Oldsmar, FL Homes

/59
$589,000

Open Sun 12PM - 2PM $10K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,428 Sq Ft
384 Wingate Cir, Oldsmar, FL 34677

Nestled on a quiet street in the desirable gated community of Bay Arbor, this lovely two-story home offers 3 bedrooms, 2.5 bathrooms, two spacious bonus/great rooms, a 2-car garage, and a spectacular custom pebble tech pool with a stunning stone waterfall, pool pump 2025 and new pool filter 2025. The back yard is completely fenced and backs up to a peaceful conservation. As you enter, you'll be

Denise Denver RE/MAX MARKETING SPECIALISTS

384 Wingate Cir, Oldsmar, FL 34677
/2
$274,000

Sold Apr 08, 2026

529 Jetstar Ln, Oldsmar, FL 34677
- 2 Beds
- 2.5 Baths
- 1,013 Sq Ft
- Built 2017
Last Sold Summary
- $270/SF
- 9 Days On Market
Current Estimated Value $272,443

Last Listing Agent Ginger Tatarzewski FUTURE HOME REALTY INC

529 Jetstar Ln, Oldsmar, FL 34677

/35
Est $479,957

Not Listed For Sale

500 Driftwood Cir W, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,830 Sq Ft
- Built 1972
500 Driftwood Cir W, Oldsmar, FL 34677

Last Sold Summary
- 1 Day On Market

/51
$359,700

$10K PRICE DROP
- 3 Beds
- 2 Baths
- 1,274 Sq Ft
206 Bedford St, Oldsmar, FL 34677

Virtually Staged. Short Sale. This beautifully updated, single-level home offers a smart, open layout with 3 bedrooms, 2 full baths, and a 2-car garage, designed for both everyday living and easy entertaining. Completely renovated in 2022, the interior has been thoughtfully updated and modernized.The main living area features high ceilings and an open floor plan that creates a bright,

Tanja Cisliek FUTURE HOME REALTY INC

206 Bedford St, Oldsmar, FL 34677
/2
$200,000

Sold May 11, 2026

412 Cedar Ridge Ct, Oldsmar, FL 34677
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Built 1984
Last Sold Summary
- $222/SF
- 9 Days On Market
Current Estimated Value $199,129

Last Listing Agent Kerin Clarkin AGILE GROUP REALTY

412 Cedar Ridge Ct, Oldsmar, FL 34677

/55
Est $375,228

Not Listed For Sale

1802 Buttonwood Dr, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,477 Sq Ft
- Built 1972
1802 Buttonwood Dr, Oldsmar, FL 34677

Last Sold Summary
- 7 Days On Market

/49
$299,000

Pending
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
30 Ingrid Place, Oldsmar, FL 34677

Under contract-accepting backup offers. Virtually Staged. This spacious townhome offers generous room sizes for everyday living & standout outdoor space, including a large private patio bordered by lush landscaping for added privacy. With three bedrooms and 2 full baths upstairs, you will enjoy a quiet separation between the sleeping quarters and the main living areas below. The first floor

Cathy McCarthy RE/MAX REALTEC GROUP INC

30 Ingrid Place, Oldsmar, FL 34677
/2
$927,000

Sold Oct 24, 2025

70 Deerpath Dr, Oldsmar, FL 34677
- 4 Beds
- 4.5 Baths
- 4,186 Sq Ft
- Built 1986
Last Sold Summary
- $221/SF
Current Estimated Value $1,004,569

Last Listing Agent Kimberly Janowiak FUTURE HOME REALTY INC

70 Deerpath Dr, Oldsmar, FL 34677

/27
Est $518,510

Not Listed For Sale

414 Maplewood Dr, Oldsmar, FL 34677
- 5 Beds
- 3 Baths
- 2,416 Sq Ft
- Built 1973
414 Maplewood Dr, Oldsmar, FL 34677

Last Sold Summary
- 157 Days On Market

/40
$205,000

$10K PRICE DROP
- 2 Beds
- 2 Baths
- 1,056 Sq Ft
83 Pelican Dr N, Oldsmar, FL 34677

Discover exceptional value in Gull-Aire Village, a vibrant 55+ community, with this meticulously maintained home ready for its next owner. Move right in! this sale includes all furnishings and contents, including a 60-inch TV, for a seamless transition. Enjoy peace of mind with a host of recent upgrades: In March of 2024 a brand-new shingle roof, 11 new hurricane windows, and 11 new solar panels

Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

83 Pelican Dr N, Oldsmar, FL 34677
/2
$705,000

Sold Apr 23, 2026

335 Palmdale Dr, Oldsmar, FL 34677
- 5 Beds
- 3 Baths
- 3,035 Sq Ft
- Built 2001
Last Sold Summary
- 19% Below List Price
- $232/SF
- 105 Days On Market
Current Estimated Value $751,149

Last Listing Agent Troy Walseth KELLER WILLIAMS GULF BEACHES

335 Palmdale Dr, Oldsmar, FL 34677

/2
Est $389,620

Not Listed For Sale

80 Woodridge Ct, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,725 Sq Ft
- Built 1987
80 Woodridge Ct, Oldsmar, FL 34677

Last Sold Summary
- 51 Days On Market

/88
$1,350,000

$150K PRICE DROP Pending
- 4 Beds
- 3 Baths
- 3,850 Sq Ft
2151 Diamond Ct, Oldsmar, FL 34677

Under contract-accepting backup offers. Welcome to 2151 Diamond Court ~ Where luxury meets everyday comfort and style. This beautifully updated residence in the exclusive, gated community of Diamond Crest at East Lake Woodlands offers stunning water and conservation views and a thoughtfully designed 3-way split floor plan with a dedicated front office.From the moment you step inside, you’ll

Michelle Johncola RE/MAX ELITE REALTY

2151 Diamond Ct, Oldsmar, FL 34677
/2
$505,000

Sold Jun 26, 2025

1765 Oak Pond Ct, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,990 Sq Ft
- Built 2000
Last Sold Summary
- 1% Below List Price
- $254/SF
- 20 Days On Market
Current Estimated Value $514,955

Last Listing Agent Bill Christopoulos SEAN DANIEL GALARIS

1765 Oak Pond Ct, Oldsmar, FL 34677

/2
Est $385,216

Not Listed For Sale

245 Woodridge Cir, Oldsmar, FL 34677
- 3 Beds
- 2.5 Baths
- 1,700 Sq Ft
- Built 1987
245 Woodridge Cir, Oldsmar, FL 34677

Last Sold Summary
- 91 Days On Market

/45
$150,000

$82K PRICE DROP Pending
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
472 Trout Ln, Oldsmar, FL 34677

Gull-Aire Village. 55+ community. Welcome to this 1998 Jacobsen home, built to newer standards and offering the perfect blend of comfort and convenience. This spacious residence features a desirable split floor plan with three bedrooms, providing ample privacy for family or guests. The chef’s kitchen is a true highlight, boasting high-quality Kraft Maid Cabinetry with custom pull-outs for

Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

472 Trout Ln, Oldsmar, FL 34677
/2
$572,500

Sold Apr 15, 2026

1703 Bayhill Dr, Oldsmar, FL 34677
- 4 Beds
- 2.5 Baths
- 1,963 Sq Ft
- Built 1994
Last Sold Summary
- 1% Below List Price
- $292/SF
- 4 Days On Market
Current Estimated Value $567,559

Last Listing Agent Vanessa Leonard KELLER WILLIAMS REALTY- PALM HARBOR

1703 Bayhill Dr, Oldsmar, FL 34677

/3
Est $394,204

Not Listed For Sale

255 Woodridge Cir, Oldsmar, FL 34677
- 3 Beds
- 2.5 Baths
- 1,700 Sq Ft
- Built 1987
255 Woodridge Cir, Oldsmar, FL 34677

Last Sold Summary

/46
$565,000
- 3 Beds
- 2 Baths
- 2,065 Sq Ft
854 Christina Cir, Oldsmar, FL 34677

Welcome to Bays End, a hidden gem community offering a peaceful setting with convenient access to everything the area has to offer. This well-maintained 3-bedroom, 2-bathroom home features a spacious and inviting layout. Enter to an open living room that flows into the dining area. The updated kitchen showcases beautiful cabinetry, generous storage, and plenty of workspace. The heart of the home

Joseph Koebel RE/MAX REALTEC GROUP INC

854 Christina Cir, Oldsmar, FL 34677
/2
$750,000

Sold Nov 25, 2025

4992 Augusta Ave, Oldsmar, FL 34677
- 3 Beds
- 3 Baths
- 2,292 Sq Ft
- Built 1994
Last Sold Summary
- $327/SF
- 2 Days On Market
Current Estimated Value $755,820

Last Listing Agent Pat Kaylor PAT KAYLOR PROPERTIES, INC.

