Single-Family Residential Developments

Orange County’s Top 10 most expensive home sales in 2021

Orange County’s luxury residential scene demanded some high prices in 2021.

Low-interest rates and elaborate marketing campaigns with flashy home showing parties and prop Lamborghinis set the stage for an extremely hot year in the luxury real estate market.


Wealthy buyers were enchanted by Disney’s Golden Oak community and drawn to the homes of pro-athletes and local developers.

Although Golden Oak had the highest volume of deals across the top ten most expensive homes sales in 2021, the highest prices took place elsewhere in places like Orlando, Winter Park and Windermere.


Among those include the home of Shaquille O’Neal, who spent years cutting his asking price and “de-shaq-ifying” the house in order to find a buyer; and the home of PGA legend Payne Stewart, which was designed just before his death in 1999.

GrowthSpotter tracked down the top-selling residences in Orange County within the past 12 months using information collected from the county’s property appraiser website.

A list of the 10 most expensive single-family home sales this year can be found below.

No. 1

An 11,565-square-foot home in Orlando sold for $12.5M in October

The most expensive home sale in 2021 sets all-time record for the Orlando Metropolitan Statistical Area. The previous record price was set in 2017 at $11 million for an estate on Interlachen Avenue in Winter Park.

Listing agent Karan Wienker with Florida Golf and Beaches told GrowthSpotter the team looked into the replacement value of the private abode along Lake Mabel Drive in Orlando and learned the cost to rebuild would be in the neighborhood of $10 million to $11 million.

“I didn’t flinch when the sellers said $12.95 million,” she said in an email. “Our competition wanted comparable sales...there are none, this is a stand-alone property.”


The nine-bedroom home sits on 13 acres overlooking Lake Mabel and is not part of an HOA. Notable features include a two-story study/library and a hand-carved limestone fireplace mantle, inspired by Cinderella’s Castle.

Medical doctors Ashish Pal and Sunita Bhanot bought the house. Kinsey Craichy and former Miss Florida Monica Craichy were the sellers.

Patricia France with Happy Days Realty LLC represented the buyers, according to

Florida Golf and Beaches’ Nina Sayad, Gloria Siegel, Max Freeman and Janna Dombrowski helped broker the deal. Megan Morris staged, that house and George Escobar with CorsaHQ provided prop Bently, Rolls-Royce, and Lamborghini car models.

No. 2

Shaquille O’Neal’s Isleworth mansion sold for $11 million in October


After more than three years on the market, Shaquille O’Neal’s Isleworth mansion finally reeled in a buyer before the end of the year.

According to a recorded deed, Seema Khanna, acting as a trustee of the Khanna Spousal Beneficiary Trust, bought the 12-bedroom, 31,000-square-foot house, which sits on 3.9 acres on the southeastern shore of Lake Butler.

The home includes a 95-foot long pool, a movie theater, a walk-in safe, an in-house basketball court, and three tile-floor garages capable of holding up to 17 cars. It’s located inside the gated Isleworth Golf and Country Club community and was put on the market in 2018 for $28 million. Before the sale, it was listed for $16.5 million.

Benjamin Hillman with Sotheby’s International Realty represented O’Neal. In a previous interview with the Orlando Sentinel, he said he removed signature traces of the basketball player, such as the Superman statue on the dock and the custom-made 17-foot round bed. Staging costs for the sale ran over $400,000.

Rob Rahter with Stockworth Realty Group brought the buyer.

No. 3


Mansion once owned by Rollins College sold for $10.65 million in September

Things do tend to get more expensive in Winter Park, and the mansions that are built within its borders are no exception. In September, a 10-bedroom, 13,855-square-foot estate on the shores of Lake Virginia sold for $10.65 million. The Mediterranean home rests on about two acres with water frontage on three sides of the property.

The house was originally built in 1925 and owned by Rollins College in the mid-20th century. In 2018, the previous owners expanded and completely renovated the interiors and exterior of the house.

Features include a circular driveway leading to the front door, a large chef’s island kitchen, an all-glass, walk-in wine room, two master suites on the first and second floor, a full gym, elevator, and an 18-car garage with hydraulic lifts and pneumatics. On the outside, you’ll find a summer kitchen, a resort-like pool and spa, a sports court, synthetic turf, and two boat docks.

Records show the family members of the late real estate developer Robert M. Picerne sold a divided interest in the home to South Dakota Trust Company LLC, which acts as a trustee of the Lago-A-Lago Trust Agreement.

Mick Night and John Pinel of Premier Sotheby’s International Realty brokered both sides of the deal, which marks the second-highest price for a home in Winter Park behind 656 N. Interlachen Ave. back in 2017 at $11 million. Night and Pinel also brokered that deal.


No. 4

Buyers dropped $7.5 million for an enchanting mansion on Disney property in June

A home in Walt Disney World’s Golden Oak neighborhood sold for $7.5 million in June.

Records show the buyer was Losfizio LLC, which is tied to Catherine Hurst Gledhill, who serves as manager of the Catherine Hurst Gledhill 2014 Living Trust, based out of Chicago, Illinois.

