Chicago Ave
Homes for Sale in Tampa, FL

All 3,559 homes for sale in Tampa, FL · median $435,000 · 548 townhomes for sale in Tampa · 112 homes for sale in 33629 · Hillsborough County homes for sale

Community in Tampa · Hillsborough County · ZIP 33629
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data11 years of closingsUpdated twice daily

As of September 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, 5,135 homes closed in the last 12 months at a median of $430,000, 38 median days on market, with 1,363 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).

Live · Chicago Ave Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Chicago Ave 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.

Nearby homes for sale

No active listings inside Chicago AveHomes for Sale in Tampa, FL 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.

1407 S MOODY AVENUE
$1.02M · 0.0 mi away
4 bd · 3 ba · 1,683 sqft
1407 S MOODY AVENUE
Listed by CENTURY 21 BILL NYE REALTY
2401 BAYSHORE BOULEVARD #609
$525K · 0.1 mi away
2 bd · 2 ba · 1,104 sqft
2401 BAYSHORE BOULEVARD #609
Listed by BHHS FLORIDA PROPERTIES GROUP
2442 W MISSISSIPPI AVENUE #14
$840K · 0.1 mi away
3 bd · 3.5 ba · 2,705 sqft
2442 W MISSISSIPPI AVENUE #14
Listed by FUTURE HOME REALTY INC
1511 S BAY VILLA PLACE
$550K · 0.1 mi away
4 bd · 3 ba · 1,992 sqft
1511 S BAY VILLA PLACE
Listed by KELLER WILLIAMS SOUTH SHORE
1401 S DESOTO AVENUE
$3.90M · 0.1 mi away
3 bd · 2.5 ba · 2,550 sqft
1401 S DESOTO AVENUE
Listed by COMPASS FLORIDA LLC
1301 S HOWARD AVENUE #B18
$190K · 0.1 mi away
1 bd · 1 ba · 540 sqft
1301 S HOWARD AVENUE #B18
Listed by FLORIDA EXECUTIVE REALTY

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

Chicago Ave 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.

Best for

  • A buyer who has already identified a specific property in Chicago Ave 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, 213 homes are on the market and 29% are under contract — a steady corner of Tampa.

Across Hillsborough County, 6,274 homes are active and 1,939 pending (24% under contract).

In ZIP 33629 (Tampa), 599 homes closed in the last 12 months at a median of $1.23M ($488/sq ft), up 15.7% year over year, with a median 40 days on market. Right now 55 active and 25 pending listings put supply at about 3.2 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.

If we were buying in Chicago Ave today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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.

Best Buy
Best for a buyer targeting a specific home or lot in Tampa rather than someone shopping by community-level statistics.
Biggest Risk
The risk is limited comparable data, which means valuation takes more direct diligence and less reliance on aggregate figures.
Sweet Spot
The sweet spot is a buyer or seller who wants a straightforward Tampa residential purchase without amenity fees or HOA-driven pricing.
Avoid If
Avoid if you are relying on published median price or days-on-market data to guide your offer strategy — it is not available here yet.

A subdivision with no packaged data yet

The MLS feed for Chicago Ave 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.

Jon Brooks · Founder, Momentum Realty

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.

Best forBest for a buyer targeting a specific home or lot in Tampa rather than someone shopping by community-level statistics.
Biggest advantageThe advantage is a quiet, low-volume pocket where pricing is set property-by-property, not by broad market momentum.
Biggest riskThe risk is limited comparable data, which means valuation takes more direct diligence and less reliance on aggregate figures.
Sweet spotThe sweet spot is a buyer or seller who wants a straightforward Tampa residential purchase without amenity fees or HOA-driven pricing.
Avoid ifAvoid if you are relying on published median price or days-on-market data to guide your offer strategy — it is not available here yet.

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Chicago Ave homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Chicago Ave.
In short
  • HOA dues reported around $75/month (about $900/yr) · median of 16 MLS listings, most billed annually
  • Any club/amenity membership is billed separately

Listings in this community report association dues of about $75 per month ($900 a year) — the median AssociationFee across 16 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.

The takeaway

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.

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.

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Real comps, not an automated estimate.
A buyer who has already identified a specific property in Chicago Ave and wants direct, comp-based guidance rather than community-wide statisticsExcellent fit
A buyer or seller comfortable with a low-volume market where pricing is negotiated per propertyExcellent fit
Someone looking for a straightforward Tampa home purchase without a community amenity package or associated feesExcellent fit
A buyer who wants to compare against a published median price or established days-on-market trend before making an offerProbably not
Someone specifically seeking a subdivision with organized community amenitiesProbably not
A buyer who prefers high-volume markets with abundant recent comparable sales to lean onProbably not

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: September 19, 2026)
Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-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.

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.

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Schools serving nearby communities

We do not have a confirmed school assignment for Chicago Ave. These are the public schools most often assigned to other communities in ZIP 33629; zones change and vary by address, so confirm with the district before you buy.

Assignments from district data for neighboring communities; grades are official Florida Department of Education school grades (2025-26).

Common questions about Chicago Ave

Where is Chicago Ave?

Chicago Ave is a community in Tampa, Hillsborough County, Florida, ZIP 33629.

Are there homes for sale in Chicago Ave right now?

No active listings inside Chicago Ave at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.

Does Chicago Ave have an HOA or CDD?

No HOA is on record for Chicago Ave in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.

Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.

Nearby Communities

Explore more neighborhoods near Chicago Ave with Momentum Realty’s local guides.

SCShaws C B0.1 mi awaySPStroud Park Condo0.1 mi awayNBNear Bay0.1 mi away · 24 homes, built 1913–18SSeabreeze0.1 mi awayCSCasey Sub0.1 mi away · 23 homes, built 1923–20BPBelfair Park Townhomes0.1 mi awaySASoho A Condo 13010.1 mi away · 1 for sale

Browse all neighborhood guides →

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Chicago Ave Sub Market Scorecard

No active listings

Chicago Ave Sub is currently a no active listings market. Limited supply, a median asking price of n/a.

n/a
Months supply
n/a
Median list
$615,000
Median sold
n/a
Per sqft
n/a
Days on mkt
0/0/1
Active/Pend/Sold

Typical home value in the 33629 ZIP is $1,041,130, about 31.9% 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.