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.

< Back to all Homes for Sale in Orlando, FL

Be the First to Know About New Orlando Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Orlando Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Homes for Sale with a Pool in Orlando, FL

$1,679,996
4 Beds ⋅ 5 Baths ⋅ O6343980 MLS
Virtually Staged. Meticulously renovated over two years, this residence reflects more than $875,600 in improvements and was independently appraised above the current asking price on July 2, 2026. Located in the coveted Lake Lawsona Historic District in the heart of downtown Orlando, this extraordinary 1920s estate sits on an oversized double lot with dual street access and features a completely reimagined saltwater pool, among the largest in the area, along with a private studio apartment (ADU) with its own entrance, full kitchen, and bath. Just blocks from acclaimed dining, boutique shops, parks, cultural venues, and entertainment, this distinguished historic residence is surrounded by majestic live oaks and offers a rare combination of privacy, outdoor living, and urban convenience. Inspired by the timeless architectural principles of Andrea Palladio, the home harmoniously blends historic character with modern luxury and exceptional craftsmanship. The property offers a 3-bedroom, 3.5-bath main residence with a private office, spacious laundry room, and an independent ADU ideal for guests, multigenerational living, a home office, or income-producing potential. Nearly every major system has been upgraded or replaced, including the 50-year concrete tile roof (2019), Pella windows, complete plumbing and drain systems, gas tankless water heater, electrical system and panel, dual HVAC systems, ductwork, and insulation (2024–2025). The rebuilt carport includes a new engineered foundation designed to support the expanded primary suite above, featuring its spa-like bath and custom walk-in closet. The expansive double lot provides exceptional privacy and future possibilities, while the completely reimagined saltwater pool retreat is surrounded by elegant white travertine decking and complemented by a covered lanai with motorized screens, creating a private resort-style experience rarely found in an urban setting. The thoughtfully designed interior features soaring ceilings, elegant living spaces, a formal dining room, and a chef’s kitchen with custom cabinetry, oversized island, premium Dacor double ovens, and gas cooktop. The primary suite includes a spa-inspired bath with a freestanding bathtub and expansive custom walk-in closet, while additional bedrooms offer comfort and privacy. Minutes from Lake Eola, Thornton Park, the Dr. Phillips Center for the Performing Arts, Winter Park, Park Avenue, Michelin-recognized dining, Orlando Health, and AdventHealth, this extraordinary residence offers a rare opportunity to own a fully reimagined historic estate in the center of Orlando’s most desirable urban lifestyle.

1408 E Church Street, Orlando
$1,675,000
5 Beds ⋅ 5 Baths ⋅ O6431503 MLS
A Rare Opportunity in Coveted South Bay — Dr. Phillips Set in one of Southwest Orlando's most sought-after communities, this custom Mediterranean style estate by a renowned architect offers something today's luxury buyer rarely finds: grandeur, scale, and private access to the legendary Butler Chain of Lakes. A brick paver circular drive and columned, arched entry set the tone, opening to a striking split staircase, soaring 16' pocket tray ceilings, and designer chandeliers throughout the formal living spaces. The kitchen — appointed with high-end GE Café appliances — flows seamlessly into an expansive family room built for grand entertaining. Five generous bedroom suites each offer a private retreat. Built to endure with solid block construction and steel-wrapped rafters, and a new air conditioning system. Outdoors, a screened living space delivers a resort experience: custom pool, spa, and fountain, plus a pool house with shower and grill. South Bay residents enjoy private tennis courts and, most notably, private dock access to the Butler Chain via Lake Tibet — a boater's dream in the heart of Dr. Phillips. Moments from Restaurant Row, Bay Hill, world-class shopping, and exemplary Dr. Phillips schools. A signature residence in an unrivaled location. Private showings by appointment.

7957 S Park Place, Orlando
$1,650,000
10 Beds ⋅ 9 Baths ⋅ O6442060 MLS
Welcome to 6103 High Seas Dr, Orlando, FL — a fantastic opportunity to own a vacation-style property designed for memorable stays and strong investment potential. This impressive home stands out with its game room located in the spacious loft, creating the perfect entertainment area for family and guests. The property also features themed bedrooms that bring a fun, immersive vacation experience to life and make the home especially appealing to short-term rental guests. Beyond its unique design and entertainment features, this property offers an exciting investment opportunity in the Orlando market. With its combination of guest-friendly amenities, distinctive themed spaces, and desirable location, it has the potential to be an attractive addition to an investor’s portfolio or an exceptional vacation home. Whether you're looking for an investment property, a vacation retreat, or a place that guests will remember, 6103 High Seas Dr is worth seeing in person. Interested in learning more? Contact us today to schedule a private visit or showing and discover everything this property has to offer!

6103 High Seas Dr, Orlando
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.