Homes with Pools for Sale in Oldsmar, FL

114 homes + 1 early access

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Oldsmar, FL:
PRICED TO SELL!!! Welcome to your dream home nestled in the coveted Cross Creek of Eastlake Woodlands, where tranquil living meets modern convenience! This charming 3-bedroom, 2-bathroom house is a true gem, boasting stunning water views that will take your breath away. As you step inside, you’ll be greeted by tall, soaring ceilings and a light-filled living space that seamlessly blends modern aesthetics with cozy charm. The heart of this home is undoubtedly the kitchen, featuring beautiful wood cabinets equipped with convenient pullout shelves and exquisite Corian countertops, perfect for culinary adventures or casual gatherings with family and friends. The spacious living area is a

$499,999

3 beds2 baths1,890 sq ft

1469 Riverdale Dr, Oldsmar, FL 34677

Corian countertops • Walk-in shower • Walk-in bath

ABOUT THIS HOME
Home with a Pool for sale in Oldsmar, FL:
Virtually Staged. Virtually Staged. Welcome Home to this first floor 2 bedroom, 2 bath condo in Woodlake Run in East Lake Woodlands. Large open living/dining area with wood-like flooring and sliders to screened in Lanai. Tranquil wooded views with no rear neighbors. Nice open Kitchen off of dining area with stainless steel appliances, lots of cabinets and breakfast bar seating. Covered porch off of the kitchen with laundry closet & washer/dryer. Large Primary Bedroom with adjoining bath, step-in shower, 2 closets and a private slider to covered Lanai. 2nd Bedroom with private slider to covered porch and adjacent bath features step-in shower. New windows in 2021 along with new electric

$195,000

2 beds2 baths924 sq ft

135 Woodlake Wynde #135, Oldsmar, FL 34677

Covered porch • Wooded views • First floor condo

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Oldsmar, FL:
BACK ON THE MARKET SELLER FINANCING FELL THROUGH. Exceptional GROUND-FLOOR CORNER UNIT with Resort-Style living AT WOODLAKE RUN! Welcome home to this DESIRABLE 2-BEDROOM, 2-BATHROOM condo offering effortless ONE-LEVEL MAINTENANCE-FREE LIVING in the premier gated community of East Lake Woodlands! Boasting 924 SQ FT OF LIGHT-FILLED LIVING SPACE, this prime END-UNIT LOCATION features an OPEN FLOOR PLAN, modern WOOD LAMINATE AND TILE FLOORING throughout (NO CARPET!), and a bright LIVING/DINING ROOM COMBO ideal for entertaining. Enjoy total peace of mind with recent high-value updates including a New electrical panel (2026), 2023 A/C SYSTEM for ultimate energy efficiency, a BRAND-NEW DISHWASHER,

$188,000

2 beds2 baths924 sq ft

10 Woodlake Pl, Oldsmar, FL 34677

Open floor plan • Community pool • End-unit location

ABOUT THIS HOME
Home with a Pool for sale in Oldsmar, FL:
Welcome to this beautiful 2-bedroom, 2-bathroom ground-floor condo in the highly sought-after East Lake Woodlands community. Built in 1979 with durable masonry construction and a slab foundation, this charming residence offers the perfect blend of comfort, character, and convenience. Enjoy peaceful pond views from the rear of the home while being surrounded by the outstanding amenities this master-planned community has to offer, including golf courses, nature trails, swimming pools, and a clubhouse. Ideally located between Hillsborough and Pinellas Counties, you'll have easy access to an incredible selection of shopping, dining, entertainment, and Gulf Coast attractions. Inside, timeless el

$189,000

2 beds2 baths1,094 sq ft

205 Martha Ln #205, Oldsmar, FL 34677

Clubhouse • Swimming pools • Golf courses

ABOUT THIS HOME
Home with a Pool for sale in Oldsmar, FL:
One look and you'll be sold! This beautifully maintained, move-in-ready villa offers the perfect combination of comfort, privacy, and convenience. Featuring three bedrooms, two bathrooms, and an attached two-car garage, this home is sure to check all the boxes. Step inside to a spacious Great Room with soaring cathedral ceilings and a cozy wood-burning fireplace, creating the perfect space for relaxing or entertaining. The home's thoughtful layout and meticulous upkeep make it truly move-in ready. One of this property's most outstanding features is its premium location on one of the most private lots in all of East Lake Woodlands. With no rear neighbors, you'll enjoy exceptional privacy whi

