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$13,000,000
10 Beds ⋅ 11 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
A Stunning Achievement in Design and Location Beyond Comparison. Incomparable Gulf views, dramatic architectural details and a highly coveted location combine for the height of luxury in this Mediterranean masterpiece overlooking the widest expanse of Clearwater Harbor. “Century Oaks” is the namesake of this storied estate that has entertained U.S. presidents, heads of state and is located on the grounds of the Ft Harrison used during the Spanish – American war. Commanding an unmatched 5.6 acres with 213 feet of direct waterfront, the 16,472 square foot mansion presents a rare opportunity to own one of the most iconic mansions in the state of Florida. Strategically positioned atop a large bluff, the sprawling residence was purposefully built to capitalize on vistas spanning Eye of the Gulf, Sand Key and the Clearwater skyline. Soaring cathedral ceilings, multiple windows and an expansive open plan create a welcoming setting for luxurious family living and entertaining—whether your guest list numbers two or 200. Truly an achievement in design and décor, the stunning 10-bedroom residence combines the artistry and grandeur of old world elegance with the sophistication and convenience of modern amenities. Beyond the distinguished porte cochere, the two-story layout offers a pleasing blend of formal and informal spaces which can accommodate any entertaining need including a grand entry hall, massive ballroom, banquet-size dining room and an inviting family room. Serving any occasion is the kitchen, equipped with everything a professional chef requires including a AGA cast iron range, two warming ovens, Subzero refrigerator, coffee station, breakfast bar, work island and casual dining space. Morning coffee is best served on the balcony as boats sail by and dolphins play steps away from your backyard. Evening cocktails become elevated on the entertainment terrace when gazing at a technicolor sunset over the sparkling waters of the Gulf of Mexico. Residents can enjoy numerous activities at home as the property includes a plush home theater, tennis and basketball courts, two swimming pools and two deep water docks that can accommodate yachts up to 60 feet. Augmenting the main house are two equally elegant guest homes. This peerless setting of waterfront splendor is conveniently located near cultural and entertainment venues, fine dining and shopping and award-winning Gulf beaches. Tampa International Airport is just a short drive away. Adjacent properties to the north and south (800 and 820 Druid Road) are available for purchase creating a large compound opportunity.

802 Druid Road S, Clearwater
$4,000,000
6 Beds ⋅ 5 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Waterfront Masterpiece in Clearwater’s Harbor Oaks. Breathtaking vistas of Clearwater Harbor and the Clearwater Beach skyline combine with manicured gardens and a coveted address to create an idyllic setting for this Greek Revival-style home in Harbor Oaks. Privately situated behind stately walls with gated access and a brick drive, the two-story home commands 1.1 acres and boasts more than 100 feet of direct waterfront along the Intracoastal Waterway. Harbor lights and city sights present a stunning backdrop for the outdoor oasis comprised of a lighted tennis court, tiered terraces, English gardens and a swimming pool. Particularly noteworthy is the exquisite observatory where spectacular Gulf sunsets are best viewed. Inside this spacious home is a sophisticated plan that redefines coastal elegance with a flair. Designed to promote comfortable family living as well as stylish entertaining, the home is appointed with an array of classic elements including crown moldings, arched doorways, custom millwork and Palladian windows. A generous display of glass doors allow natural light to fill interior spaces while also capitalizing on magnificent water views. Sized to generous proportions, the kitchen facilitates meal preparation with an abundance of storage cabinets and work space. Encompassing 6 bedrooms, 5 full and 2 half bathrooms, this waterfront masterpiece is complete with an expansive billiards room featuring a full size wetbar. The historic neighborhood of Harbor Oaks is conveniently located in the heart of Clearwater with easy access to cultural venues, recreational activities, major sporting events, world-class medical facilities and award-winning Gulf beaches.

