25 total properties
Did you mean the neighborhood Oldsmar?
View 608 TIMBER BAY CIRCLE E Oldsmar, FL MLS# TB8562343
  • Recently Listed with Virtual Tour
1 of 36
$299,000
3

Beds

2.0

Baths

924

Sq.Ft.

608 TIMBER BAY CIRCLE E

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 145 POOLE PLACE Oldsmar, FL MLS# TB8557674
  • Recently Listed with Virtual Tour
1 of 34
$229,995
2

Beds

2.0

Baths

1,380

Sq.Ft.

145 POOLE PLACE

Oldsmar, FL

Courtesy of SOUTH CEDAR REAL ESTATE, INC
View 210 GRETCHEN COURT Oldsmar, FL MLS# TB8550922
  • Virtual Tour
1 of 40
$239,000
2

Beds

2.0

Baths

1,250

Sq.Ft.

210 GRETCHEN COURT

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1925 CASTLE BAY COURT Oldsmar, FL MLS# R4912040
$300,000
3

Beds

2.0

Baths

1,368

Sq.Ft.

1925 CASTLE BAY COURT

Oldsmar, FL

Courtesy of TAMPA HOME SALES, INC.
View 135 PINEWINDS BOULEVARD Oldsmar, FL MLS# S5156711
$239,900
2

Beds

2.0

Baths

1,053

Sq.Ft.

135 PINEWINDS BOULEVARD

Oldsmar, FL

Courtesy of LA ROSA REALTY BEACHES LLC
View 105 LAKESIDE COURT ELW VI UNIT 5 Oldsmar, FL MLS# TB8545064
$230,000
2

Beds

2.0

Baths

1,150

Sq.Ft.

105 LAKESIDE COURT ELW VI UNIT 5

Oldsmar, FL

Courtesy of B & K REAL ESTATE & PROPERTY MANAGEMENT PA
View 215 WOODS LANDING TRAIL Oldsmar, FL MLS# TB8544503
$300,000
3

Beds

2.1

Baths

1,450

Sq.Ft.

215 WOODS LANDING TRAIL

Oldsmar, FL

Courtesy of CENTURY 21 COASTAL ALLIANCE
View 428 PELICAN DRIVE S Oldsmar, FL MLS# TB8544886
  • Adult Community with Virtual Tour
1 of 56
$249,000
2

Beds

2.0

Baths

1,671

Sq.Ft.

428 PELICAN DRIVE S

Oldsmar, FL

Courtesy of CONCI, REALTORS
View 279 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# TB8542613
$275,000
2

Beds

1.1

Baths

1,105

Sq.Ft.

279 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

Courtesy of REAL ESTATE FIRM OF FLORIDA, LLC
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 704 LEMONWOOD DRIVE Oldsmar, FL MLS# TB8534748
  • Virtual Tour
1 of 24
$229,900
2

Beds

2.0

Baths

1,064

Sq.Ft.

704 LEMONWOOD DRIVE

Oldsmar, FL

Courtesy of DALTON WADE 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 407 DOLPHIN DRIVE S Oldsmar, FL MLS# TB8530978
  • Adult Community with Virtual Tour
1 of 47
$247,000
2

Beds

2.0

Baths

1,320

Sq.Ft.

407 DOLPHIN DRIVE S

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 75 POOLE PLACE Oldsmar, FL MLS# TB8527830
  • Virtual Tour
1 of 55
$276,900
2

Beds

2.0

Baths

1,380

Sq.Ft.

75 POOLE PLACE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 60 ST ANDREWS PLACE 60 Oldsmar, FL MLS# TB8526165
$299,900
2

Beds

2.0

Baths

1,626

Sq.Ft.

60 ST ANDREWS PLACE 60

Oldsmar, FL

Courtesy of PROFESSIONAL REAL ESTATE MGMT
View 107 LAKEVIEW PLACE 7 Oldsmar, FL MLS# W7885525
  • Virtual Tour
1 of 30
$224,900
2

Beds

2.0

Baths

1,094

Sq.Ft.

107 LAKEVIEW PLACE 7

Oldsmar, FL

Courtesy of SAMUELSEN BUILDERS REALTY LLC
View 276 PELICAN DRIVE N Oldsmar, FL MLS# TB8510692
  • Adult Community with Virtual Tour
1 of 46
$224,400
2

Beds

2.0

Baths

984

Sq.Ft.

276 PELICAN DRIVE N

Oldsmar, FL

Courtesy of THE SOMERDAY GROUP PL
View 258 PELICAN DRIVE N Oldsmar, FL MLS# TB8508713
  • Adult Community with Virtual Tour
1 of 51
$252,000
3

Beds

2.0

Baths

1,471

Sq.Ft.

258 PELICAN DRIVE N

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 260 MICHAELS CIRCLE Oldsmar, FL MLS# TB8507054
  • Virtual Tour
1 of 44
$250,000
3

Beds

2.0

Baths

1,385

Sq.Ft.

260 MICHAELS CIRCLE

Oldsmar, FL

Courtesy of DASHER RLTY & PROP. MANAGEMENT
View 193 BLUE MARLIN DRIVE Oldsmar, FL MLS# TB8503933
  • Adult Community with Virtual Tour
1 of 41
$255,000
3

Beds

3.0

Baths

1,485

Sq.Ft.

193 BLUE MARLIN DRIVE

Oldsmar, FL

Courtesy of CONCI, REALTORS

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

208

Estimated median home price

$333,500
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 - 200K60
$200K - 300K32
$300K - 400K39
$400K - 500K30
$500K - 600K16
$600K - 700K8
$700K - 800K6
$800K - 900K5
$900K - 1M2
$1M - Max10

Homes for Sale by Type in Oldsmar, FL

Property TypeCount
Single Family101
Townhouse23
Condo51
Commercial2
Rental43
Lots and Land11
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home20
Farms0

(Data as of 10/31/2026)

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 10/31/2026.