Mindy DolleDomain Realty · Naples
(239) 851-2556
Naples, FL · Street guide

Homes for sale on Live Oak Drive

As of October 23, 2026, 5 homes are for sale in Live Oak Drive, Naples, FL, priced from $520K to $1.45M with a median asking price of $925K (about $402 per square foot).

5Active homes
$520K – $1.45MList price range
$402Median list $ / sq ft
10Closed sales, 12 months

Live from the MLS and refreshed through the day.

Free market snapshot

Get the Live Oak Drive market report

Current prices, what is for sale and what has sold, in your inbox right now. Then Mindy's occasional updates, and you can stop them any time.

By submitting, you agree to receive the Live Oak Drive market snapshot now and Mindy Dolle's market updates by email. Unsubscribe any time. No obligation. See our Privacy Policy.

Questions about Live Oak Drive

How many homes over $3M are for sale in Live Oak Drive?

There are no homes listed at $3M or more in Live Oak Drive right now, and 5 active listings overall. Listings change daily.

What do luxury homes cost in Live Oak Drive?

Current asking prices run $520K to $1.45M, with a median of $925K or roughly $402 per square foot. Floor, view, finish and, for single-family homes, lot and water frontage account for most of the spread.

What kinds of homes are in Live Oak Drive?

Live Oak Drive is a street in Naples in Naples, FL. Current listings include homes with 3 to 4 bedrooms, 1,554 sq ft to 3,350 sq ft, built 2015 to 2016.

Are homes in Live Oak Drive on the water?

Of the 5 current listings, 1 is waterfront, 4 have a private pool, per MLS data. Water type and access vary by street and building, so confirm each home's details before relying on them.

What are the association fees in Live Oak Drive?

Current listings report association fees of $1,441 to $1,646 per quarter. What a fee covers differs by building or community, so ask for the budget and the reserve and milestone-inspection documents before you buy.

How fast do homes sell in Live Oak Drive?

10 sales closed in the past 12 months at a median of $612K, with a median of about 76 days on market and a median sale-to-list ratio of 96.9%. A small number of sales means these medians are only a guide.

What should I check before buying a home in Live Oak Drive?

Start with the association: the budget, reserves and any special assessments, and what the current fees cover. Then check the flood zone and elevation, an insurance quote, any club or amenity membership and its transfer rules, and what comparable homes have actually sold for. Mindy can pull the closed sales for Live Oak Drive and walk you through the documents.

Which communities are on Live Oak Drive?

Current listings on Live Oak Drive sit in Winding Cypress (5). Each community has its own association rules, fees and amenities, so compare them before you choose.

Who can show me homes in Live Oak Drive?

Mindy Dolle, a licensed Florida real estate sales associate with Domain Realty, can arrange showings, pull comparable sales and review association documents for homes in Live Oak Drive. Call or text (239) 851-2556.

Along and near Live Oak Drive