The seller, Sabrina Yonkers bought the 0.67-acre lot from Golden Oak Development LLC in 2011 for $949,900. Residential building permits filed in Orange County show James and Sabrina Yonkers hired Derrick Builders to construct a two-story, 8925-square-foot home in 2014.

The home has four bedrooms and six bathrooms. Residential building permit documents filed in 2013 show the house was constructed with an exercise room, craft room, office, two garages, a theater room and bar, and a customized golf room. Outside the home has a large courtyard main entry and a pool and spa.


The transaction was an off-market deal.

No. 5

A home that belonged to PGA legend Payne Stewart sold for $7.12M in October

A roughly 11,000-square-foot mansion in Windermere’s exclusive Isleworth community, that once belonged to PGA legend Payne Stewart, sold for $7.12 million in October.

According to an article by GrowthSpotter, Stewart’s wife, Tracey, completed the house in 2002 and raised the couple’s two children there.

Stewart was the winner of 11 PGA tour events including three majors. The four-bedroom, five-bathroom home was designed right before his death in 1999. It sits on more than two acres on Lake Bessie and includes an underground garage, movie theater, and an indoor-outdoor pool area that has a summer kitchen, fireplace, and waterslide.


Monica Lochmandy with Isleworth Realty represented the Stewart family trust. Ron Ziolkowski with Re/Max Prime Properties represented the buyers, Jessica and Kurt O’Brien.

Kurt O’Brien was the CEO of Simply Self Storage.

No. 6

A home in the Isleworth Golf & Country Club community sells for $6.9M

In December, a French Chateau-style house in the Isleworth Golf & Country Club community in Windermere sold for $6.9 million.

The 12,300-square-foot mansion has seven bedrooms, seven-and-a-half bathrooms and sits on 0.67 acres on the shores of Lake Bessie. Features include a circular driveway entrance, custom French doors and a grand two-story foyer with a spiral tower staircase.


Other notable features include a built-in media center, game room, a temperature-controlled wine room, and a seven-car garage. Outside the home has a boat dock, an open-air pool and spa, and a screened covered terrace with a summer kitchen.

Online marketing material states the previous owners widened the driveway, installed a new air conditioning system, installed an electric car charger, and put in security cameras, among other updates and finishes prior to the deal.

Records show John T. Rich and trustee of the John T. Rich Revocable Trust was the seller and the buyers are Larry Scott Demerau and Julia Emily Demerau

Monica Lochmandy with Isleworth Realty was the listing agent. Chris Bauman with Suzi Karr Realty brought the buyers.

No. 7

Newly completed home in Golden Oak sells for $6.45M in October


A newly constructed home in Walt Disney World’s Golden Oak neighborhood sold for $7.5 million. The buyers, John and Lisa Westlake, bought the 6,510-square-foot house in June from custom homebuilder Goehring & Morgan.

Goehring & Morgan paid $1.52 million for the 0.44-acre lot in 2019. The home, completed this year. has six bedrooms and seven bathrooms. According to a residential building permit, the house features a large game room, library, elevator, summer kitchen, and a resort-style pool and cabana area.

It resides in the Four Seasons Private Residences Orlando private residential community, where most homes feature separate kitchens so Four Seasons staff may prepare meals and cater for parties.

No. 8

Golden Oak home with custom fire pit sells for $6.4M in August

Roble Dorado LLC, led by Christopher John Pettit, paid $6.4 million for a 7,367-square-foot house in Walt Disney World’s Golden Oak community.


Custome homebuilder Stonebridge Homes completed the home earlier this year. It paid $1.57 million for the property in 2019. The five-bedroom, five-and-a-half bathroom home sits on a 0.44 acre lot along Summer Meadow Way.

According to residential building permits, the house was built to feature a raised theater, large game room and elevator. The house also features a large outdoor fire table by a pool and pool deck.

It resides in the Four Seasons Private Residences Orlando community, where most homes feature separate kitchens so Four Seasons staff may prepare meals and cater for parties.

No. 9

Golden Oak resale fetches $6.195M in March

Doggy John LLC paid $6.195 million for a home in Walt Disney World’s Golden Oak community in March.


Deborah Robertson, individually and as trustee of the Deborah L. Robertson Living Trust, sold the property. Records show she had previously paid about $4.2 million for the house in 2014, after it was completed by Derrick Builders. The five-bedroom, 7,000-square-foot home features a grand staircase at its entrance and a separate, second-floor guest suite with a private balcony that overlooks the pool and wetlands.

Residents at Golden Oak have access to a private clubhouse, park transportation, signature club events, and exclusive theme park experiences.

No. 10

Nigerian tech entrepreneur buys Golden Oak home for $5.999M in March

Zuma Alpha Properties LLC, led by Nigerian tech entrepreneur Shegun Otulana paid $5.999 million for a recently built custom home by Stonebridge in March. The mortgage on the home was signed by Otulana and his wife Mary. Shegun Otulana is the CEO of the software company, TheraNest.

The 6,756-square-foot home has five bedrooms and six-and-a-half bathrooms. According to a residential building permit, the home was built to feature a grand foyer entrance, large game room, courtyard, summer kitchen, a guest suite, two garages and pool and spa.


It resides in the Four Seasons Private Residences Orlando community. Residents have access to a private clubhouse, park transportation, signature club events, and exclusive theme park experiences.

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