"Side-street opportunities." The phrase sits in a short bulleted list on the Park Avenue page of the City of Winter Park's Retail Vision document. Its neighbors on the list are "Additional soft goods cotenancy" and "Broadening of customer base." On paper, those three bullets read like planning shorthand. On the sidewalk in 2026, they describe what has happened, almost storefront by storefront.
The shops that left Park Avenue this year are mostly still in Winter Park. Many of them moved a block or two off the Avenue.
The corner at Park and New England
Tuni opened at 301 S. Park Avenue in 1986. In June, the women's boutique announced it had been given 30 days to leave and that a national retailer was expected to take the space. The shop said it was not closing and was searching for a new home.
The building's ownership had changed nearly two years earlier. Benderson Development bought Park Plaza in September 2024. That's the 25,000-square-foot property at 307 S. Park Avenue, with the 28-room Park Plaza Hotel upstairs and retail on the ground floor. Commercial real estate reports put the price at $16.25 million. At the time, Benderson called it an "iconic property" and said it planned to enhance the Park Plaza experience.
By late August, the new tenant was open. Lilly Pulitzer now occupies 301 S. Park, the corner where Tuni spent 40 years. The resort-wear brand isn't new to the Avenue. It used to operate farther north at 114-118 N. Park Avenue. That storefront is now Brandy Melville, which opened on Saturday, April 4, to lines out the door.
Follow both addresses and the chain is easy to see. One national apparel brand moved from the north end of the Avenue to the south end. A second national apparel brand took the space it left. The longtime local boutique ended up around the corner. That's "additional soft goods cotenancy" in practice: more clothing and accessories tenants sitting side by side, which draws shoppers to all of them.
Bungalower framed the turnover as a question about who benefits once a street's charm becomes valuable. Commenters on its June story asked for local businesses to stay part of the mix. As of early October, we couldn't find any City Commission action, Chamber statement, or proposed rule on retail mix in response.
Park Avenue, address by address
This is where each 2026 storefront change stands as of October 4, 2026, based on local reporting and the businesses' own pages.
| Address | Before | As of early October 2026 |
|---|---|---|
| 301 S. Park Ave. | Tuni, since 1986 | Lilly Pulitzer, open |
| 114-118 N. Park Ave. | Lilly Pulitzer | Brandy Melville, open since April 4 |
| 214 N. Park Ave. | Louise James Boutique, since 2019 | Closing announced, no final date given |
| 334 N. Park Ave. | Empty storefront near Briarpatch | Nigel's Bananas planned, no opening date announced |
| 310 S. Park Ave. | Not reported | Oak & Stone, listed as "coming soon" |
| 348 N. Park Ave., #5 | Garp & Fuss | Temporarily closed after a July fire, repairing and renovating |
Louise James is the hardest change on the list. Owner Katie Bullivant opened the pink-fronted shop in 2019, after the business started online. She designed it with her daughter. Bullivant wrote that the design gave her purpose. In late August the store was still open, with everything in the shop and online at 50% off. The city's 2023 Retail Vision lists Louise James by name on its Park Avenue page as an example of the Avenue's current positioning.
The incoming names follow the same pattern. Nigel's Bananas is a dessert shop from Seaside, Florida, founded by Simon Sullivan and Marla Carter. It started as a pop-up in December 2020 and opened its first permanent shop in May 2021. Bungalower has heard it is targeting February 2027 for Park Avenue, but the company hasn't announced a date. Oak & Stone's own Winter Park page still says "COMING SOON!" for 310 S. Park. Orlando Weekly's March roundup had forecast a fall opening.
One block west, on Fairbanks
Tuni's new address explains a lot. The boutique now runs a temporary pop-up at 143 W. Fairbanks Avenue, inside the former Miller's Hardware. Miller's closed this spring after 80 years in Winter Park. Bungalower called it "a very Winter Park kind of handoff," with one longtime local name leaving a building and another moving in.
As of early October, Tuni's website still directs shoppers to the Miller's Hardware pop-up and lists no permanent location. Hours are 10 a.m. to 6 p.m. Monday through Saturday and noon to 5 p.m. on Sunday. We found no separate redevelopment plan for the hardware building.
A temporary shop in an 80-year-old hardware store is not a permanent answer. But it puts one of Park Avenue's best-known local names on Fairbanks, a short walk from its old corner, in the kind of off-Avenue space the city's document had in mind.
What the 2023 plan described
The Park Avenue section of the Retail Vision is brief. Under "Current Positioning," it describes the Avenue this way:
Metro's premier walkable/authentic shopping destination
Under "Potential," it lists three items: more soft goods tenants, a broader customer base, and side-street opportunities. The same document says zoning, policy flexibility, and market forces are the tools that shape a district's retail mix. It describes Hannibal Square as more locally oriented and suited to destination concepts.
Separately, the city's Park Avenue Refresh project covers streetscape, safety, infrastructure, and appearance. It doesn't address who leases the storefronts. Tenant choice on the Avenue is up to property owners and the market. The 2023 plan expected exactly that: national soft goods brands on the main frontage, and room for something else just off it.
Where the side streets are filling in
Map this year's local openings and they cluster away from the Park Avenue frontage.
On Orange Avenue, the Winter Park Playhouse reopened its renovated building at 711 N. Orange Ave. after a July 7 ribbon-cutting. The theater now has 172 seats and a new cabaret space. Russell Stephens performs in that room, the Santos-Compel Cabaret Lounge, on October 7 and 8.
In Hannibal Square, The Reverie is planned for 533 W. New England Ave., the former Chez Vincent space, with a late-2026 target and no confirmed opening day. A few blocks north, Mecatos Bakery & Café is planned for 610 W. Morse Blvd. Its store page still says "OPENING SOON!" Saikō Coffee is also preparing a Winter Park shop, though the owner hasn't shared the address or an opening date.
Put Tuni on Fairbanks, the Playhouse on Orange, The Reverie on New England, and Mecatos on Morse, and the local openings form a ring around Park Avenue's frontage. That ring matches the "side-street opportunities" bullet from 2023.
A fall loop through both
This route covers the Avenue's new tenants and the streets around them, built around confirmed dates:
- October 7 or 8: Russell Stephens at the Playhouse's Santos-Compel Cabaret Lounge, 711 N. Orange Ave.
- Any Saturday morning: the Winter Park Farmers' Market at Central Park's West Meadow, New York Avenue and Morse Boulevard, 8 a.m. to 1 p.m. From there, walk to the Tuni pop-up at 143 W. Fairbanks Ave.
- Before Louise James closes: stop at 214 N. Park Ave. No final date has been announced.
- November 14 and 15: the 53rd Winter Park Autumn Art Festival in Central Park, 9 a.m. to 5 p.m. The city says the Saturday market sometimes moves to Seven Oaks Park during large events like this one, so check the market page before you go.
Tuni's permanent address, Louise James's last day, and opening dates for Nigel's Bananas, Oak & Stone, The Reverie, and Mecatos are all still open questions as of October 4.
A changing street is a reminder that how a place looks shapes who notices it. That holds for a Park Avenue storefront and for a bungalow a few blocks off Fairbanks. If you live near these corridors and want to know how your home presents in this market, Autumn Makin can walk through it with you, from staging and paint to video. Schedule your free home consultation & valuation.
