A 2023 house in Lakeland with a climate-controlled indoor pickleball court sold for $2.25 million, the highest-priced home sale reported in the Lakeland, Florida metro area for the week ending August 16, 2026.
The week’s five highest-priced reported sales combined for $6.37 million. Three of the closings were in Lakeland, and the other two were in Winter Haven and Haines City.
The five houses were built between 1995 and 2023, and they run from a golf-community estate and a gated cul-de-sac property on more than an acre to a Spanish-inspired lakefront residence on Lake Hamilton and a custom house on nearly six fenced acres. Two of them came from the same builder, Hulbert Homes.
No. 1 — $2,250,000 · 2398 Heritage Lakes Drive, Lakeland, Florida
The indoor pickleball court at 2398 Heritage Lakes Drive is climate-controlled, laid out to regulation and wired for sound, with a second-floor observation deck above it. Hulbert Homes built the house around it in 2023 inside the guard-gated Grasslands Golf & Country Club community, and it sold for $2,250,000 on August 12, 2026.
The oversized lot backs to a preserve, an extended paver driveway leads to 10-foot solid mahogany doors, and ceilings rise to 22 feet over open rooms with custom wood beams and Hinkley fixtures. Dolomite countertops, brass fixtures, Bosch appliances and an induction cooktop equip the kitchen, the first-floor primary suite opens to the pool through double doors, and five bedrooms and four and a half bathrooms fill a reported 6,705 square feet under a tile roof. The screened rear yard holds a heated saltwater pool and spa, an outdoor kitchen and a gas fireplace, and Grasslands residents have an 18-hole championship golf course, clubhouse dining, a fitness center and lighted pickleball courts.
Daniela Zoppe of Keller Williams Realty Smart 1 was the listing agent. Jenny Robles of Keller Williams Realty represented the buyer. The $2,250,000 transaction put Zoppe on the listing side of RealtyWire’s No. 1 reported home sale in the Lakeland, Florida metro area for the week ending August 16, 2026. The property previously changed hands for $340,000 in 2022, before the current residence was completed in 2023.
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No. 2 — $1,175,000 · 7375 Millbrook Oaks DR, Lakeland, Florida
The second-ranked sale sits at the end of a cul-de-sac in Millbrook Oaks, a gated community in South Lakeland. 7375 Millbrook Oaks Dr, on more than an acre, changed hands for $1,175,000 in a closing recorded August 10, 2026.
The 1997 house holds five bedrooms, four full bathrooms, a library and office and two bonus rooms across a reported 4,938 square feet, with an updated kitchen, replaced flooring and a roof replaced in 2021. Out back are a screened pool, a putting green and mature landscaping with no rear neighbors, and a bridge just beyond the property leads into Loyce E. Harpe Park, also known as Carter Road Park.
Matthew Kish of 54 Realty LLC was the listing agent. Craig Murrell of Remax Experts represented the buyer. Kish’s listing went under contract 9 days after the current listing date and ranked No. 2 in RealtyWire’s Lakeland metro area Top 5 for the week. The property previously changed hands for $875,000 in 2021.
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No. 3 — $1,150,000 · 1280 W Lake Hamilton Drive, Winter Haven, Florida
Spanish-inspired architecture and a widow’s walk mark the third sale, a 1995 custom residence on more than an acre of fenced waterfront on Lake Hamilton. 1280 W Lake Hamilton Drive in Winter Haven sold for $1,150,000 on August 11, 2026.
A circular driveway ends at a covered portico with a fountain, and double doors open on a foyer with soaring ceilings and lake views. One of the owners is a working artist, and that shows through the design. A family room with a fireplace, an office, a theater room, an enclosed Florida room across the rear and a kitchen remodeled in 2018 fill a reported 5,416 square feet, with the owner’s retreat upstairs under wraparound lake views and an artist’s perch above it. A heated salt-filtered pool completed the same year overlooks the water, and a composite dock reaches into Lake Hamilton, nearly 1,900 acres of fishing and boating water.
Michael Stone and Deanna Stone of The Stones Real Estate Firm were the listing agents. Claudia Centesimo of Lionheart Brokers represented the buyer. The lakefront listing went under contract 24 days after the current listing date and ranked No. 3 in RealtyWire’s Lakeland metro area Top 5 for the week ending August 16, 2026, the Stones’ second appearance in a RealtyWire Top 5 roundup for the metro. The property previously changed hands for $429,000 in 2018.
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No. 4 — $917,500 · 9045 Lake Hatchineha RD, Haines City, Florida
Nearly six fenced acres and a 30-by-50-foot workshop came with the fourth sale. 9045 Lake Hatchineha Rd, a custom-built 2005 house in Haines City, changed hands for $917,500 in an August 10, 2026 closing.
A gated entrance and a gravel drive lead to a front porch running the full width of the house, and the aluminum workshop, added in 2023, is wired for power. Wood-look tile floors, elevated ceilings, crown molding and a stone fireplace run through a reported 3,012 square feet, and the kitchen has custom cabinetry, granite countertops and two islands. The four-bedroom, three-bath plan is split for privacy, one guest bedroom has its own bath and a door to the pool deck, and the oversized heated pool, fitted with a waterslide, is ringed by paver decking. The roof dates to 2019, and interior paint and flooring were redone in 2024.
Zachary Lay LLC of Watson Realty Corp. was the listing agent. Zachary Lay LLC also represented the buyer. The property went under contract 23 days after the current listing date and ranked No. 4 in RealtyWire’s Lakeland metro area Top 5 for the week ending August 16, 2026. It previously changed hands for $700,000 in 2022.
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No. 5 — $875,000 · 6370 Highlands IN The Woods Avenue, Lakeland, Florida
Hulbert Homes built the fifth sale as well. 6370 Highlands in the Woods Avenue, a 2011 custom house on a landscaped 0.40-acre lot in the gated Highlands in the Woods community of South Lakeland, changed hands for $875,000 in an August 14, 2026 closing.
A paver driveway, stone accents, arched windows and decorative wrought-iron double entry doors front the house, and a new roof went on in May 2026. Inside are a formal dining room, an office behind double French doors and a living room whose glass doors pocket away entirely to open it to the lanai, while an upstairs bonus room with a full bath can serve as a guest suite or media room. Four bedrooms and four bathrooms occupy a reported 3,383 square feet, and the screened lanai carries a tongue-and-groove wood ceiling, paver decking and a saltwater pool with a waterfall.
Christine Hubbert of BHHS Florida Properties Group was the listing agent. Shawn McDonald of Shawn R Mcdonald Realtygrp Inc represented the buyer. Hubbert’s listing went under contract 5 days after the current listing date and closed $5,100 above its final asking price of $869,900, rounding out RealtyWire’s Lakeland metro area Top 5 for the week ending August 16, 2026, at No. 5. The property previously changed hands for $510,000 in 2015.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 16, 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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