Harbor Oaks Homes for Sale

Harbor Oaks Homes for Sale

Welcome to Harbor Oaks, a hidden gem nestled in the heart of Sarasota, Florida. This charming subdivision is renowned for its picturesque landscapes, friendly community atmosphere, and proximity to some of the best amenities that Sarasota has to offer. With its lush oak trees and serene waterways, Harbor Oaks provides a tranquil retreat while still being conveniently located near vibrant shopping districts, exquisite dining options, and stunning beaches.

The homes for sale in Harbor Oaks are as diverse as the residents themselves, featuring a variety of architectural styles that cater to different tastes and lifestyles. From cozy single-family homes to spacious modern residences, each property is designed with comfort and elegance in mind. Many of these homes boast beautiful outdoor spaces, perfect for enjoying the sunny Florida weather or hosting gatherings with family and friends.

Living in Harbor Oaks means embracing a lifestyle filled with leisure and recreation. Residents can take advantage of nearby parks, walking trails, and community events that foster a strong sense of belonging. The area is also known for its excellent schools and family-friendly atmosphere, making it an ideal choice for those looking to settle down and raise a family.

If you’re seeking a serene community with a vibrant spirit, look no further than Harbor Oaks. Explore the homes for sale today and discover the perfect place to call home in this idyllic Sarasota subdivision. Your dream home awaits in this charming oasis!

Newest Harbor Oaks Homes for Sale

$924,900
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Historic Harbor Oaks charm meets a backyard made to wow! Set on a gated corner lot beneath mature oaks, this beautifully remodeled 1940s bungalow pairs original character with exceptional modern upgrades. Pella impact windows, Hardie board siding, a tile-inspired metal roof and a five-car carport add to its appeal. Inside, pristine original hardwood floors, plantation shutters and a striking stone fireplace welcome you into the bright, open living room. The chef’s kitchen is a showpiece, featuring leathered granite countertops, high-end KitchenAid appliances, slate floors, glass-front cabinetry, a pot filler and a statement-making Futuro Murano range hood. The primary suite leads to an oversized bath designed for indulgence. Soak in the 72-inch copper-coated claw-foot tub beneath an overhead rain shower or unwind in the custom walk-through steam shower with mood lighting and river rock flooring. A private outdoor garden shower offers another way to recharge. You’ll also find a walk-in sauna, a TV built into the vanity mirror, heated floors in the second bath, and a new stackable washer and dryer concealed behind a glass mirror in the primary bath, keeping laundry convenient while saving valuable space. And then there’s the outdoor oasis: a private splash pad with cascading waterfalls, dual shower heads, and gusher jets. Surrounded by lush green space and an irrigated garden, it’s a setting built for relaxing or entertaining. Additionally, a spacious shed with electricity and newer AC wall unit offers flexible room for hobbies, a workshop or storage. World famous Clearwater Beach, Coachman Park, the Pinellas Trail and more are all nearby. This magnificent property is truly a MUST-SEE!

420 Druid Road W, Clearwater
$594,900
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34231 Zip Code
Some houses just have a vibe. This one has it in spades. Tucked away on a quiet dead-end street, this fully updated 3-bedroom, 3-bathroom mid-century modern home blends clean, classic lines with genuine personality — the kind of place that feels curated, not staged. Two of the three bedrooms come with their own ensuite baths, so privacy and convenience are built right in. Step inside and every detail has been thought through: newer appliances, custom closets throughout, and custom blinds that let in just the right amount of Sarasota sunshine. Out back, the good times continue. A permanent screened-in living space is made for long evenings, morning coffee, or watching the rain roll through without missing a beat. The yard is spacious and professionally landscaped, with pet turf that keeps things low-maintenance and always green — no mud, no fuss, just easy living. And then there's the bonus: a separate, private-entrance guest suite. Whether it becomes overflow space for visitors, a long-term income opportunity, or flexible living quarters for extended family, the possibilities are wide open — the layout gives you the freedom to decide what works best. Location seals the deal. This dead-end street offers a rare mix of privacy and convenience, with easy access to everything Sarasota living is known for — shopping, dining, culture, and the Gulf Coast lifestyle just minutes away. Homes that combine this level of updated detail with true flexible living space don't come around often in Sarasota's market. Come see what makes 2121 Palm Terrace special.

2121 Palm Terrace, Sarasota
$899,999
5 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34756 Zip Code
Welcome to this spacious custom pool home on a beautifully wooded half-acre lot in Montverde! Offering 5 bedrooms, 3 full baths and over 3,700 sq. ft. of heated living space, this unique split-level home provides plenty of room to live and entertain. Enjoy a kitchen with granite countertops and stainless steel appliances, formal living area with fireplace, family room, bonus/game room and flexible living spaces. Step outside to your private Florida retreat featuring a sparkling pool and spa, screened outdoor kitchen, covered porch, fire pit and mature trees offering shade and privacy. A garage-sized workshop and additional tandem garage/storage space provide plenty of room for hobbies and storage. Updates include A/C replaced in 2022, newer kitchen appliances and refinished hardwood floors. Convenient to Clermont, shopping, dining and major roadways.

16017 Harbar Oaks Drive, Montverde
$3,500,000
7 Beds ⋅ 8 Baths ⋅ Harbor Oaks SubDv. ⋅ 33756 Zip Code
Virtually Staged. A rare opportunity to own one of Harbor Oaks’ most distinguished estates. Built between 1918 and 1925, 403 Magnolia Drive pairs nearly a century of architectural character with the scale and presence of a true estate—all just one block from the water, minutes from Downtown Clearwater, and located in desirable Flood Zone X. Spanning 7,223 square feet across three levels, the seven-bedroom, seven-and-a-half-bath estate is defined by soaring natural light, original hardwood floors, beautifully preserved architectural details, and an exceptional sense of space. Floor-to-ceiling windows line the dual formal living rooms, while a sun-filled solarium with NEW windows and an adjoining Florida room create effortless transitions throughout the main level. A private library and expansive family room offer additional spaces for both intimate everyday living and large-scale entertaining. Each of the home’s seven bedrooms features its own private full bathroom, an extraordinary level of comfort and privacy for family and guests. Upstairs, two generous suites open onto a sweeping wraparound deck and feature beautifully appointed, spa-inspired baths. The entire third floor offers another private retreat with a full bath, fireplace, sun deck, and abundant storage—creating exceptional flexibility for a primary suite, guest quarters, or private living level. At the heart of the home, the kitchen is designed for both serious cooking and entertaining, featuring commercial-grade stainless steel appliances, a Dacor gas range, custom millwork, and an oversized walk-in pantry. A wet bar, tray ceilings, and French doors opening to the courtyard and outdoor living spaces further enhance the home’s ability to host with ease. Outside, the estate unfolds across a prominent corner lot of more than half an acre—an increasingly rare offering in this location. Mature surroundings create a private setting for the resort-style pool and spa, expansive deck, and outdoor entertaining areas, while a circular drive provides an impressive sense of arrival. Moments from Downtown Clearwater’s dining and entertainment, minutes from Clearwater Beach, and surrounded by some of the area’s most notable residences, 403 Magnolia Drive offers a combination of history, scale, land, and lifestyle that is truly one of a kind.

403 Magnolia Drive, Clearwater
$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
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