Oldsmar Florida Homes for Sale

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198 total properties
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View 2044 SHEFFIELD COURT Oldsmar, FL MLS# TB8542342
  • Recently Listed with Virtual Tour
1 of 26
$249,900
2

Beds

2.0

Baths

1,296

Sq.Ft.

2044 SHEFFIELD COURT

Oldsmar, FL

View 160 LAKEVIEW WAY 160 Oldsmar, FL MLS# TB8540997
  • Recently Listed with Virtual Tour
1 of 36
$169,900
2

Beds

2.0

Baths

1,094

Sq.Ft.

160 LAKEVIEW WAY 160

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 180 TADS TRAIL Oldsmar, FL MLS# TB8541050
  • Virtual Tour
1 of 38
$349,900
3

Beds

2.0

Baths

1,450

Sq.Ft.

180 TADS TRAIL

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 216 HEMINGWAY DRIVE Oldsmar, FL MLS# TB8539671
  • Recently Listed with Virtual Tour
1 of 52
$395,000
3

Beds

2.1

Baths

1,452

Sq.Ft.

216 HEMINGWAY DRIVE

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM HARBOR
View 80 FOXFIRE LANE Oldsmar, FL MLS# TB8540121
  • Recently Listed with Virtual Tour
1 of 75
$719,000
4

Beds

2.0

Baths

2,584

Sq.Ft.

80 FOXFIRE LANE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 416 CYPRESS VIEW DRIVE Oldsmar, FL MLS# TB8542008
  • Recently Listed with Virtual Tour
1 of 53
OPEN HOUSE: Sunday 8/30 1:00 PM - 3:00 PM
$550,000
4

Beds

2.0

Baths

2,069

Sq.Ft.

416 CYPRESS VIEW DRIVE

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM HARBOR
View 819 JACARANDA DRIVE Oldsmar, FL MLS# TB8539896
  • Recently Listed
1 of 34
$425,000
3

Beds

2.0

Baths

1,320

Sq.Ft.

819 JACARANDA DRIVE

Oldsmar, FL

Courtesy of PREMIER SOTHEBY'S INTL REALTY
View 135 WOODLAKE WYNDE 135 Oldsmar, FL MLS# TB8539499
  • Recently Listed with Virtual Tour
1 of 33
$195,000
2

Beds

2.0

Baths

924

Sq.Ft.

135 WOODLAKE WYNDE 135

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 20 EVELYN COURT Oldsmar, FL MLS# TB8539291
  • Recently Listed with Virtual Tour
1 of 74
$229,000
2

Beds

2.0

Baths

1,380

Sq.Ft.

20 EVELYN COURT

Oldsmar, FL

Courtesy of KELLER WILLIAMS ST PETE REALTY
View 200 FAIRFIELD STREET Oldsmar, FL MLS# TB8539338
  • Recently Listed with Virtual Tour
1 of 7
$299,000
2

Beds

1.0

Baths

1,143

Sq.Ft.

200 FAIRFIELD STREET

Oldsmar, FL

Courtesy of SUNSHINE REALTY COMPANY LLC
View 392 COBIA WAY Oldsmar, FL MLS# TB8539760
  • Recently Listed with Virtual Tour
1 of 23
$199,000
2

Beds

2.0

Baths

1,344

Sq.Ft.

392 COBIA WAY

Oldsmar, FL

View 415 MAPLEWOOD CIRCLE Oldsmar, FL MLS# TB8539039
  • Recently Listed with Virtual Tour
1 of 44
$349,900
3

Beds

1.0

Baths

1,583

Sq.Ft.

415 MAPLEWOOD CIRCLE

Oldsmar, FL

View 123 LOBLOLLY COURT A Oldsmar, FL MLS# TB8536224
  • Recently Listed with Virtual Tour
1 of 46
$129,900
2

Beds

2.0

Baths

915

Sq.Ft.

123 LOBLOLLY COURT A

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 4770 PEBBLE BROOK DRIVE Oldsmar, FL MLS# TB8535905
  • Virtual Tour
1 of 26
$549,900
3

Beds

2.0

Baths

1,860

Sq.Ft.

4770 PEBBLE BROOK DRIVE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 1723 CAPTIVA DRIVE Oldsmar, FL MLS# TB8538123
  • Recently Listed with Virtual Tour
1 of 84
$830,700
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
  • Recently Listed
1 of 13
$170,000
2

Beds

2.0

Baths

1,054

Sq.Ft.

219 PALMETTO COURT 219

Oldsmar, FL

View 214 DOLPHIN DRIVE N Oldsmar, FL MLS# TB8538126
  • Recently Listed with Virtual Tour
1 of 46
$259,000
2

Beds

2.0

Baths

1,324

Sq.Ft.

214 DOLPHIN DRIVE N

Oldsmar, FL

View 116 DOLPHIN DRIVE S Oldsmar, FL MLS# TB8537217
  • Recently Listed
1 of 37
$230,000
2

Beds

2.0

Baths

1,090

Sq.Ft.

116 DOLPHIN DRIVE S

Oldsmar, FL

View 508 WASHINGTON AVENUE Oldsmar, FL MLS# TB8537441
  • Recently Listed with Virtual Tour
1 of 50
$489,000
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
  • Recently Listed with Virtual Tour
1 of 8
$1,499,000
Studio

Beds

0.0

Baths

205 CHESTNUT STREET

Oldsmar, FL

Courtesy of SUNSHINE REALTY COMPANY LLC

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

200

Estimated median home price

$337,450
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

Price Count
$0 - 100K 1
$100K - 200K 47
$200K - 300K 40
$300K - 400K 39
$400K - 500K 22
$500K - 600K 19
$600K - 700K 6
$700K - 800K 6
$800K - 900K 4
$900K - 1M 1
$1M - Max 15

Homes for Sale by Type in Oldsmar, FL

Property Type Count
Single Family 104
Townhouse 22
Condo 46
Commercial 3
Rental 52
Lots and Land 7
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 18
Farms 0

(Data as of 8/26/2026)

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 8/27/2026.

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 8/27/2026.