The five highest-priced home sales reported in Seminole County, Florida for the week ending October 25, 2026 came to a combined $6.41 million, and they spanned the county from Winter Park to Chuluota. The group was closely bunched, with every sale landing between $1.2 million and $1.38 million.
The homes were just as varied as their settings. Two were newly built, one of them completed this year, and four of the five have two stories. Lots ran from 9,239 square feet in a gated Winter Park community to more than five acres outside Chuluota, and Winter Park accounted for two of the five sales.
No. 1 — $1,380,000 · 2873 Old Castle Drive, Winter Park, Florida
The top sale of the week was a lakefront home in the gated Bear Gully Pointe community of Winter Park, which sold for $1,380,000. The property sits on Bear Lake, a spring-fed lake of 137 acres, and its 0.59-acre lot is landscaped, with mature trees, with walking paths winding through the backyard.
Built in 1993, the two-story custom home has 4,247 square feet, four bedrooms and four bathrooms, with stucco walls and a side-facing three-car garage. Ceilings rise high in the entry, where tall windows and sliding glass doors look out toward the pool. The formal dining room has a coffered ceiling and connects to the kitchen by way of a wet bar and wine closet.
The kitchen was rebuilt down to the studs in 2016. It now has marble counters, custom cabinetry, double wall ovens, a gas cooktop, a Sub-Zero refrigerator and a breakfast nook, and a large picture window faces the pool. It opens to a family room with a gas fireplace, built-in cabinetry and windows that run from floor to ceiling. The primary suite is on the main floor, with a French door out to the pool and lanai, and its bath was remodeled in 2019 with two vanities, a soaking tub and a shower with dual heads. An office and a pool bath are nearby. Upstairs are a loft, two more bedrooms and a full bath.
Outside, a heated pool and spa sit under a covered, screened lanai. Bear Gully Pointe has sidewalks, a tennis court, a playground and a new gazebo looking out over Bear Lake. The property last sold for $600,000 in 2011.
Wendy Williams Crumit of FANNIE HILLMAN & ASSOCIATES was the listing agent, and Michelle Hochfelder of PREMIER SOTHEBY’S INTL. REALTY represented the buyer in the week’s highest-priced sale.
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No. 2 — $1,299,990 · 408 Marina Louis Point, Sanford, Florida
In second place, a newly completed home in Preserve At Deer Lakes, a gated community of 31 homes in Sanford, sold for $1,299,990. Completed in 2026, it is the newest home in this Top 5 and, at 4,309 square feet, the largest.
The two-story home was built on the Richmond floor plan with a farmhouse exterior and a front porch. Inside, the great room rises two stories, with oversized windows and a 16-foot sliding glass door that opens toward the backyard and a view of the preserve. The kitchen is built around a large island with an apron sink, quartz counters and GE appliances, and it opens to the family room.
The home has five bedrooms, five full baths and a half bath, along with a home office and a loft. The primary suite is upstairs, with two walk-in closets and a bath that has a freestanding tub and a shower with a rain showerhead. Out back, a covered patio looks onto a 0.56-acre lot with room for a pool. The community is convenient to downtown Sanford and the business districts of Lake Mary and Sanford.
The home went under contract 13 days after it was listed. Richard Selikoff of K HOVNANIAN FLORIDA REALTY was the listing agent.
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No. 3 — $1,285,000 · 2056 Alaqua Drive, Longwood, Florida
The only one-story home in the group, a Dave Brewer custom home in the 24-hour guard-gated community of Alaqua in Longwood, sold for $1,285,000. Built in 1991, it is also the oldest of the five, and it stands on a one-acre homesite.
The home has 3,768 square feet, with three bedrooms, three full baths and a half bath, plus a large private office with its own closet that could serve as a fourth bedroom. Hardwood floors run through the home, the ceilings include coffered and vaulted designs, and the family room has a fireplace. Outdoors are a screened pool, a spa and an outdoor kitchen. Golf is close by at Alaqua Country Club.
Frank Benevento of COLDWELL BANKER REALTY was on both sides of the sale, as both the listing agent and the buyer’s agent.
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No. 4 — $1,243,362 · 1117 Wading Waters Circle, Winter Park, Florida
A 2019 home by Meritage Homes in Waters Edge At Hawks Crest, a gated community in Winter Park, sold for $1,243,362. Built on the builder’s Kerrville II plan, the two-story home has 4,307 square feet, six bedrooms, the most of any home in this Top 5, and four bathrooms, on a 9,239-square-foot lot with water views.
Much of the home’s appeal is outdoors. An extended lanai leads to a heated saltwater pool and spa that clean themselves, an outdoor kitchen, and a screened enclosure fitted with lighting that changes color at night. The home also has solar panels.
Inside, the kitchen has a large center island, quartz counters and premium cabinetry, and it opens to the main living and dining areas. Formal living and dining rooms are on the first floor, along with a guest suite that has its own bathroom and easy access to the pool. The upstairs includes flexible living space that could work as a media room, office or gym. The three-car garage has overhead storage shelving. Residents of Hawks Crest share a community pool, a clubhouse, a fitness center, a playground, a putting green and a private dock on Lake Howell.
The home went under contract 22 days after it was listed, and the property last sold for $613,800 in 2019. Brian Hyser of THE AGENCY FL was the listing agent, and Monika Gupta of LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV represented the buyer.
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No. 5 — $1,200,000 · 490 Riverwoods Trail, Chuluota, Florida
Rounding out the week, a new custom home on 5.02 acres in Chuluota sold for $1,200,000. The lot is the largest in this Top 5, and the property last sold for $240,000 in 2006, before the current home was built.
Completed in 2025, the two-story home has 3,093 square feet, four bedrooms, three full baths and a half bath, and an attached two-car garage. Its walls are concrete block with core-fill insulation and HardiPlank-type siding, and spray foam between the two floors cuts down on sound traveling between them. Luxury vinyl plank flooring runs throughout, and the showers are built with the Schluter waterproofing system. The primary bedroom is on the main floor and has a custom walk-in closet with built-in storage.
Covered porches at the front and rear are finished with tongue-and-groove wood ceilings and recessed lighting. A large bonus room was designed so it can be divided into two more bedrooms, and the septic system was laid out with a future pool in mind.
The home went under contract 29 days after it was listed. Justin Core of EXP REALTY LLC was the listing agent, and Bonnie Endrick of COLDWELL BANKER 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 25, 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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