TANGLEWOOD

Tanglewood is an established single-family neighborhood in south Fort Myers (ZIP 33919), off McGregor Boulevard and bordering the Whiskey Creek area, about six miles south of downtown. Most houses were built in the mid-1960s and 1970s, some by Michigan Homes, on platted sections such as Tanglewood 1st Addition, with a few newer rebuilds mixed in (MLS records, 2026). Streets include Tanglewood Parkway, Woodwind Court, Kingswood Court, Covington Circle, Northampton Drive and Westminster Drive. The neighborhood shares its name with Tanglewood Elementary, one of the assigned schools.
Homes and Prices
Homes are one-story block ranches of roughly 1,200 to 3,000 sq ft, many on lots of about a quarter acre, and some with pools. Across 29 closings from June 2025 through September 2026, prices ran from $330,000 to $670,000 with a median near $430,000 (Subdivisions.com, Sep 2026). A 1965 pool home on a corner lot on Tanglewood Parkway sold for $610,000 in March 2026, slightly above its asking price (MLS via Bex Realty, Mar 2026). One Kingswood Court house sold for $350,000 in June 2025 and again for $670,000 in May 2026.
Amenities and Lifestyle
There is no clubhouse or neighborhood pool, and Tanglewood has no golf course of its own, though owners can buy an optional membership at the neighboring Whiskey Creek Country Club (MLS, 2026). Golf carts are common on the quiet interior streets, and about 86 percent of parcels are homesteaded, so most owners live here full time (Florida DOR roll via Move With Momentum, 2025).
HOA and Fees
No mandatory HOA applies to most homes. Listings describe a voluntary association with dues of roughly $75 a year, though a few 2026 listings showed $75 to $85 a month, so confirm what any fee covers (Subdivisions.com, 2026). Deed restrictions apply on some sections. Flood status varies by street; several 2026 listings were outside the special flood hazard area, including Zone X and X500 lots.
Location
McGregor Boulevard leads north to downtown and south toward Sanibel and Fort Myers Beach, each roughly 10 to 20 minutes away according to listing remarks. Cypress Lake Middle and Fort Myers High are among the assigned schools.
Browse current listings on our Fort Myers homes for sale page or the broader Fort Myers area guide. Tanglewood owners can review the Fort Myers flat fee listing. Sal DiBenedetto, Licensed Real Estate Broker, The DiBe Group, brokered by eXp Realty, takes calls at 239-256-5005.
Also in south Fort Myers, Pine Manor offers smaller block homes at lower prices.