Chicago
Homes for Sale in St. Petersburg, FL
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 4 recorded sales closed at a median of $653,750, $429 per square foot, a median 73 days on market, sellers accepting 96% of original asking. Homes listed or recently sold were built 1921–2025 with 1 new construction. At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $12,670 ($11,860 with the full homestead exemption).
Chicago 3 is trading with a median price of $653,750 and a median price per square foot of $428.52, but the read here comes with a caveat: this snapshot is built on just four closings. That is not enough volume to call a trend line — it is enough to tell you what the last few buyers were willing to pay, not what the next one will pay.
The median days on market, just over 70 days, points to a market that is not moving fast. Homes here are sitting through more than one showing cycle before going under contract, which usually means pricing precision matters more than speed. For a seller, that argues for pricing to the comp, not the hope. For a buyer, it argues for taking the time to negotiate rather than assuming you need to move at first sight.
Nearby homes for sale
No active listings inside Chicago Sub 3 right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Chicago market snapshot (as of September 12, 2026): the median sale price is about $654K ($429 per sq ft over the trailing 12 months of closed sales), and a median 73 days on market for closed sales.
In ZIP 33701 (St Petersburg), 1,156 homes closed in the last 12 months at a median of $1.65M ($833/sq ft), up 7.1% year over year, with a median 20 days on market. Right now 169 active and 32 pending listings put supply at about 2.7 months — a healthy market. See the live ZIP 33701 housing market and the Pinellas County market.
Stellar MLS sales records identify 35 homes in Chicago that have changed hands since 2007, built between 1913 and 2025 (median 1926), with a median living area of about 1,376 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Chicago 3 is a small, low-volume corner of the St Petersburg market in Pinellas County, where per-square-foot value sits well above $400 but the sample size is thin enough that each closing carries real weight in the numbers.
Who Chicago is best for.
Best for
- A buyer focused on a specific home in Chicago 3 rather than shopping the subdivision broadly for options
- A buyer comfortable negotiating over a longer marketing window rather than expecting a fast, competitive-offer environment
- A buyer who wants value in the property and its location, without a built-in amenity package
Probably not for
- A buyer who wants a large, active comp set to validate pricing before writing an offer
- A buyer expecting on-site community amenities as part of the purchase
- A buyer who needs a fast close and is not prepared for a market running well past a month on average
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($654K) IS the median in the snapshot above.
Windows contain 0 to 4 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2026. Deemed reliable but not guaranteed.
Chicago Sub 3 Market Scorecard
Chicago Sub 3 is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 33701 ZIP is $750,349, about 117.6% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Chicago on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
The Chicago buying strategy.
If we were buying in Chicago today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Chicago.
A market defined by thin data, not thin value
With only four closings feeding this snapshot, Chicago 3 does not behave like a high-volume subdivision with a predictable price curve. The median price per square foot, $428.52, tells you homes here are commanding a real premium on a square-footage basis, but with so few data points, one unusually large or unusually finished home can move that median meaningfully in either direction.
No community amenities are identified from current MLS listings, which means the value proposition here is the home and the location itself — not a clubhouse, pool, or gated entry. That is worth knowing going in: buyers paying up per square foot are paying for the property and its position in St Petersburg, not for a shared amenity package.
The location and the amenities are priced into every listing in Chicago. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A market this thin on closings is easy to misread from the outside — a single comp can look like a trend when it is really an outlier. We pull the full closing history behind the snapshot, not just the median, so you are pricing or offering against what actually happened, not against a headline number.
Chicago in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Chicago buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Chicago sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chicago, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chicago home worth?
Get a no-obligation home value based on real comparable sales in Chicago, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See homes for sale in Chicago on the map →
Frequently Asked Questions
What is the median home price in Chicago?
How long do homes in Chicago take to sell?
Who is the best real estate agent for Chicago?
How do I find a top St Petersburg real estate agent who knows Chicago?
Can Momentum Realty connect me with an agent for Chicago?
Should you buy in Chicago?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 13, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2012 (15 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Chicago 3 fits the bigger picture — live prices, inventory, and Momentum Scores:
Schools serving nearby communities
We do not have a confirmed school assignment for Chicago. These are the public schools most often assigned to other communities in ZIP 33701; zones change and vary by address, so confirm with the district before you buy.
- St. Petersburg High School · Public · FLDOE grade A (assigned to 4 nearby communities)
- John Hopkins Middle School · Middle · FLDOE grade B (assigned to 4 nearby communities)
- Shore Acres Elementary School · Elementary · FLDOE grade A (assigned to 2 nearby communities)
- Northeast High School · High · FLDOE grade A (assigned to 2 nearby communities)
Assignments from district data for neighboring communities; grades are official Florida Department of Education school grades (2025-26).
Nearby Communities
Explore more neighborhoods near Chicago with Momentum Realty’s local guides.