4992 Augusta Ave, Oldsmar, FL 34677

/59
Est $398,750

Not Listed For Sale

50 Woodridge Cir, Oldsmar, FL 34677
- 3 Beds
- 3 Baths
- 1,820 Sq Ft
- Built 1984
50 Woodridge Cir, Oldsmar, FL 34677

Last Sold Summary
- 6 Days On Market

/30
$629,000

$40K PRICE DROP
- 4 Beds
- 3 Baths
- 2,587 Sq Ft
4007 Palm Key Ave, Oldsmar, FL 34677

Walk in the front door and look straight out to the water. Head out to the screened-in back porch to hang out and enjoy the views, from dolphins and mother duck with her ducklings, to the pink & orange glowing sunsets. This unit comes with floodplain X zoning tied to the title, which means you’re grandfathered in, and the cheap flood insurance is transferable to you (less than $800/yr.). Soaring

JACOB GROSS CHARLES RUTENBERG REALTY INC

4007 Palm Key Ave, Oldsmar, FL 34677
/2
$670,000

Sold Aug 08, 2025

5156 Pinnacle Dr, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,972 Sq Ft
- Built 1994
Last Sold Summary
- 1% Below List Price
- $340/SF
- 25 Days On Market
Current Estimated Value $673,519

Last Listing Agent Angie Clark WIKLE INCORPORATED

5156 Pinnacle Dr, Oldsmar, FL 34677

/2
Est $397,973

Not Listed For Sale

30 Woodridge Cir, Oldsmar, FL 34677
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
- Built 1984
30 Woodridge Cir, Oldsmar, FL 34677

Last Sold Summary
- 49 Days On Market

/2
Price To Be Determined

New Construction
- 3 Beds
- 3.5 Baths
- 2,341 Sq Ft
Alto Plan at Odeon Square, Oldsmar, FL 34677

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DRB Homes Builder

504 St Petersburg Dr St E Unit 40570367, Oldsmar, FL 34677
/2
$485,000

Sold May 29, 2026

420 Cypress View Dr, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,870 Sq Ft
- Built 1998
Last Sold Summary
- $259/SF
- 2 Days On Market
Current Estimated Value $530,737

Last Listing Agent Jeffrey Borham EXP REALTY LLC

420 Cypress View Dr, Oldsmar, FL 34677

/2
Est $357,241

Not Listed For Sale

20 Woodridge Cir, Oldsmar, FL 34677
- 2 Beds
- 2 Baths
- 1,883 Sq Ft
- Built 1984
20 Woodridge Cir, Oldsmar, FL 34677

Last Sold Summary
- 3 Days On Market

/61
$635,000
- 3 Beds
- 2 Baths
- 1,886 Sq Ft
5163 Pinnacle Dr, Oldsmar, FL 34677

Offering over $23,000 in upgrades! Located in X Flood Zone with no flood insurance required, this beautifully maintained residence offers one of the best values currently available in the highly sought-after gated golf community of East Lake Woodlands. This is one of the newer homes in the community and an exceptional opportunity to own a high-quality property at one of the lowest entry points in

Jenny Neumeyer KELLER WILLIAMS REALTY- PALM HARBOR

5163 Pinnacle Dr, Oldsmar, FL 34677
/2
$520,000

Sold Sep 25, 2025

1600 Gray Bark Dr, Oldsmar, FL 34677
- 4 Beds
- 2.5 Baths
- 2,270 Sq Ft
- Built 1996
Last Sold Summary
- 17% Below List Price
- $229/SF
- 223 Days On Market
Current Estimated Value $565,386

Last Listing Agent Noah Rich PINEYWOODS REALTY LLC

1600 Gray Bark Dr, Oldsmar, FL 34677

/27
Est $275,090

Not Listed For Sale

50 Lance Ct, Oldsmar, FL 34677
- 2 Beds
- 2 Baths
- 1,250 Sq Ft
- Built 1981
50 Lance Ct, Oldsmar, FL 34677

Last Sold Summary
- 75 Days On Market

/19
$129,000

Pending
- 2 Beds
- 2 Baths
- 1,054 Sq Ft
201 Palmetto Ct Unit 21, Oldsmar, FL 34677

Welcome to this beautiful 2 bedroom, 2 bathroom condominium located in the heart of desirable Oldsmar. This inviting home features an open-concept layout perfect for comfortable everyday living and entertaining. The spacious living and dining areas flow seamlessly to a private screened back porch, creating the ideal spot to relax and enjoy the Florida lifestyle. The kitchen is equipped with sleek

