If you left Cypress Woods for the North in April and only came back last week, the drive between Northbrooke Drive and I-75 looks the same. The plazas do not. Between January and March, six restaurants inside a four-mile stretch of Immokalee Road either opened, rebranded, or closed for good, and the shorthand most members use for "where we go on a Tuesday" is now out of date. Add a clubhouse kitchen project on your own property and a course renovation scheduled for the 2027 season, and this is the summer you will spend more nights outside the gate than any recent one. It is worth knowing which doors are open.
What Changed Between the Gate and I-75
The turnover clustered in three plazas members already pass on the way to Publix. Here is the honest state of play as of mid-July 2026.
| Plaza | What's new | What it replaced |
|---|---|---|
| Cameron Commons (Immokalee & Collier) | Tipsy Corner, opened January | Pelican Larry's Raw Bar & Grill |
| Cameron Commons | Uma Sushi, opened March | Sakura Buffet |
| The Strand | ChaChaCha Fusion Cuban Cuisine | Skillet's |
| Granada Shoppes (Immokalee & U.S. 41) | Connors Steak & Seafood, 950 Immokalee Road | Dollar Tree, previously Walgreens |
| Pebblebrooke Center | Bernwood Tavern & Cucina | Shabo's Bistro |
| Mercato | Shake Shack, opened late February | New build |
A few of these deserve more than a table row.
Tipsy Corner came from the owners of New York Pizza & Pasta, who took the shuttered Pelican Larry's box in Cameron Commons and turned it into a restaurant-and-bar concept. It has already started building its own calendar of member-adjacent events, including a Sunday exotic car show with live music that ran in June and drew a crowd from the Immokalee golf communities north of the interchange.
Connors Steak & Seafood is the biggest arrival on the corridor by a wide margin. Its Granada Shoppes location covers roughly 9,000 square feet on about a half-acre at 950 Immokalee Road, with more than 250 seats, a 46-seat patio, and 23 seats at the full bar. The kitchen uses mesquite wood grills, and signature cuts arrive with a soup, Caesar or house salad, and a baked potato. For members who have driven to the Coconut Point location in Estero for a decade, the new address cuts that trip roughly in half.
ChaChaCha in The Strand is worth a mention only because Skillet's was, for years, the default breakfast stop for anyone doing a nine-hole loop and heading out early. The Cuban replacement is a dinner concept, and the neighborhood has not yet backfilled the breakfast slot Skillet's occupied.
Two closings matter enough to save you a wasted trip. Cheddar's Scratch Kitchen at Granada Shoppes permanently closed in early 2026, along with Sonic Drive-In at Naples Town Centre, and neither location was backfilled with a replacement. And Kelly's Roast Beef shut down all three of its Southwest Florida locations, including the Founders Square drive-thru that had operated since August 2023 and the Gateway Shoppes location that only opened in March 2025. The Founders Square vacancy is the one you will notice, since it sits directly across from the South Street patio.
The Construction Timing on Your Own Property
The corridor turnover would be interesting on its own. What makes it useful is the timing against two projects inside the Cypress Woods gate.
The first is the clubhouse kitchen improvement project, funded through a special assessment. A current condo listing at 3545 Laurel Greens confirms the assessment amount at $3,800, which the seller in that unit has already paid in full. Members closing on resales this summer should read the estoppel carefully, because whether the assessment travels with the unit or gets prorated is the kind of line item that changes a deal by four figures.
The second is the course itself. Rental listings currently on the market flag that the golf course will be newly renovated for 2027, which points to work windows inside the 2026 off-season that will overlap with reduced clubhouse dining capacity during the kitchen buildout. For members, that means the value of knowing what is open on Immokalee Road stops being lifestyle content and starts being logistics.
The good news is the fundamentals of the club itself are not changing. This is still the Gordon Lewis routing that opened in 1999, playing to a par 72 and a 133 slope over 110 acres of lakes, marshes, and preserves, with Bermuda greens and fairways under the care of superintendent Cisco Navas and head pro Chris Phillips. The renovation is a refresh of the surfaces, not a redesign of the golf.
One under-used note for members hosting visitors this summer: the Grill Room at the clubhouse operates as a local hangout that is open to the public, which means friends staying at a rental down the street can meet you for lunch without a member sponsor form. If the main dining room goes offline during kitchen work, that flexibility is worth remembering.
South Street's Summer Tribute Nights, Five Minutes East
South Street at Founders Square sits at 8845 Founders Square Drive, roughly five minutes east of Northbrooke Drive, and its summer calendar is doing more work than the Fifth Avenue venues right now. The tribute-band lineup members can actually get to without a downtown parking hunt:
- Friday, July 17 — Beer For My Horses, an 8 p.m. show that leans country
- Friday, August 21 — a double bill of Get Lucky, a Loverboy tribute, and Aerosmith Rocks, also at 8 p.m.
- Friday, September 18 and Saturday, October 10 — additional South Street shows already on sale through the venue's ticketing partners
The pattern to notice: South Street has moved most of its ticketed music into Friday and Saturday slots, which pairs cleanly with a pre-show dinner at Connors or Tipsy Corner and a short drive home. The Kelly's Roast Beef vacancy directly across the plaza will almost certainly draw a replacement operator before the 2026 season, and if the pattern from Cameron Commons holds, expect an independent rather than another regional chain.
Two Corridor Projects That Change the Drive Home
Two developments further east on Immokalee Road are worth watching from behind the Cypress Woods gate.
NC Square, the mixed-use project on the southwest corner of Immokalee Road and Catawba Street, about 1.5 miles west of Wilson Boulevard, has been proposed as a commercial strip with four restaurants and additional retail units on more than seven acres, directly across Immokalee Road from the Twin Eagles golf community. The developer recently proposed reducing the commercial square footage from 44,400 to 36,500 square feet by dropping a day care center while increasing residential density from 129 townhomes to 205 apartments, and the Board of County Commissioners postponed its decision after the April 8 meeting to a May 13 hearing. Whatever the final vote, the corridor east of Wilson is going to get denser, and that means the drive to Ave Maria's Umami Ave restaurant and the shops at Founders Square will feel busier by next season.
On the medical side, NCH Healthcare System announced a $350 million expansion at its North Naples campus in partnership with Nicklaus Children's Hospital, adding a four-story, 156,000-square-foot pavilion. The construction footprint sits closer to the Immokalee-U.S. 41 intersection than most members realize, and lane shifts during the buildout will affect the fastest route from Cypress Woods to Vanderbilt Beach on weekends.
Where This Leaves You
If the last two years at Cypress Woods have been about the club itself, the next twelve months are about the corridor. The kitchen assessment gets built, the course gets prepped for its 2027 debut, and the plazas outside the gate absorb five new dining rooms and one national chain that will pull members off-property more often than usual. The residents who treat that as inconvenience will spend the summer complaining about detours. The ones who treat it as a lineup will end 2026 with a shorter list of default reservations and a longer list of favorites.
If you are weighing a move within the community, or you own here and want a considered read on how the assessment and course timing intersect with resale value this season, the team at Ryan Batey tracks Cypress Woods block by block. Get Your Instant Home Valuation to see where your unit sits against the current market before the fall listing wave.
