O'Neil Property Group
Tall Grass is south Naperville’s prairie-themed master plan south of 95th Street and west of Route 59 — clubhouse, pool, tennis, and trails, with Fry Elementary and Scullen Middle School essentially at the neighborhood’s doorstep.
Tall Grass came out of the ground between 1999 and 2008, when south Naperville was building its last generation of large master-planned communities, and it aged into one of the area’s most consistent performers. The community sits south of 95th Street and west of Route 59 in Will County’s Wheatland Township, organized around ponds, walking trails, and a prairie-landscape theme that gave it its name — with a clubhouse, community pool, and tennis courts on Deering Bay Drive at its center.
The homes are the south side’s signature product: predominantly four- and five-bedroom two-stories, typically 3,500+ square feet with three-car garages and full basements, built by Wilshire Development, Brittany Homes, Westmore Builders, and Len-Mark. Townhomes at the community’s perimeter add an attached option. Recent sales tell the story of demand — single-family closings over the 2024–2026 window ran roughly $810K to just over $1M with a median around $870K, and active listings in late 2026 averaged in the high $800s.
What sets Tall Grass apart operationally is the school geography: Fry Elementary sits on Deering Bay Drive within the community and Scullen Middle School borders it on Mistflower Lane, so a large share of the neighborhood walks to both. The master association funds the clubhouse, pool, and tennis — and fields the Tall Grass Lightning, the community’s Naperville Swim Conference team. Exact master dues aren’t published online; we confirm them with the association on every transaction.
Pricing reflects Tall Grass sales and active listings as of late summer 2026.
The attached homes at the community’s edge — the entry point into Tall Grass’s amenity package and school geography, with exterior maintenance handled by their sub-association.
See listings →The community’s center of gravity: 3,500+ square-foot two-stories with three-car garages and full basements from the 1999–2008 build-out. The median sale over the recent window ran about $870K.
See listings →The biggest floor plans — up to roughly 6,400 square feet — and homes on pond-backing or trail-adjacent lots. Recent top sales have cleared $1M.
See listings →Inventory in Tall Grass is limited and moves quickly — search all Naperville listings below, or call or text Kealan at 630-381-4995 for current and coming-soon Tall Grass homes.
The community clubhouse on Deering Bay Drive anchors a pool-and-tennis campus that runs on the master association — and hosts the Tall Grass Lightning, the neighborhood’s Naperville Swim Conference team.
Walking and biking trails wind through the community’s ponds and prairie-themed landscaping — the plan reserved green corridors between sections rather than building lot-to-lot.
Fry Elementary sits inside the community and Scullen Middle School borders it — much of Tall Grass reaches both on internal sidewalks.
The Route 59 corridor’s retail — groceries, dining, and services — runs minutes east, and the 95th Street corridor adds the library and more shopping westward.
Tall Grass is served by Indian Prairie School District 204. Verify current attendance boundaries with the district — most of the community feeds Waubonsie Valley via Scullen, but assignments should be confirmed per address.
On Deering Bay Drive within the Tall Grass community — much of the neighborhood walks. Confirm the current boundary with IPSD 204.
On Mistflower Lane at the community’s edge. Adjacent to the neighborhood; verify assignment per address.
The high school serving most of the Tall Grass area per current sources; some sources note Neuqua Valley for certain addresses — verify with the district.
The 95th Street and Route 59 corridors put groceries, the 95th Street Library, and daily services within five minutes. Springbrook Prairie’s 1,800 acres of trails sit just northeast, and downtown Naperville is about 15–20 minutes north.
The Route 59 Metra station is roughly 15 minutes north, with BNSF expresses reaching Union Station in about 35–45 minutes. Drivers reach I-88 via Route 59 in about 15–20 minutes, and the I-55 corridor via Route 59 south.
Tall Grass sits in Will County’s Wheatland Township, where effective tax rates run somewhat higher than DuPage-side Naperville — typically around the mid-2% range. We pull the actual bill on every home so the monthly math is real before you offer.
We track every Tall Grass listing, sale, and coming-soon home. Get real answers about pricing, fees, and what’s coming to market.