183 total properties
Did you mean the neighborhood Oldsmar?
View 1909 CASTLE BAY COURT Oldsmar, FL MLS# TB8535099
  • Recently Listed with Virtual Tour
1 of 53
$365,000
3

Beds

2.0

Baths

1,410

Sq.Ft.

1909 CASTLE BAY COURT

Oldsmar, FL

View 129 NANCY DRIVE Oldsmar, FL MLS# TB8533834
  • Recently Listed with Virtual Tour
1 of 68
$149,900
2

Beds

2.0

Baths

1,094

Sq.Ft.

129 NANCY DRIVE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 366 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# TB8534362
  • Recently Listed with Virtual Tour
1 of 23
$229,500
2

Beds

2.1

Baths

1,110

Sq.Ft.

366 COUNTRYSIDE KEY BOULEVARD

Oldsmar, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 204 SHORE DRIVE W Oldsmar, FL MLS# TB8534439
  • Recently Listed with Virtual Tour
1 of 18
$299,900
3

Beds

2.0

Baths

1,374

Sq.Ft.

204 SHORE DRIVE W

Oldsmar, FL

Courtesy of DALTON WADE INC
View 613 CHESTNUT STREET Oldsmar, FL MLS# TB8534625
  • Recently Listed with Virtual Tour
1 of 9
$299,900
5

Beds

4.0

Baths

2,572

Sq.Ft.

613 CHESTNUT STREET

Oldsmar, FL

Courtesy of DALTON WADE INC
View 704 LEMONWOOD DRIVE Oldsmar, FL MLS# TB8534748
  • Recently Listed with Virtual Tour
1 of 24
$259,900
2

Beds

2.0

Baths

1,064

Sq.Ft.

704 LEMONWOOD DRIVE

Oldsmar, FL

Courtesy of DALTON WADE INC
View 1504 MERLOT COURT Oldsmar, FL MLS# TB8532311
  • Virtual Tour
1 of 55
$355,000
3

Beds

2.1

Baths

1,525

Sq.Ft.

1504 MERLOT COURT

Oldsmar, FL

View 158 BRENT CIRCLE Oldsmar, FL MLS# OM728969
  • Virtual Tour
1 of 67
$530,000
3

Beds

3.0

Baths

1,834

Sq.Ft.

158 BRENT CIRCLE

Oldsmar, FL

Courtesy of FLORIDA REAL ESTATE LIFESTYLES
View 331 SHORE DRIVE E Oldsmar, FL MLS# TB8531357
  • Virtual Tour
1 of 6
$450,000
3

Beds

2.0

Baths

2,064

Sq.Ft.

331 SHORE DRIVE E

Oldsmar, FL

View 407 DOLPHIN DRIVE S Oldsmar, FL MLS# TB8530978
  • Adult Community with Virtual Tour
1 of 34
$247,000
2

Beds

2.0

Baths

1,320

Sq.Ft.

407 DOLPHIN DRIVE S

Oldsmar, FL

View 5250 PINEHURST COURT Oldsmar, FL MLS# TB8529582
$665,000
3

Beds

2.0

Baths

2,074

Sq.Ft.

5250 PINEHURST COURT

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 222 CARYL WAY Oldsmar, FL MLS# TB8530417
  • Virtual Tour
1 of 63
$216,000
2

Beds

2.0

Baths

1,094

Sq.Ft.

222 CARYL WAY

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 80 SUMMERWINDS LANE Oldsmar, FL MLS# TB8529421
  • Virtual Tour
1 of 57
$425,000
3

Beds

2.0

Baths

1,560

Sq.Ft.

80 SUMMERWINDS LANE

Oldsmar, FL

View 208 CLAYS TRAIL 208 Oldsmar, FL MLS# TB8530374
  • Virtual Tour
1 of 39
$399,000
3

Beds

2.0

Baths

1,835

Sq.Ft.

208 CLAYS TRAIL 208

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 450 CYPRESS CREEK CIRCLE Oldsmar, FL MLS# TB8529291
$599,900
3

Beds

2.1

Baths

2,139

Sq.Ft.

450 CYPRESS CREEK CIRCLE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 75 POOLE PLACE Oldsmar, FL MLS# TB8527830
  • Virtual Tour
1 of 55
$279,900
2

Beds

2.0

Baths

1,380

Sq.Ft.

75 POOLE PLACE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 2410 ARCH AVENUE Oldsmar, FL MLS# TB8529492
  • Virtual Tour
1 of 36
$429,500
3

Beds

2.1

Baths

1,888

Sq.Ft.

2410 ARCH AVENUE

Oldsmar, FL

Courtesy of KELLER WILLIAMS TAMPA PROPERTIES
View 102 SHORE DRIVE E Oldsmar, FL MLS# O6425984
  • Virtual Tour
1 of 34
$444,000
3

Beds

2.0

Baths

1,416

Sq.Ft.

102 SHORE DRIVE E

Oldsmar, FL

Courtesy of LPT REALTY, LLC
View 3087 DUANE AVENUE Oldsmar, FL MLS# TB8527948
  • Virtual Tour
1 of 30
$365,000
3

Beds

2.0

Baths

1,296

Sq.Ft.

3087 DUANE AVENUE

Oldsmar, FL

Courtesy of AMERICAN HERITAGE REALTY, INC.
View 416 MAPLEWOOD DRIVE Oldsmar, FL MLS# TB8527873
  • Virtual Tour
1 of 68
$449,000
3

Beds

2.0

Baths

1,395

Sq.Ft.

416 MAPLEWOOD DRIVE

Oldsmar, FL

Courtesy of FUTURE HOME 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

204

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

PriceCount
$0 - 100K1
$100K - 200K49
$200K - 300K41
$300K - 400K39
$400K - 500K23
$500K - 600K17
$600K - 700K9
$700K - 800K4
$800K - 900K4
$900K - 1M1
$1M - Max16

Homes for Sale by Type in Oldsmar, FL

Property TypeCount
Single Family107
Townhouse21
Condo46
Commercial3
Rental52
Lots and Land8
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home19
Farms0

(Data as of 8/19/2026)

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 8/20/2026.

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 8/20/2026.