$425,000

3 beds2 baths1,560 sq ft

80 Summerwinds Ln, Oldsmar, FL 34677

Wooded preserve • Premium location • No rear neighbors

Property at 214 Dolphin Dr N, Oldsmar, FL 34677, 2 beds, 2 baths

$259,000

2 beds2 baths1,324 sq ft

214 Dolphin Dr N, Oldsmar, FL 34677

Property at 402 Shore Dr W, Oldsmar, FL 34677, 4 beds, 2.5 baths

$725,000

4 beds2.5 baths1,711 sq ft

402 Shore Dr W, Oldsmar, FL 34677

Property at 219 Palmetto Ct #219, Oldsmar, FL 34677, 2 beds, 2 baths

$170,000

2 beds2 baths1,054 sq ft

219 Palmetto Ct #219, Oldsmar, FL 34677

Property at 1404 East Lake Woodlands Pkwy, Oldsmar, FL 34677, 4 beds, 3 baths

$1,100,000

4 beds3 baths4,312 sq ft

1404 East Lake Woodlands Pkwy, Oldsmar, FL 34677

Property at 123 Loblolly Ct Unit A, Oldsmar, FL 34677, 2 beds, 2 baths

$129,900

2 beds2 baths915 sq ft

123 Loblolly Ct Unit A, Oldsmar, FL 34677

Property at 4931 Turtle Creek Trl, Oldsmar, FL 34677, 4 beds, 3 baths

$1,055,000

4 beds3 baths3,189 sq ft

4931 Turtle Creek Trl, Oldsmar, FL 34677

Property at 230 Balsam Dr, Oldsmar, FL 34677, 2 beds, 2 baths

$225,000

2 beds2 baths1,250 sq ft

230 Balsam Dr, Oldsmar, FL 34677

Property at 208 Clays Trl #208, Oldsmar, FL 34677, 3 beds, 2 baths

$399,000

3 beds2 baths1,835 sq ft

208 Clays Trl #208, Oldsmar, FL 34677

Property at 366 Countryside Key Blvd, Oldsmar, FL 34677, 2 beds, 2.5 baths

$229,500

2 beds2.5 baths1,110 sq ft

366 Countryside Key Blvd, Oldsmar, FL 34677

Property at 2013 Sunset Wind Loop, Oldsmar, FL 34677, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths1,667 sq ft

