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

Homes for sale on San Mateo Drive

As of November 3, 2026, 3 homes listed at $3M and up are for sale in San Mateo Drive, Bonita Springs, FL, priced from $3.27M to $4.5M with a median asking price of $4.35M (about $1,100 per square foot).

3Active homes $3M+
$3.27M – $4.5MList price range
$1,100Median list $ / sq ft

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Homes on San Mateo Drive

3 at $3M+
211 San Mateo Dr, Bonita SpringsNew today1 / 50
$4,505,000
211 San Mateo DrSouthport On The Bay · Bonita Springs
4 bd4 ba4,000 sf
Listing courtesy of Premier Sotheby's Int'l Realty
195 San Mateo Dr, Bonita SpringsGulf access1 / 46
$4,350,000
195 San Mateo DrSouthport On The Bay · Bonita Springs
4 bd3.5 ba4,333 sf
Listing courtesy of John R Wood Properties
197 San Mateo Dr, Bonita SpringsGulf access1 / 50
$3,275,000
197 San Mateo DrSouthport On The Bay · Bonita Springs
4 bd3 ba2,976 sf
Listing courtesy of John R Wood Properties
207 San Mateo Dr, Bonita SpringsWaterfront1 / 45
$2,995,000
207 San Mateo DrSouthport On The Bay · Bonita Springs
5 bd4.5 ba4,954 sf
Listing courtesy of John R Wood Properties
201 San Mateo Dr, Bonita SpringsGulf access1 / 39
$2,595,000
201 San Mateo DrSouthport On The Bay · Bonita Springs
4 bd3 ba2,404 sf
Listing courtesy of John R Wood Properties

Listings are shown courtesy of the listing brokerages. Information is deemed reliable but not guaranteed.

Questions about San Mateo Drive

How many homes over $3M are for sale in San Mateo Drive?

3 homes priced at $3M or more are listed for sale in San Mateo Drive, Bonita Springs, FL, according to the MLS as of November 3, 2026, out of 5 active listings overall. The list changes daily.

What do luxury homes cost in San Mateo Drive?

Current asking prices at $3M and up run $3.27M to $4.5M, with a median of $4.35M or roughly $1,100 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 San Mateo Drive?

San Mateo Drive is a street in Bonita Springs in Bonita Springs, FL. Current listings include homes with 4 bedrooms, 2,976 sq ft to 4,333 sq ft, built 1998 to 2023.

Are homes in San Mateo Drive on the water?

Of the 3 current listings, 3 are waterfront, 2 have Gulf access, 3 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 San Mateo Drive?

Current listings report association fees of $5,166 per year. What a fee covers differs by building or community, so ask for the budget and the reserve and milestone-inspection documents before you buy.

Are there new or modern homes in San Mateo Drive?

1 current listing here was built in 2018 or later (newest 2023). Finishes and floor plans vary by year, so compare homes of similar age.

What should I check before buying a home in San Mateo 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 San Mateo Drive and walk you through the documents.

Which communities are on San Mateo Drive?

Current listings on San Mateo Drive sit in Southport on the Bay (5). Each community has its own association rules, fees and amenities, so compare them before you choose.

Who can show me homes in San Mateo 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 San Mateo Drive. Call or text (239) 851-2556.

Along and near San Mateo Drive