These are the highest-priced home sales reported in Orlando / Orange County, Florida for the week ending November 8, 2026, and together they came to $16.375 million. Three of the five were in Windermere, with one each in Orlando and Winter Park, and all five are single-family homes. They were built across more than three decades, and their lots range from about a quarter acre to two acres.
No. 1 — $4,750,000 · 9875 & 9893 Kilgore Road, Orlando, Florida
The week’s top sale was an equestrian property on Kilgore Road in Southwest Orlando, where two private, electrically secured gates open onto two fenced acres zoned for horses. Classic four-board fencing divides the land, which has pasture, corrals, a workshop and a custom barn with four American Stall Works stalls built for full-sized horses. The property sold for $4,750,000.
The main residence is a two-story ranch-style home built in 2023, with six bedrooms, five full baths and three half baths in 4,740 square feet. A 10-foot-wide wraparound porch of Trex composite decking runs around all four sides. Impact-resistant PGT and Andersen windows and concrete architectural shingles give the exterior a European rustic look. Inside, cathedral and vaulted ceilings are finished with custom woodwork, the living room and the family room each have a fireplace, and a private elevator links the levels.
The kitchen is built around a La Cornue gas range and oven with hand-finished trim. It also has a 64-inch Sub-Zero refrigerator, a Bosch wall oven and dishwasher, and a pair of porcelain farmhouse sinks. The primary suite has a walk-through shower and an oversized clawfoot soaking tub. A separate guest house has its own full kitchen, one bedroom, one bath and 850 square feet of living space. The property also has a four-car garage, an outdoor kitchen, a Generac whole-home backup generator, two wells and two septic systems.
Leslie Heimer of PREMIER SOTHEBYS INT’L REALTY and Janet Scott, also of PREMIER SOTHEBYS INT’L REALTY, were the listing agents on the week’s highest-priced sale. Brian Teach of COLDWELL BANKER REALTY represented the buyer.
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No. 2 — $3,725,000 · 4906 Aviva Garden Court, Windermere, Florida
Inside the guarded gates of Isleworth, in the enclave known as the Gardens of Isleworth, a custom Mediterranean home built by Wyatt in 2016 sold for $3,725,000. At 6,605 square feet it is the largest of the week’s five homes, while its 0.26-acre lot on a cul-de-sac is the smallest.
The two-story home has four bedrooms, three full baths and three half baths. Its interiors have inlaid wood and travertine floors and custom ceiling details, and wide sliding glass pocket doors open the living spaces to the outdoors. A copper hood rises over the Viking appliances in the kitchen, which also has a butler’s pantry, a concealed walk-in pantry, a wet bar and an oversized island. The primary suite adds a private lounge, a two-sided fireplace and two walk-in closets, and its bath has an indoor-outdoor shower. Elsewhere are a private theater, an elevator and a whole-house generator.
The outdoor living area centers on a heated saltwater pool and spa, with a fire pit, a summer kitchen and an outdoor shower. A covered lanai with retractable screens overlooks the water, and the property comes with lake privileges and a private boat ramp. Its six-car garage, the most garage space of any home this week, includes four separate single-car garages, two of them fitted with vehicle lifts. The property last sold for $2.9 million in 2021.
Simon Simaan of THE SIMON SIMAAN GROUP was the listing agent, and Rob Rahter of STOCKWORTH REALTY GROUP represented the buyer.
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No. 3 — $2,800,000 · 801 Via Lombardy, Winter Park, Florida
On Via Lombardy in Winter Park’s Sicilian Shores neighborhood, a Mediterranean home built in 1998 sold for $2,800,000. The listing describes its setting as the Winter Park Vias, with the Winter Park Racquet Club a short walk away. The two-story home has five bedrooms and five full baths in 4,105 square feet, on a level, landscaped corner lot of 0.44 acres with a circular driveway and a three-car garage. The primary bedroom is on the main floor, and the family room has a fireplace. A saltwater pool is set in a secluded backyard, and the property also has an in-ground spa. The property last sold for $1.275 million in 2005.
Maria Van Warner of FANNIE HILLMAN & ASSOCIATES was the listing agent. Catherine D’Amico, also of FANNIE HILLMAN & ASSOCIATES, represented the buyer, putting the firm on both sides of the sale.
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No. 4 — $2,750,000 · 5379 Isleworth Country Club Drive, Windermere, Florida
The oldest home of the five, and the only single-story one, is on the 17th hole of the Isleworth Country Club golf course in Windermere, with frontage on the course and views of the lake. Built in 1989, it has four bedrooms, three full baths and a half bath in 3,872 square feet, the smallest living area this week. The 0.56-acre lot has an in-ground pool, and the home has high ceilings, an open floor plan and a three-car attached garage. The listing presented it as a candidate for a remodel or for a new custom home. It sold for $2,750,000, and the property last sold for $2.625 million in 2025.
Mindy Silva of LOKATION was the listing agent, and Riley Whittall of SELLING FLORIDA REAL ESTATE INC represented the buyer.
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No. 5 — $2,350,000 · 12722 S Lake Sawyer Lane, Windermere, Florida
A private gate leads to this Windermere home on about 80 feet of Lake Sawyer shoreline, and the lake connects with Little Lake Sawyer for boating and swimming. Beyond the pool, a private dock and boathouse have a covered boat lift and two Jet Ski lifts. The two-story Mediterranean home, built in 2007 and extensively renovated in 2019, sold for $2,350,000.
The home has five bedrooms and four baths in 5,139 square feet, on 1.46 acres. A two-story foyer with a winding staircase opens toward the formal living room and its two-sided fireplace, with the screened deck, the pool and the lake in view beyond. The renovated kitchen has white cabinetry that reaches the ceiling, quartz counters and backsplash, a contrasting island that seats four, and a professional-style gas range with a pot filler under a custom hood. A glass-enclosed wine closet is close by, and a wet bar joins the formal dining room to the kitchen.
The primary suite is on the first floor, with a tray ceiling, a large custom dressing closet and its own door to the covered outdoor living area. Its bath has a freestanding soaking tub and an oversized shower with two entrances and herringbone tile. Upstairs, four more bedrooms and two full baths share the floor with a living area, a theater and a bonus room, and a covered balcony looks out over the lake. Large glass doors at the rear open to the screened pool and spa, the deck and the covered lanai. The property last sold for $980,000 in 2014.
Padgett McCormick of KELLY PRICE & COMPANY LLC was the listing agent, and Alice Anne Jackson of CORCORAN PREMIER REALTY represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 8, 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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