Englewood Real Estate

Homes for Sale with a Pool in Englewood, FL

Welcome to your dedicated resource for homes for sale with a pool in Englewood, 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 Englewood, 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 Englewood, FL

$4,490,000
5 Beds ⋅ 4 Baths ⋅ A4689647 MLS
To experience this breathtaking beach-to-bay residence is to understand what true, uncompromised Gulf Coast luxury feels like. Situated at 756 N Manasota Key Road, this commanding dual-waterfront sanctuary represents one of the rarest and most significant home and land assets on Florida’s entire coastline. Spanning seamlessly from 155 feet of pristine, turquoise Gulf of Mexico beach frontage to an additional approximate 155 feet of protected deep-water frontage on Lemon Bay, this extraordinary legacy estate delivers an unrepeatable coastal lifestyle defined by absolute privacy, natural grandeur, and timeless elegance. Cherished by the same family for nearly three decades, the expansive, compound-sized setting captures sweeping, unobstructed water views in every direction, offering front-row seats to spectacular Gulf sunsets each evening and tranquil, glowing bay sunrises every morning across nearly 300 feet of depth. The estate offers 4,033 square feet of impeccably crafted living space thoughtfully designed to accommodate multi-generational living or seamless host-guest separation, featuring a 3-bedroom, 3-bath main residence alongside a fully private, independent 2-bedroom guest apartment above the garage complete with its own dedicated living room. Inside the main home, dramatic cathedral ceilings, warm rich cypress accents, integrated surround sound, and custom built-ins frame an airy, open-concept living space that flows effortlessly through multiple windowed doors to the screened pool area and private grounds. A dedicated bayfront dining room framed by high-end Andersen windows fills with soft morning light, while the premium chef’s kitchen features solid wood cabinetry, two pantries, a Thermador cooktop, GE Monogram appliances, breakfast bar seating, and direct water views right from the sink. Designed to celebrate outdoor living at its finest, step out to a heated pool and an expansive 18x48 open lanai sitting just steps from the soft sand, or stroll over to your private 89-foot dock—re-decked in 2025 and fully equipped with water, electric, and a fish cleaning station—offering effortless, deep-water boating along Lemon Bay and immediate access through Stump Pass straight out to the open Gulf. Curate the ultimate Florida day by taking the boat to favorite nearby waterfront spots like Magnolias on the Bay, The Lighthouse Grill, or The Waverly Restaurant & Bar, or take advantage of optional memberships at the local Manasota Key Club and nearby cultural gems like the Hermitage Artist's Retreat. Positioned on the highly coveted, private, gated north end of the Key, this fully fenced estate also delivers remarkable peace of mind backed by major capital improvements, including a high 12.9 foot site elevation, several impact windows and doors, a 2021 metal roof, three newer AC systems, modern PVC plumbing, a 2016 septic system, and a brand-new 2025 pool cage. Whether envisioned as an architectural masterpiece, a cherished family compound, or a preserved tropical sanctuary, properties of this frontage, structural integrity, and scale simply cannot be duplicated—contact the listing agent directly today to request a comprehensive feature dossier or to arrange your private, confidential tour.

756 N Manasota Key Road, Englewood
$4,300,000
2 Beds ⋅ 2 Baths ⋅ A4690960 MLS
OWNER FINANCING AVAILABLE!! A rare and irreplaceable oceanfront estate offering an exceptional blend of refined coastal living and high-performing income potential. Situated on an expansive 0.63 acre oceanfront lot, zoned RMF 7.5 an acre, this private compound features two distinct residences and is currently operating as a successful luxury Airbnb retreat. Designed for both exclusivity and flexibility, the dual-residence layout is ideal for a private owner’s enclave, multi-generational living, or a premier short-term rental investment. With limited oceanfront properties offering this level of scale and versatility, opportunities like this are becoming increasingly scarce. Enjoy sweeping ocean views from the rooftop deck—perfect for sunset entertaining—while the private pool and spacious grounds create a resort-style setting for relaxation and guest enjoyment. The direct oceanfront setting delivers an unparalleled connection to the water and a true luxury lifestyle experience. The primary oceanfront residence presents a compelling value-add opportunity, finishing renovations are underway, and this allows a discerning buyer to fully customize finishes, design, and appointments to their exact vision. With completion, the property is well-positioned to command a significantly higher market value in line with other fully renovated luxury oceanfront estates, offering meaningful upside potential for both end-users and investors. Located just moments from restaurants, shopping, and the main beach, this is a rare chance to secure a premier beachfront compound with both immediate income, and long-term appreciation potential. Take a short stroll through the sand to the vibrant turquoise teal ocean, and feel the serenity. Offers rental flexibility as short term rentals are permitted.

2630 N Beach Road, Englewood
$3,990,000
12 Beds ⋅ 8 Baths ⋅ D6147829 MLS ⋅ Na BLDG.
Established 7-Unit Short-Term Vacation Rental Property on Manasota Key! Rare opportunity to purchase an established licensed short-term vacation rental property currently accommodating nightly, weekly, monthly, and seasonal rentals on the desirable southern end of Manasota Key. Offered as a package, the property consists of two adjacent buildings with a total of seven rental units. The Main House is a two-story building featuring five remodeled rental suites, including three 1-bedroom, 1-bathroom suites, one 2-bedroom, 1-bathroom suite on the lower level, and a spacious 3-bedroom, 2-bathroom suite occupying the entire upper level. The lower-level suites feature open floor plans, updated kitchens with granite countertops and stainless-steel appliances, updated bathrooms with tiled walk-in showers, and private outdoor patios. The upper-level 3-bedroom, 2-bathroom suite provides flexibility for owner occupancy or additional rental income and features a full kitchen, living area, ensuite primary bedroom, private balconies, and partial Gulf views. The Pool House is a renovated single-story duplex featuring two side-by-side 2-bedroom, 1-bathroom suites connected by a shared screened front porch and offering access to a private heated swimming pool and tiki bar area. Designed to create a memorable guest experience, the property features lush tropical landscaping, evening landscape lighting, private patios and outdoor seating areas for each suite, outdoor dining spaces, Weber grilling stations, outdoor showers, shell and shark tooth cleaning stations, on-site laundry facilities, and Wi-Fi. A two-car gathering garage provides additional guest space with lawn games, a full-size refrigerator with a freezer, a large-screen TV, and seating for 32. The Pool House offers even more amenities with a private heated swimming pool, tiki bar gathering area, and outdoor entertainment space. This setup allows for a multitude of rental options for large groups, families, or the single couple looking for a peaceful vacation spot. Located on the southern end of Manasota Key, the property is within walking distance of nearby beach access and just moments from Stump Pass Beach State Park. Guests enjoy convenient access to Gulf beaches, boating, fishing, shelling, wildlife viewing, waterfront dining, tiki bars and nightly entertainment, marinas, shopping, golf courses, and numerous local attractions. Few properties offer the combination of scale, flexibility, guest amenities, and island charm found in this unique Manasota Key investment offering, creating an exceptional opportunity in today's vacation rental market.

1120 Gulf Boulevard, Englewood
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