Caldwells
Homes for Sale in Gulfport, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 10 closed sales in Caldwells Rep in Gulfport, FL since 2006, the most recent in April 2026. Across Gulfport as a whole, 263 homes closed in the last 12 months at a median of $385,000, 54 median days on market, with 90 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $7,460 ($6,650 with the full homestead exemption).
The facts we can stand behind for Caldwells Rep are thin: a Gulfport location in Pinellas County, tracked on the Stellar feed, current as of mid-2026. That means the honest read here is about place, not price. We don't have a median, an inventory count, or a days-on-market figure to anchor to, so treat any pricing you see elsewhere as unverified until we pull current comps for this specific pocket.
What we can say is that Gulfport is a small-footprint, character-driven part of Pinellas, and pricing in places like this tends to be condition-driven and lot-specific rather than formula-driven. For a buyer, that argues for underwriting each property on its own merits. For a seller, it argues for pricing off recent, comparable closings rather than a neighborhood average. Come to us for the live numbers before you make a move.
Nearby homes for sale
No active listings inside Caldwells Rep 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
Caldwells Rep sits in Gulfport, on the Pinellas County side of the bay. It is a compact, location-first pocket where the individual home and lot matter more than any headline neighborhood figure.
Stellar MLS sales records identify 10 homes in Caldwells that have changed hands since 2009, built between 1947 and 2011 (median 2003), with a median living area of about 1,614 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.
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 Caldwells is best for.
Best for
- Buyers set on a specific Gulfport location who will underwrite each home individually
- Buyers comfortable moving on a property once we confirm live comps rather than waiting for a published neighborhood average
- Sellers who want pricing built from recent comparable closings in this exact pocket
Probably not for
- Buyers who need a broad, uniform inventory to compare against
- Buyers who want a firm median and days-on-market figure before they will start looking
- Sellers expecting a single neighborhood benchmark to set their list price
The market around Caldwells
Caldwells is too small for its own price trend, so here is the market around it.
In ZIP 33707, 338 homes are on the market and 19% are under contract — a steady corner of Gulfport.
Across Pinellas County, 6,628 homes are active and 1,729 pending (21% under contract).
In ZIP 33707 (Gulfport), 729 homes closed in the last 12 months at a median of $385K ($307/sq ft), down 1.1% year over year, with a median 48 days on market. Right now 192 active and 46 pending listings put supply at about 4.9 months — a buyer's market. See the live ZIP 33707 housing market and the Pinellas County market.
ZIP and county figures describe the wider market, not Caldwells specifically. Momentum Research analysis of MLS records.
The Caldwells buying strategy.
If we were buying in Caldwells 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 Caldwells.
The location and the amenities are priced into every listing in Caldwells. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small Gulfport pocket like Caldwells Rep, the difference between a good deal and a costly one is local, property-level detail — condition, lot, and a handful of genuinely comparable closings. We pull the live Stellar data for this specific area rather than lean on a neighborhood average, and we will tell you plainly when a listing or a list price does not hold up.
Caldwells 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 Caldwells 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 Caldwells sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Caldwells, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Caldwells home worth?
Get a no-obligation home value based on real comparable sales in Caldwells, 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 Gulfport →
Should you buy in Caldwells?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2006 (10 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 Caldwells Rep fits the bigger picture — live prices, inventory, and Momentum Scores:
Schools serving nearby communities
We do not have a confirmed school assignment for Caldwells. These are the public schools most often assigned to other communities in ZIP 33707; zones change and vary by address, so confirm with the district before you buy.
- Boca Ciega High School · High · FLDOE grade C (assigned to 3 nearby communities)
- Azalea Middle School · Middle · FLDOE grade C (assigned to 2 nearby communities)
- Boca Ciega High among area schools · By address (assigned to 2 nearby communities)
Assignments from district data for neighboring communities; grades are official Florida Department of Education school grades (2025-26).
Common questions about Caldwells
Where is Caldwells?
Caldwells is a community in Gulfport, Pinellas County, Florida, ZIP 33707.
Are there homes for sale in Caldwells right now?
No active listings inside Caldwells at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Caldwells have an HOA or CDD?
No HOA is on record for Caldwells 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 Caldwells with Momentum Realty’s local guides.
Caldwells Rep Market Scorecard
Caldwells Rep is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 33707 ZIP is $367,339, about 7.4% 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.