Harbor Oaks Real Estate

Harbor Oaks Real Estate

Welcome to Harbor Oaks, a picturesque subdivision nestled in the heart of Florida's vibrant landscape. This charming community offers a unique blend of serene living and modern convenience, making it an ideal choice for families, retirees, and everyone in between.

Harbor Oaks is characterized by its beautifully landscaped streets, lined with stunning homes that reflect a variety of architectural styles. From cozy single-family residences to spacious waterfront properties, there’s something to suit every taste and lifestyle. Residents enjoy the tranquility of lush greenery and the gentle sounds of nature, all while being just a short drive away from the bustling energy of nearby urban areas.

One of the standout features of Harbor Oaks is its commitment to community living. The subdivision boasts a range of amenities designed to enhance the quality of life for its residents. Enjoy leisurely strolls through well-maintained parks, or take advantage of the community clubhouse, perfect for hosting gatherings and events. Families will appreciate the proximity to top-rated schools, recreational facilities, and shopping centers, ensuring that everything you need is just around the corner.

For outdoor enthusiasts, Harbor Oaks offers easy access to Florida’s stunning beaches and waterways. Spend your weekends soaking up the sun, fishing, or exploring the scenic coastal trails. The area is also known for its vibrant local culture, with an array of dining, shopping, and entertainment options that reflect the unique charm of Florida living.

Discover the warm community spirit and idyllic lifestyle that Harbor Oaks has to offer. Your dream home awaits in this enchanting subdivision!

Newest Listings in Harbor Oaks

$3,000,000
7 Beds ⋅ 8 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Virtually Staged. This exceptional residence offers a rare opportunity to acquire one of Harbor Oaks' most storied addresses. Built between 1918 and 1925 within the coveted "Florida Heritage" district, 403 Magnolia Drive stands just blocks from downtown Clearwater — a seven bedroom, seven and a half bathroom estate of 7,223 square feet, gracefully arranged across three levels. Floor-to-ceiling windows trace the twin formal living rooms, allowing the day to unfold from room to room in a continuous wash of natural light. At the same time, rich original hardwood floors carry warmth throughout every level. A sun-filled solarium and an adjoining Florida room extend this openness further still, complemented by a private library and a spacious family room. Each of the home's seven bedrooms is appointed with its own full, private bathroom — Upstairs, two primary suites open onto a sweeping wraparound deck, each accompanied by a spa-inspired Restoration-style bath of exceptional finish. The entire third floor is reserved for the primary suite, complete with a full bath, fireplace, sun deck, and generous storage, offering a graceful degree of separation and privacy from the rest of the home. The kitchen is outfitted with commercial-grade stainless appliances, a Dacor gas range, crown molding, and a walk-in pantry of considerable scale — a room designed as much for the passionate cook as for the discerning host. A wet bar and tray ceilings polish the home's entertaining spaces, while French doors along the main level open onto a private courtyard and balcony, softening the boundary between interior and exterior life. Beyond its walls, the estate unfolds across a corner lot of over half an acre, anchored by a resort-caliber pool and spa deck. A circular drive welcomes you home, while Downtown shopping and dining are just minutes away, and the white sands of Clearwater Beach are a mere five-minute drive. Floor plans and a full tour are available upon request — 403 Magnolia Drive is a rare opportunity to own a true piece of Harbor Oaks history.

403 Magnolia Drive, Clearwater
$499,000
Harbor Oaks SubDv. ⋅ 32127 Zip Code
SUBJECT PARCEL IS A 1.47+ ACRE COMMERCIAL SITE (MU) WITH OVER 210 LF ALONG S RIDGEWOOD AVENUE HAVING GOOD SITUS AND A SIGNALIZED INTERSECTION CONNECTING WITH SR 5A (S NOVA ROAD) & EAST PALM AVENUE. THE PARCEL HAS THE REMNANTS OF A 1924 STRUCTURE ON SITE WITH UTILITY CONNECTIONS STILL AVAILABLE AND A FIRE HYDRANT AT THE NW CORNER OF THE PARCEL.

