Harbor Oaks Real Estate

Harbor Oaks Real Estate

Welcome to Harbor Oaks, a hidden gem nestled in the heart of Florida’s picturesque landscape. This charming subdivision offers a unique blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle surrounded by nature.

Harbor Oaks boasts beautifully landscaped streets lined with mature trees and vibrant flora, creating a warm and inviting atmosphere. The community features a variety of meticulously maintained homes, each with its own character and charm. Whether you’re looking for a cozy single-family residence or a spacious modern home, Harbor Oaks has something to suit every taste and budget.

One of the standout features of Harbor Oaks is its proximity to stunning waterfront views and recreational activities. Residents can enjoy easy access to local parks, walking trails, and waterfront access for fishing, kayaking, and leisurely strolls along the shore. The community also offers a sense of camaraderie, with friendly neighbors and regular community events that foster connections and create lasting friendships.

Convenience is key in Harbor Oaks, as it is strategically located near shopping centers, dining options, and top-rated schools. Whether you're in the mood for a casual bite to eat or a day of retail therapy, everything you need is just a short drive away.

Discover the enchanting lifestyle that Harbor Oaks has to offer. With its beautiful homes, friendly community, and prime location, it’s no wonder that this subdivision is one of Florida’s most sought-after places to call home. Come experience the charm of Harbor Oaks for yourself!

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
$469,777
4 Beds ⋅ 2 Baths ⋅ Harbor Oaks SubDv. ⋅ 34231 Zip Code
Excellent opportunity to own a well-maintained duplex in a highly desirable Sarasota location just minutes from world-famous Siesta Key Beach, Downtown Sarasota, shopping, dining, and transit. This property features two separate 2-bedroom, 1-bathroom units, making it ideal for investors seeking strong rental income or owner-occupants looking to offset their mortgage with rental revenue. Both entrances have enclosed lanai areas. The front unit lanai has laundry hookups. Tile flooring throughout, large kitchens, tub with tiled shower walls. Ceiling fans in bedrooms. Fenced on back and side of building. Both units offer comfortable floor plans with central air conditioning and charming fireplaces that add character and appeal. The rear unit includes a valuable two-car carport, dedicated storage area, and laundry hookups, providing additional convenience for tenants. 2011 Metal Roof, 2021 & 2022 HVAC. Owner pays water, electric separately metered. Attractive units and setup for long-term renters. Situated on a quiet street with easy access to Sarasota's beaches, cultural attractions, restaurants, and everyday conveniences, this duplex combines location, functionality, and investment potential. Buyer to verify all measurements, rental information, and property details.

2110 Palm Terrace, Sarasota
$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
$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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