Diamond Loop Drive, Kissimmee, FL

Everything we know about Diamond Loop Drive in Kissimmee: 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.

30 homes sit on Diamond Loop Drive in Kissimmee, FL (ZIP 34744), built 2015–2018, a typical 1,846 sq ft with 4 bedrooms. 1 is for sale right now from $419,990. Homes that sold since 2023 went for a median $393,500.

For sale on Diamond Loop Drive now

1576 Diamond Loop Drive, home for sale on Diamond Loop Drive
$419,990
4 bd · 2 ba · 1,846 sq ft · built 2017
1576 Diamond Loop Drive
Listing courtesy of VESTI LLC

The homes on Diamond Loop Drive

30 single-family. Built by decade: 2010s 30.

Last recorded sales (parcel record)

AddressSoldDateBuiltSq ft
1519 Diamond Loop Drive$375,0002026-03-2620171,846
1514 Diamond Loop Drive$437,0002025-12-0920172,674
1565 Diamond Loop Dr$389,0002025-11-2520171,846
1593 Diamond Loop Drive$375,0002025-05-0920171,690
1404 Diamond Loop Drive$540,0002024-11-0120162,851
1526 Diamond Loop Drive$410,0002024-02-2320171,846
1573 Diamond Loop Drive$390,0002024-02-1220171,676
1507 Diamond Loop Drive$425,0002023-12-0520182,038
1522 Diamond Loop Drive$393,5002023-06-2720171,846
1408 Diamond Loop Drive$480,0002022-11-1820162,383
1580 Diamond Loop Drive$397,0002022-06-0220171,690
1569 Diamond Loop Drive$490,0002022-06-0220172,674
1512 Diamond Loop Drive$327,0002021-07-2120171,846
1576 Diamond Loop Drive$320,0002021-06-0120171,846
1572 Diamond Loop Drive$295,0002019-09-2520172,674
1543 Diamond Loop Drive$247,0002019-09-2520171,676
1531 Diamond Loop Drive$270,0002019-02-2720171,846
1475 Diamond Loop Drive$278,0002019-01-1320162,883
1495 Diamond Loop Drive$324,0002018-07-0220182,787
1530 Diamond Loop Drive$253,9902018-06-1520171,751

Communities along Diamond Loop 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 3,084 homes for sale in Kissimmee, homes for sale in 34744.

Hiring an agent in Kissimmee, FL?

Nearby streets

Get matched with the right local expert.

Tell us your goal in Kissimmee, FL and we’ll connect you with the Momentum agent who knows it best — backed by a RealTrends 500 brokerage. No pressure, no obligation.

Prefer to talk now? Call (904) 351-6461.

Work with a local Kissimmee, FL expert

A real conversation with a local specialist, usually within one business day.

or call (904) 351-6461

Common questions

How many homes are on Diamond Loop Drive in Kissimmee?

30 homes in the parcel and MLS record, built between 2015 and 2018.

Are there homes for sale on Diamond Loop Drive?

1 listed right now, from $419,990.

What do homes on Diamond Loop Drive sell for?

Homes that sold since 2023 went for a median $393,500.