Orlando Real Estate

Homes for Sale with a Pool in Orlando, FL

Welcome to your dedicated resource for homes for sale with a pool in Orlando, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Orlando, FL agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Orlando, FL

$1,395,000
3 Beds ⋅ 4 Baths ⋅ O6412528 MLS
Virtually Staged. Welcome to this beautifully maintained lakefront estate located on the pristine shores of Lake Jessamine, offering a rare opportunity to own in one of the area’s most coveted lake communities. Nestled on a sprawling lot with 120 feet of lake frontage, this home effortlessly blends luxury, comfort, and serene natural beauty. As you enter through a beautifully landscaped courtyard with a horseshoe driveway, you’re immediately greeted by the charm and grandeur of this exceptional property. The interior boasts 3 spacious bedrooms plus a flexible 4th bedroom, currently transformed into a custom California Closets-designed primary walk-in closet. The heart of the home is a modern chef’s kitchen complete with premium appliances, double ovens, expansive counter space, and a massive butler’s pantry/bonus kitchen, perfect for entertaining. Adjacent, the living area is both inviting and impressive, featuring two gas fireplaces, French doors, and large windows that frame breathtaking lake views with downtown Orlando as your scenic backdrop. Step outside to a custom-designed patio with an elegant fireplace, and a fully equipped outdoor kitchen, perfect for hosting gatherings overlooking the tranquil waters. The estate also features an oversized heated pool and spa with a covered 16 x 60 deck area, plus a private boat dock with electric lift, creating endless opportunities for lakefront leisure and entertainment. Additional highlights include; Roof replaced in 2022, upgraded pool & spa equipment 2024, Custom wet bar with built-in wine storage, integrated speaker system and hidden security system, Travertine tile throughout bathrooms, dining room, and a spa-inspired primary bath with custom finishes, Ample storage space with custom built-in shelving throughout, AC unit replaced 2023, floating jet ski dock recently installed, and custom garage cabinetry. This estate offers privacy and elegance while being just minutes from Orlando’s premier shopping, dining, entertainment, and city center. Experience the perfect balance of luxury living with the tranquility of a lakeside retreat.

5400 Kenmore Lane, Orlando
$1,390,000
4 Beds ⋅ 3 Baths ⋅ O6433115 MLS
COME LIVE THE LAKE LIFE — Completely Remodeled Lakefront Retreat on Lake Jessamine Welcome to 430 Bywater Dr, a fully remodeled lakefront estate on the shores of Lake Jessamine in the heart of Orlando, where every finish has been reimagined for today's buyer. Set on a beautifully landscaped lot with a private boathouse and dock, this home delivers front-row seats to some of the most spectacular sunsets in Central Florida to the west — and it's ready for its next owner to move in and start living the lake life immediately. Spanning over 4,058 square feet under roof, the home offers four bedrooms and three full baths, plus a flexible bonus room and gathering room, and a separate playroom or home theater room — ideal for movie nights, a home gym, or a private retreat. Inside, the transformation is complete: wide-plank flooring, designer lighting, and warm white oak cabinetry set the tone throughout. The chef's kitchen anchors the main living space with an oversized quartz island, custom cabinetry, a pot filler, and a suite of high-end stainless appliances, opening directly to the dining and living areas beneath a striking wood-beamed ceiling and a sleek linear fireplace — perfect for entertaining. The primary suite is a true escape, wrapped in a rich wood-plank ceiling and anchored by a spa-inspired bath with a freestanding soaking tub, oversized rain shower, and brushed-brass fixtures. Step outside to the screened and covered lanai, where a sparkling pool and spa overlook the lake, framed by mature oaks and swaying palms. Down at the water's edge, the covered boathouse and dock are ready for the boat and the jet skis — with evenings made for watching the sun drop over Lake Jessamine. All of this in a no-HOA setting minutes from Belle Isle, the Conway chain of lakes, sought-after Cornerstone Charter School, ORMC, and the excitement of Orlando's theme parks, including the brand-new Epic Universe. Fully remodeled lakefront homes like this don't last — schedule your private showing today. Lake Jessamine a 294-acre lake with a ski course and wakeboarding, located just 15 minutes from downtown Orlando and the Orlando International Airport. RV parking as well. (Note: the nearby public boat ramp closes/locks at dusk daily.)

430 Bywater Drive, Orlando
$1,379,000
8 Beds ⋅ 8 Baths ⋅ O6374187 MLS ⋅ 5773 BLDG.
Don’t miss this luxury vacation home opportunity at Paradiso Grande! This remarkable new construction with PREMIUM LOT, never occupied features an 8-bedroom, 8-bathroom Lagoon II floor plan, complete with an inviting loft area perfect for relaxation or entertainment. Located in the premier vacation community by Park Square Homes in Orlando, you’ll be just minutes from SeaWorld, Universal Studios, premium outlets and Disney. This property boasts amazing features, including additional laundry rooms on each floor, two refrigerators and dishwashers, granite countertops, gray cabinets, and a screen-enclosed pool. The seller has added numerous upgrades during construction, such as a Summer Kitchen Pre-Plumb with hot/cold water, drain pre-plumb, exterior J-box, and gas drop to elevate your outdoor entertaining experience. The upgraded 15x30 pool includes a spa and fountains, along with four flush-mount can lights in all bedrooms. Step outside to your private pool area, where you can enjoy stunning water views. Key features include an EV car charger and gas heaters for both the house and pool, ensuring comfort year-round. The Summer Kitchen pre-plumb is installed for your convenience. Inside, the open-concept kitchen is a chef’s dream, equipped with two refrigerators, two dishwashers, granite countertops, and elegant gray cabinetry. The first-floor master suite adds convenience, while the transformed 2-car garage doubles as a spacious game room. Paradiso Grande offers exclusive access to the luxurious Aquarius Clubhouse, featuring a resort-style pool, lazy river, café, game room, and fitness center. This property is perfect for both short-term rentals and long-term living. Don’t miss your chance to own this exceptional property in the heart of Orlando!

5773 High Seas Drive, Orlando
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