The 2006 Mediterranean house at 1180 Via Lugano was custom-built by Maroon Fine Homes, renovated in 2024 by Greg Hardwick and given a new pool, turf courtyard and sport court this year. Its $4 million sale on September 14, 2026 was one of five home sales reported in the Orlando, Florida metro area for the week ending September 20, 2026, a group that combined for $14.05 million.
Winter Park accounted for three of the week’s closings, with the others in Windermere and Montverde. Two houses on the list were finished in 2026 and the oldest dates to 2003. The Windermere and Montverde sales closed at matching prices of $2.4 million.
No. 1 — $4,000,000 · 1180 Via Lugano, Winter Park, Florida
A double lot of nearly half an acre in the Vias section of Winter Park carried the week’s highest reported price: $4 million for a 2006 custom build with five bedrooms, six bathrooms and a reported 4,961 square feet. The sale closed on September 14, 2026. The property previously changed hands for $2,950,000 in 2021.
Listing materials credit Maroon Fine Homes with the 2006 build and Greg Hardwick with the 2024 renovation. Solid wood arched doors open into a foyer of porcelain marble tile set off by an iron circular staircase, and the dining and living rooms share a temperature-controlled wine cellar finished in seamless glass. A kitchen with an eat-in area and counter seating, a family room facing the rear yard and a wet bar fill out the main level, along with the primary suite, which sits behind privacy doors with a home office, two custom-fitted walk-in closets and a bath whose shower encloses a soaking tub. A guest suite is split from that wing, and three more ensuite bedrooms are upstairs.
The outdoor spaces were reworked this year by Signature Landscaping around a new pool with a sun shelf, a turf courtyard, a sport court and a covered lanai with a summer kitchen. A gas fire pit anchors a seating area, Japanese blueberry trees and Podocarpus hedges screen the grounds, and a side-yard dog run adjoins them. An air-conditioned three-car garage and a circular drive complete a property within reach of Park Avenue, Rollins College, the Winter Park Golf Course and Kraft Azalea Gardens.
Alison Mosley and Frank Mosley of Premier Sotheby’s Intl. Realty were the listing agents. The transaction ranked No. 1 in RealtyWire’s Orlando Metro Area Top 5 for the week, and it is Alison Mosley’s second appearance in the metro’s roundup.
See this property in Google Street View →
No. 2 — $2,925,000 · 1597 Oakhurst Avenue, Winter Park, Florida
On a brick street in Comstock Park, a 2015 custom house sold for $2,925,000, closing $226,000 above its final asking price of $2,699,000. The sale was completed September 16, 2026, and the property previously changed hands for $1,665,000 in 2019.
The five-bedroom, five-bath house carries a reported 4,410 square feet on two levels. Its current owners reconfigured the main living level for a more open flow, renovated the kitchen and installed wide-plank oak flooring across both floors, and both HVAC systems have been replaced recently. Vaulted ceilings, exposed beams and generous room proportions run through an interior reached from the old-world exterior by way of a courtyard and a covered patio.
Two bedroom suites occupy the main level, including the primary retreat, while the second floor holds an oversized family-room loft, further bedrooms and baths and generous storage. At the rear, the main rooms open to a large covered terrace and a pool. The house stands on one of Winter Park’s established brick streets, near Phelps Park, the YMCA and the shops and restaurants of Park Avenue.
Robert Kurzreiter PA of Keller Williams Realty AT The Parks was the listing agent. Mick Night of Premier Sotheby’s Intl. Realty represented the buyer. The listing drew a contract 2 days after the current listing date and closed above asking, putting Robert Kurzreiter PA on the listing side of the metro’s No. 2 reported sale for the week.
See this property in Google Street View →
No. 3 — $2,400,000 · 1408 Lake Whitney Drive, Windermere, Florida
A lakefront house in the guard-gated Reserve at Belmere community in Windermere sold for $2,400,000 on September 15, 2026. The 2003 custom build has five bedrooms, six baths and a reported 5,433 square feet on the shore of Lake Whitney. The property previously changed hands for $1,549,000 in 2003.
