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SARASOTA

3920 RED ROCK WAY

4 Beds

4 Baths

4,144 Sq.Ft.

$5,500,000

MLS#: A4635399

One or more photo(s) has been virtually staged. Custom-built riverfront estate on 18.5 acres in the gated Seaside Landings community of Flagler Beach, offering luxury coastal living with no expense spared. This stunning residence features over 6,200 sq ft of living space with 5 bedrooms, 6.5 baths, a 6-car garage, and a massive 65 ft x 42 ft outbuilding perfect for RVs, boats, car collections, or a serious workshop. A separate, detached 32 ft x 26 ft game room serves as a true entertainment pavilion, complete with a wet bar, home theater, and bath, providing guests with their own private retreat away from the main home. Rich wood flooring runs throughout and captures incredible river views from many rooms, including the riverfront dining room, executive office, and inviting living room with double-sided fireplace and custom built-ins. The main level also offers a large utility room, bedroom, and three baths, providing flexible space for multigenerational living or extended-stay guests. The gourmet kitchen impresses with quartz countertops, quartz backsplash, and a huge, well-equipped butler's pantry designed for effortless entertaining. Upstairs, the owner's suite is a private sanctuary with sweeping river views and a massive walk-in closet with custom built-ins, while three additional guest bedrooms, all en-suite, ensure comfort and privacy for family and visitors. Outdoor living is resort-caliber, with a covered lanai overlooking the pool and hot tub, summer kitchen, and travertine flooring, plus an additional screened lanai with a fireplace for cozy evenings by the water. The private dock with boat house provides direct access to the Matanzas River and Intracoastal Waterway, ideal for boating, fishing, and paddle sports right from your backyard. Seaside Landings itself is an exclusive, Intracoastal-front, gated community known for its Old Florida ambiance, majestic oaks, and wide canals, offering a peaceful, upscale environment for boaters and nature lovers. Residents enjoy a true coastal lifestyle with direct Intracoastal access, scenic Florida vistas, and an intimate, low-density neighborhood feel, all just minutes from Flagler Beach's shoreline, local restaurants, and A1A, with convenient access to I-95, and multiple nearby airports. An active social environment and community gathering spots along the Intracoastal, including a screened gazebo, fire pit, barbecue area, benches, and kayak rack, further enhance the relaxed yet refined lifestyle that makes Seaside Landings so desirable.

FLAGLER BEACH

239 SEASIDE LANDINGS DRIVE S

5 Beds

6 Baths

6,201 Sq.Ft.

$5,500,000

MLS#: V4949052

This parcel is one of two contiguous properties (1420 Gulf and 1440 Gulf) that may be acquired individually or together, offering a unique opportunity to secure a meaningful stretch of Gulf frontage today, with the option to expand into a nearly one-acre estate. Whether as a standalone homesite or part of a larger assembled holding, the flexibility here is rarely available on the Pinellas coastline.
With proportions ideally suited for a custom coastal residence, the property supports a thoughtful architectural program, including a gracious arrival sequence from Gulf Boulevard, expansive outdoor living, and direct beach access. The depth allows for the kind of front-to-back design seen in the most desirable estates of Palm Beach and Jupiter Island, with the residence oriented to capture unobstructed Gulf views and sunset exposure.
Belleair Shore is exclusive by design. Spanning just a quarter-mile of coastline, with only 58 single-family residences permitted in perpetuity, the town offers a level of privacy and permanence increasingly difficult to find.
For those seeking a premier Gulf-front homesite, with the rare ability to expand or create a larger legacy holding, this offering presents a compelling opportunity.
Photos may include AI-enhanced images showing the property with existing structures removed (scheduled for demolition pending permits). Do not walk the property without listing agent present.

BELLEAIR BEACH

1420 GULF BOULEVARD

None Beds

None Baths

0.47 acres

$5,500,000

MLS#: TB8502634

CAPTIVA

16205 CAPTIVA DRIVE

4 Beds

4 Baths

3,890 Sq.Ft.

$5,500,000

MLS#: A4693267

ST PETERSBURG

1237 BRIGHTWATERS BOULEVARD NE

5 Beds

5 Baths

5,733 Sq.Ft.

$5,500,000

MLS#: TB8474777

Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

WINDERMERE

5138 FAIRWAY OAKS DR

4 Beds

5 Baths

4,330 Sq.Ft.

