Harbor Oaks Homes with Street Lights Community Features

Harbor Oaks Homes with Street Lights Community Features

Welcome to Harbor Oaks, an enchanting subdivision nestled in the heart of Longboat Key, Florida, within Sarasota County. This idyllic community embodies the perfect blend of coastal charm and modern living, making it an ideal destination for those seeking a serene yet vibrant lifestyle.

Harbor Oaks is characterized by its beautifully designed homes, each featuring unique architectural styles that complement the picturesque surroundings. The thoughtfully planned layout of the community includes well-maintained streets adorned with charming street lights, creating a warm and inviting atmosphere as evening descends. As you stroll through the neighborhood, you’ll appreciate the sense of safety and community that these illuminated pathways provide.

The natural beauty of Longboat Key surrounds Harbor Oaks, offering residents easy access to stunning beaches, lush parks, and vibrant local attractions. Whether you enjoy sunbathing on pristine shores, indulging in water sports, or exploring the local dining scene, this subdivision places you in the heart of it all.

In addition to its prime location, Harbor Oaks boasts a strong sense of community, where neighbors become friends and every day feels like a vacation. The community features include well-maintained common areas and a commitment to preserving the natural beauty of the landscape, ensuring that residents can enjoy the outdoors year-round.

If you’re seeking a place where tranquility meets convenience, look no further than Harbor Oaks. Here, you’ll find not just a home, but a lifestyle enriched by the sun, sea, and the warmth of a close-knit community. Come discover your dream home in this enchanting Florida paradise!

Newest Harbor Oaks Homes with Street Lights Community Features

$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
$1,495,000
3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code
3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

2101 Harbourside Drive Unit 1103, Longboat Key
$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
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