185 total properties
Did you mean the neighborhood Oldsmar?
View 1637 GRAY BARK DRIVE Oldsmar, FL MLS# TB8440841
$589,988
4

Beds

3.0

Baths

2,146

Sq.Ft.

1637 GRAY BARK DRIVE

Oldsmar, FL

Courtesy of LISA HALL REALTY, INC
View 20 SYLVIA PLACE Oldsmar, FL MLS# TB8439639
$337,000
4

Beds

2.0

Baths

1,550

Sq.Ft.

20 SYLVIA PLACE

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 204 BAY ARBOR BOULEVARD Oldsmar, FL MLS# TB8440310
$639,900
3

Beds

2.0

Baths

2,026

Sq.Ft.

204 BAY ARBOR BOULEVARD

Oldsmar, FL

Courtesy of RE/MAX ACTION FIRST OF FLORIDA
The time to sell is now! THE TIME TO SELL IS NOW!
View 106 DOLPHIN DRIVE E Oldsmar, FL MLS# TB8438561
  • Adult Community with Virtual Tour
1 of 35
$224,000
2

Beds

2.0

Baths

1,092

Sq.Ft.

106 DOLPHIN DRIVE E

Oldsmar, FL

Courtesy of AH REALTY SERVICES, LLC
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 1802 CHINABERRY DRIVE Oldsmar, FL MLS# TB8439498
$389,500
2

Beds

2.0

Baths

1,358

Sq.Ft.

1802 CHINABERRY DRIVE

Oldsmar, FL

Courtesy of FOXX AND ASSOCIATES
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 140 JOANNE PLACE Oldsmar, FL MLS# TB8439226
  • Virtual Tour
1 of 16
$289,900
2

Beds

2.0

Baths

1,250

Sq.Ft.

140 JOANNE PLACE

Oldsmar, FL

Courtesy of COMMUNITY REALTY ASSOCIATES
View 1223 CLAYS TRAIL Oldsmar, FL MLS# TB8436662
  • Virtual Tour
1 of 15
$359,000
4

Beds

2.1

Baths

2,600

Sq.Ft.

1223 CLAYS TRAIL

Oldsmar, FL

Courtesy of REALTY OF RIVERVIEW LLC
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 105 WOODLAKE LANE #105 Oldsmar, FL MLS# TB8438925
$210,900
2

Beds

2.0

Baths

924

Sq.Ft.

105 WOODLAKE LANE #105

Oldsmar, FL

Courtesy of MARC JOSEPH REALTY, INC
View 1654 BAYHILL DRIVE Oldsmar, FL MLS# TB8438417
  • Virtual Tour
1 of 56
$610,000
4

Beds

2.1

Baths

2,320

Sq.Ft.

1654 BAYHILL DRIVE

Oldsmar, FL

Courtesy of ECKERT REALTY & PROPERTY MGMT
View 505 OAKWOOD BOULEVARD Oldsmar, FL MLS# TB8432340
$449,000
4

Beds

2.0

Baths

1,993

Sq.Ft.

505 OAKWOOD BOULEVARD

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 281 CYPRESS LANE #281 Oldsmar, FL MLS# TB8435538
$207,500
2

Beds

2.0

Baths

1,054

Sq.Ft.

281 CYPRESS LANE #281

Oldsmar, FL

Courtesy of UNITED REAL ESTATE SUNCOAST
View 1909 CASTLE BAY COURT Oldsmar, FL MLS# TB8436254
  • Virtual Tour
1 of 52
OPEN HOUSE: Saturday 12/13 3:00 PM - 6:00 PM
$390,000
3

Beds

2.0

Baths

1,410

Sq.Ft.

1909 CASTLE BAY COURT

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM H
View 411 OAKLEAF BOULEVARD #B Oldsmar, FL MLS# TB8434683
$300,000
2

Beds

2.1

Baths

1,360

Sq.Ft.

411 OAKLEAF BOULEVARD #B

Oldsmar, FL

Courtesy of APPLE HOMES CORP
View 5163 PINNACLE DRIVE Oldsmar, FL MLS# TB8435206
  • Virtual Tour
1 of 55
$619,700
3

Beds

2.0

Baths

1,886

Sq.Ft.

5163 PINNACLE DRIVE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 1744 MAPLELEAF BLVD Oldsmar, FL MLS# TB8434852
  • Virtual Tour
1 of 23
$625,000
6

Beds

3.0

Baths

3,124

Sq.Ft.

1744 MAPLELEAF BLVD

Oldsmar, FL

Courtesy of FIRST IN REAL ESTATE SERVICES
View 2044 SHEFFIELD COURT Oldsmar, FL MLS# TB8327277
$190,000
2

Beds

2.0

Baths

1,296

Sq.Ft.

2044 SHEFFIELD COURT

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 315 WOODS LANDING TRAIL Oldsmar, FL MLS# TB8433357
$319,900
2

Beds

2.1

Baths

1,200

Sq.Ft.

315 WOODS LANDING TRAIL

Oldsmar, FL

Courtesy of MIHARA & ASSOCIATES 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 12/8/2025.