800 Druid Road S, Clearwater
$2,925,000
4 Beds ⋅ 5 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Under Construction. Under Construction- Ready November 2025 - This stunning Magnolia Construction Home features the best of what any builder has to offer! Located in the heart of Downtown Clearwater in the Harbor Oaks neighborhood, this home has it all! Four full bedrooms, an office/den, a loft/recreation room, a dedicated oversized dining room plus a separate dining nook. This Energy Star beauty offers a perfect blend of luxury and historic charm. Past the entry is an office/den to the left and formal dining room. The foyer then opens up to an expansive family room with a gas fireplace, and stairwell to the second floor. The kitchen boasts custom built inset cabinets to the ceiling, an oversized pantry and a dedicated breakfast nook. With high end panel ready appliances and a large island that can easily seat four to five, this gourmet kitchen has everything for the most acquired chef! The first of two laundry rooms is also on this level. Moving to the second floor, there is a large recreation/loft area that is perfect for entertaining and includes a beverage cooler. The primary suite is located on the second floor with an enormous walk-in closet, free standing soaker tub, large shower, and split vanities with plenty of drawer space plus a dedicated makeup area. There is also an oversized rear lanai off of the master to look down upon the beautiful pool. Three separate guest bedrooms – with dedicated full bathrooms are also on this level. Finally, a second laundry room is also on this level. French doors lead from the family room to an expansive covered lanai with outdoor kitchen and plenty of room for patio sets. The yard features a heated spa & pool below with plenty of back yard left over. Other features include: Icynene spray foam insulation; impact windows and doors; custom built-ins and so much more! See the full list of upgrades, colored rendering and floor plans in the images. Don’t miss out on the opportunity to own this brand new Harbor Oaks gem!

407 Jasmine Way, Clearwater
$2,675,000
4 Beds ⋅ 6 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Tucked along one of the most coveted streets in **Historic Harbor Oaks, Clearwater’s first developed neighborhood**, this 1925 Spanish Mediterranean Revival blends old-world character with thoughtfully updated modern living. Surrounded by mature oaks, the home feels like a private European retreat just minutes from the water. Inside, natural light pours through five sunrooms that wrap the residence, creating warm, inviting living spaces throughout. A grand staircase welcomes you into the main level featuring a gracious living room with wood-burning fireplace, a cozy library nook, formal dining room, breakfast room, and an elegant kitchen with AGA dual-fuel range, Fisher & Paykel appliances, British Shaws of Darwen ceramic sinks and a butler’s pantry with wine refrigeration. Upstairs are three spacious bedrooms, each with en-suite baths, including a serene primary suite with its own private sunroom overlooking the oak canopy. A coral garden path leads to the detached 1-bedroom, 1-bath carriage house with kitchenette, ideal for guests, a private office, or creative studio, installed with separate wifi. Extensive renovations done over three years restore the home’s historic integrity while upgrading every major system. Improvements include new electrical and plumbing (2023), new exterior sewer line (2026), new roof (2019), new Trane split HVAC system with separate temperature control for each level (2023), a 26kW Generac whole-house generator, and a custom whole-house water filtration system designed to remove chemicals and microplastics. Architectural woodwork and copper downspouts were restored, and interiors feature custom Plain English cabinetry built in London, restored heart-pine floors, and handmade terracotta tiles imported from Siena, Italy. Outside, lush landscaping, new sod, and full irrigation. No HOA. Flood Zone X. Located just a short stroll from the Harbor Oaks pier for sunset views and minutes from Clearwater Beach, the Pinellas Trail, and Coachman Park with BayCare Sound. Renderings of the pool and wellness room are digitally created to illustrate the potential vision and design possibilities for these spaces. Historic charm. European soul. Completely turnkey for modern living.

