windermere home sold for $3.337 million. Built in 1988, it is the oldest of the week’s top five, and its grounds have since been redone.
A wall of glass now encloses the pool area, keeping open the views of the golf course and the lake. The pool deck has new pavers, and the outdoor kitchen has been upgraded with granite counters, a built-in grill, a pizza oven and a sink. A fire pit, new turf and fresh landscaping fill out the yard.
Inside, porcelain tile covers the main level, where the living room has a fireplace and a large built-in finished in slate with lighted shelves. The primary suite is on the main floor, with a sitting area, a walk-in closet and a bath with a soaking tub and a separate shower. A home office, a formal dining room and a kitchen with a center island and a casual dining area complete that level. Two more bedrooms upstairs open to a balcony. The home has three bedrooms, four bathrooms (three full and one half bath) and 4,751 square feet on 0.54 acre, with a three-car attached garage.
The property last sold for $3.02 million in 2022. Michelle Corbin and Sarah Longwell, both of ISLEWORTH REALTY LLC, were the listing agents, and Chuck Whittall of SELLING FLORIDA REAL ESTATE INC represented the buyer.
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No. 4 — $3,250,000 · 528 N Pollard Street, Oakland, Florida
The week’s fourth-highest sale, at $3.25 million, is for a home that has not been built yet. It is planned for a 0.58-acre homesite in Briley Farm, a community of custom homes in Oakland, and Element Home Builders is to build it.
The plans call for five bedrooms, seven bathrooms (five full and two powder baths) and about 5,148 square feet over two stories, with a two-car attached garage. They also include two home offices, a private gym, a gas fireplace, engineered hardwood floors and high ceilings. Outside, the plans show an in-ground pool, a courtyard and an outdoor kitchen with a grill, and the exterior is to combine block, brick and HardiPlank-type siding.
Briley Farm sits within small-town Oakland, and the listing puts it minutes from the West Orange Trail and downtown Winter Garden.
Alexis Anderson and Heather Spirazza, both of REGENCY REAL ESTATE LLC, were the listing agents. Tammi Pipkin of FLORIDA REALTY INVESTMENTS represented the buyer.
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No. 5 — $2,500,000 · 8600 Hata Street, Orlando, Florida
A waterfront home in Lake Nona South, in Orlando, sold for $2.5 million to round out the week. Built in 2019 in a warm, modern-transitional style, it has five bedrooms, six full bathrooms and 5,718 square feet on 0.71 acre, with a three-car garage.
Four of the bedrooms are on the main level, among them the primary suite, which has two large walk-in closets and a spa-style bath. Formal living and dining rooms, a home office and a laundry room share that floor. The kitchen has frameless contemporary cabinetry, a large center island and Wolf and Sub-Zero appliances, and it opens into the great room and a Florida room that lead outdoors. Upstairs are the fifth bedroom and a multipurpose room.
Landscaped grounds look out over conservation land. The backyard has a heated pool and spa, a summer kitchen with Bull appliances, a covered outdoor living area with a fireplace and a basketball court. The gated community has a clubhouse, a pool, tennis courts, a park and a playground.
The property last sold for $1.45 million in 2021. Humberto Cuevas of LA ROSA REALTY LLC was the listing agent, and Cathy Williams of LAKE NONA REALTY LLC represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 18, 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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