5919 S Ridgewood Avenue, Port Orange
$725,000
4 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34231 Zip Code
Fully furnished with a full price... Stunning Turn-Key Dual-Unit Income Property | Fully Renovated Top to Bottom | Prime Sarasota Location This meticulously renovated single-family residence with 4 bedrooms and 3 bathrooms has been completely transformed into a modern, income-producing gem on a spacious 10,048 sq ft lot (approx. 0.23 acres). The property features extensive updates throughout, including brand-new plumbing, electrical, roof, and air conditioning systems. The interior has been beautifully refreshed with a renovated kitchen featuring granite countertops, new cabinets, and an open-concept design, along with tile flooring throughout and fully renovated bathrooms. The exterior boasts fresh stucco paint for enhanced curb appeal. The interior floor plan has been thoughtfully reconfigured to include a completely independent studio unit with its own private entrance, full kitchenette, dedicated washer and dryer, and complete autonomy — ideal for multi-generational living, guests, or maximizing rental income. Both units are beautifully furnished and move-in ready, making this a true turn-key opportunity. Each unit enjoys its own private backyard space, while the generous lot size offers plenty of room to add a pool in the backyard if desired. The property also provides ample parking for multiple vehicles. Perfect for investors or owner-occupants seeking strong short- and mid-term rental performance, this home comes with proven rental records available upon request. The thoughtful design provides privacy and functionality for both living spaces. This fully renovated property offers unbeatable central Sarasota location — just minutes to Siesta Key Beach, downtown Sarasota, and surrounded by an abundance of restaurants, shopping, and entertainment options. Whether you're looking for a low-maintenance primary residence with income potential or a high-performing investment property, this fully updated and furnished dual-unit home delivers exceptional value in one of Sarasota’s most convenient and desirable neighborhoods. Don’t miss this rare opportunity — schedule your showing today!

2107 Pine Terrace, Sarasota
$599,000
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34231 Zip Code
Backyard retreat + income-producing detached studio + steps to Trader Joe’s! Quiet dead-end street near Siesta Key & Downtown Sarasota—privacy meets prime location. Extensively updated and ideally located, this Sarasota home offers the perfect blend of lifestyle and convenience—just minutes to Downtown, Siesta Key Beach, Sarasota Memorial Hospital, and SRQ Airport. The private backyard is a true highlight, featuring lush landscaping, custom hardscaping, a pergola, and a striking mural—fully fenced (2023) for privacy and perfect for entertaining or relaxing outdoors year-round. Inside, the home is move-in ready with fresh paint, custom feature wall, built-in closets, blackout blinds, and hurricane-rated windows and doors for peace of mind and natural light. The kitchen includes a Bosch dishwasher (2025), Samsung range and microwave (2023), plus LG washer/dryer (2023). Additional upgrades include whole-home water filtration with reverse osmosis (2022), air purification (2024), generator with transfer switch (2025), updated plumbing, maintained HVAC, and a new 28-gallon water heater (2026). The upgraded garage features waterproof flooring, built-ins, insulation, and mini-split AC (2025)—ideal for a gym, workshop, or flex space. The detached studio adds exceptional versatility with a private entrance, outdoor space, kitchenette, full bath, washer/dryer, and dedicated AC (2023). The studio has been successfully rented, offering strong income potential or flexibility for guests or a private office. A rare opportunity combining privacy, flexibility, and a highly desirable Sarasota location.

2121 Palm Terrace, Sarasota
$800,000
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
$799,000
Harbor Oaks SubDv. ⋅ 32127 Zip Code
SUBJECT PROPERTY IS A .62 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 275 FT DEEP (~27,547 SF) WITH LARGE BEAUTIFUL OAKS, CONCRETE BOAT RAMP WITH ROOM TO BUILD A CUSTOM BOAT DOCK TO HOUSE & MOOR YOUR WATER CRAFT. THE PARCEL PROVIDES ACCESS TO THE INTRACOASTAL WATERWAY VIA MILL CREEK PROVIDING AMPLE DRAFT. THIS PARCEL HAS PLENTY OF AREA TO BUILD YOUR CUSTOMIZED HOME ON THIS DEEP LOT TO ENJOY OUR FLORIDA SUNSETS OVER THE SOUTH END OF ROSE BAY.

5948 Riverside Drive, Port Orange
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