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

756 N Manasota Key Road, Englewood
$4,290,000
5 Beds ⋅ 4 Baths ⋅ A4689647 MLS
A rare, irreplaceable Gulf-to-Bay legacy compound situated on the private, gated north end of North Manasota Key: 756 North Manasota Key Road commands an extraordinary coastal position spanning from 155 feet of private Gulf of Mexico beach frontage to 155 feet of protected deep-water dockage on Lemon Bay. Cherished by the same family for nearly three decades, this compound-sized parcel captures both glowing bay sunrises and vibrant Gulf sunsets across nearly 300 feet of pristine depth. Anchored by an exceptional 12.9-foot site elevation and comprehensive capital infrastructure—including a 2021 metal roof, three updated HVAC units, modern PVC plumbing, a 2016 septic system, a 2025 pool cage, and selected impact-rated openings within a fully fenced perimeter—this estate delivers rare barrier island peace of mind. Offering 4,033 square feet of living area, the property is thoughtfully configured for multi-generational living or refined host-guest separation. The main residence features 3 bedrooms, 3 full baths, soaring cathedral ceilings with rich cypress accents, custom millwork, integrated surround sound, and Andersen windows framing sweeping water views. At its center, the chef’s kitchen is appointed with solid wood cabinetry, dual pantries, a Thermador cooktop, and GE Monogram appliances that look directly out over Lemon Bay. Providing ultimate privacy, a self-contained 2-bedroom guest apartment with its own dedicated living room is set above the garage. Outdoor living is engineered for world-class recreation. Step from the main living area to the heated screened pool and an expansive 18x48 open lanai just strides from the sand, or walk to the protected bay side to your private 89-foot deep-water dock—newly re-decked in 2025 and equipped with power, water, and a cleaning station. Boating is effortless with sheltered mooring on Lemon Bay and bridge-free navigation through Stump Pass straight into the Gulf, as well as easy cruising to local waterfront dining. Whether enjoyed immediately as an authentic coastal sanctuary or reimagined into an architectural showpiece, opportunities pairing this caliber of dual frontage, high elevation, and seclusion are virtually impossible to replicate. Contact the listing team directly to request the complete property dossier or arrange a private, confidential tour.

756 N Manasota Key Road, Englewood
1120 Gulf Boulevard, Englewood
$4,180,000
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
8017 Manasota Key Road, Englewood
$3,850,000
5 Beds ⋅ 7 Baths ⋅ A4708940 MLS
Virtually Staged. Set on nearly a full acre with 214 feet of direct bay frontage, this Manasota Key waterfront estate offers a true bay-to-Gulf lifestyle, combining deep-water boating access with convenient deeded beach access just across the street. Positioned along a quiet stretch of Manasota Key Road, the property delivers privacy, scale, and unobstructed water views across Lemon Bay. Built in 2001 by Newport Home Builder, the residence spans more than 5,200 square feet across two living levels and has been meticulously maintained with thoughtful updates, including a new tile roof in 2024 and new impact-rated garage doors serving the oversized four-car garage. Impact glass windows and sliders throughout the home frame the bay while enhancing storm protection and energy efficiency. The main living level is designed for everyday comfort and entertaining. Diagonal tile flooring connects the living room—opening directly to the screened bayfront lanai—with the formal dining area and expansive kitchen. The chef’s kitchen features solid-wood cabinetry, granite countertops, center island, breakfast bar, informal dining space with wine bar built-in, and walls of glass sliders that open to the covered patio and summer kitchen. The adjacent family room enjoys panoramic bay views and seamless outdoor connection. The primary suite is located on the main level, offering a private retreat with a stone-encased fireplace, morning kitchen, custom walk-in closet, en-suite bath, and direct access to the bayfront patio. Two additional guest suites, a dedicated office or study, and a laundry room complete the first floor. Upstairs, guests enjoy a loft-style sitting area, and two spacious bedroom suites overlooking the bay (one suite is large enough to be an additional primary suite), providing flexibility for multi-generational living, work-from-home needs, or extended stays. Outdoor living is a defining feature. The panoramic screened pool deck, completed with travertine flooring, surrounds a resurfaced PebbleTec pool and raised spa, creating a comfortable setting for waterfront entertaining. Boating enthusiasts will appreciate the deep-water dock, updated in 2016 and equipped with a boat lift, electric, and water—offering no fixed bridges and direct access to open bay waters and the Gulf of Mexico. Deeded beach access is conveniently located just across the street. Ideally positioned on Manasota Key, this estate offers quick access to local waterfront dining, marinas, and nature preserves, while remaining close to Englewood, Venice, and Sarasota’s Cultural Coast. Championship golf courses, shopping, and dining are nearby, with world-class beaches lining both Manasota Key and nearby barrier islands. A rare opportunity to secure a direct bayfront property with beach access, acreage, and deep-water boating—delivering the best of Southwest Florida coastal living.

8017 Manasota Key Road, Englewood
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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.

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