403 Jasmine Way, Clearwater
$1,450,000
5 Beds ⋅ 4 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Tucked away on one of Clearwater’s most exclusive and historic streets in the coveted Harbor Oaks neighborhood, this newer construction masterpiece—built in 2022—combines Italianate-inspired architecture with modern sophistication. A timeless treasure, the residence features 5 bedrooms and 3.5 bathrooms, including a luxurious primary suite conveniently located on the first floor. Designed for both elegance and function, the open floor plan is enhanced by abundant natural light, exceptional storage, and refined finishes throughout. An upstairs loft offers additional living space, perfect for a home office, media room, or lounge. Every detail reflects quality and comfort—from hurricane-rated windows, Bosch appliances, and custom Closets by Design systems in every closet, to a 14x16 spa offering the ultimate in relaxation. Modern innovation elevates daily living with solar panels, a gas tankless water heater, and an electric vehicle charging station. Ideally located in a non-flood, non-evacuation zone, the home also offers peace of mind alongside its luxury features. Just steps away, residents enjoy the iconic Magnolia Fishing Dock, where evenings unfold with breathtaking sunsets over the Gulf. The home is also just a short distance from the reimagined Coachman Park, world-class entertainment at the Capitol Theatre and The Sound, and the vibrant shops and restaurants of Downtown Clearwater. Outdoor enthusiasts will appreciate nearby golf courses, the Pinellas Trail, Belleair Country Club, marinas, and of course, and the powder-soft sands of Clearwater Beach—just minutes away by foot or bike. Blending the timeless character of Harbor Oaks with today’s finest luxuries, this residence offers a rare opportunity waiting for you.

405 Jasmine Way, Clearwater
$1,125,000
Harbor Oaks SubDv. ⋅ 33756 Zip Code
Prime Downtown Clearwater office property on highly visible S Ft Harrison Ave, adjacent to Harbor Oaks neighborhood. The offering includes two office buildings on two parcels totaling 3,515 SF (2,140 SF and 1,375 SF), with 20 parking spaces and Office zoning. Ideal for an investor or owner-user, the property offers multiple options: maintain existing medical tenants for income, occupy one space and lease the other, or utilize the full 3,515 SF. A rare opportunity for flexible office use in a strong location.

908 S Fort Harrison Avenue, Clearwater
$915,000
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
NEW PRICE: Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42 villas in Harbour Circle with a community pool and spa and membership access to the deeded private beach club. This home boasts vaulted ceilings, multiple hurricane skylights, hurricane windows, sliders and front door, private atrium and new roof with trusses in 2025, coming completely furnished. Enjoy your morning coffee and dozens of magnificent sunsets on your large two level lanai. Enjoy a walk to Publix, CVS and several Banks close to your community. Only a short drive to Saint Armand's Circle and downtown Sarasota where you will find numerous options for shopping, dinning, theatres, ballet, opera and galleries.

2367 Harbour Oaks Drive, Longboat Key
$850,000
3 Beds ⋅ 2 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
A fully renovated, designer curated residence in Bay Isles — offering upgrades, furnishings, and lifestyle advantages rarely found at this price point. This turnkey 3BD/2BA, second story condo, stands apart with high impact windows and sliders, new community roofing and siding, rich engineered hardwoods, custom millwork, and upgraded lighting. The fireplace has been brought back to full working order and finished with a sleek Carrera marble front, blending craftsmanship with modern design. These improvements significantly reduce future maintenance costs and elevate long term value. The professionally redesigned kitchen features premium appliances, induction cooking, and a large island ideal for everyday living and entertaining. The primary suite offers dual walk ins, Stark wool carpeting, balcony access, and a spa level marble shower — finishes typically reserved for higher priced homes. A private balcony with motorized SPF screen captures sweeping golf course and sunset views, while the two car garage with epoxy flooring and a mini-split air conditioner provides like a single family home convenience. Ownership includes access to the newly renovated Bay Isles Beach Club, 24/7 gated security, a community pool/spa within walking distance, and proximity to the Longboat Key Club Moorings, St. Regis, and St. Armands. With its extensive upgrades, curated furnishings, and prime Bay Isles location, this residence delivers exceptional long term value and a truly elevated Longboat Key lifestyle.

