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$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
$1,125,000
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
$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