Caldwells
Homes for Sale in Gulfport, FL
All 152 homes for sale in Gulfport, FL · median $375,000 · 120 homes for sale in 33707 · Pinellas 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 10 closed sales in Caldwells Rep in Gulfport, FL since 2006, the most recent in April 2026. Across Gulfport as a whole, 268 homes closed in the last 12 months at a median of $363,750, 50 median days on market, with 130 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $7,050 ($6,240 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.
Figures in this note are as of July 14, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Caldwells 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.
County records show 9 qualified sales in Caldwells across 2024–2025 (3 in 2024, 6 in 2025), median $350,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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, 323 homes are on the market and 18% are under contract — a steady corner of Gulfport.
Across Pinellas County, 6,539 homes are active and 1,627 pending (20% under contract).
In ZIP 33707 (Gulfport), 174 homes closed in the last 12 months at a median of $475K ($319/sq ft), down 7.7% year over year, with a median 46 days on market. Right now 107 active and 31 pending listings put supply at about 7.4 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.
Homes For Sale Right Now in Caldwells
Live MLS inventory for Caldwells. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Caldwells listings as of 2026-11-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026. Tap any home to ask about it.
Schools
- Pinellas County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Gulfport Elementary-PN · Elementary
- Azalea Middle-PN · Middle
- Boca Ciega High-PN · High
Zoned schools reflect the assignments reported on recent Caldwells listings and can change; always confirm with Pinellas County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Caldwells address.
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.
A closer look at the Caldwells market
The housing stock is 76 homes built between 1910 and 2022, and 55% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
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.
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 →
| Location | Gulfport, Pinellas County, FL · ZIP 33707 |
|---|---|
| Homes in the community | 76 (FL DOR 2025 assessment roll) |
| Years built | 1910–2022 (median 1948.5) |
| Typical living area | 1,490 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 55% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Caldwells key facts,” movewithmomentum.com/neighborhoods/caldwells-rep, data as of September 20, 2026.
Housing distress & ownership in Caldwells Rep, Gulfport
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.
Every Home for Sale in Caldwells Rep Right Now (1)
All 1 active and pending Caldwells Rep listings with a detail page, newest first, refreshed twice a day from the MLS.
- 5879 27th Avenue · $443,000 · 3 bd / 1 ba · listed Oct 10, 2026 · listed by Gulfport Realty
More Gulfport home searches
- All homes for sale in Gulfport, FL
- Homes for sale in Pinellas County, FL
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- Gulfport home values: what is my house worth?
Gulfport guides & data
- Market data
- Property taxes (Pinellas County)
- Homestead exemption (Pinellas County)
- Home insurance cost
- New construction (Pinellas County)
- ZIP codes
- Home builders (Pinellas County)
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
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- 27Th Avenue S (7 homes on record)
Email me new listings in Caldwells
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 Caldwells
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Caldwells will answer, and the answer is published on this page for the next buyer.
18% of homes for sale in ZIP 33707 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 (2026-11-14).
Recent Developments in Caldwells Rep
Development, infrastructure, retail, and school activity affecting Caldwells Rep, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Market
North St. Petersburg FedEx warehouse sells for $58.2M, $36M below 2021 price
A 236,976 square foot FedEx Ground distribution center at 1950 102nd Avenue N. on about 63 acres near I-275 sold for $58.2 million, versus $94.5 million in 2021. FedEx has operated there since 2017 and the deed shows no change to its lease. The article ties the sale to higher borrowing costs facing the prior owner.
What it may mean for the marketThe sale points to repricing in Pinellas industrial property while the last-mile logistics hub keeps operating near I-275. The project is about 4 miles southeast of Caldwells Rep, elsewhere in Pinellas County.
Source: St. Pete Catalyst - October 2026Development
Humane Society of Tampa Bay to open Clearwater clinic on State Road 590
The nonprofit's clinic at 2907 State Road 590, Suite 5, near its Clearwater shelter opens Nov. 2, with a grand opening Nov. 12. It offers vaccinations, wellness exams, microchipping, lab work and X-rays by appointment, with spay and neuter services planned later.
What it may mean for the marketA new low-cost veterinary option near the SR 590 corridor adds a neighborhood service amenity in central Clearwater. The project is about 5 miles north of Caldwells Rep, elsewhere in Pinellas County.
Source: St. Pete Catalyst - October 2026Development
ClearView apartments complete at $1 billion Echelon City Center in St. Petersburg
The 363-unit ClearView community, with ground-floor retail, is complete within the Echelon City Center development by Third Lake Partners and Echelon. A 3rd & 3rd residential high-rise with ground-floor retail is expected to open in the first quarter of 2027.
What it may mean for the marketNew downtown apartments and walkable retail add rental inventory and amenities in central St. Petersburg. The project is about 10 miles southeast of Caldwells Rep, elsewhere in Pinellas County.
Source: Tampa Bay Business and Wealth - August 2026Infrastructure
Four firms vie to build Tampa International Airport's $150 million control tower
TPA narrowed the field to four builders for a new blast-resistant air traffic control tower on about 2 acres northwest of the main terminal. The budget is about $150 million, with board selection expected Oct. 1 and substantial completion targeted for March 2029.
What it may mean for the marketAirport capital spending supports construction employment and long-term air service capacity for the region. The site is about 12 miles northeast of Caldwells Rep.
Source: Tampa Bay Business and Wealth - July 2026Development
St. Pete advances housing plan for nine vacant city lots
The St. Petersburg City Council unanimously approved a first reading of an ordinance to place a measure on the November 3 ballot that would remove nine vacant city lots in Methodist Town from the city's Charter Park and Waterfront Map. The change would allow up to 41 units of affordable or workforce housing, with four lots planned for single family homes and five larger parcels for multifamily housing. The lots have held park designations since 1984 but have remained vacant.
What it may mean for the marketAdvances a plan to convert nine vacant city lots into new single family and multifamily housing, adding to local housing inventory. Placing the parcels on the ballot could open long dormant land for residential construction. The project is about 10 miles southeast of Caldwells Rep, elsewhere in Pinellas County.
Source: St Pete Catalyst - July 2026Development
Blake-Related team selected to redevelop 86-acre Historic Gas Plant District
St. Petersburg selected a bid led by Blake Investment Partners, with the Related Group as co-developer, to redevelop the 86-acre Historic Gas Plant District at the Tropicana Field site. The roughly 8.1 billion dollar mixed use plan calls for more than 3,600 income-restricted residential units, a 13-acre central park, and office, retail, hotel and civic space over an estimated 20-year buildout. The developers plan to purchase about 58 acres while the city retains roughly one third.
What it may mean for the marketAdds a large mixed use district with thousands of new residential units, a central park, and office, retail, hotel and civic space to the downtown St. Petersburg market. Redevelopment of the Tropicana Field site reshapes the surrounding property landscape and expands housing supply. The project is about 11 miles south of Caldwells Rep, elsewhere in Pinellas County.
Source: Florida YIMBY
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
How many homes are in Caldwells?
What share of Caldwells is owner-occupied?
When were the homes in Caldwells built?
Who is the best real estate agent for Caldwells?
How do I find a top Gulfport real estate agent who knows Caldwells?
Can Momentum Realty connect me with an agent for Caldwells?
Where is Caldwells, and what county is it in?
Should you buy in Caldwells?
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 33707)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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.
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