Homes with Pools for Sale in 34744, FL

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ABOUT THIS HOME
Home with a Pool for sale in 34744, FL:
Welcome to your next home in the prestigious gated community of Kissimmee Bay Country Club! This spectacular, fully renovated residence blends luxury, advanced technology, and comfort, all set in a breathtaking natural environment overlooking the majestic Lake Toho. The home offers 5 spacious bedrooms and 4.5 bathrooms. The primary suite, located on the first floor, features private access to the pool and kitchen, plus a spa-style bathroom with a sauna—perfect for relaxation. A second bedroom on the main floor can be used as an office or guest suite. Upstairs, you’ll find three additional bedrooms: one with a private bath and two sharing a full bathroom. The elegant interior fea

$1,100,000

5 beds4.5 baths3,845 sq ft

1407 Water Lilly Ln, Kissimmee, FL 34744

Spa style bathroom • Chef's dream kitchen • Open concept design

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in 34744, FL:
Sitting on over a third of an acre, this 6-bedroom, 4.5-bath pool home gives you the kind of space and layout that’s just hard to find — especially this close to Lake Nona. Right when you pull up, you’ll notice it feels a little different. The wide driveway, mature landscaping, and clean curb appeal set the tone. Inside, it opens up into a bright, functional layout that actually works — not one of those homes that looks good in photos but makes no sense in person. The kitchen was completely redone in 2024 and it shows — modern cabinetry, clean finishes, and a big center island that opens up to the dining area. It feels like the kind of space you’ll actual

$699,000

6 beds4.5 baths2,821 sq ft

3149 Twisted Oak Loop, Kissimmee, FL 34744

Remodeled kitchen • Screened-in patio • Double primary suite

ABOUT THIS HOME
Home with a Pool for sale in 34744, FL:
"Beautiful Location" Modern Comfort, Security, & Resort-Style Living! This cozy and beautifully designed 3-bedroom, 2-bathroom home offers an open-concept living space, perfectly blending comfort and modern convenience. The sleek kitchen is a chef’s dream, featuring stainless steel appliances, a spacious pantry, and stylish finishes. The covered lanai provides a perfect outdoor retreat, while the master suite offers a private oasis with a walk-in closet and dual vanity. Built with a solid concrete block structure, this home ensures durability and is equipped with smart home technology, allowing you to control various features from your devices. A complete fence surround

$384,990

3 beds2 baths1,516 sq ft

1648 Heart Bar Rd, Kindred, FL 34744

Spacious pantry • Walk-in closet • Dual vanity

ABOUT THIS HOME
Home with a Pool for sale in 34744, FL:
Beautiful 3 bedroom 2.5 bath townhouse in desirable area of Kissimmee. Townhouse features a 1 car attached garage in a Gated community. Community features a pool and 2 playgrounds. Close to shopping, stores and turnpike.

$335,000

3 beds2.5 baths1,758 sq ft

2575 Aventurine St, Kissimmee, FL 34744

Gated community • Attached garage • Playgrounds

ABOUT THIS HOME
Home with a Pool for sale in 34744, FL:
4 Bed, 3 Bath Pool Home – Fully Furnished & Move-In Ready! Welcome to 2705 Prestwick Lane – a spacious 4 bedroom, 3 bathroom home with a private pool, located on a quiet corner lot in a well-kept Kissimmee neighborhood. Whether you're looking for a turnkey vacation rental or a comfortable primary home, this one checks all the boxes. The home comes fully furnished, so you can move right in or start renting it out immediately. The open layout, generous bedrooms, and private pool area make it great for families, guests, or just enjoying a relaxed Florida lifestyle. You're a short drive from shopping, dining, golf, and plenty of local attractions—without all the theme

