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An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis
Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining.

While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life.

The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary.

Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the entire home.

While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets.

Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center, community pool, and exclusive Johns Lake access. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping.

This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.

WINTER GARDEN

16614 HARBOR SAIL WAY

6 Beds

5 Baths

4,882 Sq.Ft.

$1,495,000

MLS#: O6414639

Natural light moves with intention through this three-story townhome, where a private elevator connects all levels and a rare dual-exposure design brings brightness and balance to each floor. Private balconies extend the living experience outdoors, overlooking a dynamic downtown waterfront setting where live music and coastal energy become part of the backdrop. From the front-facing windows, views overlook a gazebo, cascading waterfall, and thoughtfully designed landscaping... adding a sense of calm and visual interest.

Set within Gramercy Court, the residence is thoughtfully positioned near parking and community gathering spaces, offering a seamless blend of accessibility and privacy. Interiors reflect a refined, cohesive aesthetic. Walls finished in Sherwin-Williams “Ice Cube” are paired with vinyl plank flooring in “Chatter Oak,” creating a calm, neutral foundation throughout, complemented by 8-foot solid wood doors, tailored millwork, and a discreetly integrated office nook. Remote-controlled blinds and ceiling fans are installed throughout every room, while a Nest thermostat provides streamlined climate control.

The kitchen is designed with both precision and presence... gray shaker cabinetry, quartz countertops in “Dove Beach,” and a full-height subway tile installation are paired with a professional-grade appliance suite, including Sub-Zero refrigeration, a Wolf gas range with hood and microwave, and a Cove dishwasher. A walk-in pantry adds further functionality without compromising design.

Three bedrooms and 3.5 bathrooms continue the home’s elevated material palette, featuring granite countertops, brushed nickel fixtures, and glass shower enclosures. The primary suite offers a spacious walk-in closet and a dual-sink vanity designed for everyday ease.

A whole-home water softener, an instant tankless water heater and laundry on the same floor as the primary makes life simpler. The garage is finished with durable epoxy flooring, includes two walk in storage closets, and is equipped with an electric vehicle charging station.

In just a few steps, you’re in the heart of Downtown Dunedin, home to vibrant weekly markets, seasonal festivals, and community parades, the area also features live music, local gatherings, and a strong sense of connection providing a lively yet well-balanced ambiance where you can enjoy the energy from a comfortable distance.

Enjoy award-winning restaurants and craft breweries, scenic waterfront parks, a full-service marina, and convenient access to the Pinellas Trail. A golf-cart-friendly setting where everything is close and the energy is always coastal and connected… with three gorgeous beaches just minutes away. This is Dunedin living at its finest.

A composed and well-executed residence offering low-maintenance living with a level of finish and design rarely found in townhome communities. See... Fall in Love... Make it Your Own!!!

DUNEDIN

946 HIGHLAND AVENUE 16

3 Beds

3 Baths

1,970 Sq.Ft.

$4,000

MLS#: TB8517206

Beautifully updated 2-bedroom, 2-bath first-floor condo featuring an additional oversized storage closet. This well-maintained unit offers updated flooring and bathrooms, with tile in all wet areas and carpet in the bedrooms. The bathrooms feature modern vanities, sinks, and countertops. Enjoy the convenience of an in-unit washer and dryer, ceiling fans, and a sleek, modern appliance package.

Located in the desirable "Gallery at Bayport" community off Hillsborough Avenue, residents have access to a community pool, tennis courts, and fitness center. Conveniently situated near I-275, the Veterans Expressway, Oldsmar, Clearwater, and the airport.

Don’t miss this opportunity to lease a move-in ready condo in a prime location. Tenant occupied through 6/30/26. Please call to schedule a showing.

TAMPA

5602 BAYWATER DRIVE

2 Beds

2 Baths

1,080 Sq.Ft.

$1,875

MLS#: TB8510767

Discover the perfect canvas for your Florida dream home! This oversized 0.24-acre lot offers plenty of room to design the home you've always envisioned. Located in a developing area of Lehigh Acres, you'll enjoy a peaceful setting while remaining close to everyday conveniences, outdoor recreation, and Southwest Florida's beautiful beaches. Whether you're ready to build or looking to secure land for the future, this property is a fantastic opportunity.

