Chicago
Homes for Sale in St Petersburg, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Over the 12 months ending 2026-09-20, 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; none of the 4 geocoded homes sit in a FEMA special flood hazard zone (median elevation 38 ft). 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 Sub 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.
Figures in this note are as of July 21, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Chicago 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 20, 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), 1,166 homes closed in the last 12 months at a median of $1.65M ($836/sq ft), up 6.9% year over year, with a median 20 days on market. Right now 165 active and 28 pending listings put supply at about 2.6 months — a healthy market. See the live ZIP 33701 housing market and the Pinellas County market.
County records show 7 qualified sales in Chicago across 2024–2025 (3 in 2024, 4 in 2025), median $596,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Chicago is a community of 132 homes in St Petersburg, Pinellas County, built between 1900 and 2022 (median 1925.0), with a median living area of about 2,035 square feet. 58% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Chicago Sub 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.
The setting & the homes.
Aerial and on-site photos of Chicago. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Chicago
Chicago
Chicago
ChicagoPhotos from Stellar MLS listings in Chicago; content deemed reliable but not guaranteed.
Who Chicago is best for.
Best for
- A buyer focused on a specific home in Chicago Sub 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 20 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.
15% of homes for sale in ZIP 33701 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-23).
Chicago Market Scorecard
Chicago is currently a balanced market..
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. 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 contributors.
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 Sub 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 →
Last 30 days in Chicago: 1 new listing (median asking $565,000). As of October 24, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
| Location | St Petersburg, Pinellas County, FL · ZIP 33701 |
|---|---|
| Homes in the community | 132 (FL DOR 2025 assessment roll) |
| Years built | 1900–2022 (median 1925.0) |
| Typical living area | 2,035 sq ft (median) |
| Sale prices, last 12 months | $653,750 median across 4 closed sales · $429 per sq ft |
| Days on market (closed sales) | 73 median |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 58% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Chicago key facts,” movewithmomentum.com/neighborhoods/chicago-sub-3, data as of September 20, 2026.
Housing distress & ownership in Chicago Sub 3, St Petersburg
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period October 2026 through October 2026. Deemed reliable but not guaranteed.
More St Petersburg home searches
- All homes for sale in St Petersburg, FL
- Homes for sale in Pinellas County, FL
- St Petersburg pool homes for sale
- St Petersburg waterfront homes for sale
- Gated communities in St Petersburg
- St Petersburg golf course homes
- Homes under $300K in St Petersburg
- Homes from $300K to $500K in St Petersburg
- 4-bedroom homes for sale in St Petersburg
- St Petersburg home values: what is my house worth?
St Petersburg guides & data
- Market data
- Cost of living
- Best neighborhoods (ranked by data)
- Best neighborhoods
- Flood zones
- Property taxes (Pinellas County)
- Homestead exemption (Pinellas County)
- New construction
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
Real estate agent in St Petersburg? Join Momentum in St Petersburg: 100% commission, one $12K cap.
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- 10Th Avenue S (16 homes on record)
- 9Th Avenue S (10 homes on record)
- 9Th Avenue (2 homes on record)
Email me new listings in Chicago
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Chicago
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Chicago will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
What is the median home price in Chicago?
How long do homes in Chicago take to sell?
How many homes are in Chicago?
What share of Chicago is owner-occupied?
When were the homes in Chicago built?
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?
Where is Chicago, and what county is it in?
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: October 17, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 33701)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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 Sub 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.