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

$2,790,000
2 Beds ⋅ 3 Baths ⋅ O6391143 MLS ⋅ The Sanctuary BLDG.
Exquisitely remodeled and thoughtfully curated, this Penthouse at 100 S Eola Dr PH 116, tucked in the heart of highly coveted South Eola, offers the perfect blend of refined luxury, privacy, and vibrant, walkable downtown living. Expansive windows bathe the open living and dining areas in soft natural light while showcasing postcard-worthy views of Lake Eola and a dramatic, glittering city skyline. The gourmet chef’s kitchen is meticulously designed for both everyday cooking and effortless entertaining, featuring sleek cabinetry, striking white quartz countertops, built-in appliances, and a generous waterfall island that flows seamlessly into the main living space for easy gathering. The spacious primary suite feels like a serene private retreat with a spa-inspired bath, oversized glass-enclosed shower, elegant finishes, and generous custom closet space. An inviting additional bedroom suite is ideal for overnight guests, extended family, or a dedicated, polished home office, offering flexibility without compromising comfort or style. The balcony creates an easy indoor-outdoor lifestyle, perfect for quiet morning coffee, al fresco dining, or evening cocktails overlooking the twinkling city lights and lakeside panorama. Located in a sought-after, boutique, concierge-style building, this penthouse provides secure entry, 2 reserved garage parking spaces, and resort-style amenities such as a sparkling pool, a well-equipped fitness center, a stylish resident lounge, and a summer kitchen on the pool deck for effortless entertaining. Step outside your front door to enjoy Lake Eola Park, Sunday farmers markets, neighborhood cafés, chef-driven fine dining, wine bars, and vibrant nightlife, all just moments away along tree-lined, brick-paved streets. With its contemporary design, generous square footage, and unmatched high-end finishes, this supremely walkable South Eola address presents an exceptional opportunity for buyers seeking sophisticated, upscale urban living in the heart of downtown Orlando. Additional amenities include Full-time Front Desk Concierge and Building Operations Team, Full-time Manager, Five High-Speed Elevators, 14 Guest Parking Spaces and 2 EV charging stations.

100 S Eola Drive Unit PH 116, Orlando
$2,750,000
4 Beds ⋅ 5 Baths ⋅ O6409134 MLS
Welcome to Chiltern Garden Drive, a beautifully rebuilt home offering over 3,400sf of thoughtfully designed living space with 4 bedrooms & 4.5 baths. Completely expanded & reimagined, this exceptional residence blends elevated modern design, quality craftsmanship, & comfortable living in a way that feels sophisticated & inviting. Originally rebuilt as the personal residence of a nationally recognized contractor & structural engineer, this home was reconstructed with an extraordinary level of care, engineering, & attention to detail. The property underwent a total rebuild, with only three perimeter walls & the garage floors remaining from the original structure. The extensive reconstruction included all new framing, electrical, plumbing, & mechanical systems, including the addition of a roof dehumidifier system for enhanced climate control & efficiency. Additional improvements include a new roof, windows, doors, & garage doors, professionally installed stucco system, waterproofing of all interior masonry walls, interior foam insulation, & upgraded 3/4-inch drywall throughout for enhanced durability & sound control. Inside, warm white oak flooring flows throughout the home, complemented by custom-built millwork, designer wallpaper, & beautiful lighting selections that add warmth & character to each space. Statement chandeliers in the foyer & dining room create elegant focal points, while natural light fills the interiors & highlights the thoughtfully curated finishes. Level 5 wall finishes further elevate the clean & sophisticated aesthetic. Designed for both entertaining & everyday living, the open-concept layout seamlessly connects the kitchen, dining area, & family room. The completely reconfigured gourmet kitchen is both stunning & functional, featuring custom two-tone cabinetry, new top-of-the-line appliances, dramatic quartzite countertops, & a large center island that naturally becomes the heart of the home. Beautiful stone selections continue throughout, creating a cohesive & timeless feel. The family room offers a warm & inviting atmosphere centered around a sleek contemporary firebar that adds both ambiance & modern elegance to the space. Each bathroom was thoughtfully designed with custom vanities, imported tile, exotic stone selections, & statement lighting, creating spa-inspired spaces that feel elevated yet comfortable. The outdoor living space feels like a private retreat & serves as a seamless extension of the home. The covered lanai features motorized screens, tongue-and-groove ceilings, a dramatic accent wall, & a modern electric firebar, creating the perfect setting for year-round entertaining & relaxation. Beyond the lanai, the extended patio, pergola, & stainless steel spa tub provide additional spaces to enjoy the beautifully designed outdoor setting. Colored concrete driveways, curbs, & patio areas further enhance the home’s curb appeal & outdoor areas. Additional features include a whole-home generator, security system, security cameras, Sonos system, & professionally designed router locations for optimized connectivity. Thoughtfully rebuilt with exceptional craftsmanship, engineering, & intentionally selected finishes throughout, this extraordinary home offers a rare opportunity to own a truly turnkey residence with the feel & quality of custom new construction. Year built of 2025 per builder/owner is different than the property tax record of 1990 (house knocked down except garage slab & 3 exterior walls).

10220 Chiltern Garden Drive, Orlando
$2,750,000
5 Beds ⋅ 6 Baths ⋅ O6300031 MLS
Introducing a rare opportunity to own a truly exceptional residence in the guard-gated enclave of Turtle Creek, one of Orlando’s most coveted luxury communities. This breathtaking estate has been fully remodeled in 2024 and also features a brand new tile roof and fully resurfaced pool. Boasting over 5,800 square feet of meticulously curated living space, 5 spacious bedrooms, 5.5 designer bathrooms, and direct access to the famed Butler Chain of Lakes. Step through the stately double doors and into a grand foyer where the interior unfolds with two-story ceilings, expansive living spaces, and sleek porcelain tile flooring that flows seamlessly throughout the entire home. The heart of the home is a show-stopping chef’s kitchen designed to impress. Outfitted with custom cabinetry, quartz countertops, high-end Thermador appliances, and an oversized island with waterfall edges, it is truly the chef enthusiast's dream. The kitchen flows effortlessly into an expansive family room featuring a stylish electric fireplace, a full wet bar with a wine fridge, and tons of windows with views of the canal and backyard. The first-floor primary suite is a true private retreat. Generously sized and elegantly appointed, it features a sitting area with water views, a large walk-in closet, and a spa-inspired bathroom complete with a freestanding soaking tub, oversized walk-in shower, and dual vanities adorned with designer finishes. Upstairs, additional guest bedrooms are well-appointed, each offering ample space, natural light, and beautifully renovated bathrooms with modern touches. Additional upstairs amenities include a versatile living area, a dedicated office, and a gym. Step outside into your own private resort. The newly resurfaced pool is framed by a spacious screened-in patio and covered lanai, ideal for lounging, dining, and entertaining. Beyond the pool lies the crown jewel of the property: your private boat dock nestled along a tranquil canal with direct access to the Butler Chain of Lakes. As a part of the Turtle Creek community, residents enjoy 24-hour guard gated security, tennis courts, a playground, and a serene setting just minutes from renowned dining on Restaurant Row, world-class shopping, championship golf courses, and Orlando’s most elite private schools. Don’t miss the opportunity to make this amazing fully remodeled home yours.

10849 Emerald Chase Drive, Orlando
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