205 total properties
Did you mean the neighborhood Oldsmar?
View 135 WOODLAKE WYNDE 135 Oldsmar, FL MLS# TB8539499
$185,000
2

Beds

2.0

Baths

924

Sq.Ft.

135 WOODLAKE WYNDE 135

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 317 WOODLAKE WYNDE Oldsmar, FL MLS# TB8544505
$197,500
2

Beds

2.0

Baths

924

Sq.Ft.

317 WOODLAKE WYNDE

Oldsmar, FL

Courtesy of EXP REALTY LLC
View 392 COBIA WAY Oldsmar, FL MLS# TB8539760
  • Adult Community with Virtual Tour
1 of 23
$189,000
2

Beds

2.0

Baths

1,344

Sq.Ft.

392 COBIA WAY

Oldsmar, FL

Courtesy of LIPPLY REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 415 MAPLEWOOD CIRCLE Oldsmar, FL MLS# TB8539039
$344,900
3

Beds

1.0

Baths

1,583

Sq.Ft.

415 MAPLEWOOD CIRCLE

Oldsmar, FL

Courtesy of COLDWELL BANKER REALTY
View 123 LOBLOLLY COURT A Oldsmar, FL MLS# TB8536224
$129,900
2

Beds

2.0

Baths

915

Sq.Ft.

123 LOBLOLLY COURT A

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 1723 CAPTIVA DRIVE Oldsmar, FL MLS# TB8538123
  • Virtual Tour
1 of 94
$799,000
4

Beds

3.0

Baths

2,736

Sq.Ft.

1723 CAPTIVA DRIVE

Oldsmar, FL

Courtesy of COASTAL PROPERTIES GROUP INTERNATIONAL
View 219 PALMETTO COURT 219 Oldsmar, FL MLS# TB8538433
$168,000
2

Beds

2.0

Baths

1,054

Sq.Ft.

219 PALMETTO COURT 219

Oldsmar, FL

Courtesy of COLDWELL BANKER REALTY
View 214 DOLPHIN DRIVE N Oldsmar, FL MLS# TB8538126
  • Adult Community with Virtual Tour
1 of 46
$259,000
2

Beds

2.0

Baths

1,324

Sq.Ft.

214 DOLPHIN DRIVE N

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 508 WASHINGTON AVENUE Oldsmar, FL MLS# TB8537441
$473,900
4

Beds

2.0

Baths

1,507

Sq.Ft.

508 WASHINGTON AVENUE

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
View 205 CHESTNUT STREET Oldsmar, FL MLS# TB8537182
$999,000
0.0

Baths

205 CHESTNUT STREET

Oldsmar, FL

Courtesy of SUNSHINE REALTY COMPANY LLC
View 1730 CAPTIVA DRIVE Oldsmar, FL MLS# TB8537101
  • Virtual Tour
1 of 68
$745,000
4

Beds

3.0

Baths

2,523

Sq.Ft.

1730 CAPTIVA DRIVE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 650 TIMBER BAY CIRCLE W Oldsmar, FL MLS# TB8536069
$310,000
3

Beds

1.0

Baths

924

Sq.Ft.

650 TIMBER BAY CIRCLE W

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
View 1916 HUDSON COURT Oldsmar, FL MLS# TB8528046
  • Virtual Tour
1 of 20
$340,000
3

Beds

2.0

Baths

1,333

Sq.Ft.

1916 HUDSON COURT

Oldsmar, FL

Courtesy of MARK SPAIN REAL ESTATE
View 163 DOLPHIN DRIVE E Oldsmar, FL MLS# TB8535936
  • Adult Community with Virtual Tour
1 of 60
$300,000
2

Beds

2.0

Baths

1,255

Sq.Ft.

163 DOLPHIN DRIVE E

Oldsmar, FL

Courtesy of CONCI, REALTORS
View 205 MARTHA LANE 205 Oldsmar, FL MLS# TB8536581
$189,000
2

Beds

2.0

Baths

1,094

Sq.Ft.

205 MARTHA LANE 205

Oldsmar, FL

Courtesy of KEYS TO THE BAY REAL ESTATE
View 1909 CASTLE BAY COURT Oldsmar, FL MLS# TB8535099
$360,000
3

Beds

2.0

Baths

1,410

Sq.Ft.

1909 CASTLE BAY COURT

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 129 NANCY DRIVE Oldsmar, FL MLS# TB8533834
  • Virtual Tour
1 of 68
$149,900
2

Beds

2.0

Baths

1,094

Sq.Ft.

129 NANCY DRIVE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 366 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# TB8534362
$229,500
2

Beds

2.1

Baths

1,110

Sq.Ft.

366 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

Courtesy of CENTURY 21 INTEGRA
View 204 SHORE DRIVE W Oldsmar, FL MLS# TB8534439
  • Virtual Tour
1 of 18
$299,900
3

Beds

2.0

Baths

1,374

Sq.Ft.

204 SHORE DRIVE W

Oldsmar, FL

Courtesy of DALTON WADE INC
View 613 CHESTNUT STREET Oldsmar, FL MLS# TB8534625
$299,900
5

Beds

4.0

Baths

2,572

Sq.Ft.

613 CHESTNUT STREET

Oldsmar, FL

Courtesy of DALTON WADE INC

About Oldsmar

The Oldsmar area enjoys the distinction of offering the county’s only contiguous land connection to the City of Tampa and Hillsborough County.  Perhaps this “no bridges” location has helped to foster the area’s rapid growth in lovely residential communities. Local attractions include the thoroughbred horse racing at Tampa Bay Downs Race Track, the bargains at Oldsmar Flea Market, and the skating rink at the Tampa Bay Skating Academy.  Housing ranges from spacious single-family homes to executive homes and estates or stately older residences in the heart of town.  The regional Upper Tampa Bay Chamber of Commerce headquartered in Oldsmar also covers the unincorporated communities of Town and Country and Northwest Hillsborough.

Listings in Oldsmar, FL

207

Estimated median home price

$329,000
Oldsmar FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Oldsmar, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Oldsmar, FL.

Homes for Sale by Price in Oldsmar, FL

PriceCount
$0 - 100K2
$100K - 200K54
$200K - 300K40
$300K - 400K39
$400K - 500K27
$500K - 600K15
$600K - 700K8
$700K - 800K6
$800K - 900K2
$900K - 1M3
$1M - Max11

Homes for Sale by Type in Oldsmar, FL

Property TypeCount
Single Family102
Townhouse21
Condo48
Commercial2
Rental41
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home21
Farms0

(Data as of 10/7/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is 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.

Data is updated as of 10/8/2026.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 10/8/2026.