2195 Harbourside Drive Unit 404, Longboat Key
$775,000
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
Welcome to effortless coastal living in this beautifully maintained, fully furnished end-unit villa on Longboat Key. Offering nearly 2,400 square feet of thoughtfully designed living space, this exceptional residence combines the spaciousness and privacy of a single-family home with the convenience of maintenance-free living—all just moments from the Gulf's renowned white-sand beaches. From the moment you step inside, soaring vaulted ceilings, abundant natural light, and an open, airy floor plan create a warm and inviting atmosphere. Designed for both comfortable everyday living and effortless entertaining, the home offers multiple gathering spaces, including a formal living room with a charming wood-burning fireplace and expansive sliding glass doors that open to an impressive 740-square-foot private terrace overlooking peaceful pond views. The kitchen is both stylish and functional, featuring granite countertops, updated cabinetry, rich wood flooring, plantation shutters, and a skylight that fills the space with natural light. Recent upgrades, including a new roof and new air-conditioning system completed in 2025, provide added comfort and peace of mind. Adding to the home's unique character are two private atriums that bring the outdoors in, creating bright, tranquil spaces throughout the residence. A versatile office with a built-in Murphy bed offers the flexibility to easily serve as a fourth bedroom, while the spacious primary suite provides a relaxing retreat with comfortable accommodations for family and guests. Additional highlights include a private two-car garage with organized storage, a heated community pool and spa, and exclusive membership to the gated Bay Isles Beach Club, where residents enjoy private Gulf-front beach access and dedicated parking. Perfectly located near world-class beaches, boating, waterfront restaurants, boutique shopping, and the renowned Longboat Key Club's golf, tennis, pickleball, marina, and dining amenities, this residence places the very best of island living right at your doorstep. Beautifully furnished, impeccably maintained, and move-in ready, this is an exceptional opportunity to enjoy the relaxed elegance and coastal lifestyle that make Longboat Key one of Florida's most sought-after destinations.

2326 Harbour Oaks Drive, Longboat Key
$750,000
Harbor Oaks SubDv. ⋅ 32127 Zip Code
SUBJECT PROPERTY IS A .51 ACRE SECLUDED SINGLE FAMILY RESIDENTIAL WATER FRONT LOT LOCATED AT THE SOUTH END OF RIVERSIDE DRIVE IN PORT ORANGE RIGHT ON SCENIC ROSE BAY. THE LOT IS A 100 FT WIDE BY ~ AVG. OF 229 FT DEEP (~22,373 SF) WITH LARGE BEAUTIFUL OAKS AND A CONCRETE SEAWALL WITH AN OPPORTUNITY TO REBUILD THE PRESENT BOAT DOCK IN DISREPAIR TO MOOR YOUR WATER CRAFT. THE PARCEL PROVIDES ACCESS TO THE INTRACOASTAL WATERWAY, VIA MILL CREEK, PROVIDING AMPLE DRAFT FOR MOST VESSELS. THERE IS A SOLID CONCRETE BLOCK STRUCTURE THAT CAN BE RE-PURPOSED INTO AN OUTDOOR PAVILION WITH AN OUTDOOR FIREPLACE AND GRILLING/KITCHEN AREA. THIS PARCEL HAS PLENTY OF AREA TO BUILD YOUR CUSTOMIZED HOME ON THIS DEEP PARCEL TO ENJOY OUR FLORIDA SUNSETS OVER THE SOUTH END OF ROSE BAY.