A circular driveway with a center fountain and mature landscaping fronts the house, which has a side-entry three-car garage. The foyer opens to a formal living and great room where seamless glass windows frame the water, under soaring ceilings and ornate trim. The kitchen pairs stainless steel appliances and granite counters with a breakfast nook and a family room built around a fireplace, and a wood-paneled executive home office, a formal dining room and a billiard room with a wet bar extend the plan. The primary suite has a sitting area with direct patio access and two walk-in closets; upstairs are a home theater with a full bar, a games room opening to a private balcony and a home gym.
The grounds reach a private dock on Lake Whitney and a vanishing-edge pool with a fountain and an integrated heated spillover spa, resurfaced with new equipment in 2024, the year the exterior was repainted. A covered lanai holds an outdoor fireplace and a full outdoor kitchen, with a putting green to one side of the patio and a garden to the other. The community adds a clubhouse, fitness center, playground and tennis, basketball and sand volleyball courts, minutes from historic downtown Windermere.
Alice Anne Jackson of Corcoran Premier Realty represented the listing side of the No. 3 sale in RealtyWire’s Orlando Metro Area Top 5 for the week. The buyer was represented by Andrew Kincaid of BHHS Florida Realty.
See this property in Google Street View →
No. 4 — $2,400,000 · 17414 Pesce Loop, Montverde, Florida
In Montverde, a newly built Toll Brothers house in the Bella Collina golf community sold for $2,400,000 and closed at its full asking price. The September 14, 2026 closing covered five bedrooms, five baths and a reported 4,254 square feet on a half-acre homesite.
Built to the builder’s Corbeil Transitional plan, the house opens through a two-story entry into a living room with 20.9-foot ceilings and a wall of glass facing Lake Siena. The kitchen has quartz counters, stainless steel JennAir appliances, a walk-in pantry and a center island that connects the casual dining area to a sunlit great room. The primary suite occupies a private first-floor wing, a guest suite with a walk-in closet also sits on that level, and an open loft, a private media room and two more ensuite bedrooms are upstairs.
A covered lanai with a pool bath overlooks the pool and spa. Listing materials describe the house as under construction while it was marketed, with completion expected in August. Bella Collina residents have two restaurants, tennis courts, a fitness center and a community pool complex, along with an 18-hole golf course designed by Sir Nick Faldo.
Sharon Walisky and Matthew Matthews of Orlando Tbi Realty LLC were the listing agents. The house closed at its full asking price as the No. 4 sale in the metro’s Top 5 for the week, and Sharon Walisky has one earlier Top 5 sale in the Orlando metro area.
See this property in Google Street View →
No. 5 — $2,325,000 · 1630 Elm Avenue, Winter Park, Florida
On Elm Avenue, in Winter Park’s Tree Streets, a house finished this year sold for $2,325,000. It closed September 16, 2026. The five-bedroom, five-bath house carries a reported 3,408 square feet and was built by LUIH Homes; the property previously changed hands for $799,000 in 2025, before the current residence was completed in 2026.
A contemporary facade fronts a dining room with a custom wine bar and wine cooler and a living room with a statement accent wall and an electric fireplace. The kitchen has Calacatta quartz counters, custom cabinetry, a hidden walk-in pantry and a full suite of Thermador appliances. The first-floor primary suite has a bath with a freestanding soaking tub, dual vanities, an expansive walk-in shower and a large custom walk-in closet, and a second first-floor bedroom can serve guests, multi-generational living or a home office.
Upstairs, a loft, a hidden homework room and three more bedrooms complete the plan. Outside, a covered lanai with a summer kitchen, grill and sink faces a pool and spa with space for lounging and dining. The Tree Streets sit a short walk from Phelps Park and the YMCA and minutes from the boutiques and restaurants of Park Avenue.
Christopher Christensen and Jane Peterson of ONE Luxury International LLC were the listing agents. The house went under contract 16 days after the current listing date and closed as the No. 5 reported sale in the Orlando metro area for the week, Christopher Christensen’s second appearance in RealtyWire’s Top 5 for the metro.
See this property in Google Street View →
RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, September 20, 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.
Were you involved in one of these transactions? Contact RealtyWire to verify or correct your professional credit or submit information for a future edition.
See full market data on our Orlando, Florida market page.
