Homes with Pools for Sale in Osceola County, FL

3,572 homes + 1 early access

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
ACTIVE TRANSFERABLE REUNION RESORT MEMBERSHIP AVAILABLE. Immaculate 3 Bedroom 3 Bath GROUND FLOOR Condo with GOLF VIEWS of Hole #16 on the Tom Watson Signature Course at Reunion Resort. Located in the Villas North Community this well maintained and tastefully updated condo is being offered FULLY FURNISHED! As you enter the condo you will notice the open concept floor plan providing an inviting atmosphere to relax and entertain family and friends. Recent updates to the unit NEW LUXURY VINYL FLOORING throughout the living and dining areas, as well as all three bedrooms. NO CARPET! Additional BRAND NEW UPGRADES include living room couches, dining room table and chairs, BRAND NEW BEDS including

$309,900

3 beds3 baths1,630 sq ft

1102 Sunset View Cir #103, Reunion, FL 34747

Golf views • Ground floor condo • Fully furnished

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Luxurious Carlyle Condo built by Issa Builder located in the heart of downtown Celebration. This spacious 3 bedroom and 2.5 bath is light and bright with plenty of room for entertaining guests! This popular open floor plan is perfectly situated on the 2nd floor. You can enjoy the beautiful and serene views of the tree lined streets. Large foyer features powder room and flows to the Kitchen and family room area. Spacious kitchen opens to a large family room area with charming french doors that lead to a balcony for relaxing. Kitchen has 42 inch maple cabinets and gorgeous granite counter tops with stainless steel appliances. Charming wine storage closet! Beautiful crown molding, elegant woo

$749,999

3 beds2.5 baths1,898 sq ft

600 Edwards St #7202, Celebration, FL 34747

Open floor plan • Large family room • Carlyle condo

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
This is a tastefully furnished six-bedroom 4-bathroom home with a South West facing pool and spa, it is also a turnkey short term rental property on Windsor Hills 4 miles from Disney Parks. Margaritaville is less than a mile away with an abundance of shops and restaurants and so many others close by as well you will be spoilt for choice. Walking into the beautifully decorated main living room gives you a WOW factor and then through the main dining area to the comfortable family room and roomy kitchen. Here you will find stone counter tops and stainless-steel appliances and all the items you need to prepare your breakfast or a full family meal if you choose. Then you have sliding doors to t

$695,000

6 beds4 baths2,812 sq ft

2564 Archfeld Blvd, Kissimmee, FL 34747

Games area • Covered lanai • King master bedroom

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Priced to sell as is! This 4-bedroom, 2.5-bath Poinciana home sits on a generous 1/4-acre lot and offers a formal dining room, living room, and bonus space for flexible living. Enjoy Florida days on the screened lanai overlooking the inground pool. Two-car garage. Kitchen and bath cabinets, countertops, and carpet are ready for your updates, so bring your vision and build instant equity in a prime Poinciana location.

$319,900

4 beds2.5 baths1,759 sq ft

816 Alpine Ct, Kissimmee, FL 34758

Formal dining room • Screened lanai • Inground pool

ABOUT THIS HOME
Home with a Pool for sale in Osceola County, FL:
Welcome to 8997 Azalea Sands Lane, a beautifully maintained 2-bedroom, 2-bathroom corner-unit condominium located in the sought-after ChampionsGate community! Built in 2017, this spacious residence offers 1,409 square feet of comfortable living space, an attached one-car garage, and a thoughtfully designed open floor plan that blends style and functionality. Step inside to discover a bright and inviting interior featuring high ceilings, neutral finishes, and beautiful tile flooring throughout the main living areas. The spacious kitchen showcases rich wood cabinetry, solid-surface countertops, stainless steel appliances, a convenient breakfast bar, and stylish pendant lighting. Overlooking t

