Southside Village Pool Homes for Sale · Page 4

100 homes with a private pool for sale in Southside Village, median asking price $2,050,000, mostly $650,000 – $5,606,000. ZIP 34239: Southside Village and the surrounding neighborhoods (Cherokee Park, Harbor Acres and others). As of Oct 9, 2026.

3537 SCHOOL AVENUE, SARASOTA
Active

$669,000

3537 SCHOOL AVENUE

SARASOTA, FL 34239

3 bed
2 bath
1,988 sqft

MLS# A4691686 · Listing courtesy of COLDWELL BANKER REALTY

2912 HAWTHORNE STREET, SARASOTA
Active

$299,999

2912 HAWTHORNE STREET

SARASOTA, FL 34239

2 bed
2 bath
1,016 sqft

MLS# R4911184 · Listing courtesy of PREMIER PLUS REALTY

2823 MARSHALL DRIVE, SARASOTA
Active

$1,199,000

2823 MARSHALL DRIVE

SARASOTA, FL 34239

3 bed
3 bath
1,856 sqft

MLS# A4690497 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

1704 FORTUNA STREET, SARASOTA
Active

$1,395,000

1704 FORTUNA STREET

SARASOTA, FL 34239

3 bed
3 bath
2,435 sqft

MLS# A4689929 · Listing courtesy of COLDWELL BANKER REALTY

1714 WALDEMERE STREET, SARASOTA
Active Under Contract

$1,650,000

1714 WALDEMERE STREET

SARASOTA, FL 34239

4 bed
3 bath
2,003 sqft

MLS# A4688029 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1794 CUNLIFF LANE, SARASOTA
Active

$2,997,000

1794 CUNLIFF LANE

SARASOTA, FL 34239

4 bed
3 bath
3,377 sqft

MLS# A4685523 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1504 LODGE DRIVE, SARASOTA
Active

$6,950,000

1504 LODGE DRIVE

SARASOTA, FL 34239

4 bed
4 bath
5,450 sqft

MLS# A4683855 · Listing courtesy of COLDWELL BANKER REALTY

1731 CUNLIFF LANE, SARASOTA
Active Under Contract

$2,750,000

1731 CUNLIFF LANE

SARASOTA, FL 34239

3 bed
3 bath
3,239 sqft

MLS# A4684577 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

2314 PROSPECT STREET, SARASOTA
Active

$2,345,000

2314 PROSPECT STREET

SARASOTA, FL 34239

5 bed
6 bath
3,651 sqft

MLS# A4684572 · Listing courtesy of RE/MAX ALLIANCE GROUP

2564 ARLINGTON STREET, SARASOTA
Active

$2,300,000

2564 ARLINGTON STREET

SARASOTA, FL 34239

4 bed
6 bath
3,117 sqft

MLS# A4683569 · Listing courtesy of RE/MAX ALLIANCE GROUP

2207 WISTERIA STREET, SARASOTA
Active

$1,995,250

2207 WISTERIA STREET

SARASOTA, FL 34239

4 bed
4 bath
3,120 sqft

MLS# A4683417 · Listing courtesy of LOYD ROBBINS & CO. LLC

1535 HARBOR DRIVE, SARASOTA
Pending

$4,749,000

1535 HARBOR DRIVE

SARASOTA, FL 34239

4 bed
6 bath
3,524 sqft

MLS# A4683125 · Listing courtesy of HB REALTY GROUP INC.

2045 GOLDENROD STREET, SARASOTA
Active

$2,000,000

2045 GOLDENROD STREET

SARASOTA, FL 34239

5 bed
5 bath
3,784 sqft

MLS# A4681259 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1959 WISTERIA STREET, SARASOTA
Active

$3,150,000

1959 WISTERIA STREET

SARASOTA, FL 34239

3 bed
4 bath
2,844 sqft

MLS# A4683340 · Listing courtesy of MAJESTIK REALTY, INC

3000 SOUTHWEST DRIVE, SARASOTA
Active

$11,995,000

3000 SOUTHWEST DRIVE

SARASOTA, FL 34239

5 bed
7 bath
8,125 sqft

MLS# A4672971 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1340 HARBOR DRIVE, SARASOTA
Active

$11,450,000

1340 HARBOR DRIVE

SARASOTA, FL 34239

4 bed
7 bath
5,157 sqft

MLS# A4680096 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1500 BAYVIEW DRIVE, SARASOTA
Active

$8,750,000

1500 BAYVIEW DRIVE

SARASOTA, FL 34239

5 bed
5 bath
4,031 sqft

MLS# A4678945 · Listing courtesy of RE/MAX ALLIANCE GROUP

1389 TANGIER WAY, SARASOTA
Active Under Contract

$5,985,000

1389 TANGIER WAY

SARASOTA, FL 34239

4 bed
5 bath
5,310 sqft

MLS# A4677509 · Listing courtesy of DOUGLAS ELLIMAN

1958 MORRIS STREET, SARASOTA
Active Under Contract

$1,099,900

1958 MORRIS STREET

SARASOTA, FL 34239

4 bed
3 bath
2,362 sqft

MLS# A4677121 · Listing courtesy of WAGNER REALTY

1509 FLOWER DRIVE, SARASOTA
Active

$5,375,000

1509 FLOWER DRIVE

SARASOTA, FL 34239

5 bed
5 bath
4,989 sqft

MLS# A4665815 · Listing courtesy of GRECO REAL ESTATE

2079 HIBISCUS STREET, SARASOTA
Active

$1,895,000

2079 HIBISCUS STREET

SARASOTA, FL 34239

4 bed
4 bath
2,750 sqft

MLS# A4672247 · Listing courtesy of THE REAL ESTATE STORE

2069 HIBISCUS STREET, SARASOTA
Active

$1,649,000

2069 HIBISCUS STREET

SARASOTA, FL 34239

3 bed
4 bath
2,454 sqft

MLS# A4672246 · Listing courtesy of THE REAL ESTATE STORE

2305 TEMPLE STREET, SARASOTA
Active

$2,149,000

2305 TEMPLE STREET

SARASOTA, FL 34239

5 bed
7 bath
3,386 sqft

MLS# A4670467 · Listing courtesy of KW COASTAL LIVING III

2163 WALDEMERE STREET, SARASOTA
Active

$2,290,000

2163 WALDEMERE STREET

SARASOTA, FL 34239

5 bed
6 bath
3,334 sqft

MLS# A4669073 · Listing courtesy of KW COASTAL LIVING III

More in Southside Village

Pool Homes for Sale nearby

Questions about Southside Village Pool Homes for Sale

How many homes with a private pool are for sale in Southside Village?

100 homes with a private pool are listed on this site as of Oct 9, 2026, from Stellar MLS. The list updates every hour.

What is the median asking price of homes with a private pool in Southside Village?

The median asking price is $2,050,000; most are listed between $650,000 and $5,606,000. These are asking prices, not sale prices.

Can George help me buy in Southside Village?

Yes. George Predescu, REALTOR® with Horizon Realty International, can set up showings for any listing here, including ones listed by other brokers. Call or text (941) 899-3045.

Want to see one of these homes with a private pool?

George Predescu, REALTOR® with Horizon Realty International, can answer questions and set up showings.

Call (941) 899-3045Text GeorgeSend a message

Listings courtesy of Stellar MLS as distributed by MLS GRID

Based on information submitted to the MLS GRID as of Oct 9, 2026, 5:30 PM EDT. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some IDX listings have been excluded from this website. Full IDX / DMCA disclaimer