$5,500,000

MLS#: O6401757

SARASOTA

2043 ALAMEDA AVENUE

None Beds

None Baths

0.87 acres

$5,500,000

MLS#: A4694103

Pre-Construction. To be built. Prime development opportunity.Unlock the potential of this 13-acre development site, strategically positioned in a booming Marion County / Dunnellon hub. this site is already County-approved for 38 flex/warehouse units, this property is a rare find for developers and investors looking to capitalize on the growing demand for modern flex space. Featuring ample acreage, prime visibility, and easy access to a major road (US HWY 41), this site offers the perfect canvas to bring a high-yield commercial project to life. An exceptional opportunity to build, lease, and hold in one of the region’s most dynamic markets. This property is ready for immediate construction. Don’t miss the chance to secure a high-value project site with approvals in place.

DUNNELLON

TBD US HWY 41

None Beds

None Baths

79,514 Sq.Ft.

$5,500,000

MLS#: S5134025

5 Bedrooms | 5 Full Baths | 3 Half Baths | Lake front-Private Pool | 4-Car Climate-Controlled Garage

Experience refined living in this custom-built, lakefront ( Lake Apopka) estate in the exclusive, guard-gated community of Bella Collina. Designed for both grand entertaining and everyday luxury, the open-concept main living area features soaring ceilings, a stone fireplace wall, and expansive sliding glass doors that blur the line between indoor and outdoor living. The chef’s kitchen is a true showpiece with a waterfall-edge quartz island, Thermador appliances, custom cabinetry, and a spacious walk-in pantry—perfect for hosting gatherings or preparing intimate meals.

The main level boasts a custom-built bar with dual wine refrigerators, an entertainment lounge that flows seamlessly to the lanai, a home office, a guest suite with en-suite bath, and two designer guest baths. The luxurious primary suite is a private retreat, featuring a stone fireplace, morning bar with Thermador coffee system, spa-style bath, and private lanai with fireplace—ideal for unwinding while overlooking the serene pool and landscaped grounds.

Upstairs offers three additional en-suite bedrooms boasting balcony access, perfect for enjoying morning coffee or evening sunsets, a bonus/media room, and half bath, ensuring comfort and privacy for family and guests alike. Outdoors, the home transforms into a resort-inspired retreat with a fully equipped summer kitchen, covered lounge and dining areas, and multiple spaces designed for both relaxation and entertainment. Host sunset gatherings poolside, enjoy weekend brunch under the wood-paneled lanai, play golf in your private putting green with bunkers from an elevated 70-yard (approx.) tee or take in the views while lounging by the sparkling pool framed by lush landscaping.

Premium upgrades include a Crestron Home Automation System which allows the control of lights, shades, temperature, music, security and more from a single platform, elevator, built-in speaker system, water filtration, and a climate-controlled 4-car garage with utility area. Located within a short distance to the amenity-rich setting of Bella Collina, featuring a Nick Faldo Championship golf course, a luxurious spa, Har-Tru tennis courts, pickleball courts, clubhouse, outdoor pool complex, cutting-edge fitness center with complimentary fitness classes, lake views and monthly culinary and/or wine events. Don’t miss the opportunity to own this one-of-a-kind luxury retreat in Central Florida’s premier private community.

BELLA COLLINA

16834 ARTIMINO LOOP

5 Beds

5 Baths

6,676 Sq.Ft.

$5,500,000

MLS#: O6334958

Under contract-accepting backup offers. Once in a lifetime, El Cerro - The Ultimate Caribbean Retreat perched on a hilltop with Expansive Caribbean Views is now being offered for sale. This unique hilltop property consists of thirty acres and includes three different homes. Each allows solitude from the others yet they are connected by the privacy experienced within the confines of the fenced estate. The property comprises eight bedrooms and nine bathrooms and includes a beautiful swimming pool and sauna. The convenient access is from the nearby Esperanza Village and is entered via electronic access control and boasts a haven of privacy and unparalleled views of the Caribbean.

The Main House has four luxurious bedrooms all with en suite bathrooms. This home also offers spacious living, dining and kitchen areas and extraordinary Caribbean views. The Rock House has three bedrooms and three bathrooms, living, dining and kitchen areas all with birds eye Caribbean views. The Pool House has one bedroom and full bathroom. It also has kitchen, living and dining areas and a sauna all situated adjacent to the gorgeous swimming pool which has an additional exterior bathroom.

