Harbor Oaks Real Estate

Harbor Oaks Real Estate

Welcome to Harbor Oaks, a premier subdivision located in the beautiful state of Florida. Nestled in the heart of the Sunshine State, Harbor Oaks offers the perfect blend of luxury living and natural beauty.

Harbor Oaks is renowned for its upscale homes, lush landscaping, and a strong sense of community. Residents enjoy access to top-rated schools, pristine beaches, and a variety of recreational activities. Whether you prefer relaxing on the sandy shores, exploring nature trails, or dining at local restaurants, Harbor Oaks has something for everyone.

With its convenient location near major highways and airports, Harbor Oaks provides easy access to all that Florida has to offer. Whether you're looking for a peaceful retreat or a vibrant community, Harbor Oaks is the perfect place to call home.

Come experience the charm and elegance of Harbor Oaks. Discover why so many people choose to make this exclusive subdivision their home. Live the Florida lifestyle you've always dreamed of in Harbor Oaks.

Newest Listings in Harbor Oaks

$850,000
4 Beds 3 Baths Harbor Oaks SubDv. 34231 Zip Code
An extraordinary opportunity presents itself to acquire a magnificent Mid-century modern residence, ideally situated mere moments away from the exquisite shores of Siesta Key, consistently rated amongst the finest in the nation. The sprawling 2,016 square foot abode boasts four bedrooms and three baths, nestled within a serene oasis backyard encompassing just under a quarter of an acre in the exclusive Oyster Bay enclave. Upon entering the property, be greeted by a generous parking area accommodating six or more vehicles, all seamlessly crafted with shell and concrete. Step into the grand, open-concept living space with stunning tile flooring, offering panoramic vistas of one's own private bamboo grove and majestic old-growth trees evocative of a bygone era. Toward the rear, the kitchen beckons with a charming, classic entrance leading to a fully screened lanai that overlooks the expansive and tranquil backyard paradise. A versatile concrete slab promises a world of possibilities - an ideal location for a utility room, miniature dwelling, barbecue enclave, or any number of enhancements limited only by the imagination of the fortunate new owner. The property has undergone a complete and meticulous renovation from roof to floor, including state-of-the-art HVAC systems and jaw-dropping design enhancements such as sleek cabinetry, open-concept layouts, and timeless finishes that breathe new life into this classic gem of the sixties. The primary living quarters are comprised of three bedrooms and two baths, while a separate mother-in-law suite with its own private entrance offers a bedroom, living area, kitchenette, and dedicated laundry facilities - showcasing the exceptional flexibility and income potential of the residence. The heart of the home, the kitchen, boasts lustrous quartz countertops, high-end cabinetry, top-of-the-line appliances, a central island, breakfast bar, and a quaint dinette area - perfect for casual dining and entertaining. One of the bedrooms is treated to an exclusive en-suite bath, with ample space remaining outside for the addition of a luxurious pool. This truly exceptional property is a must-see for both discerning investors and homeowners, with both units thoughtfully curated for maximum comfort and usability. Don't miss this opportunity to own a piece of historical charm seamlessly blended with modern luxury in a highly desirable location, minutes from the best of Sarasota's shopping, dining, and recreation.

2107 Pine Terrace, Sarasota

$1,050,000
6 Beds Harbor Oaks SubDv. 34231 Zip Code
PRICE IMPROVEMENT! SELLER MOTIVATED! RARE 4plex investment opportunity in the heart of Sarasota, 6% cap rate, with potential for further income growth!! ! This well-maintained fully rented 4-plex is ideally situated in a the heart of Sarasota on a quiet dead-end street, within one of the best school districts in the area. The units boast modern updates with new kitchens, new flooring, open floor plans, and plenty of natural light. This property offers unparalleled convenience, with Trader Joe’s and Publix within walking distance and the stunning Siesta Key beaches just a 10-minute drive away. Tenants are already in place in all 4 units, ensuring a stable income stream. The expansive lot offers ample backyard space with a privacy fence. Thoughtfully designed driveway and parking area accommodate all units. Key updates included a new metal roof installed 2021 and roof clipping was completed in May 2022, significantly lowering insurance costs. Units A and B received new central A/C systems in 2020-2021, Unit C had a window unit installed in 2021 and Unit D a window unit installed in 2023. All units have been completely remodeled with new kitchens with new cabinets, granite countertops, subway tile backsplash, stunning fixtures and matching appliances. Units A & B boast LVP flooring and units C and D had tile floors, all installed between 2022 and 2023. Additional improvements include a new electrical panel and breakers in April 2022. On-site laundry facilities are currently operated by a third party, presenting an opportunity for additional revenue if switched to owner-operated machines. A termite bond is in place, providing extra peace of mind. With strong rental demand, excellent income potential, and significant recent updates, this 4-plex is an outstanding addition to any real estate portfolio. Don’t miss out on this rare chance to own a valuable piece of Sarasota real estate! Please do not disturb tenants. Ask about special financing options.

