O'Neil Property Group
Seasons Ridge is one of Montgomery’s most established communities — singles, townhomes, and condos built 1988–2003 off Douglas Road, including the Lakeside ranch section, recently trading from about $215K to $450K in Oswego SD 308.
Seasons Ridge came before Montgomery’s 2000s boom — Primus Corporation developed it from 1988 through 2003 on the village’s east side off Douglas Road, adjacent to Boulder Hill. That earlier start shows in the best ways: matured trees, a wide mix of floor plans (27 single-family models plus townhome and condo sections), and a price spread that runs from roughly $215K attached units to $450K for the largest singles.
The community’s variety is its advantage. Two-story singles up to roughly 4,800 square feet anchor the interior streets, townhomes and condos cluster near Douglas Road, and the Lakeside section offers true ranch-style attached living — one of the only dedicated single-level pockets in the village, and a persistent favorite with downsizers. Briarcliff Woods park and the community’s pond add green space, and unlike most of Montgomery, Seasons Ridge is served by the Oswegoland Park District.
Fees stay light on the detached side — many singles pay little or no HOA — while townhome and condo sections run roughly $199–$312 a month and Lakeside about $75. We found no active SSA here, which is genuinely unusual for Montgomery and worth real money against newer subdivisions; as always, we verify the exact tax bill on every address before clients offer.
Pricing reflects Seasons Ridge sales and active listings as of mid-2026.
The attached sections near Douglas Road plus the Lakeside single-level pocket — roughly 1,000–1,600 sq ft. The ranch-style units are among the most requested and quickest-selling homes in the village.
Two-story and split-level singles from 1,400 to roughly 4,800 sq ft across 27 original models. The 2025 median landed near $348K; matured lots and varied streetscapes set it apart from the 2000s subdivisions.
Every active Seasons Ridge listing, updated in real time from the MLS.
Three decades of growth give Seasons Ridge the shade and settled feel newer subdivisions are still waiting on.
Neighborhood park space and water features inside the community, with sidewalks and connections toward the Virgil Gilman Trail.
A dedicated single-level attached pocket (~$75/mo association) — one of the village’s only true ranch communities and a downsizer favorite.
Seasons Ridge (with Marquis Pointe) sits in the Oswegoland Park District — programs, facilities, and Fox Bend Golf Course privileges differ from the Fox Valley Park District that covers most of Montgomery.
Seasons Ridge is served by Oswego Community Unit School District 308. Verify current attendance boundaries with the district before purchase.
Immediately adjacent in the Boulder Hill area — the typical elementary assignment for Seasons Ridge addresses.
In nearby Oswego; the typical junior high assignment for the community.
The district high school serving most Montgomery SD 308 addresses, on Route 71 in Oswego.
Douglas Road’s locally owned storefronts run along the community’s edge, with downtown Montgomery’s riverfront five minutes west and the Route 30 retail corridor just south.
US 30 and Route 25 connect to Aurora in under 10 minutes; Oswego’s Route 34 corridor is about 10 minutes south. Orchard Road reaches I-88 in roughly 15–20 minutes.
The Aurora Transportation Center is about 10 minutes north — BNSF Metra trains reach Union Station in roughly an hour. Driving runs 60–75 minutes to the Loop outside rush hour.
Our office is minutes from Seasons Ridge, and we know every section of the community. Get real answers about pricing, fees, and what’s coming to market.