5952 S Riverside Drive, Port Orange
$740,000
3 Beds ⋅ 2 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
Situated behind gates of the coveted Bay Isles on Longboat Key is the private enclave of Harbour Oaks. This meticulously renovated second floor residence offers an effortless blend of comfort, refinement, and coastal living. Offering an expansive 3 bedrooms, 2 bathrooms as well as a 2-car garage overlooking one of the most pristine Longboat Key Club golf courses. Furniture conveys with a few personal exceptions. Vaulted ceilings as well as skylights allow natural light to flood through the entire space. The custom modern kitchen is well-appointed with KitchenAid appliances including a 36-inch induction cooktop, built-in oven, refrigerator and dishwasher as well as a dedicated wine refrigerator within the expansive kitchen island. The master bedroom offers vaulted ceilings with a connected terrace to enjoy your morning coffee or watch beautiful Gulf sunsets. The primary bath exudes a sense of being at a spa with its tiled shower, glass shower door and double sink vanity. The third bedroom is currently being used as an office and gym, however could easily be set up as a bedroom. Harbour Oaks is also pet friendly and close to shopping, golf, tennis, beach and bay. Walks and bike rides can be enjoyed in one of the most scenic areas on Longboat Key. Bay Isles offers an exceptional coastal lifestyle including two fully staffed, 24-hour security entrances and exclusive access to a private, gated Gulf-front beach club. Residents have access to a thoughtfully appointed beachside retreat featuring a shaded pavilion, picnic spaces, restrooms, dedicated beach chair storage, grilling stations, and generous parking. Within minutes, access the famous St Armand’s Circle with its exceptional shopping and dining amenities. Cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining. Additional amenities are available within Bay Isles upon joining the Longboat Key Club.

2155 Harbourside Drive Unit 804, Longboat Key
$740,000
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
PRICED TO SELL! Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks community on Longboat Key. This one-story, 3-bedroom, 2.5-bath residence spans 2,219 sq. ft. and offers a host of desirable features—including a private pool, 2-car garage, and deeded beach access through the exclusive Bay Isles Beach Club. A new roof (2025) and fresh interior paint ensure peace of mind and a move-in-ready experience. High ceilings fill the home with natural light, enhancing the spacious feel throughout. The expansive living room, anchored by a wood-burning fireplace, seamlessly connects to the outdoor living area via pocket sliding glass doors, opening to two large screened lanais—ideal for both relaxing and entertaining. The chef’s kitchen is outfitted with granite countertops, stainless steel appliances, rich wood cabinetry, a breakfast bar, and a skylight for added brightness. The primary suite is a private retreat featuring a walk-in closet, two additional closets, updated master bath, and sliding doors leading to the terrace. A guest suite with en suite bath provides comfort and privacy for visitors. Additional highlights include an interior laundry room with sink, a newer AC unit (2018), and natural gas line for adding a pool heater. All furnishings are included. Residents of Harbour Oaks enjoy a resort-style lifestyle with access to a community pool, spa, and lushly landscaped surroundings—just minutes from Longboat Key’s vibrant Town Center. As part of Bay Isles, you’ll have exclusive access to the Bay Isles Beach Club, a private, gated Gulf-front oasis with a pavilion, picnic areas, BBQ grills, beach chairs, restrooms, and ample parking—perfect for sunset viewing or relaxing on Longboat Key’s pristine white sands. Optional membership opportunities at the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deep-water slips offer even more ways to elevate your coastal lifestyle.

2181 Harbourside Drive Unit 1403, Longboat Key
$575,000
4 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 32127 Zip Code
One or more photo(s) has been virtually staged. Port Orange on Rose Bay with detached in-law or STR!!! Enjoy waterfront living with a private dock, a deep lot, and a fully equipped, detached in-law suite. Set on a deep homesite with a private dock, the property captures wide water views and a peaceful natural setting, complemented by mature trees and classic Old Florida charm. The main home with 3 bedrooms and 2 bathrooms features spacious, light filled living areas with wood flooring and vaulted ceilings creating a bright, open atmosphere. The spacious living room flows seamlessly into the dining area and kitchen, where granite countertops, stainless steel appliances, and ample wood cabinetry provide both function and style. A separate family room features a vaulted wood ceiling, a striking stone fireplace, and large windows that frame the backyard and water beyond, offering an inviting space for gathering or relaxing. The primary bedroom is filled with natural light and includes generous closet space, while two additional bedrooms provide flexibility for family, guests, or a home office. The private, detached in-law suite offers a well-designed and versatile living space. Inside, the suite features a spacious living area filled with natural light, a fully equipped kitchenette with cabinetry and appliances, a generously sized bedroom with ample closet space, and a full bathroom with a tiled walk-in shower. An additional laundry closet adds everyday convenience, making the suite well-suited for extended living arrangements or short-term rental while maintaining privacy from the main living areas. The outdoor setting truly shines with a broad lawn stretching to the shoreline, mature oaks and palms, inviting patio and porch areas, and a private, floating dock that makes it easy to enjoy boating, fishing, or simply taking in the views. Notable improvements include a 2022 A/C, a 2018 metal roof and storm shutters, adding peace of mind to this exceptional waterfront property. With no HOA, the property offers added flexibility and fewer restrictions. Conveniently located near local waterways, parks, and coastal amenities, this home provides a well-rounded waterfront lifestyle. All information recorded in the MLS is intended to be accurate but cannot be guaranteed.

