Southside Village Luxury Homes for Sale · Page 4

91 luxury homes for sale in Southside Village, median asking price $2,199,000, mostly $1,225,000 – $5,750,000. Homes with an asking price of $1M or more. ZIP 34239: Southside Village and the surrounding neighborhoods (Cherokee Park, Harbor Acres and others). As of Oct 9, 2026.

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

1538 ORANGE AVENUE, SARASOTA
Active

$1,950,000

1538 ORANGE AVENUE

SARASOTA, FL 34239

3 bed
4 bath
2,550 sqft

MLS# A4672485 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

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

2232 GROVE STREET, SARASOTA
Active Under Contract

$2,395,000

2232 GROVE STREET

SARASOTA, FL 34239

4 bed
6 bath
3,800 sqft

MLS# A4670786 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

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

1775 STAPLETON STREET, SARASOTA
Active

$1,475,000

1775 STAPLETON STREET

SARASOTA, FL 34239

5 bed
4 bath
2,853 sqft

MLS# A4670359 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

1759 WALDEMERE STREET, SARASOTA
Active

$4,099,999

1759 WALDEMERE STREET

SARASOTA, FL 34239

4 bed
5 bath
4,513 sqft

MLS# A4666725 · Listing courtesy of PREFERRED SHORE LLC

1642 BAHIA VISTA STREET, SARASOTA
Active Under Contract

$3,700,000

1642 BAHIA VISTA STREET

SARASOTA, FL 34239

4 bed
5 bath
3,809 sqft

MLS# A4667508 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

1541 FLOWER DRIVE, SARASOTA
Active

$1,870,000

1541 FLOWER DRIVE

SARASOTA, FL 34239

4 bed
4 bath
3,302 sqft

MLS# A4656365 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

2327 HILLVIEW STREET, SARASOTA
Active

$2,100,000

2327 HILLVIEW STREET

SARASOTA, FL 34239

6 bed
7 bath
3,500 sqft

MLS# A4644963 · Listing courtesy of KW COASTAL LIVING III

3502 BAHIA VISTA STREET, SARASOTA
Active

$1,095,000

3502 BAHIA VISTA STREET

SARASOTA, FL 34239

7 bed
7 bath
3,432 sqft

MLS# A4615828 · Listing courtesy of LOYD ROBBINS & CO. LLC

More in Southside Village

Luxury Homes for Sale nearby

Questions about Southside Village Luxury Homes for Sale

How many luxury homes are for sale in Southside Village?

91 luxury homes 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 luxury homes in Southside Village?

The median asking price is $2,199,000; most are listed between $1,225,000 and $5,750,000. 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 luxury homes?

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

Listings courtesy of Stellar MLS as distributed by MLS GRID

Based on information submitted to the MLS GRID as of Oct 9, 2026, 4:30 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