2111 Palm Terrace, Sarasota

$6,200,000
5 Beds 3.5 Baths Harbor Oaks SubDv. 33756 Zip Code
The house is a historic venue located on the bluffs overlooking Clearwater Harbor in the Harbor Oaks section of Clearwater. Its beauty provides a historical classical Mediterranean street view when you first approach. The entrance is through a beautiful antique Tiffany glass door leading to a majestic center hall with a grand stairway to the upstairs with a classic wrought iron banister and railing. The floors throughout are beautiful oak and maple wood finished in a light blonde natural color. The kitchen is marble and the sunrooms are stone and terrazzo. The kitchen is ready for the chef with all appliances and a connected pantry. There is also a mud room at the rear access to the house and a connecting hallway to the dining room for grand affairs. The grand stairway leads to an upstairs surround balcony with matching wrought iron railing. All 5 of the bedrooms access from the surrounding hall balcony. There are three beautiful tiled full bathrooms on the second floor with a grandiose master bath. Two bedrooms have balconies overlooking the harbor. There is a third balcony facing the front entrance. Traversing the property to the rear is a beautiful terraced pool with spa and fountain. Located next to the pool is the original carriage house with an upstairs potential mother/daughter apartment ready for finishing which has a patio facing the waterfront and a 4 car garage below. The property slopes down to a second gated entry by the waterfront with a boathouse and room for a private dock. One of the most beautiful sunset views over the waterfront in all of Florida.

205 Magnolia Drive, Clearwater

$6,350,000
5 Beds 5.5 Baths Harbor Oaks SubDv. 33756 Zip Code
Discover a timeless treasure nestled within the historic Harbor Oaks neighborhood of Clearwater. This stunning waterfront residence, boasting a rich century-old legacy, has been meticulously renovated to marry its historic charm with contemporary luxury. From the moment you step inside, you're greeted by an atmosphere of refined elegance and quality craftsmanship. Architectural marvels abound, including intricate woodwork, majestic stone fireplace mantles, and pristine original wood floors that whisper tales of the past. The heart of the home lies in its spacious kitchen, where Saltillo tile floors, wood cabinets, and Corian countertops create a perfect blend of functionality and style. Step outside into the serene courtyard, complete with a soothing fountain, accessible from the kitchen for delightful al fresco dining experiences. Entertaining is effortless with a plethora of gathering spaces, including a grand dining room, inviting living room, cozy family room, and a versatile game room that promises endless enjoyment for family and friends. Ascend the grand stairway to the upper level, where an awe-inspiring primary bedroom suite awaits, offering breathtaking water and pool views through floor-to-ceiling French doors and a private balcony for moments of tranquil reflection. The ensuite bathroom is a haven of relaxation, boasting a walk-in closet with custom built-ins, a double sink vanity, and a luxurious walk-in shower. Your guests will feel pampered in the additional light-filled bedrooms, each offering ample closet space and a serene ambiance. Step outside into the lush oasis of the backyard, where swaying palms and a glistening pool beckon for leisurely afternoons of relaxation. A charming pool house and Casita offer additional convenience, providing ample storage for pool and water toys, as well as a private retreat for guests with a full bath and kitchenette. For the avid fisherman or boater, a floating dock, slip, and lift stand ready to facilitate countless adventures on the water. Beyond its exquisite amenities, this remarkable home holds a special place in Clearwater's rich history, residing in the city's first planned subdivision, founded in 1913. It's not just a home; it's a living testament to a bygone era, where every corner whispers stories of days gone by. Embrace the timeless allure of this waterfront masterpiece and become a part of Clearwater's storied past.

208 Magnolia Drive, Clearwater

$1,700,000
6 Beds 4.5 Baths Harbor Oaks SubDv. 33756 Zip Code
HISTORIC HARBOR OAKS DREAM HOME! Welcome to the timeless allure of the Historic Harbor Oaks community, a living masterpiece steeped in rich heritage. Built in 1925, this architectural gem effortlessly marries the grandeur of yesteryear with modern comfort, situated on a historic street, lined with a canopy of century old live oaks. This lovely home boasts a main house with 4 bedrooms/3.5 baths, and a detached 2 car garage with a 2 bedroom/1 bathroom/2 story guest house. As you step inside, you are met with a feeling of being home! You are greeted by stunning hardwood floors that exude warmth and character, graceful archways and high ceilings. The abundance of large windows and many French doors throughout the home allow for natural light to fill the space, creating a bright and inviting atmosphere. The living room boasts a cozy fireplace, hardwood floors, and 3 sets of French doors. The family room features yet another fireplace, hardwood floors, and French doors that open to a lovely, enclosed sunroom. The living spaces are ideal for entertaining, seamlessly blending the living areas, kitchen and dining areas, and large covered screened porch in the back. The updated kitchen features bamboo flooring, granite countertops and tiered island, brick walls, recessed LED lighting, and SS appliances. Just off the kitchen is an adorable powder room, typical of the 1920’s. The dining room has huge windows, hardwood floors, and a built-in hutch original to the home. Make your way up the gleaming hardwood stairs to the 2nd level, with hardwood floors throughout. The master bedroom, with WATER VIEWS, is lovely, featuring a walk-in closet, a spacious sitting/dressing room with 3 walls of windows, and a gorgeous, completely updated ensuite bathroom with wood cabinetry, walk in shower with rain head, dual sinks and granite. The 2nd bedroom has an updated ensuite bath, and the 2 other bedrooms are spacious and lovely as well, sharing an updated full hall bath. There is a 3rd level to the home, which can be utilized as an office or a large closet/dressing room. The entire home has beautiful high baseboards, and crown molding throughout. Outside, you’ll find a true oasis in the lush, tropical, mature landscape that surrounds the property. The spacious backyard is a serene and private retreat to enjoy with a screened in covered porch, and an outdoor kitchen, wonderful for family gatherings and entertaining. The 2-car detached garage, also boasts a separate guest house, featuring two bedrooms, one bath, fully modern kitchen and laundry, and living area. Enjoy easy access the famous Harbor Oaks Magnolia Dock where you may fish, relax, and take in the sunsets and beautiful views of Clearwater Harbor. This home is also near the Pinellas Trail, restaurants, shopping, Morton Plant Hospital, golf courses, Belleair Country Club, marinas, downtown Clearwater, Capitol Theater, the new Sound stage. Beautiful Clearwater Beach and the Gulf of Mexico are only minutes away, (walking or biking distance) and airports are in close proximity. Indulge in the allure of the past while embracing the comforts of the present, don’t miss the opportunity to own this stunning piece of history.

