154 total properties
Did you mean the neighborhood Oldsmar?
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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.
View 300 DOUGLAS ROAD W Oldsmar, FL MLS# TB8434164
$450,000
Studio

Beds

0.0

Baths

300 DOUGLAS ROAD W

Oldsmar, FL

Courtesy of LPT REALTY, LLC
View 646 TIMBER BAY CIRCLE W Oldsmar, FL MLS# W7879421
$409,000
3

Beds

2.0

Baths

1,554

Sq.Ft.

646 TIMBER BAY CIRCLE W

Oldsmar, FL

Courtesy of RE/MAX CHAMPIONS
View 260 BALSAM DRIVE Oldsmar, FL MLS# TB8433742
  • Virtual Tour
1 of 25
$289,900
2

Beds

2.0

Baths

1,250

Sq.Ft.

260 BALSAM DRIVE

Oldsmar, FL

Courtesy of MARC JOSEPH REALTY, INC
View 2007 PALM KEY AVENUE Oldsmar, FL MLS# TB8430845
$479,900
3

Beds

2.1

Baths

1,888

Sq.Ft.

2007 PALM KEY AVENUE

Oldsmar, FL

Courtesy of BHHS FLORIDA PROPERTIES GROUP
View 115 PALMETTO COURT #115 Oldsmar, FL MLS# TB8432105
$164,000
2

Beds

2.0

Baths

1,054

Sq.Ft.

115 PALMETTO COURT #115

Oldsmar, FL

Courtesy of TAYLORMADE PROPERTIES, INC.
View 256 CYPRESS LANE Oldsmar, FL MLS# TB8417068
  • Virtual Tour
1 of 31
$179,000
2

Beds

2.0

Baths

1,053

Sq.Ft.

256 CYPRESS LANE

Oldsmar, FL

Courtesy of SMITH & ASSOCIATES REAL ESTATE
View 129 WOODLAKE WYNDE #129 Oldsmar, FL MLS# TB8426049
$223,500
2

Beds

2.0

Baths

924

Sq.Ft.

129 WOODLAKE WYNDE #129

Oldsmar, FL

Courtesy of BILTMORE GROUP INC
View 1915 DOVER COURT Oldsmar, FL MLS# TB8430739
  • Virtual Tour
1 of 24
$380,000
4

Beds

2.0

Baths

1,401

Sq.Ft.

1915 DOVER COURT

Oldsmar, FL

Courtesy of REDFIN CORPORATION
View 887 LUCAS LANE Oldsmar, FL MLS# TB8430489
  • Virtual Tour
1 of 38
$469,900
3

Beds

2.0

Baths

1,610

Sq.Ft.

887 LUCAS LANE

Oldsmar, FL

Courtesy of LIPPLY REAL ESTATE
View 504 CABERNET WAY Oldsmar, FL MLS# TB8430681
$344,000
3

Beds

2.1

Baths

1,525

Sq.Ft.

504 CABERNET WAY

Oldsmar, FL

Courtesy of ELITE TAMPA BAY REALTY LLC
View 100 INGRID PLACE Oldsmar, FL MLS# TB8427672
  • Virtual Tour
1 of 51
$299,000
3

Beds

2.1

Baths

1,755

Sq.Ft.

100 INGRID PLACE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 206 CARYL WAY #1 Oldsmar, FL MLS# TB8427572
  • Virtual Tour
1 of 15
$224,900
2

Beds

2.0

Baths

948

Sq.Ft.

206 CARYL WAY #1

Oldsmar, FL

Courtesy of VITA LUXURY REALTY LLC
View 271 HEMINGWAY DRIVE Oldsmar, FL MLS# TB8426952
  • Virtual Tour
1 of 31
$410,000
3

Beds

2.1

Baths

1,452

Sq.Ft.

271 HEMINGWAY DRIVE

Oldsmar, FL

Courtesy of COLDWELL BANKER REALTY

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.