O'Neil Property Group
Timber Trails is the established core of Gilberts — a Ryland Homes community from the early 2000s north of Big Timber Road, mixing singles, townhomes and condos across parks, tennis courts and ponds, with the widest price range in the village.
Timber Trails is where modern Gilberts began. Ryland Homes built the community through the early-to-mid 2000s on the village’s north side — north of Big Timber Road and west of Tyrrell Road — and it remains the largest and most varied neighborhood in town: two-story and ranch singles, townhome rows and condo buildings sharing one street network, one park system and one association framework. When buyers say they want “into Gilberts,” this is usually the door they come through.
The variety is the point. Condo flats and older townhome sections trade from the mid $200s; updated townhomes and the community’s smaller singles run through the $300s; and the larger detached homes — up to about 3,706 square feet — have sold into the $500s. That spread, rare for a single subdivision, means residents can move up or downsize without leaving the neighborhood, and it keeps turnover steady in a village where listings are scarce. Homes here average two decades newer than similar price points in the towns east, which is the quiet engine of Timber Trails demand.
Ownership costs stay moderate: average tax bills run near $7,200 — the most attainable of the village’s major subdivisions — and association fees vary widely by section, from modest single-family dues to fuller-service attached-home fees. The practical note for buyers is that section matters: fee structures, what they cover and pond or park adjacency all shift street by street, so we verify the specific section’s numbers on every showing sheet.
Pricing reflects Timber Trails sales and active listings as of mid-2026.
The village’s entry market: two- and three-bedroom flats and townhomes from 2001 onward, roughly 1,100–1,600 square feet with garages. Association fees vary by section — run the full monthly math against the list price.
See listings →Three-bedroom two-stories and the community’s ranch plans. Original-finish homes price below the band; updated kitchens and baths push toward the top of it and sell fastest.
See listings →The community’s biggest detached homes, up to about 3,706 square feet with four-plus bedrooms. Recent top sales have reached the $500s — pond-adjacent lots and finished basements drive the premiums.
See listings →Subdivision-level MLS feeds for Timber Trails are being configured. Until then, browse every active Gilberts listing — we can flag the Timber Trails homes the moment they hit the market.
The community’s park system includes tennis courts, playground equipment and open field space threaded between the housing sections — most streets are a short walk from one of them.
Stocked ponds and retention lakes give many sections water views, and the community’s path network ties into the village sidewalk system.
Timber Trails sits on the village’s north side, minutes from Big Timber Road — the Metra station in Elgin is about a 10-minute drive, the closest of any Gilberts subdivision.
The condo-to-townhome-to-single spread means residents change homes without changing neighborhoods — a real factor in why Timber Trails resales draw local buyers first.
Timber Trails is served by Community Unit School District 300. School assignments in Gilberts split by address and boundaries can change — always confirm current attendance boundaries with the district for any specific home.
The village’s elementary school serves Timber Trails addresses. Confirm the current attendance boundary with D300 for any specific address.
Sources differ on the middle school feeder for Timber Trails addresses — assignments split between the Dundee and Hampshire feeders by address. Verify with D300 before you buy.
High school assignments in Gilberts split between H.D. Jacobs (Algonquin) and Hampshire High School depending on address and can change. Confirm the current assignment with the district.
Big Timber Road connects east toward Elgin and west into the village; Route 72 and Galligan Road are minutes away, with Town Center Park and the village calendar about five minutes south.
The Randall Road interchange at I-90 is roughly 10 minutes, putting Schaumburg about 25–30 minutes out and O’Hare around 40. Randall Road’s retail corridor is five to ten minutes east.
The Big Timber Road Metra station is about a 10-minute drive — the Milwaukee District West line reaches Union Station in roughly 70–90 minutes. Driving I-90 runs about an hour off-peak.
We track every Timber Trails listing and sale, and we know what drives value here. Get real answers about pricing, fees, and what’s coming to market.