The five highest-priced home sales reported in the Orlando metro area for the week ending October 4, 2026, totaled $17.598 million. All five are single-family homes, and they range from a one-story home built in 1990 to one completed this year, with addresses in four cities across Orange, Osceola and Seminole counties.
Two of the sales were in the city of Orlando, one in the established streets of Baldwin Park and one in a gated golf community at Lake Nona. The others were in Kissimmee, Oakland and Longwood, and several of the homes were planned around extended family, with guest quarters or a private apartment alongside the main living space.
No. 1 — $4,600,000 · 8590 Apache Trail, Kissimmee, Florida
Behind a private gate on five acres in Kissimmee, the top sale of the week is a custom estate built in 2009. It sold for $4,600,000. With 11,138 square feet of living space, it is the largest home in this Top 5, and its five-acre lot is the biggest of the group.
The entry sets the scale. A curving marble staircase rises under a Swarovski crystal chandelier, and a stone gas fireplace and soaring ceilings give the main rooms their height. Rich woodwork runs through the formal dining room and the living room, where sliding glass doors open at the corner to the outdoor living areas. The home has five bedrooms, each with its own bath and a large walk-in closet, plus nine bathrooms in all, five full and four half. The primary bedroom is on the main floor and includes a sitting area, and an elevator serves the two stories.
The home was built for entertaining and for staying in. There is a media room with theater seating and a chandelier that the listing says was commissioned from Tiffany’s in New York, along with a wine cellar, a wet bar finished in custom woodwork and coffered ceilings with printed panels. A gym with a steam room and a combined office and library round out the main living spaces, and an upstairs game room looks out over a large covered balcony.
Outside, mature oaks and full landscaping surround a large pool and spa, an outdoor kitchen, generous covered seating and tennis courts. An attached garage has room for five cars. The property last sold for $300,000 in 2007, before the current home was built.
Brian Hyser of THE AGENCY FL was the listing agent. Jamie Bevelacqua of DENIZ REALTY PARTNERS LLC represented the buyer in the week’s highest-priced sale.
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No. 2 — $3,799,000 · 4601 New Broad Street, Orlando, Florida
Derrick Builders designed this Baldwin Park home in the Georgian tradition, and its front shows it: a symmetrical facade with a columned veranda across the front, a balcony above, dormers and black shutters. The home sits on a 0.33-acre corner lot looking out on the cascading water feature along New Broad Street, with mature trees around it. It sold for $3,799,000.
Built in 2003, the home has 6,220 square feet on three levels, with six bedrooms and seven bathrooms, six full and one half. It has the most bedrooms of any home in this Top 5. The main level has formal living and dining rooms, an office and a guest bedroom, and a large kitchen with an oversized island that opens to a casual dining area, a family room and a small home-management space. French doors lead out to a covered brick terrace. The primary suite is upstairs, with a sitting area, built-ins, a walk-in dressing room and a bath with a freestanding soaking tub. The third floor is given over to recreation, with a large entertainment room, a gym and a wet bar.
Over the three-car garage is a private apartment of about 626 square feet, with its own entrance, a living area, a kitchenette and a full bath, suited to relatives, long-stay guests or household help. Behind the home, the covered brick terrace has an outdoor kitchen that looks over a pool with a sun shelf and a fountain. A brick fire pit sits under the trees, and a hedge of Japanese blueberry, crape myrtles and bamboo screens the grounds. Baldwin Park Village Center and Lake Baldwin are a short distance away. The property last sold for $3.6 million in 2024.
Emma Kaplan of BALDWIN PARK REALTY LLC was the listing agent, and JJ Mackle of PREMIER SOTHEBY’S INTL. REALTY represented the buyer. The home went under contract 21 days after it was listed and sold at its full asking price.
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No. 3 — $3,399,000 · 515 N Nixon Street, Oakland, Florida
The newest home in this Top 5 was completed in 2026 in Briley Farm, a community on 111 acres in Oakland, and it is the week’s only new construction. It sold for $3,399,000. The two-story home is in the Florida Colonial style, with stucco and cement siding, and sits on a level, landscaped lot of 0.52 acres.