$225,000

2 beds2 baths1,409 sq ft

8997 Azalea Sands Ln #8997, Davenport, FL 33896

Corner unit • $667 HOA • Garage

Property at 3261 Whooping Crane Run, Kissimmee, FL 34741, 3 beds, 2 baths

$449,900

3 beds2 baths1,579 sq ft

3261 Whooping Crane Run, Kissimmee, FL 34741

Property at 8302 Portofino Dr #101, Davenport, FL 33896, 3 beds, 2 baths

$174,990

3 beds2 baths1,248 sq ft

8302 Portofino Dr #101, Davenport, FL 33896

Property at 2481 Winchester Blvd, Kissimmee, FL 34743, 3 beds, 2 baths

$360,000

3 beds2 baths1,023 sq ft

2481 Winchester Blvd, Kissimmee, FL 34743

Property at 1218 Bermuda Lakes Ln #203, Kissimmee, FL 34741, 2 beds, 2 baths

$184,900

2 beds2 baths1,103 sq ft

1218 Bermuda Lakes Ln #203, Kissimmee, FL 34741

Property at 2723 N Poinciana Blvd #157, Kissimmee, FL 34746, 3 beds, 2 baths

$205,000

3 beds2 baths1,287 sq ft

2723 N Poinciana Blvd #157, Kissimmee, FL 34746

Property at 5046 Down Ct, Saint Cloud, FL 34772, 5 beds, 3 baths

$460,000

5 beds3 baths3,197 sq ft

5046 Down Ct, Saint Cloud, FL 34772

Property at 3000 Maingate Ln #420, Kissimmee, FL 34747, 1 bed, 1 bath

$50,000

1 bed1 bath304 sq ft

3000 Maingate Ln #420, Kissimmee, FL 34747

Property at 4819 Cumbrian Lakes Dr, Kissimmee, FL 34746, 4 beds, 3 baths

$390,000

4 beds3 baths1,728 sq ft

4819 Cumbrian Lakes Dr, Kissimmee, FL 34746

Property at 2539 Old Kent Cir, Kissimmee, FL 34758, 3 beds, 3 baths

$238,000

3 beds3 baths1,504 sq ft

2539 Old Kent Cir, Kissimmee, FL 34758

Property at 4522 Narrative Ln, Kissimmee, FL 34746, 8 beds, 5 baths

$810,000

8 beds5 baths4,289 sq ft

4522 Narrative Ln, Kissimmee, FL 34746

Property at 3817 Shoreside Dr, Kissimmee, FL 34746, 6 beds, 4 baths

$849,999

6 beds4 baths4,565 sq ft

3817 Shoreside Dr, Kissimmee, FL 34746

Property at 3452 Bellissimo Ave, Kissimmee, FL 34746, 4 beds, 3 baths

$298,000

4 beds3 baths2,043 sq ft

3452 Bellissimo Ave, Kissimmee, FL 34746

Property at 580 Muirfield Loop, Reunion, FL 34747, 9 beds, 11 baths

$3,185,000

9 beds11 baths6,756 sq ft

580 Muirfield Loop, Reunion, FL 34747

Property at 961 Leader St, Davenport, FL 33896, 5 beds, 5 baths

$515,000

5 beds5 baths3,081 sq ft

961 Leader St, Davenport, FL 33896

Property at 5163 Jack Brack Rd, Saint Cloud, FL 34771, 3 beds, 2 baths

$415,000

3 beds2 baths1,227 sq ft

5163 Jack Brack Rd, Saint Cloud, FL 34771

Property at 231 Minton Loop, Kissimmee, FL 34747, 6 beds, 6 baths

$580,000

6 beds6 baths2,831 sq ft

231 Minton Loop, Kissimmee, FL 34747

Property at 7677 Fairfax Dr, Kissimmee, FL 34747, 9 beds, 8.5 baths

$950,000

9 beds8.5 baths5,030 sq ft

7677 Fairfax Dr, Kissimmee, FL 34747

Property at 7789 Four Seasons Blvd, Kissimmee, FL 34747, 3 beds, 2.5 baths

$499,900

3 beds2.5 baths2,360 sq ft

7789 Four Seasons Blvd, Kissimmee, FL 34747

Property at 115 Cheltenham Pl, Kissimmee, FL 34758, 4 beds, 2 baths

$314,900

4 beds2 baths1,604 sq ft

115 Cheltenham Pl, Kissimmee, FL 34758

Property at 2622 Hunley Loop, Kissimmee, FL 34743, 4 beds, 2 baths

$394,999

4 beds2 baths1,874 sq ft

2622 Hunley Loop, Kissimmee, FL 34743

Property at 7593 Gathering Dr #708, Reunion, FL 34747, 1 bed, 1 bath

$220,000

1 bed1 bath1,128 sq ft

7593 Gathering Dr #708, Reunion, FL 34747

Property at 7704 Westland Dr, Kissimmee, FL 34747, 10 beds, 9 baths

$1,195,000

10 beds9 baths5,138 sq ft

7704 Westland Dr, Kissimmee, FL 34747

Property at 4190 Bull St, Saint Cloud, FL 34772, 5 beds, 3.5 baths

$530,000

