The highest-priced home sales reported in the Orlando metro area for the week ending October 11, 2026, came to a combined $19.25 million. Two of the five homes are in Winter Park, two are in Orlando and one is in Fern Park, in Seminole County, and all five are single-family homes.
Water runs through much of the list, from a private ski lake to the shoreline of Lake Temple, and the homes span more than a quarter century, from a 1999 home in Lake Nona Estates to one finished this year. The second- and third-ranked sales closed at the same price, and in three of the five sales the same agent was on both sides.
No. 1 — $4,650,000 · 2525 Temple Drive, Winter Park, Florida
The week’s top sale was a lakefront compound at 2525 Temple Drive in the Lake Maitland neighborhood of Winter Park, which sold for $4,650,000. Gallimore Homes completed the Mediterranean-style home in 2019 on 1.32 acres along Lake Temple, the largest lot in this group. The home sits well back from the street behind mature plantings and a walled courtyard with a security gate.
The main living space is a great room with a gas fireplace and high, vaulted ceilings, where EuroWall glass doors fold back across 15 feet to open the room to the yard and the lake. The kitchen has Sub-Zero and Wolf appliances, including a six-burner Wolf range, along with a large island, a walk-in pantry and a dry bar. The primary suite is on the first floor, with two walk-in closets, and an upstairs bonus room is plumbed for a future bath and kitchenette. In all, the home has five bedrooms, five bathrooms and 4,542 square feet, plus a three-car garage and room to park a boat.
Outside, a covered lanai with Phantom screens includes a wood-fired Argentine grill and a wet bar. The heated saltwater pool has an infinity edge, a sun shelf and a composite wood deck facing the water, and the lawn slopes down to the shore under an oak tree more than a century old. A detached guest house of about 480 square feet has its own kitchen, living room and covered front porch. The Winter Park Racquet Club is a few blocks away, and Interlachen Country Club is less than three miles off. The property last sold for $520,000 in 2017, before the current home was built.
The home went under contract nine days after it was listed. MaryStuart Day and Sara Robbins of FANNIE HILLMAN & ASSOCIATES were the listing agents, and Dela Armstrong, PA, of C BRENNER INC represented the buyer. It was one of two homes in this Top 5 listed by FANNIE HILLMAN & ASSOCIATES, which also had the fifth-ranked sale.
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No. 2 — $4,000,000 · 9662 Blandford Road, Orlando, Florida
A one-story home at 9662 Blandford Road in Lake Nona Estates, Orlando, sold for $4,000,000, tying for second place with the sale at 229 Alexander Place. Built in 1999, it is the oldest home in this group, set on 0.48 acres near the golf course in the gated Lake Nona Golf & Country Club community, with lake frontage and a circular driveway.
The listing says the home was in the middle of a complete renovation by Mrcela Custom Homes, with completion expected in August 2026. The plans call for a modern exterior with a charcoal standing-seam metal roof and limestone accents, new windows and doors, a reworked interior and a larger kitchen opening to the main living area, along with new hardscaping and landscaping. The home has four bedrooms, five bathrooms, 4,315 square feet and a three-car garage. It also has a sauna, a gas fireplace, a dry bar and a saltwater pool with an in-ground spa. The property last sold for $1.7 million in 2025.
Amanda Hoppenjans and Marisela Torres of LAKE NONA REALTY LLC were the listing agents, and Jessica Lyons, also of LAKE NONA REALTY LLC, represented the buyer, keeping both sides of the sale within one firm.
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No. 3 — $4,000,000 · 229 Alexander Place, Winter Park, Florida
The contemporary home at 229 Alexander Place in Winter Park was designed by architect Phil Kean, and the National Association of Home Builders originally commissioned it as its International Showcase Home. Completed in 2011, it sold for $4,000,000, the same price as the second-ranked sale. The home stands on a cul-de-sac two blocks from Park Avenue, between the Alfond Inn and Lake Osceola.
