Active residential listings in Gillespie and the surrounding Macoupin County area — represented by Apex Realty agents who live nearby and know the local market.
Listings represented directly by Apex Realty across the Gillespie/Macoupin County area. For the full Gillespie MLS inventory, scroll down to the browse map.
Click any photo — opens that active Macoupin County listing.
Gillespie sits in central Macoupin County along IL-4 in Macoupin County — population around ~3,200. Anchored by Gillespie CUSD #7, it offers former coal-mining town with affordable inventory and a strong school district.
Apex Realty is headquartered in downtown Jacksonville at 1515 W. Walnut, Suite #4 — but every Apex agent works the full Macoupin County market and the surrounding service area. We know which Gillespie streets turn over fastest, which corners of the market reward patience, and which deals never reach the MLS at all. The kind of local intelligence you can't get from a Zillow algorithm.
Whether you're relocating for St. Louis metro (45 mi) and Springfield (50 mi), looking for a starter home, downsizing into a ranch, or buying acreage just outside town — we work every street in Gillespie and every rural pocket within reach.
Meet the Apex teamLive data from the RMLS Alliance MLS — every active residential listing across Macoupin County (including Gillespie) from every brokerage. Click any pin to see details, photos, and pricing.
Schools shape every Gillespie home search — what's in-boundary, what attendance line you're on the wrong side of, which streets feed which building. Here's the local read.
Gillespie CUSD #7 serves the city of Gillespie and the adjacent village of Benld plus the surrounding rural attendance area. About 1,000 students K–12 across three buildings, anchored in Gillespie's central campus. The district has a long coal-mining history — its sports culture and community identity are deeply tied to the town's working-class roots.
Gillespie Elementary serves K–5, Gillespie Middle School takes 6–8, and Gillespie High School (the Miners) handles 9–12 — a mascot that names the town's coal-mine past explicitly. The Miners compete in the South Central Conference; football, basketball, and softball are the strongest historic programs. The campus is on the east side of town off IL-4.
St. Joseph's Catholic School in Benld offers K–8 parochial education for Gillespie-area families. For Catholic high school, the commute options are Marquette (Alton) or Father McGivney (Glen Carbon). Gillespie's location 45 miles from the St. Louis metro means Catholic-school commute is doable but not casual.
Gillespie's district covers a wider footprint than the city limits suggest — most of central Macoupin County between Carlinville and Mt. Olive feeds Gillespie. The line on the east side near the Bond County border can be tricky; confirm the assignment before writing on rural acreage.
Gillespie is small enough that "neighborhood" usually means a few blocks of pre-war homes near downtown, the streets along central Macoupin County along IL-4, and the rural acreage just outside town. We work every part of it. Tap the map below for live listings, or talk to an Apex agent for the off-MLS situations.
Gillespie's residential market has been one of the steadier in the Macoupin County area — anchored by Gillespie CUSD #7 and shaped by commuter demand from St. Louis metro. Days-on-market for well-priced homes typically lands in the two-to-four-week window.
That's where Gillespie's first-time buyers, relocations, and downsizers compete. Move-in-ready homes in that range often see multiple offers in the first weekend. Above the top of the band, days-on-market climbs sharply. Below the bottom of the band usually signals deferred maintenance — worth a structural look before writing.
For sellers, this means strategic pricing matters more than aggressive listing. We've seen Gillespie homes priced 5% above market sit for 90+ days while identical homes priced at fair market close in two weeks. For buyers, this means preparation matters: pre-approval letter in hand, agent on speed-dial, and a willingness to write within 48 hours of a tour are what separate winning offers from also-rans.
In a community this size, many of the best transactions never list publicly. Apex agents hear about properties through neighbors, contractors, estate attorneys, and twelve years of past clients. If you're a serious buyer with clear criteria, tell us — we'll work the network alongside the MLS.
For market data on specific Gillespie streets or price bands — recent sold comparables, average days-on-market, school-zone trends — contact us directly. We'll pull the report and walk through it with you, no obligation.
Median sale prices in Gillespie have run in the $80K–$140K range over the past 18 months. Pricing varies by age of home, lot size, and location within the city. The Apex featured listings carousel above and the full MLS browse map show real-time pricing for every active property.
Gillespie CUSD #7 is the primary public district. Specific school-attendance boundaries are listed on every MLS detail page; we factor those into the conversation when school zone matters to a family.
Effective tax rates in Gillespie typically run around 2.0–2.3% of assessed value, depending on the exact township and school district overlay. Specific tax amounts are listed on every MLS detail page; we factor them into the affordability conversation early.
For long-term rental income, Gillespie can offer favorable price-to-rent ratios compared to most US markets — entry-point single-family rentals can cash-flow with conventional financing where tenant demand is stable. Dagmar Schroetter on our team specializes in investment analysis if you want a deeper read.
Gillespie to St. Louis metro and Springfield (50 mi) is 45 mi. Plenty of Apex buyers split the difference — they work in the nearby employment hub and live in Gillespie for cost-of-living and pace-of-life reasons.
For MLS-listed properties accepting showings, tours can usually be scheduled within 24 hours — often same-day for Apex or other Macoupin-County brokerage listings. Call the office at 217-960-8474 or use the contact form, and we'll get you in.
Yes. We represent buyers and sellers across all of Macoupin County and the surrounding service area — including Benld, Mount Olive, Carlinville. Whether you're buying acreage 15 minutes outside town or selling a farm-and-house in a neighboring township, the same agents and the same process apply.
Whether you're three years out or three weeks from moving, an Apex agent will walk you through the Gillespie market — what's available, what's coming, and what you should actually pay attention to. No pressure, no obligation, just a real conversation.
Browse homes for sale and local market insight in the communities surrounding Gillespie — all within Apex Realty’s Macoupin County coverage.
Drill into Gillespie’s neighborhoods and school-district zones — each with live MLS listings and local context from Apex Realty.