2013 Sunset Wind Loop, Oldsmar, FL 34677

Property at 75 Poole Pl, Oldsmar, FL 34677, 2 beds, 2 baths

$279,900

2 beds2 baths1,380 sq ft

75 Poole Pl, Oldsmar, FL 34677

Property at 158 Brent Cir, Oldsmar, FL 34677, 3 beds, 3 baths

$510,000

3 beds3 baths1,834 sq ft

158 Brent Cir, Oldsmar, FL 34677

Property at 112 Lakeview Pl #12, Oldsmar, FL 34677, 2 beds, 2 baths

$169,000

2 beds2 baths1,094 sq ft

112 Lakeview Pl #12, Oldsmar, FL 34677

Property at 123 Loblolly Ct Unit B, Oldsmar, FL 34677, 2 beds, 2 baths

$110,000

2 beds2 baths915 sq ft

123 Loblolly Ct Unit B, Oldsmar, FL 34677

Property at 85 Kelleys Trl, Oldsmar, FL 34677, 5 beds, 3 baths

$1,100,000

5 beds3 baths3,390 sq ft

85 Kelleys Trl, Oldsmar, FL 34677

Property at 900 Lucas Ln, Oldsmar, FL 34677, 3 beds, 2 baths

$495,000

3 beds2 baths1,685 sq ft

900 Lucas Ln, Oldsmar, FL 34677

Property at 470 Hickorynut Ave, Oldsmar, FL 34677, 4 beds, 2.5 baths

$739,000

4 beds2.5 baths2,922 sq ft

470 Hickorynut Ave, Oldsmar, FL 34677

Property at 190 Water Oak Way, Oldsmar, FL 34677, 3 beds, 2.5 baths

$619,990

3 beds2.5 baths2,061 sq ft

190 Water Oak Way, Oldsmar, FL 34677

Property at 407 Dolphin Dr S, Oldsmar, FL 34677, 2 beds, 2 baths

$247,000

2 beds2 baths1,320 sq ft

407 Dolphin Dr S, Oldsmar, FL 34677

Property at 260 Michaels Cir, Oldsmar, FL 34677, 3 beds, 2 baths

$260,000

3 beds2 baths1,385 sq ft

260 Michaels Cir, Oldsmar, FL 34677

Property at 222 Caryl Way, Oldsmar, FL 34677, 2 beds, 2 baths

$204,000

2 beds2 baths1,094 sq ft

222 Caryl Way, Oldsmar, FL 34677

Property at 380 Rosalind Ln, Oldsmar, FL 34677, 3 beds, 2.5 baths

$599,000

3 beds2.5 baths2,423 sq ft

380 Rosalind Ln, Oldsmar, FL 34677

Property at 10 Arbor Ln, Oldsmar, FL 34677, 4 beds, 2 baths

$669,000

4 beds2 baths2,318 sq ft

10 Arbor Ln, Oldsmar, FL 34677

Property at 10 Lesley Ln, Oldsmar, FL 34677, 2 beds, 2 baths

$288,000

2 beds2 baths1,250 sq ft

10 Lesley Ln, Oldsmar, FL 34677

Property at 115 Windward Pl #15, Oldsmar, FL 34677, 2 beds, 2 baths

$180,000

2 beds2 baths879 sq ft

115 Windward Pl #15, Oldsmar, FL 34677

Property at 60 ST Andrews Pl #60, Oldsmar, FL 34677, 2 beds, 2 baths

$299,900

2 beds2 baths1,626 sq ft

60 ST Andrews Pl #60, Oldsmar, FL 34677

Property at 94 Sugar Bear Dr #55, Safety Harbor, FL 34695, 2 beds, 2 baths

$139,000

2 beds2 baths1,040 sq ft

94 Sugar Bear Dr #55, Safety Harbor, FL 34695

Property at 2328 Warwick Dr, Oldsmar, FL 34677, 4 beds, 3.5 baths

$829,000

4 beds3.5 baths3,294 sq ft

2328 Warwick Dr, Oldsmar, FL 34677

Property at 1795 Bayhill Dr, Oldsmar, FL 34677, 3 beds, 2 baths

$499,900

3 beds2 baths1,844 sq ft

1795 Bayhill Dr, Oldsmar, FL 34677

Property at 193 Blue Marlin Dr, Oldsmar, FL 34677, 3 beds, 3 baths

$300,000

3 beds3 baths1,485 sq ft

193 Blue Marlin Dr, Oldsmar, FL 34677

Property at 163 Dolphin Dr E, Oldsmar, FL 34677, 2 beds, 2 baths

$300,000

2 beds2 baths1,255 sq ft

163 Dolphin Dr E, Oldsmar, FL 34677

Property at 410 Dolphin Dr S, Oldsmar, FL 34677, 2 beds, 2 baths

$175,000

2 beds2 baths1,266 sq ft

410 Dolphin Dr S, Oldsmar, FL 34677

Property at 2034 Montego Ct, Oldsmar, FL 34677, 1 bed, 1 bath

$214,900

1 bed1 bath1,024 sq ft

2034 Montego Ct, Oldsmar, FL 34677

Property at 119 Brent Cir, Oldsmar, FL 34677, 3 beds, 3 baths

$525,000

3 beds3 baths1,834 sq ft

119 Brent Cir, Oldsmar, FL 34677

Property at 126 Cypress Ct #26, Oldsmar, FL 34677, 2 beds, 2 baths

$184,900

2 beds2 baths1,054 sq ft

126 Cypress Ct #26, Oldsmar, FL 34677

Property at 133 Sabal Ct Unit G, Oldsmar, FL 34677, 2 beds, 2 baths

$110,000

2 beds2 baths915 sq ft

133 Sabal Ct Unit G, Oldsmar, FL 34677

Viewing page 2 of 3

Based on information submitted to the MLS GRID as of Mon Sep 21 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Oldsmar

There are currently 115 homes with pools for sale in Oldsmar at a median listing price of $383K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oldsmar stay on the market for 94 days. Popular neighborhoods include Gull Aire Village, Bridgeport, East Lake Woodlands, and Briar Creek. This map is refreshed with the newest listings in Oldsmar every 15 minutes.

In the past month, 16 homes have been sold in Oldsmar. In addition to houses in Oldsmar, there were also 16 condos, 23 townhouses, and 1 multi-family unit for sale in Oldsmar last month. Find your dream home in Oldsmar using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Oldsmar are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oldsmar. Our Oldsmar real estate stats and trends will give you more information about home buying and selling trends in Oldsmar. If you're looking to sell your home in the Oldsmar area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oldsmar with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Oldsmar, FL

Nearby Cities

Neighborhoods

Zip Codes

Nearby Cities with Homes with Pools

Nearby Neighborhoods with Homes with Pools

More to explore in Oldsmar, FL

How to buy a house in Oldsmar, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

6 Redfin agents serving Oldsmar

177

Deals*

4.7

Satisfaction

1234

Homes closed*

* Data from the last year

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.