75 total properties
Did you mean the neighborhood Oldsmar?
View 396 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# A4654401
$280,000
2

Beds

2.1

Baths

1,110

Sq.Ft.

396 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

Courtesy of EXP REALTY, LLC
View 2004 SHEFFIELD COURT Oldsmar, FL MLS# TB8443044
$279,999
2

Beds

2.0

Baths

1,296

Sq.Ft.

2004 SHEFFIELD COURT

Oldsmar, FL

Courtesy of KELLER WILLIAMS SOUTH TAMPA
View 50 INGRID PLACE #50 Oldsmar, FL MLS# TB8394672
  • Virtual Tour
1 of 51
$275,000
2

Beds

2.0

Baths

1,380

Sq.Ft.

50 INGRID PLACE #50

Oldsmar, FL

Courtesy of MIHARA & ASSOCIATES INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 207 CLAYS TRAIL #207 Oldsmar, FL MLS# TB8437924
$275,000
2

Beds

2.0

Baths

1,237

Sq.Ft.

207 CLAYS TRAIL #207

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 60 BIRDSONG COURT Oldsmar, FL MLS# TB8398415
$270,000
2

Beds

2.0

Baths

1,053

Sq.Ft.

60 BIRDSONG COURT

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 123 DOLPHIN DRIVE S Oldsmar, FL MLS# TB8447450
  • Adult Community with Virtual Tour
1 of 21
$270,000
2

Beds

2.0

Baths

1,248

Sq.Ft.

123 DOLPHIN DRIVE S

Oldsmar, FL

Courtesy of PAM RYAN REALTY INC
View 215 CORKWOOD LANE Oldsmar, FL MLS# TB8441702
  • Virtual Tour
1 of 88
$265,000
2

Beds

2.0

Baths

900

Sq.Ft.

215 CORKWOOD LANE

Oldsmar, FL

Courtesy of COASTAL PROPERTIES GROUP INTERNATIONAL
View 121 DOLPHIN DRIVE S Oldsmar, FL MLS# TB8370574
  • Adult Community with Virtual Tour
1 of 48
$264,500
2

Beds

2.0

Baths

1,392

Sq.Ft.

121 DOLPHIN DRIVE S

Oldsmar, FL

Courtesy of AH REALTY SERVICES, LLC
View 168 MANTA CIRCLE Oldsmar, FL MLS# TB8449969
  • Recently Listed with Virtual Tour
1 of 35
$252,900
2

Beds

2.0

Baths

1,128

Sq.Ft.

168 MANTA CIRCLE

Oldsmar, FL

Courtesy of AH REALTY SERVICES, LLC
View 416 WOODWARD AVENUE Oldsmar, FL MLS# TB8448302
  • Virtual Tour
1 of 31
$250,000
4

Beds

2.0

Baths

2,420

Sq.Ft.

416 WOODWARD AVENUE

Oldsmar, FL

Courtesy of COLDWELL BANKER REALTY
View 1718 AZALEA COURT #B Oldsmar, FL MLS# P4935316
  • Virtual Tour
1 of 59
$249,999
2

Beds

2.1

Baths

1,285

Sq.Ft.

1718 AZALEA COURT #B

Oldsmar, FL

Courtesy of HUT TEAM REALTY
View 145 BLUE MARLIN DRIVE Oldsmar, FL MLS# TB8345454
  • Adult Community with Virtual Tour
1 of 36
$249,900
3

Beds

2.0

Baths

1,504

Sq.Ft.

145 BLUE MARLIN DRIVE

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
View 250 WOODS LANDING TRAIL Oldsmar, FL MLS# TB8411225
$249,900
2

Beds

2.1

Baths

1,200

Sq.Ft.

250 WOODS LANDING TRAIL

Oldsmar, FL

Courtesy of COMPASS FLORIDA LLC
View 421 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# TB8401283
$249,000
2

Beds

2.1

Baths

1,105

Sq.Ft.

421 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

Courtesy of RED SASH REALTY LLC
View 106 LAKEVIEW PLACE #106 Oldsmar, FL MLS# TB8411641
$249,000
2

Beds

2.0

Baths

1,094

Sq.Ft.

106 LAKEVIEW PLACE #106

Oldsmar, FL

Courtesy of SOUTHERN LIFE REALTY
View 347 CANAL WAY Oldsmar, FL MLS# TB8436926
  • Adult Community with Virtual Tour
1 of 48
$249,000
2

Beds

2.0

Baths

1,080

Sq.Ft.

347 CANAL WAY

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 117 E CYPRESS COURT #117 Oldsmar, FL MLS# TB8443086
$249,000
2

Beds

2.0

Baths

1,054

Sq.Ft.

117 E CYPRESS COURT #117

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 367 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# TB8400747
$245,000
2

Beds

1.1

Baths

1,105

Sq.Ft.

367 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 273 COUNTRYSIDE KEY BOULEVARD #N/A Oldsmar, FL MLS# TB8439412
$245,000
2

Beds

2.1

Baths

1,110

Sq.Ft.

273 COUNTRYSIDE KEY BOULEVARD #N/A

Oldsmar, FL

Courtesy of KELLER WILLIAMS TAMPA PROP.
View 209 CORKWOOD LN Oldsmar, FL MLS# TB8396745
  • Virtual Tour
1 of 32
$244,900
2

Beds

2.0

Baths

900

Sq.Ft.

209 CORKWOOD LN

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY 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

252

Estimated median home price

$389,000
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 - 100K0
$100K - 200K28
$200K - 300K57
$300K - 400K50
$400K - 500K33
$500K - 600K20
$600K - 700K15
$700K - 800K12
$800K - 900K7
$900K - 1M4
$1M - Max26

Homes for Sale by Type in Oldsmar, FL

Property TypeCount
Single Family146
Townhouse33
Condo38
Commercial6
Rental55
Lots and Land13
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home15
Farms0

(Data as of 11/11/2025)

Information deemed reliable but not guaranteed.

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 12/9/2025.