LEHIGH ACRES

1121 DAMEN STREET E

None Beds

None Baths

0.24 acres

$25,000

MLS#: O6415198

Virtually Staged. MARGARITAVILLE is the place to enjoy retirement. 2 Bed 2 Bath 2 Car Garage for easy living. Option to rent or purchase. Enjoy Fins Up for full gym experience. Indoor lap pool, as well as Hot Tub. Full service restaurant at the Chill located between resort style pool & Town Square.

DAYTONA BEACH

562 LANDSHARK BOULEVARD

2 Beds

2 Baths

1,160 Sq.Ft.

$2,600

MLS#: TB8517676

Virtually Staged. Enjoy elevated living in this beautiful, like-new home perched on a premium lot with scenic views. Offering the perfect blend of modern design and natural beauty, this well-maintained residence features a spacious open-concept floor plan that seamlessly connects the living, dining, and kitchen areas—ideal for entertaining or relaxing at home.

Abundant natural light fills the interior, showcasing stylish finishes and creating a warm, inviting atmosphere throughout. Step outside to the covered rear porch, where you can unwind with your morning coffee while taking in breathtaking sunrises and peaceful surroundings.

The professionally maintained yard provides plenty of space to enjoy the outdoors, whether hosting friends and family or simply appreciating the view. Nestled in a quiet neighborhood while remaining conveniently close to shopping, dining, schools, and major roadways, this home offers the perfect balance of comfort and convenience.

Residents are enrolled in a $95 monthly Resident Benefits Package (RBP), which includes lawn care, pest control, air filter delivery, and additional valuable services designed to enhance your living experience.

Don't miss this opportunity to make this exceptional property your next home!

GROVELAND

338 RIDGEMARK AVENUE

4 Beds

2 Baths

1,824 Sq.Ft.

$2,300

MLS#: O6415525

Recently avilable the areas best kept secret - Swifton Villas, a Florida Registered 55+ Community. Just 1.2 miles to the water, via the locals secret beach access. Bike, walk, or take a ride share for quick daily access to the sand and sun. Also a short 1/8 mile walk next to Swifton Villas, a shopping plaza featuring Detweiller's Grocery, CVS, Ace Hardware and so much more. Residents frequently walk mornings for conversation with the neighbors and in the evening, enjoy the pool which is heated to 90 degrees year round. The clubhouse is very popular. Full kitchen and bathroom, large tv, a library filled with books and DVDs, and even a puzzle table. The villa itself, located facing the clubhouse and pool, so walk out back and enjoy. This very popular two bedroom, 2 bath layout is nicely updated with luxury vinyl plank, shiplap kitchen ceiling adornments and a large functional lanai with blinds for privacy and windows that open for those Gulf breezes. This villa may be leaseed turnkey furnished...preferably actually. While we cannot invite pets for tenants leasing due to board rules, we are happy to accomodate medically necessary service animals in accordance with the law. Testing the waters of living in paradise? This is the perfect spot! The neighbors are very friendly and helpful. Call today for a private showing.

SARASOTA

2814 SWIFTON DRIVE 108

2 Beds

2 Baths

934 Sq.Ft.

$2,150

MLS#: A4696686

Beautiful 3-bedroom, 2.5-bath townhome in a desirable newer community! Featuring a spacious open floor plan, modern finishes, and a prime location with easy access to I-4, 27 HWY , shopping, dining, and major attractions. Conveniently located near top-rated schools and community amenities. Available June 30th. Don't miss this exceptional rental opportunity—schedule your showing today!

DAVENPORT

2743 FETCHING TRL

3 Beds

2 Baths

1,699 Sq.Ft.

$2,100

MLS#: O6415834

#O6415631

ORLANDO

11520 WESTWOOD 527

2 Beds

2 Baths

971 Sq.Ft.

$1,900

MLS#: O6415631

INVERNESS

598 S CHAMBERS WAY

None Beds

None Baths

1.22 acres

$64,900

MLS#: OM726356

Student Friendly. Available for move-in on August 10th. 5 Bedroom home located 5 Minutes from UCF. Screened in patio with lots of extra living space. Corner lot for easier parking. Washer & Dryer and Lawn maintenance is included. Applicants must have co-signer and be in school. No pets please. Renters insurance required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.

