Chicago Ave
Homes for Sale in Tampa, FL
All 3,772 homes for sale in Tampa, FL · median $429,000 · 541 townhomes for sale in Tampa · 176 homes for sale in 33629 · Hillsborough County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of November 2026, the MLS records 7 closed sales in Chicago Ave Sub in Tampa, FL since 2015, the most recent in December 2025. Across Tampa as a whole, 7,766 homes closed in the last 12 months at a median of $430,000, 35 median days on market, with 3,282 homes for sale today. At that median and Hillsborough County's FY2025-26 rate of 15.73 mills, annual property tax runs about $6,760 ($6,140 with the full homestead exemption).
Chicago Ave Sub is a small, established subdivision in Tampa, and the current MLS feed does not carry enough active or recent sold data to support a pricing narrative here. That absence is itself informative: this is a thin, low-turnover pocket rather than a high-volume resale market, so any pricing conversation needs to be built from direct comps and a walk-through rather than aggregate stats.
For a buyer or seller, that means the usual market-heat shortcuts do not apply. Positioning a listing or an offer here takes pulling individual closed sales in Hillsborough County near this subdivision and reading the property itself, not leaning on a community-wide median or days-on-market figure that simply is not populated yet.
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 Ave 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 Ave Sub sits in Tampa, Hillsborough County, and current MLS records show no community amenities tied to active listings — this reads as a straightforward residential subdivision rather than an amenitized development.
Stellar MLS sales records identify 9 homes in Chicago Ave that have changed hands since 2015, built between 1983 and 1983 (median 1983), with a median living area of about 1,511 sq ft and a typical 3-bedroom, 2.5-bath layout; 100% are townhomes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Chicago Ave is best for.
Best for
- A buyer who has already identified a specific property in Chicago Ave Sub and wants direct, comp-based guidance rather than community-wide statistics
- A buyer or seller comfortable with a low-volume market where pricing is negotiated per property
- Someone looking for a straightforward Tampa home purchase without a community amenity package or associated fees
Probably not for
- A buyer who wants to compare against a published median price or established days-on-market trend before making an offer
- Someone specifically seeking a subdivision with organized community amenities
- A buyer who prefers high-volume markets with abundant recent comparable sales to lean on
The market around Chicago Ave
Chicago Ave is too small for its own price trend, so here is the market around it.
In ZIP 33629, 207 homes are on the market and 28% are under contract — a steady corner of Tampa.
Across Hillsborough County, 6,324 homes are active and 1,810 pending (22% under contract).
In ZIP 33629 (Tampa), 242 homes closed in the last 12 months at a median of $1.20M ($484/sq ft), up 3.5% year over year, with a median 28 days on market. Right now 48 active and 12 pending listings put supply at about 2.4 months — a healthy market. See the live ZIP 33629 housing market and the Hillsborough County market.
ZIP and county figures describe the wider market, not Chicago Ave specifically. Momentum Research analysis of MLS records.
The Chicago Ave buying strategy.
If we were buying in Chicago Ave 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 Ave.
A subdivision with no packaged data yet
The MLS feed for Chicago Ave Sub does not currently return the volume of listings needed to establish a median price, typical days on market, or inventory trend. That is not unusual for smaller platted subdivisions inside larger Tampa submarkets — sales can be sparse enough that a snapshot simply will not populate meaningful statistics in a given window.
No community amenities are identified from current listings either, which suggests this is likely a subdivision built around individual lots and homes rather than a planned community with shared facilities. Anyone evaluating a property here should treat it as a standalone home purchase inside Tampa, and lean on direct comparable sales and a site-specific walkthrough rather than community-level marketing data.
The location and the amenities are priced into every listing in Chicago Ave. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
When a subdivision's MLS data is this thin, the value of an agent shifts from reciting stats to doing the legwork: pulling off-platform comps, tracking down recent closings in the immediate area, and evaluating the specific home and lot on its own terms rather than a community average that does not exist yet.
Chicago Ave in 15 seconds.
Tools for a Chicago Ave 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 Ave sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chicago Ave, 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 Ave home worth?
Get a no-obligation home value based on real comparable sales in Chicago Ave, 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 all homes for sale in Tampa →
| Location | Tampa, Hillsborough County, FL · ZIP 33629 |
|---|---|
| Homes in the community | 21 (FL DOR 2025 assessment roll) |
| Years built | 1983–1983 (median 1983) |
| Typical living area | 1,670 sq ft (median) |
| Amenities listed by sellers | Deed Restrictions |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 90% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Chicago Ave key facts,” movewithmomentum.com/neighborhoods/chicago-ave-sub, data as of September 20, 2026.
Housing distress & ownership in Chicago Ave Sub, Tampa
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 November 2026 through November 2026. Deemed reliable but not guaranteed.
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Email me new listings in Chicago Ave
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 Ave
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Chicago Ave will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
How many homes are in Chicago Ave?
What share of Chicago Ave is owner-occupied?
When were the homes in Chicago Ave built?
Who is the best real estate agent for Chicago Ave?
How do I find a top Tampa real estate agent who knows Chicago Ave?
Can Momentum Realty connect me with an agent for Chicago Ave?
Where is Chicago Ave, and what county is it in?
Should you buy in Chicago Ave?
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: November 12, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 33629)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2015 (7 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.
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See how Chicago Ave Sub fits the bigger picture — live prices, inventory, and Momentum Scores: