Holiday Harbor Homes for Sale

Welcome to Holiday Harbor, a hidden gem nestled in the heart of Jacksonville, Florida! This charming subdivision offers a perfect blend of tranquility and convenience, making it an ideal locale for families, retirees, and anyone seeking the quintessential Florida lifestyle.

Holiday Harbor boasts a picturesque setting with lush greenery and serene waterways, providing residents with a peaceful retreat from the hustle and bustle of city life. The community is known for its friendly atmosphere, where neighbors become friends and gatherings are a regular delight. With easy access to the scenic St. Johns River, residents can enjoy a variety of outdoor activities such as boating, fishing, and kayaking right in their backyard.

The homes for sale in Holiday Harbor are as diverse as the community itself, featuring a range of architectural styles and sizes to suit every taste and budget. Whether you’re looking for a cozy bungalow or a spacious family home, you’ll find options that combine modern amenities with classic charm. Many properties come equipped with beautiful outdoor spaces, perfect for entertaining or simply enjoying the warm Florida sunshine.

In addition to its stunning homes, Holiday Harbor is conveniently located near top-rated schools, shopping centers, and recreational facilities, ensuring that all your daily needs are just a stone's throw away. With its welcoming community spirit and prime location, Holiday Harbor is not just a place to live; it’s a place to thrive. Explore the homes for sale today and discover the enchanting lifestyle that awaits you in this wonderful Jacksonville subdivision!

Newest Holiday Harbor Homes for Sale

$697,000

4 Beds ⋅ 2 Baths ⋅ 2171314 MLS

Truly a one of a kind property! Full of curb appeal and coastal charm, this beautifully refreshed 4-bedroom, 2-bath home features thoughtfully chosen details you won't find just anywhere! Inside, an open floor plan filled with natural light connects the cozy living room, spacious dining area, and an entertainer's dream kitchen featuring an oversized island, abundant cabinetry, farmhouse sink, and new stainless-steel appliances. The split-bedroom layout offers privacy, while the primary suite feels like a retreat of its own with tropical inspired wallpaper, custom wall sconces, and shiplap ceilings. Both bathrooms have been beautifully refreshed with high-end vanities and elevated fixtures. New LVP flooring and fresh interior and exterior paint complete the home's inviting feel. Outside, the large, fenced in backyard is made for Florida living, featuring a resurfaced pool with a new pool pump, newly installed pavers, and a custom pergola perfect for entertaining or unwinding. Situated in a welcoming neighborhood near parks and schools, this one-of-a-kind home brings together distinctive coastal-inspired design, everyday comfort, and effortless indoor/outdoor living. Schedule your private tour TODAY!

2440 Peg Leg Road, Jacksonville

Courtesy of RIVER CITY RENTALS AND REALTY

Listing courtesy of RIVER CITY RENTALS AND REALTY.

Listing courtesy of NIMA TOGHIYANI from RIVER CITY RENTALS AND REALTY.

$829,000

3 Beds ⋅ 3 Baths ⋅ 2170928 MLS

Beautifully remodeled and full of charm, this move-in-ready home offers modern upgrades, timeless character, and inviting indoor-outdoor living. Enjoy peace of mind with a new roof installed in 2025 and a new water filtration system. The completely updated kitchen features new appliances and a spacious walk-in pantry, while the beautifully renovated bathrooms, hardwood flooring, terrazzo, and new window coverings add style and comfort throughout. A wood-burning fireplace creates a warm, welcoming atmosphere, and included laundry appliances add everyday convenience. Step outside to enjoy your private pool and outdoor hot-and-cold shower, perfect for relaxing and entertaining. A 16' x 16' shed provides versatile additional space, while the two-car carport and ample enclosed storage offer excellent functionality. With extensive renovations and desirable features inside and out, this exceptional property is ready for its next chapter!

2278 Windjammer Lane E, Jacksonville

Courtesy of HERRON REAL ESTATE LLC

Listing courtesy of HERRON REAL ESTATE LLC.

Listing courtesy of ELODIE LATSON from HERRON REAL ESTATE LLC.

$1,900,000

4 Beds ⋅ 3 Baths ⋅ A4701902 MLS

Welcome to this immaculate, move-in ready Sarasota estate on a quiet, no-outlet cul-de-sac west of the Trail, just minutes from both the world-famous beaches of Siesta Key and the cultural amenities of downtown Sarasota. Just around the corner, Hidden Harbor Marina provides convenient boat storage and access to the Intracoastal and the Gulf for those who choose to join. Completely renovated in 2006, with the original 1959 structure fully redone, this professionally curated, single-story home offers 4 bedrooms, 2.5 baths, and 3,269 heated square feet on an oversized, fully private lot with no HOA, and is available optionally furnished. Arriving along the paver driveway, you are welcomed by custom tropical landscaping and oversized bespoke double glass doors featuring a custom heron overlay. Inside, the heron theme continues on a unique grasscloth wallcovering, leading to an open living and dining area with vaulted ceilings, skylights, and Italian porcelain plank flooring. Two sets of impact sliders frame picturesque views of the pool and established gardens. The expansive chef's kitchen features white raised-panel cabinetry, leaded glass uppers, granite counters, a marble backsplash with a handcrafted marble medallion above the cooktop, and a navy island with a prep sink and breakfast bar seating. A Bosch wall oven, microwave, and cooktop, stainless steel appliances, a built-in bar with wine storage, and a breakfast nook with arched windows complete the space, with a laundry room featuring an LG washer and dryer and a utility sink nearby. The split bedroom plan places the primary suite on its own side of the home, with a bay window overlooking the colorful garden and patio doors opening directly to the pool deck. The en suite bath offers dual granite vanities, a spa tub, a walk-in shower, and a private water closet, while the custom walk-in closet provides abundant hanging space, shoe storage, and built-in dressers. On the opposite side, two guest bedrooms share a bath with marble tile and a walk-in rain shower, the fourth bedroom is currently set up as an office, and a half bath serves guests. Closets with built-in shelving, extra tall solid wood doors, plantation shutters, and LED lighting carry throughout. Outside, the expansive paver patio surrounds an oversized Pebble Tec pool and an inviting pergola, all enclosed by Clusia hedges and a vinyl privacy fence. Professional landscape lighting showcases the lush gardens, and an irrigation system keeps them thriving. Additional highlights include two separate HVAC systems, an air-conditioned utility room off the garage, and a flood zone X500 designation. Just moments away, the Tamiami Trail and Beneva Road corridor is becoming a South Sarasota hub, with a new Trader Joe's on the way and the former Sarasota Square Mall being transformed into a mixed-use destination anchored by Whole Foods. FURNISHINGS NEGOTIABLE. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

7780 Holiday Drive N, South Sarasota

Listing courtesy of KW COASTAL LIVING III. murraycoleman@kw.com

$1,299,999

4 Beds ⋅ 4 Baths ⋅ 2158482 MLS

Waterfront living with no HOA or CDD on 0.65 acres in Holiday Harbor. At the end of a quiet cul-de-sac, this 4-bedroom, 3.5-bath home offers Intracoastal views, navigable tidal canal frontage, and shared dock access, minutes from the beaches and Mayo Clinic. A 2024 backyard retreat features a 30x20 pool and 10x10 spa, sun shelf, bubblers, LED lighting, Pentair automation, shell stone decking, and an extended-view screen enclosure. Inside, 3,300+ sq ft offer a split-bedroom plan with a flexible in-law layout, media room, and great room with soaring ceilings, a wood-burning fireplace, and water views. The kitchen includes granite countertops, stainless appliances, a breakfast bar, and sunny nook. The owner's suite features a sitting area and private waterfront balcony. Wood and travertine floors, crown molding, and zoned HVAC complete the interior. Mature landscaping and thoughtful positioning provide privacy while preserving the views. Enjoy a shared dock on navigable tidal water, while the home's thoughtful positioning offers exceptional privacy, creating a tranquil setting that's perfect for both everyday living and entertaining.

13957 Ketch Cove Place, Jacksonville

Courtesy of FLUID REALTY, LLC.

Listing courtesy of FLUID REALTY, LLC..

Listing courtesy of HEATHER PEREZ-HOLLIS LLC from FLUID REALTY, LLC..

$1,145,000

3 Beds ⋅ 2 Baths ⋅ 2151467 MLS

BOAT TO JAGS GAMES, THE OCEAN, RESTAURANTS AND MORE! Waterfront renovated pool home offering the ultimate Florida lifestyle. Nestled just off San Pablo Boulevard- conveniently close to the renowned Mayo Clinic- this stunning property features direct Intracoastal access navigable to the ocean, peaceful preserve views, a private dock, and a 10,000-pound boat lift- making it easy to boat to waterfront dining, downtown events, and even Jaguars games. Designed for year-round enjoyment, the resort-style backyard is fully fenced and beautifully enhanced by professional landscaping and irrigation. Enjoy endless days by the newly converted saltwater pool featuring a new pump, then gather with family and friends at the covered outdoor entertaining area complete with a wet bar and outdoor grill. The spacious Florida room further extends the living space and offers endless possibilities for relaxation and entertaining. A circular driveway welcomes you home, while just inside, the grand living room immediately impresses with soaring ceilings, exposed beam details, expansive windows that fill the home with natural light, a wood-burning fireplace, and a show-stopping iron spindle staircase leading to an open loft- perfect as a home office, game room, or additional living space. Designed for both comfort and versatility, this open, light-filled home offers three bedrooms and two bathrooms, including two main-level primary suites ideal for multigenerational living or hosting guests. New wide-plank white oak flooring extends throughout the main living areas and primary bedroom, while elegant crown moulding and fresh interior paint add a refined finishing touch. The kitchen is beautifully appointed with granite countertops, a stone backsplash, double ovens, a cozy breakfast nook, a new LG dishwasher, and abundant space for everyday living and entertaining. The primary suite serves as a private sanctuary, featuring direct access to the pool and a fully renovated, spa-inspired bathroom complete with a soaking tub, dual walk-in shower, double vanity, and a custom closet system. For added peace of mind, the home also features a new roof installed in 2024, newer heat pump from 2023 and a/c unit 2018, making this exceptional waterfront property as practical as it is beautiful. Ideally located just minutes from Jacksonville's beautiful beaches, premier shopping, and popular dining destinations, this exceptional property also offers convenient access to J. Turner Butler Boulevard, making it easy to enjoy everything Northeast Florida has to offer. Combining the tranquility of waterfront living with the convenience of an unbeatable location, this is more than a home--it's a lifestyle.

14073 Pine Island Drive, Jacksonville

Courtesy of COMPASS FLORIDA LLC

Listing courtesy of COMPASS FLORIDA LLC.

Listing courtesy of EDWARD LANE from COMPASS FLORIDA LLC.

$1,575,000

4 Beds ⋅ 3 Baths ⋅ 2148936 MLS

Rare opportunity to own a beautifully remodeled waterfront estate just off San Pablo Road. Set on a spacious 1/3 acre lot, this exceptional property offers approximately 2,661 square feet of updated living space with direct boating access from a private dock. Fully renovated, the home features an open-concept layout, luxury vinyl plank flooring, and a stunning kitchen with quartz countertops and ample workspace. Major updates include a new roof, HVAC system, and water heater. Large windows fill the home with natural light and showcase scenic water views. Outside, enjoy a 20,000-gallon saltwater pool overlooking the canal, where manatees and fish are frequent visitors. Boaters will appreciate the 25' x 46' dock, 13,000-pound boat lift, and 8' x 20' floating Ipe wood dock.

2310 Shipwreck Circle W, Jacksonville

Courtesy of BETTER HOMES & GARDENS REAL ESTATE LIFESTYLES REALTY

Listing courtesy of BETTER HOMES & GARDENS REAL ESTATE LIFESTYLES REALTY.

Listing courtesy of BONNIE SCHUETZ from BETTER HOMES & GARDENS REAL ESTATE LIFESTYLES REALTY.

$870,000

3 Beds ⋅ 3 Baths ⋅ A4691644 MLS

Wonderfully charming street along HIDDEN HARBOR MARINA high and dry this lovely turn key home has 3 beds and 2.5 baths, a heated pool and large fenced yard.. NO HOA Country restrictions only Sarasota County restrictions. Home has many updates including a light and bright kitchen, window treatments, a king bed en-suite bath with French doors to a covered patio with plenty of lounging furniture and TV set up. This home comes turnkey furnished and has IMPACT RESISTANT, ENERGY EFFICIENT WINDOWS AND SLIDERS and a newer metal roof. You will love this HIDDEN HARBOR neighborhood with plenty of charm. Minutes to Siesta Key shopping and dining. A new shopping area to be completed by 2026 includes a new WHOLE FOODS and TRADER JOES as well as shopping and dining.

7860 Holiday Drive, South Sarasota

Listing courtesy of CENTURY 21 ROSEBAY. 941-366-7673

$1,950,000

4 Beds ⋅ 3 Baths ⋅ 2102048 MLS

Waterfront Paradise Awaits! Discover Luxury Living in this stunning 3 year young home featuring everything you've been dreaming of. With breathtaking views, open concept design, and high-end finishes throughout, this home is the ultimate Florida lifestyle package. Experience the perfect blend of indoor-outdoor living in this beautifully designed waterfront retreat. Featuring 4 spacious bedrooms, a versatile flex-room, 3 full bathrooms and Gourmet Kitchen this home is perfect for both relaxation and entertaining. Step outside to your Resort style outdoor living with your covered lanai complete with custom summer kitchen and huge granite bar ideal for hosting family and friends. Take a dip in the sparkling private pool or lounge in the relaxation areas, all while enjoying peaceful water views. With your very own private dock, enjoy direct access to the water perfect for boating, fishing or simply soaking in the coastal lifestyle. Live where others Vacation, make your Dreams a Reality.!

13879 Ketch Cove Drive, Jacksonville

Courtesy of THE LEGENDS OF REAL ESTATE

Listing courtesy of THE LEGENDS OF REAL ESTATE.

Listing courtesy of LIZ MC MAHAN from THE LEGENDS OF REAL ESTATE.

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Holiday Harbor Homes for Sale

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