$437,000

4 beds3 baths1,719 sq ft

2705 Prestwick Ln, Kissimmee, FL 34744

Quiet corner lot • Private pool • Fully furnished

Property at 1502 Jadewood Way, Kindred, FL 34744, 4 beds, 2 baths

$359,900

4 beds2 baths1,846 sq ft

1502 Jadewood Way, Kindred, FL 34744

Property at 2723 Callaway Ln, Kissimmee, FL 34744, 4 beds, 3.5 baths

$447,900

4 beds3.5 baths2,513 sq ft

2723 Callaway Ln, Kissimmee, FL 34744

Property at 2921 Puerta Del Sol Blvd, Kissimmee, FL 34744, 3 beds, 2 baths

$266,999

3 beds2 baths1,274 sq ft

2921 Puerta Del Sol Blvd, Kissimmee, FL 34744

Property at 1565 Leaf Ln, Kissimmee, FL 34744, 4 beds, 3 baths

$545,000

4 beds3 baths2,456 sq ft

1565 Leaf Ln, Kissimmee, FL 34744

Property at 1408 Diamond Loop Dr, Kindred, FL 34744, 4 beds, 3 baths

$495,000

4 beds3 baths2,374 sq ft

1408 Diamond Loop Dr, Kindred, FL 34744

Property at 148 Harwood Cir, Kissimmee, FL 34744, 3 beds, 2.5 baths

$395,000

3 beds2.5 baths2,232 sq ft

148 Harwood Cir, Kissimmee, FL 34744

Property at 1749 Fulfillment Dr, Kissimmee, FL 34744, 3 beds, 2.5 baths

$365,000

3 beds2.5 baths1,528 sq ft

1749 Fulfillment Dr, Kissimmee, FL 34744

Property at 1723 Happiness Row, Kissimmee, FL 34744, 3 beds, 2.5 baths

$434,000

3 beds2.5 baths1,802 sq ft

1723 Happiness Row, Kissimmee, FL 34744

Property at 3016 Madelia Ln, Kissimmee, FL 34744, 4 beds, 2 baths

$425,000

4 beds2 baths1,784 sq ft

3016 Madelia Ln, Kissimmee, FL 34744

Property at 1983 Fortune Rd, Kissimmee, FL 34744, 1 bed, 1 bath

$50,000

1 bed1 bath420 sq ft

1983 Fortune Rd, Kissimmee, FL 34744

Property at 1384 E Lake Shore Blvd, Kissimmee, FL 34744, 4 beds, 4 baths

$999,900

4 beds4 baths3,606 sq ft

1384 E Lake Shore Blvd, Kissimmee, FL 34744

Property at 1882 Rustic Falls Dr, Kindred, FL 34744, 4 beds, 3.5 baths

$515,500

4 beds3.5 baths2,851 sq ft

1882 Rustic Falls Dr, Kindred, FL 34744

Property at 417 Benita St, Kissimmee, FL 34744, 3 beds, 1.5 baths

$284,000

3 beds1.5 baths1,186 sq ft

417 Benita St, Kissimmee, FL 34744

Property at 1542 Colony Ave, Kissimmee, FL 34744, 3 beds, 2 baths

$357,000

3 beds2 baths1,185 sq ft

1542 Colony Ave, Kissimmee, FL 34744

Property at 339 Magical Way, Kissimmee, FL 34744, 4 beds, 3 baths

$430,000

4 beds3 baths1,797 sq ft

339 Magical Way, Kissimmee, FL 34744

Property at 1074 Berkeley Dr, Kissimmee, FL 34744, 6 beds, 4 baths

$625,000

6 beds4 baths3,460 sq ft

1074 Berkeley Dr, Kissimmee, FL 34744

Property at 3184 Skyline Loop, Kissimmee, FL 34758, 2 beds, 2 baths

$280,000

2 beds2 baths1,187 sq ft

3184 Skyline Loop, Kissimmee, FL 34758

Property at 1501 Sunset Pointe Pl, Kissimmee, FL 34744, 5 beds, 3.5 baths

$1,599,000

5 beds3.5 baths3,685 sq ft

1501 Sunset Pointe Pl, Kissimmee, FL 34744

Property at 1465 Riviera Dr, Kissimmee, FL 34744, 4 beds, 3.5 baths

$739,900

4 beds3.5 baths2,528 sq ft

1465 Riviera Dr, Kissimmee, FL 34744

Property at 3225 Parkwood Ct, Kissimmee, FL 34744, 4 beds, 3.5 baths

$300,000

4 beds3.5 baths2,808 sq ft

3225 Parkwood Ct, Kissimmee, FL 34744

Property at 107 Benita St, Kissimmee, FL 34744, 3 beds, 1 bath

$158,900