Inside are 5,092 square feet, five bedrooms and seven bathrooms, five full and two half. Vaulted and tray ceilings open up the main rooms, and the kitchen and family room run together around a gas fireplace. The primary bedroom is on the main floor. A dedicated office and a private sauna are among the interior features, and a separate casita gives guests or extended family their own space.
Covered porches wrap the home on the front, side and rear, and the outdoor kitchen and grill sit near a heated pool and spa. The three-car garage is oversized and faces the side. Briley Farm residents have pickleball and tennis courts, a community pool, a splash pad and golf-cart access to Downtown Winter Garden.
Alexis Anderson and Heather Spirazza, both of REGENCY REAL ESTATE LLC, were the listing agents. Carol Ortiz of OLYMPUS EXECUTIVE REALTY INC represented the buyer.
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No. 4 — $3,000,000 · 10348 Kensington Shore Drive, Orlando, Florida
In the gated Lake Nona Golf & Country Club, within the Lake Nona Estates neighborhood of Orlando, this 2022 home on a 0.26-acre lot looks out over two ponds with no neighbors behind it. It sold for $3,000,000.
Marble floors carry through the 3,963 square feet of the two-story home. The open kitchen centers on an oversized island with a waterfall edge, stone counters and custom cabinetry, and it flows into the living areas, where an electric fireplace sits beside wide sliding glass doors to the backyard. All four bedrooms have their own baths, and the home has five bathrooms in all, four full and one half. The primary suite is on the main level, with a large walk-in closet and its own laundry, and an upstairs loft can work as an office or media room. Smart-home controls, paired refrigerators, dishwashers and laundry machines finish the practical side.
The backyard has a heated saltwater pool and spa, a screened outdoor kitchen, two fire pits and an outdoor fireplace set in landscaped gardens. The garage has room for three cars plus a golf cart. Club residents have a golf course, a clubhouse with dining, a fitness center, a pool, and tennis and pickleball courts, and the community has staffed gates around the clock.
Mark Sayad and TJ Cosgrove, both of REAL BROKER, LLC, were the listing agents. Marisela Torres of LAKE NONA REALTY LLC represented the buyer.
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No. 5 — $2,800,000 · 2228 Earleaf Court, Longwood, Florida
At the end of a quiet cul-de-sac in the Markham Woods Corridor of Longwood, this home backs to Wekiwa Springs State Park, with a pond and wooded conservation land as its view. Built in 1990, it is the oldest home in this Top 5 and the only one on a single story, and a comprehensive renovation has remade the interior. It sold for $2,800,000.
The fenced 1.04-acre property is entered through private gates onto a brick paver circular drive, with a porte-cochere and a motor court in front. A pivot door five feet wide and eight feet tall opens to a foyer of porcelain tile and white oak. Beyond it, 14-foot ceilings and walls of glass run over an open plan in which the living, dining, family and kitchen areas share one space, divided by a double-sided wood-burning fireplace between the kitchen and family room. The kitchen has Wolf appliances, built-in refrigeration and a waterfall-edge island that seats six.
The home has 7,696 square feet, five bedrooms and six bathrooms. The primary suite looks out on the water and woods, and its bath has leather-finished stone counters, two vanities, a soaking tub and a steam shower. One of its two walk-in closets conceals a safe room. An office, a bonus room and a gym add flexible space, and a flex room between the main residence and the guest quarters opens to the lanai and a pool bath. The guest quarters have two bedrooms, two baths, a great room, a full kitchen, their own laundry and separate access from a motor court. Outside, a travertine lanai leads to a large heated pool and spa with the pond and conservation land beyond.
The property last sold for $1.3 million in 2025. This time it sold above its $2.785 million asking price. Mel Bernstein of PREMIER SOTHEBYS INT’L REALTY was the listing agent, and Rob Breese, III of RE/MAX TOWN & COUNTRY REALTY represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 4, 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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