Nisim Korkus HIGHLIGHT REALTY CORP/LW

201 Palmetto Ct Unit 21, Oldsmar, FL 34677
/2
$150,000

Sold Jun 05, 2026

106 W Cypress Ct Unit 106, Oldsmar, FL 34677
- 2 Beds
- 2 Baths
- 1,054 Sq Ft
- Built 1980
Last Sold Summary
- 9% Below List Price
- $142/SF
- 8 Days On Market
Current Estimated Value $185,518

Last Listing Agent Stacy Kitchell ENGEL & VOELKERS UPPER TAMPA BAY

106 W Cypress Ct Unit 106, Oldsmar, FL 34677

/2
Est $279,267

Not Listed For Sale

170 Ashley Ln, Oldsmar, FL 34677
- 2 Beds
- 2 Baths
- 1,250 Sq Ft
- Built 1981
170 Ashley Ln, Oldsmar, FL 34677

Last Sold Summary
- 7 Days On Market

/60
$760,000

$25K PRICE DROP
- 4 Beds
- 3 Baths
- 2,652 Sq Ft
4761 Stonebriar Dr, Oldsmar, FL 34677

Back on the Market.....PASSED 4point and Wind Mitigation. This is Florida luxury living at its finest in one of the area’s most desirable gated communities. Exclusive executive home located in the highly sought-after Stonebriar community within East Lake Woodlands, a desirable gated golf club community. Zoned for top-rated schools and ideally situated less than 30 minutes from Tampa International

Nichole Gaytan PRIME INT'L REAL ESTATE GROUP

4761 Stonebriar Dr, Oldsmar, FL 34677
/2
$563,000

Sold Oct 03, 2025

632 Lake Cypress Cir, Oldsmar, FL 34677
- 4 Beds
- 2 Baths
- 1,906 Sq Ft
- Built 1998
Last Sold Summary
- 4% Below List Price
- $295/SF
- 111 Days On Market
Current Estimated Value $569,341

Last Listing Agent Don Moore KELLER WILLIAMS REALTY- PALM HARBOR

632 Lake Cypress Cir, Oldsmar, FL 34677

/2
Est $367,657

Not Listed For Sale

60 Ashley Ln, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,850 Sq Ft
- Built 1981
60 Ashley Ln, Oldsmar, FL 34677

Last Sold Summary
- 71 Days On Market

/29
$385,000
- 3 Beds
- 2 Baths
- 1,293 Sq Ft
416 Country Club Dr, Oldsmar, FL 34677

Nestled in the highly deisrable City of Oldsmar, this home has been tastefuly renovated. You'll love the updated kitchen with new stainless steel appliances, stone counter top and lovely build in desk. This modern kitchen has beautiful black cabinets, double sink, new range, refrigerator, dishwasher, and microwave. There are new ceiling fans throughout the home and plenty of decorator lighting.

Jenny Meers MURRAY BELL REAL ESTATE LLC

416 Country Club Dr, Oldsmar, FL 34677
/2
$160,000

Sold Jul 17, 2025

601 Park Blvd, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,080 Sq Ft
- Built 1948
Last Sold Summary
- 36% Below List Price
- $148/SF
- 72 Days On Market
Current Estimated Value $226,790

Last Listing Agent Ginger Tatarzewski FUTURE HOME REALTY INC

601 Park Blvd, Oldsmar, FL 34677

/56
Est $326,931

Not Listed For Sale

50 Ashley Ln, Oldsmar, FL 34677
- 3 Beds
- 2 Baths
- 1,745 Sq Ft
- Built 1981
50 Ashley Ln, Oldsmar, FL 34677

Last Sold Summary
- 2 Days On Market

/57
$615,000
- 3 Beds
- 2.5 Baths
- 2,452 Sq Ft
586 Kingsmill Ct, Oldsmar, FL 34677

Virtually Staged. Welcome to this inviting single-family home in the sought-after Kingsmill neighborhood of East Lake Woodlands—a premier gated community celebrated for its security, lush Florida landscapes, and vibrant lifestyle. Offering 2,453 square feet of living space, this beautifully updated residence features a grand total of three bedrooms, two full bathrooms, and a modernized half bath.

Susanne Jones REDFIN CORPORATION

586 Kingsmill Ct, Oldsmar, FL 34677

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Florida Pinellas County Oldsmar

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Oldsmar, FL Homes

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