The property has a manager/caretaker home that is attached to the garages used for the storage of equipment and vehicles. This magnificent and one of a kind Vieques estate borders thousands of acres of grazing land owned by the Municipality of Vieques adding unprecedented privacy surrounded by nature.

VIEQUES

1 EL CERRO

8 Beds

9 Baths

7,665 Sq.Ft.

$5,500,000

MLS#: PR9106479

An extraordinary and increasingly rare offering in the State of Florida — ±147 acres of legacy land defined by privacy, scale, and natural permanence. This assemblage presents a configuration seldom encountered: multiple parcels entirely enveloped by conservation and government-owned lands, creating a protective buffer that ensures enduring seclusion and an unmatched sense of control over one’s surroundings. Expansive, improved pastures sit high and dry, framed by native landscapes that reflect Old Florida at its finest.

Towering oak hammocks shelter abundant wildlife including whitetail deer, Osceola turkey, and a diverse array of native species, while a distinct section of the property preserves planted witness trees dating back to the early 1800s — a living testament to Florida’s earliest surveying history and a feature virtually impossible to replicate. Of the seven parcels, three carry approved building opportunities, allowing a future owner to thoughtfully steward the land while establishing a private compound, equestrian estate, or multi-generational retreat without compromising the integrity of the landscape.

An additional dimension of value exists through ±77 acres connected via deeded easements approximately two miles away, paired with a separate ±70-acre tract offering strategic flexibility for a discerning buyer. Whether envisioned as a premier recreational facility, a private hunting preserve, or a secondary enclave dedicated to the heritage lifestyle of rural Florida, these opportunities provide scale and optionality rarely found within a single acquisition strategy.

Currently utilized for agricultural purposes, the owner operates a cow-calf program supported by leased surrounding lands, underscoring the property’s functional productivity as well as its investment credibility. This is not merely acreage — it is Florida as it once was and increasingly will never be again. A generational holding for those who value privacy over proximity, permanence over convenience, and stewardship over spectacle. An opportunity to secure, preserve, and cherish a vanishing way of life.

GROVELAND

LAKE ERIE ROAD

None Beds

None Baths

147.3 acres

$5,500,000

MLS#: W7883334

GUAYNABO

FELIPE LA VOZ RODRIGUEZ

None Beds

None Baths

48.55 acres

$5,500,000

MLS#: PR9122054

Perfectly positioned on approximately 130 feet of deep sailboat water, this exceptional waterfront estate offers an extraordinary opportunity to experience the very best of Sarasota’s luxury lifestyle.

Encompassing over 6,100 square feet, the residence was thoughtfully designed to balance grand-scale entertaining with comfortable everyday living. A dramatic two-story living room, sweeping staircase, extensive custom millwork, and walls of glass create a sense of timeless elegance while framing breathtaking water views throughout the home.

The gourmet kitchen serves as the heart of the residence, seamlessly connecting to multiple gathering spaces and opening effortlessly to the expansive waterfront terrace. Corner sliding glass doors dissolve the boundaries between indoors and out, revealing a resort-style infinity-edge pool, summer kitchen, covered entertaining areas, and sparkling bay views beyond.

The luxurious primary suite is a private waterfront retreat featuring a separate dressing room, generous dual closets, and serene water vistas. Additional guest suites provide exceptional comfort and privacy for family and visitors alike.

Designed for both recreation and relaxation, the home also features a private office/library, elevator access, media and game room with full bar, and a four-car split garage.

Outside, the lifestyle continues with a private dock, boat lift, fishing pier, and immediate access to Sarasota Bay. Whether enjoying sunset cruises, waterfront dining, or simply relaxing poolside while watching dolphins and boats pass by, every day feels like a vacation.

Rarely does a property combine this level of space, waterfront presence, boating access, and location. Just minutes from downtown Sarasota, St. Armands Circle, and the area’s renowned beaches, this is a home designed for those who expect the very best.

SARASOTA

1541 CARIBBEAN DRIVE

5 Beds

4 Baths

6,035 Sq.Ft.

$5,500,000

MLS#: A4695466

SARASOTA

7524 WESTMORELAND DRIVE

6 Beds

5 Baths

6,215 Sq.Ft.

$5,500,000

MLS#: A4695898

DUNEDIN

1720 SANTA BARBARA DRIVE

6 Beds

5 Baths

5,833 Sq.Ft.

$5,500,000

MLS#: U8201320

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