3 beds1 bath1,010 sq ft

107 Benita St, Kissimmee, FL 34744

Property at HARPER Plan, Kissimmee, FL 34744, 4 beds, 2 baths

$400,990

4 beds2 baths1,665 sq ft

HARPER Plan, Kissimmee, FL 34744

Listing provided by Zillow

Property at 2518 Bowmer Dr, Kissimmee, FL 34744, 3 beds, 2 baths

$359,900

3 beds2 baths1,523 sq ft

2518 Bowmer Dr, Kissimmee, FL 34744

Property at 1380 E Lake Shore Blvd, Kissimmee, FL 34744, 4 beds, 4 baths

$699,900

4 beds4 baths3,637 sq ft

1380 E Lake Shore Blvd, Kissimmee, FL 34744

Property at 4147 Boggy Creek Rd, Kissimmee, FL 34744, 4 beds, 3 baths

$1,850,000

4 beds3 baths2,932 sq ft

4147 Boggy Creek Rd, Kissimmee, FL 34744

Property at 720 Shore Dr, Kissimmee, FL 34744, 2 beds, 2 baths

$449,900

2 beds2 baths1,503 sq ft

720 Shore Dr, Kissimmee, FL 34744

Property at Miramar II Plan, Kissimmee, FL 34744, 5 beds, 3 baths

$553,432

5 beds3 baths2,571 sq ft

Miramar II Plan, Kissimmee, FL 34744

Listing provided by Zillow

Property at Freedom Plan, Kissimmee, FL 34744, 4 beds, 3 baths

$530,295

4 beds3 baths2,109 sq ft

Freedom Plan, Kissimmee, FL 34744

Listing provided by Zillow

Property at Autumn Plan, Kissimmee, FL 34744, 3 beds, 2.5 baths

$409,340

3 beds2.5 baths1,795 sq ft

Autumn Plan, Kissimmee, FL 34744

Listing provided by Zillow

Property at Sierra Plan, Kissimmee, FL 34744, 4 beds, 3.5 baths

$431,540

4 beds3.5 baths2,522 sq ft

Sierra Plan, Kissimmee, FL 34744

Listing provided by Zillow

Property at Undisclosed address, Kissimmee, FL 34744

$3,300,000

— beds— baths— sq ft

Undisclosed address, Kissimmee, FL 34744

Property at 717 Boyd St, Kissimmee, FL 34744

$89,000

— beds— baths— sq ft

717 Boyd St, Kissimmee, FL 34744

Property at 4250 High Plains Ln, Kissimmee, FL 34744

$5,000,000

— beds— baths— sq ft

4250 High Plains Ln, Kissimmee, FL 34744

Property at High Plains Ln, Kissimmee, FL 34744

$5,000,000

— beds— baths— sq ft

High Plains Ln, Kissimmee, FL 34744

Property at 1056 Shawnda Ln, Kissimmee, FL 34744

$175,000

— beds— baths— sq ft

1056 Shawnda Ln, Kissimmee, FL 34744

Property at 4345 Boggy Creek Rd, Kissimmee, FL 34744

$4,250,000

— beds— baths— sq ft

4345 Boggy Creek Rd, Kissimmee, FL 34744

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. 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 34744

There are currently 377 homes with pools for sale in 34744 at a median listing price of $422K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 34744 stay on the market for 79 days and receive 4 offers. This map is refreshed with the newest listings in 34744 every 15 minutes.

In the past month, 70 homes have been sold in 34744. In addition to houses in 34744, there was also 1 condo, 58 townhouses, and 1 multi-family unit for sale in 34744 last month. Find your dream home in 34744 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 34744 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 34744. If you're looking to sell your home in the 34744 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 34744 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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