302 Druid Road W, Clearwater

$7,495,000
3 Beds 3 Baths Harbor Oaks SubDv. 33756 Zip Code
Unsurpassed Views and A Chance to Own a Piece of History awaits the buyer of the ‘South House’, a magical 2.75-acre property once associated with the legendary ‘Century Oaks Estate’—which was built on the site of the original Fort Harrison. Positioned at the water’s edge of the deepest and widest part of Clearwater Harbor, the view-inspired residence offers show-stopping views of the Gulf, Sand Key Bridge and the Clearwater skyline. Situated behind a private gate and surrounded by meticulously maintained gardens, the 3,046 square foot single-story design reflects an ambiance of casual elegance throughout. The open floor plan merges the family and dining rooms into one extra-large area that is ideal for entertaining as well as fine Florida living. A fireplace adds warmth and character to primary spaces while walls of glass doors reveal unobstructed Gulf views and open to an expansive terrace and adjoining boat dock. A charming gazebo adorned with stately Corinthian columns makes a delightful conversation area and combines with a swimming pool for an idyllic retreat. The adjacent kitchen is outfitted with an array of storage cabinets, granite countertops, breakfast bar and a cozy nook for casual dining. Private accommodations within the 3-bedroom plan include a master suite of generous proportions featuring a dramatic exposed beamed ceiling and a fireplace. The opportunity to build on the upper bluff of this property is significant for its stunning views and 50-feet elevation above sea level—a rarity for waterfront properties in Florida and precluded from flood insurance requirements. Conveniently located in the heart of Clearwater, the home affords easy access to award-winning Gulf beaches, medical facilities, shopping and dining, and is a short drive to Tampa International Airport, downtown Tampa and St. Petersburg. Formerly known as the estate’s ‘Boat House’, this offering may again be joined with the Century Oaks property which is separately listed.

820 Druid Road S, Clearwater

$49,995,000
19 Beds 16.5 Baths Harbor Oaks SubDv. 33756 Zip Code
Discover Historic Century Oaks, an enchanting 4.45-acre waterfront estate in Pinellas that embodies the ultimate luxury lifestyle. Nestled atop a sloping bluff surrounded by lushly ornamental gardens cascading down to the water, this spectacular property boasts sweeping views of Clearwater Bay. The estate features a main house, a 5,000 sq/ft North guest house and third guest house that offer a total of 19 spacious bedrooms, 16 full and 5 half baths, and an array of exceptional amenities, including 3 pools, a tennis court, a basketball court, carriage house, and boat docks. Behind the walled grounds, meandering brick pathways shaded by soaring Live-Oak trees wind past fountains, the historic bell tower, and a gazebo, creating an idyllic setting for relaxation and entertainment. The main house is a masterpiece of architectural design, featuring 23,159 sq/ft of luxurious living space that exudes elegance and refinement. The custom finishes throughout the home are a testament to its impeccable craftsmanship. The home's two guest wings, formal and informal dining and living spaces, library, theatre room, music studio, sunroom, trophy room, and ballroom offer unparalleled luxury and comfort. The expansive terraces provide a perfect setting for outdoor entertainment and breathtaking views of the lavish grounds. The North guest house offers a serene retreat with 4 spacious bedrooms, 5 full and 2 half baths, music and sun rooms, a fireplace, a full gym, a billiard room, a bar, and a suite of offices. The estate can accommodate covered parking for ten plus vehicles, which includes an air-conditioned garage and several open-air parking areas to facilitate large events. With open Gulf waters just minutes away and no bridge obstructions, this property is a boater's paradise. Located just blocks from downtown Clearwater and thirty minutes to Tampa International Airport, Historic Century Oaks is the epitome of luxury living. Don't miss your chance to own one of the most exquisite estates in Pinellas.

802 Druid Road S, Clearwater

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