Maddie Drive, Haines City, FL

Everything we know about Maddie Drive in Haines City: what is for sale, what has sold, what the homes are like and which communities the street runs through — from the MLS record and county parcel data, refreshed nightly.

135 homes sit on Maddie Drive in Haines City, FL (ZIP 33844), built 2023–2025, a typical 1,850 sq ft with 4 bedrooms. 7 are for sale right now from $279,000 to $399,900. Homes that sold since 2023 went for a median $334,945.

For sale on Maddie Drive now

5381 Maddie Drive, home for sale on Maddie Drive
$399,900
5 bd · 3 ba · 3,011 sq ft · built 2023
5381 Maddie Drive
Listing courtesy of FLORIDA REALTY INVESTMENTS
5377 Maddie Drive, home for sale on Maddie Drive
$399,000
5 bd · 2.5 ba · 2,539 sq ft · built 2023
5377 Maddie Drive
Listing courtesy of WC REALTY PARTNERS & ASSOCIATES LLC
5508 Maddie Drive, home for sale on Maddie Drive
$362,000
3 bd · 2 ba · 1,615 sq ft · built 2024
5508 Maddie Drive
Listing courtesy of LA ROSA REALTY CENTRAL FLORIDA LLC
5342 Maddie Drive, home for sale on Maddie Drive
$343,990
4 bd · 2 ba · 2,100 sq ft · built 2023
5342 Maddie Drive
Listing courtesy of NAIM REAL ESTATE LLC
5326 Maddie Drive, home for sale on Maddie Drive
$325,000
4 bd · 2.5 ba · 1,938 sq ft · built 2023
5326 Maddie Drive
Listing courtesy of RE/MAX PRIME PROPERTIES
5599 Maddie Drive, home for sale on Maddie Drive
$289,990
3 bd · 2 ba · 1,492 sq ft · built 2025
5599 Maddie Drive
Listing courtesy of RE/MAX ASSURED
5632 Maddie Drive, home for sale on Maddie Drive
$279,000
3 bd · 2 ba · 1,320 sq ft · built 2023
5632 Maddie Drive
Listing courtesy of NURI REALTY LLC

The homes on Maddie Drive

135 single-family. Built by decade: 2020s 135.

Last recorded sales (parcel record)

AddressSoldDateBuiltSq ft
5604 Maddie Drive$287,0002026-10-0220231,483
5479 Maddie Drive$272,0002026-09-2520231,405
5535 Maddie Drive$319,9902026-09-0820251,564
5543 Maddie Drive$309,9902026-08-2020251,564
5587 Maddie Drive$357,9902026-05-2920252,072
5563 Maddie Drive$349,9902026-05-1220252,072
5310 Maddie Drive$365,0002026-03-2720232,107
5591 Maddie Drive$313,9902025-10-0220251,680
5579 Maddie Drive$339,9902025-10-0120252,072
5536 Maddie Drive$271,9002025-05-3020251,479
5544 Maddie Drive$271,9002025-05-3020251,479
5467 Maddie Drive$285,0002025-04-2920231,405
5675 Maddie Drive$270,0002025-04-2820241,486
5532 Maddie Drive$369,9002025-04-2020242,587
5540 Maddie Drive$278,9002025-04-2020251,486
5520 Maddie Drive$344,9992025-03-3120242,226
5595 Maddie Drive$356,0902025-03-2820252,072
5516 Maddie Drive$333,9992025-03-1920242,039
5499 Maddie Drive$313,9002025-03-1620241,715
5524 Maddie Drive$379,9952025-03-1420242,470

Communities along Maddie Drive

How to read this

Home counts, build years, sizes and last sales come from the county parcel record joined to MLS history; listings and 12-month closings from the live MLS feeds as of October 15, 2026. Listings appear courtesy of the listing brokerage under IDX rules; information deemed reliable but not guaranteed. See also all 599 homes for sale in Haines City, homes for sale in 33844.

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Common questions

How many homes are on Maddie Drive in Haines City?

135 homes in the parcel and MLS record, built between 2023 and 2025.

Are there homes for sale on Maddie Drive?

7 listed right now, from $279,000.

What do homes on Maddie Drive sell for?

Homes that sold since 2023 went for a median $334,945.