239 total properties
Did you mean the neighborhood Oldsmar?
View 114 CLAYS TRAIL 114 Oldsmar, FL MLS# TB8379057
$329,900
3

Beds

2.0

Baths

1,668

Sq.Ft.

114 CLAYS TRAIL 114

Oldsmar, FL

Courtesy of ADVANCED REALTY GROUP INC
View 1803 ELMWOOD DRIVE Oldsmar, FL MLS# TB8461337
$325,000
2

Beds

2.0

Baths

1,290

Sq.Ft.

1803 ELMWOOD DRIVE

Oldsmar, FL

Courtesy of EXP REALTY LLC
View 807 JACARANDA DRIVE Oldsmar, FL MLS# TB8490680
  • Virtual Tour
1 of 17
$325,000
3

Beds

2.0

Baths

1,341

Sq.Ft.

807 JACARANDA DRIVE

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 634 TIMBER BAY CIRCLE W Oldsmar, FL MLS# TB8489706
  • Recently Listed with Virtual Tour
1 of 27
OPEN HOUSE: Saturday 4/18 1:00 PM - 3:00 PM
$324,900
3

Beds

2.0

Baths

1,056

Sq.Ft.

634 TIMBER BAY CIRCLE W

Oldsmar, FL

Courtesy of AMERICAN HERITAGE REALTY, INC.
View 1206 SAWGRASS COURT Oldsmar, FL MLS# TB8449708
  • Virtual Tour
1 of 10
$323,000
3

Beds

2.0

Baths

1,204

Sq.Ft.

1206 SAWGRASS COURT

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 0 ST PETERSBURG DRIVE Oldsmar, FL MLS# U8068220
$320,000
Studio

Beds

0.0

Baths

0 ST PETERSBURG DRIVE

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
View 0 ST PETERSBURG DRIVE Oldsmar, FL MLS# U8107571
$320,000

0 ST PETERSBURG DRIVE

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
View 108 DOLPHIN DRIVE E Oldsmar, FL MLS# TB8482185
  • Adult Community with Virtual Tour
1 of 32
$319,000
3

Beds

2.0

Baths

1,372

Sq.Ft.

108 DOLPHIN DRIVE E

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 208 HEMINGWAY DRIVE Oldsmar, FL MLS# TB8490712
  • Recently Listed with Virtual Tour
1 of 36
$314,900
2

Beds

2.0

Baths

1,207

Sq.Ft.

208 HEMINGWAY DRIVE

Oldsmar, FL

Courtesy of RE/MAX MARKETING SPECIALISTS
View 215 CLAYS TRAIL 215 Oldsmar, FL MLS# TB8452814
  • Virtual Tour
1 of 29
OPEN HOUSE: Saturday 4/18 11:00 AM - 1:30 PM
$305,000
2

Beds

2.0

Baths

1,237

Sq.Ft.

215 CLAYS TRAIL 215

Oldsmar, FL

Courtesy of RE/MAX COLLECTIVE
View 308 Congress STREET Oldsmar, FL MLS# U8233209
$300,000
3

Beds

2.0

Baths

1,446

Sq.Ft.

308 Congress STREET

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 163 DOLPHIN DRIVE E Oldsmar, FL MLS# TB8357645
  • Adult Community with Virtual Tour
1 of 28
$299,999
3

Beds

2.0

Baths

1,255

Sq.Ft.

163 DOLPHIN DRIVE E

Oldsmar, FL

Courtesy of BLAKE REAL ESTATE INC
View STRATHMORE AVENUE Oldsmar, FL MLS# TB8396827
  • Virtual Tour
1 of 27
$299,000
Studio

Beds

0.0

Baths

STRATHMORE AVENUE

Oldsmar, FL

Courtesy of ALIGN RIGHT REALTY CARROLLWOOD
View 40 SYLVIA PLACE Oldsmar, FL MLS# TB8487410
  • Recently Listed with Virtual Tour
1 of 40
$299,000
3

Beds

2.0

Baths

1,385

Sq.Ft.

40 SYLVIA PLACE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 645 TIMBER BAY CIRCLE E Oldsmar, FL MLS# TB8443970
$295,000
3

Beds

2.0

Baths

1,274

Sq.Ft.

645 TIMBER BAY CIRCLE E

Oldsmar, FL

Courtesy of MARK SPAIN REAL ESTATE
View 209 HEMINGWAY DRIVE Oldsmar, FL MLS# TB8483445
$294,900
2

Beds

2.0

Baths

1,086

Sq.Ft.

209 HEMINGWAY DRIVE

Oldsmar, FL

Courtesy of SMITH & ASSOCIATES REAL ESTATE
View 1203 CLAYS TRAIL 406 Oldsmar, FL MLS# W7871895
  • Virtual Tour
1 of 49
$285,000
2

Beds

2.0

Baths

1,910

Sq.Ft.

1203 CLAYS TRAIL 406

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 140 JOANNE PLACE Oldsmar, FL MLS# TB8439226
  • Virtual Tour
1 of 16
$284,900
2

Beds

2.0

Baths

1,250

Sq.Ft.

140 JOANNE PLACE

Oldsmar, FL

Courtesy of COMMUNITY REALTY ASSOCIATES
View 235 WOODS LANDING TRAIL 235 Oldsmar, FL MLS# TB8474969
$279,900
2

Beds

2.0

Baths

1,201

Sq.Ft.

235 WOODS LANDING TRAIL 235

Oldsmar, FL

Courtesy of SOUTHERN LIFE REALTY
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

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

239

Estimated median home price

$382,000
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 - 100K1
$100K - 200K42
$200K - 300K45
$300K - 400K45
$400K - 500K29
$500K - 600K21
$600K - 700K14
$700K - 800K6
$800K - 900K8
$900K - 1M4
$1M - Max24

Homes for Sale by Type in Oldsmar, FL

Property TypeCount
Single Family131
Townhouse31
Condo40
Commercial4
Rental41
Lots and Land11
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home21
Farms0

(Data as of 4/13/2026)

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 4/14/2026.