5 beds3.5 baths3,266 sq ft

4190 Bull St, Saint Cloud, FL 34772

Property at 381 Pineywoods St, Saint Cloud, FL 34772, 3 beds, 2 baths

$350,000

3 beds2 baths1,552 sq ft

381 Pineywoods St, Saint Cloud, FL 34772

Property at 2711 Oakwater Dr #2711, Kissimmee, FL 34747, 3 beds, 2 baths

$299,900

3 beds2 baths1,255 sq ft

2711 Oakwater Dr #2711, Kissimmee, FL 34747

Property at 2863 Middleton Cir, Kissimmee, FL 34743, 4 beds, 2 baths

$415,000

4 beds2 baths2,071 sq ft

2863 Middleton Cir, Kissimmee, FL 34743

Property at 5424 Marylebone Dr, Saint Cloud, FL 34771, 5 beds, 3 baths

$489,000

5 beds3 baths3,075 sq ft

5424 Marylebone Dr, Saint Cloud, FL 34771

Property at 3075 Seaview Castle Dr, Kissimmee, FL 34746, 3 beds, 2.5 baths

$349,000

3 beds2.5 baths1,540 sq ft

3075 Seaview Castle Dr, Kissimmee, FL 34746

Property at 299 Magical Way, Kissimmee, FL 34744, 4 beds, 3 baths

$400,000

4 beds3 baths1,790 sq ft

299 Magical Way, Kissimmee, FL 34744

Property at 4324 Paradise Cove Ct, Kissimmee, FL 34746, 3 beds, 2.5 baths

$269,000

3 beds2.5 baths1,769 sq ft

4324 Paradise Cove Ct, Kissimmee, FL 34746

Property at 2190 Preston Ln, Kissimmee, FL 34746, 3 beds, 2 baths

$360,000

3 beds2 baths1,677 sq ft

2190 Preston Ln, Kissimmee, FL 34746

Property at 2321 Silver Palm Dr, Kissimmee, FL 34747, 3 beds, 3 baths

$349,000

3 beds3 baths1,440 sq ft

2321 Silver Palm Dr, Kissimmee, FL 34747

Property at 4854 Poolside Dr, Saint Cloud, FL 34769, 3 beds, 2.5 baths

$290,000

3 beds2.5 baths1,832 sq ft

4854 Poolside Dr, Saint Cloud, FL 34769

Property at 3293 Wauseon Dr, Saint Cloud, FL 34772, 3 beds, 2.5 baths

$619,900

3 beds2.5 baths2,580 sq ft

3293 Wauseon Dr, Saint Cloud, FL 34772

Property at 1540 Maidstone Ct, Davenport, FL 33896, 8 beds, 5 baths

$765,000

8 beds5 baths3,909 sq ft

1540 Maidstone Ct, Davenport, FL 33896

Property at 2775 Corvette Ln, Kissimmee, FL 34746, 4 beds, 3.5 baths

$309,900

4 beds3.5 baths1,852 sq ft

2775 Corvette Ln, Kissimmee, FL 34746

Viewing page 6 of 88

Based on information submitted to the MLS GRID as of Sun Nov 08 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 Osceola County

There are currently 3573 homes with pools for sale in Osceola County at a median listing price of $400K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Osceola County stay on the market for 104 days and receive 1 offers. This map is refreshed with the newest listings in Osceola County every 15 minutes.

In the past month, 655 homes have been sold in Osceola County. In addition to houses in Osceola County, there were also 729 condos, 1246 townhouses, and 19 multi-family units for sale in Osceola County last month. Find your dream home in Osceola County 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 Osceola County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Osceola County. If you're looking to sell your home in the Osceola County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Osceola County 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 Osceola County, FL

Cities

Nearby Counties

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Osceola County, FL

How to buy a house in Osceola County, 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

9 Redfin agents serving Osceola County

227

Deals*

4.9

Satisfaction

1205

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.

Redfin Brokerage Licenses

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.