Ten-foot mahogany doors lead into a private courtyard, where a heated pool is set within the landscaping. Inside, the ceilings reach 14 feet, and the living spaces, lined by a 40-foot gallery wall, open to the outdoors. The kitchen has Gaggenau, Monogram and JennAir appliances, with a media lounge and a wet bar close by.
The primary suite occupies the entire second floor, reached by a floating staircase or an elevator, and has three private terraces, a marble vanity and a smart-controlled shower. On the first floor are an office, a guest suite and a fitness room with its own steam shower, and a casita sits by the pool. A whole-home generator, smart-home controls and automatic Lutron shades are built in. The home has four bedrooms, six bathrooms, 4,431 square feet and a three-car garage on 0.27 acres. The property last sold for $2.9 million in 2017.
Brandon Geers and John Nagell of COMPASS FLORIDA LLC were the listing agents, and Geers also represented the buyer, so the same agent was on both sides of the sale.
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No. 4 — $3,700,000 · 692 Gladwin Avenue, Fern Park, Florida
At 6,240 square feet, the home at 692 Gladwin Avenue in Fern Park is the largest in this Top 5, and with six bedrooms it also has the most. It sold for $3,700,000. Completed in 2023 in a contemporary Florida style, it sits on 0.98 acres fronting Prairie Lake, a private lake of 124 acres where skiing is allowed and seaplanes may land for private use.
The waterfront has a covered boat slip with an electric lift, a dock for two jet skis, a private boat ramp and beach access. Inside, white oak planks and honed marble run beneath high ceilings and Kolbe windows, LaCantina folding doors open the living areas to the outdoors, and a 73-inch gas fireplace is the focus of the main room. The kitchen has Omega cabinetry, quartz counters, a 14-foot waterfall island and a 48-inch Bluestar gas range.
The primary suite is on the main floor, with lake views, French doors to the pool deck, a soaking tub and two walk-in closets. Upstairs are a second living area overlooking the lake and a theater with a 120-inch screen, and there is a laundry room on each floor. Outside are a saltwater pool with a waterfall and fire bowls, a swim spa, a summer kitchen and a fire pit by the lake. The home has five bathrooms and a three-car garage, and it is convenient to Winter Park, Maitland, Altamonte Springs and Lake Mary. The property last sold for $480,000 in 2020, before the current home was built.
Tammy Jo Gaylord of CHARLES RUTENBERG REALTY INC was the listing agent and also represented the buyer, putting the same agent on both sides of the sale.
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No. 5 — $2,900,000 · 1236 Chichester Street, Orlando, Florida
The newest home in this Top 5 was finished this year at 1236 Chichester Street in the Beverly Shores neighborhood of Orlando, and it sold for $2,900,000. The custom two-story home has five bedrooms, six bathrooms and 3,501 square feet on a lot of 10,125 square feet, with a two-car garage. The property last sold for $430,000 in 2018, before the current home was built.
White oak sets the tone, laid in a herringbone pattern in the foyer and in wide planks in the living room, where a gas fireplace has a marble surround and a Venetian plaster face framed by built-in cabinetry. In the kitchen, quartzite counters top two-tone cabinetry, and an eight-burner ILVE range with brass trim sits under a Venetian plaster hood, joined by Thermador appliances and a full-height wine refrigerator. A separate scullery adds a second sink and more storage.
The primary suite is on the main floor, with a vaulted ceiling crossed by exposed white oak beams, a freestanding tub and a closet that includes its own washer and dryer. A first-floor room can serve as an office or a fifth bedroom. Upstairs, a loft opens to three bedrooms, each with a walk-in closet and its own bath. Out back, a covered veranda with a tongue-and-groove ceiling and motorized screens leads to a summer kitchen, a pool bath and a saltwater pool with a heated spa and sun shelf.
Lisa Shear of FANNIE HILLMAN & ASSOCIATES was the listing agent and also represented the buyer, so the same agent was on both sides of the sale. FANNIE HILLMAN & ASSOCIATES also listed the week’s top sale, giving the firm two of the five listings in this Top 5.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 11, 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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