O'Neil Property Group
Blackberry Crossing is an established Ryland-built community on Montgomery’s Orchard Road corridor — singles, townhomes, and condos from the early-to-mid 2000s, recently trading from the high $200s to about $450K in Oswego SD 308.
Blackberry Crossing sits on Montgomery’s Orchard Road corridor just south of US 30 — a Ryland Homes community whose core built out 2002–2006, with attached sections continuing to roughly 2014. Street names like Prairie Crossing Drive, Hillsboro Lane, and Gallant Fox Circle mark a community that mixes three- to five-bedroom singles with townhomes and condos, all a short hop from the village’s main retail.
Singles run roughly 1,700 to 3,686 square feet and have recently traded toward $450K at the top, with the 2026 median near $420K; attached homes historically trade in the $230K–$310K band. Attached sections carry associations around $192–$194 a month, singles little or none — and the village’s SSA #7 is active here, flagged on MLS sheets, so we price it into every payment estimate.
One clarity note, because the name causes real confusion: this is Blackberry Crossing, distinct from Blackberry Crossing West (a separate, newer community across Dickson Road) and unrelated to Blackberry Creek in Elburn or Aurora’s Blackberry Farm. Schools here are Oswego SD 308, with Lakewood Creek Elementary the typical assignment — the same walkable school anchor as the neighboring subdivision it borders.
Pricing reflects Blackberry Crossing sales and active listings as of mid-2026.
Two- and three-bedroom attached homes from roughly 1,110–1,850 sq ft with ~$192–$194/mo associations — recent attached volume is thin, so well-priced units draw quick attention.
Ryland two-stories from 1,700 to 3,686 sq ft; the 2026 median sale landed near $420K. Ponds and waterfront lots add premiums on select streets.
A dedicated Blackberry Crossing listings feed is coming soon. In the meantime, browse every active Montgomery listing — updated daily from the MLS — and tell us you’re watching Blackberry Crossing; we’ll alert you the moment anything lists here.
Neighborhood green space with bike trails and pond lots inside the community, plus a newer Fox Valley Park District park adjacent.
The typical SD 308 elementary assignment sits in the neighboring subdivision — a short walk or drive for most of the community.
Orchard Crossing (Walmart, Aldi, Walgreens) and the growing Orchard Road restaurant corridor are minutes away.
Orchard Road runs straight north to I-88 at North Aurora in about 15 minutes — among the best commuter positioning in the village.
Blackberry Crossing is served by Oswego Community Unit School District 308. Verify current attendance boundaries with the district before purchase.
In the adjacent Lakewood Creek subdivision at 2301 Lakewood Creek Drive — the typical elementary assignment.
In nearby Oswego; the common junior high assignment (some addresses feed Traughber — verify).
The district high school serving most Montgomery SD 308 addresses, on Route 71 in Oswego.
Orchard Crossing retail is effectively across the street, downtown Montgomery’s riverfront is about five minutes northeast, and Jericho Lake Park is five minutes northwest.
Orchard Road to I-88 at North Aurora runs about 15 minutes; Aurora’s west side and Rush Copley are about 10 minutes.
The Aurora Transportation Center is about 12 minutes — BNSF Metra trains reach Union Station in roughly an hour. Driving runs 60–75 minutes outside rush hour.
Our office is minutes from Blackberry Crossing, and we know every section of the community. Get real answers about pricing, fees, and what’s coming to market.