5508 W Bayshore Drive, Port Orange
$495,000
5 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 32952 Zip Code
Welcome to this beautifully renovated 5-bedroom, 2.5-bathroom home located in the heart of Merritt Island. Combining modern upgrades with spacious living, this home offers the perfect setting for both everyday comfort and entertaining. From the moment you arrive, you'll be impressed by the inviting curb appeal, manicured landscaping, and welcoming exterior. Inside, luxury vinyl plank flooring flows throughout the main living areas, creating a bright and contemporary atmosphere. The updated kitchen is designed to impress, featuring quartz countertops, stainless steel appliances, ample cabinetry, and plenty of workspace for preparing meals and hosting guests. The spacious living room is anchored by a charming fireplace, creating a warm focal point for gatherings and relaxing evenings at home. Large windows throughout the home fill each room with natural light, enhancing the open and airy feel. The primary suite serves as a private retreat with a beautifully updated bathroom featuring a modern vanity and a tiled walk-in shower. The additional bedrooms offer flexibility for family, guests, a home office, or hobby space. Step outside to the fenced backyard, where you'll find plenty of room for entertaining, outdoor activities, and enjoying Florida's year-round sunshine. Conveniently located near shopping, dining, parks, waterways, and the beaches of the Space Coast, this move-in-ready home offers the perfect blend of style, comfort, and location.

1760 Harbor Oaks Place, Merritt Island
$425,000
3 Beds ⋅ 2 Baths ⋅ Harbor Oaks SubDv. ⋅ 34231 Zip Code
Location, Location, Location!!!! New, New, New!!! Located in the heart of the action, right off the Tamiami Trail, just 5 or 6 minutes from downtown Sarasota and also 5 or 6 minutes from Siesta Key Beach, the #1 beach in the USA, yet incredibly peaceful on a quiet cul-de-sac with zero traffic. The metal roof is only 3 years old, brand-new plumbing, new electrical panel, new bathrooms, new kitchen, brand new A/C units with 10-year warranty, new hurricane safe windows and doors—even the garage door is new. I don't think there's another property in this area with similar conditions for under a million dollars. Non flood zone (X), No HOA.

2138 Pine Terrace, Sarasota
$336,000
5 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 32952 Zip Code
Multiple offers received, H&B requested by 3pm Wednesday 2/4. Merritt Island 254- New Found Harbor — Investor special with serious upside potential. This 5 bedroom, 2.5 bath, 2-car garage home offers 2,767 sqft on a generous .26 acre lot, providing the size, layout, and lot depth that value-add investors look for. The floor plan delivers strong rental or resale appeal with multiple living areas, large bedrooms, and flexible space for modern updates. With cosmetic renovation and system upgrades, this property presents a clear opportunity to force appreciation and build equity. Roof appears to be from 2004 and AC from 2006, priced accordingly for buyers planning improvements. The oversized lot offers room to enhance outdoor living, add amenities, or reposition the property for top market value. Ideal for fix-and-flip, buy-and-hold, or long-term portfolio investors seeking square footage and margin. Buyer to verify all measurements, restrictions, and property details. Opportunities with this size and lot footprint are rare — bring your vision and unlock the potential.

1760 Harbor Oaks Place, Merritt Island