ORLANDO

4300 IVEYGLEN AVENUE

5 Beds

2 Baths

2,120 Sq.Ft.

$3,099

MLS#: O6415659

SANFORD

3316 W 5TH STREET

None Beds

None Baths

1,360 Sq.Ft.

$425,000

MLS#: V4949596

This 2,340 SF office condo is available for sale in the beautifully maintained Peridia Office Park. Peridia Office Park offers a professional atmosphere within a quiet setting featuring both medical and professional offices. Join THB Med Spa, Associated Family Physicians, TrustMed Billing Solution, Romero Law Firm, Fidelity Mortgage Loans, State Farm Insurance Agent, CenterWell Home Health, Lakewood Dental Excellence, APC Pediatrics, Costal Luxury Partners Real Estate, Hendricks Wealth & Real Estate Management, and more.

This corner condo unit features a welcoming front entrance that opens into a spacious, open-concept floorplan, currently configured as a physical therapy practice. Upon entry, visitors are greeted by a reception area and a large private office conveniently located to the right.

The layout includes three additional private offices along the right side of the suite, as well as a smaller office or potential storage/closet space near the front left corner. Two ADA-accessible restrooms are located in the rear left portion of the unit and are equipped with a washer and dryer, providing added convenience for medical, therapy, or service-oriented uses.

This highly versatile space is well-suited for a variety of professional applications, including medical or therapy practices, collaborative office environments, call centers, and traditional office layouts. The expansive open area offers flexibility for future customization, including the addition of a dedicated reception area, private offices, treatment rooms, or workstations to meet specific business needs. The rear right corner is currently open and could easily be enclosed to create a conference room, training space, or additional private office.

BRADENTON

3911 GOLF PARK LOOP 105

None Beds

None Baths

2,340 Sq.Ft.

$645,000

MLS#: A4696598

TOWNHOME located in the beautiful MADISON PLACE Community, offers 3 bedrooms / 2.5 bathrooms. Enjoy the privacy of this Interior Unit overlooking the pool, offering specious kitchen with stainless steel appliances, granite countertops. Dining room and Living Room filled with plenty of daylight throughout the first floor. Three bedrooms located on the second floor. The private master suite offers a large walk-in closet. Washer and dryer is included. Madison Place Community is conveniently located 3 miles from I4, minutes away from Heart of Florida Hospital, and one of the best shoppings you will experience at Posner Park. Community offers swimming pool, and playground. Landscape maintenance is included. Tenant will pay $40 application fee per adult person.

DAVENPORT

394 MADISON DRIVE

3 Beds

2 Baths

1,421 Sq.Ft.

$1,700

MLS#: O6415758

Large deeded RV Lot – Full time AND Part time – Come enjoy the easy living on this Lot with beautiful pavers. Offers plenty of room in the rear of lot for landscaping hobbies or just to relax. Don’t let this upgraded Lot pass you up! Shade is provided throughout the resort with large oaks and hickory trees adorned with Spanish moss that dances in the breeze. Sand hill cranes wander about. Your canoe is at hand for an early morning fishing trip along the shoreline or take the kayak if you prefer. For the boaters you may take an afternoon slow cruise around the lake. Glorious sunsets will prompt oohs and aahs from your visitors or friends as the sunsets are breathtaking. Come enjoy all the amenities of the park which include a clubhouse, 2 swimming pools, tennis court & shuffleboard, to name a few. Centrally located to Ocala, Palatka and only hour or so from Daytona Beach! Your golf cart will get you to the nearby stores and post office. Your electric bike will propel you around the paved streets of the resort – for the more adventurous grab the mountain bike and enjoy all the nearby trails. The 2018 Rockwood Signature Ultra Light 8335BSS RV can remain on the property and will be between the Sellers & Buyer(s) or seller will possibly remove.

SALT SPRINGS

25244 NE 143RD ST 180

None Beds

None Baths

0.09 acres

$75,000

MLS#: OM726384

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