Southside Village Pool Homes for Sale · Page 2

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.

1960 BOYCE STREET, SARASOTA
Active

$3,895,000

1960 BOYCE STREET

SARASOTA, FL 34239

4 bed
5 bath
3,674 sqft

MLS# A4704619 · Listing courtesy of COLDWELL BANKER REALTY

3536 JAFFA DRIVE, SARASOTA
Active

$599,000

3536 JAFFA DRIVE

SARASOTA, FL 34239

3 bed
2 bath
1,839 sqft

MLS# N6145472 · Listing courtesy of COMPASS FLORIDA LLC

2410 SIESTA DRIVE, SARASOTA
Active Under Contract

$1,295,000

2410 SIESTA DRIVE

SARASOTA, FL 34239

4 bed
3 bath
2,360 sqft

MLS# A4704038 · Listing courtesy of LUXE COASTAL PROPERTIES

1722 NORTH DRIVE, SARASOTA
Active

$2,690,000

1722 NORTH DRIVE

SARASOTA, FL 34239

3 bed
2 bath
2,193 sqft

MLS# A4703853 · Listing courtesy of COLDWELL BANKER REALTY

3624 LOCKWOOD RIDGE ROAD, SARASOTA
Active

$1,375,000

3624 LOCKWOOD RIDGE ROAD

SARASOTA, FL 34239

4 bed
4 bath
4,013 sqft

MLS# A4703672 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

1740 ORANGE AVENUE, SARASOTA
Active

$5,500,000

1740 ORANGE AVENUE

SARASOTA, FL 34239

5 bed
6 bath
5,583 sqft

MLS# A4703787 · Listing courtesy of RE/MAX ALLIANCE GROUP

2419 HILLVIEW STREET, SARASOTA
Active

$2,650,000

2419 HILLVIEW STREET

SARASOTA, FL 34239

5 bed
6 bath
4,761 sqft

MLS# A4703714 · Listing courtesy of RE/MAX ALLIANCE GROUP

1907 MAGNOLIA STREET, SARASOTA
Active Under Contract

$1,495,000

1907 MAGNOLIA STREET

SARASOTA, FL 34239

3 bed
3 bath
1,824 sqft

MLS# A4703284 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

3606 PALONIA COURT, SARASOTA
Active

$2,299,000

3606 PALONIA COURT

SARASOTA, FL 34239

3 bed
3 bath
2,700 sqft

MLS# A4703404 · Listing courtesy of COLDWELL BANKER REALTY

3424 OLD OAK DRIVE, SARASOTA
Active

$1,039,000

3424 OLD OAK DRIVE

SARASOTA, FL 34239

3 bed
2 bath
1,368 sqft

MLS# A4702989 · Listing courtesy of EXP REALTY LLC

2631 PURITAN TERRACE, SARASOTA
Active

$2,150,000

2631 PURITAN TERRACE

SARASOTA, FL 34239

4 bed
4 bath
3,675 sqft

MLS# A4699231 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1671 ARLINGTON STREET, SARASOTA
Active

$3,050,000

1671 ARLINGTON STREET

SARASOTA, FL 34239

5 bed
6 bath
3,564 sqft

MLS# A4703257 · Listing courtesy of COMPASS FLORIDA LLC

1354 TEAROSE PLACE, SARASOTA
Active

$1,625,000

1354 TEAROSE PLACE

SARASOTA, FL 34239

3 bed
3 bath
1,974 sqft

MLS# A4702710 · Listing courtesy of RE/MAX ALLIANCE GROUP

1444 HARBOR DRIVE, SARASOTA
Active

$6,999,900

1444 HARBOR DRIVE

SARASOTA, FL 34239

5 bed
7 bath
5,001 sqft

MLS# A4703040 · Listing courtesy of STARZ REAL ESTATE, LLC

1426 OSPREY AVENUE, SARASOTA
Active

$2,999,000

1426 OSPREY AVENUE

SARASOTA, FL 34239

4 bed
4 bath
2,915 sqft

MLS# A4703064 · Listing courtesy of COMPASS FLORIDA LLC

1959 HIBISCUS STREET, SARASOTA
Pending

$2,220,000

1959 HIBISCUS STREET

SARASOTA, FL 34239

3 bed
3 bath
2,720 sqft

MLS# A4702810 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

2440 ARLINGTON STREET, SARASOTA
Active Under Contract

$1,150,000

2440 ARLINGTON STREET

SARASOTA, FL 34239

3 bed
2 bath
1,859 sqft

MLS# A4702167 · Listing courtesy of RE/MAX ALLIANCE GROUP

2306 VALENCIA DRIVE, SARASOTA
Active Under Contract

$1,175,000

2306 VALENCIA DRIVE

SARASOTA, FL 34239

3 bed
3 bath
1,949 sqft

MLS# A4701639 · Listing courtesy of COMPASS FLORIDA LLC

2070 HYDE PARK STREET, SARASOTA
Active

$745,000

2070 HYDE PARK STREET

SARASOTA, FL 34239

3 bed
2 bath
1,714 sqft

MLS# A4701591 · Listing courtesy of COLDWELL BANKER REALTY

1640 WALDEMERE STREET, SARASOTA
Active

$5,400,000

1640 WALDEMERE STREET

SARASOTA, FL 34239

5 bed
6 bath
5,270 sqft

MLS# A4701346 · Listing courtesy of COMPASS FLORIDA LLC

2590 FLOYD STREET, SARASOTA
Active

$1,499,000

2590 FLOYD STREET

SARASOTA, FL 34239

3 bed
4 bath
2,954 sqft

MLS# A4701670 · Listing courtesy of KW COASTAL LIVING III

2069 BOUGAINVILLEA STREET, SARASOTA
Active

$1,550,000

2069 BOUGAINVILLEA STREET

SARASOTA, FL 34239

6 bed
5 bath
3,249 sqft

MLS# A4701696 · Listing courtesy of EXP REALTY LLC

2532 FRUIT TREE DRIVE, SARASOTA
Active

$2,295,000

2532 FRUIT TREE DRIVE

SARASOTA, FL 34239

6 bed
6 bath
3,931 sqft

MLS# A4700943 · Listing courtesy of COMPASS FLORIDA LLC

2395 HYDE PARK STREET, SARASOTA
Active

$1,400,000

2395 HYDE PARK STREET

SARASOTA, FL 34239

3 bed
3 bath
2,126 sqft

MLS# A4700669 · Listing courtesy of HARRY ROBBINS ASSOC INC

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, 5:00 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