Harbor Island Real Estate, Homes, Condos for Sale in Fleming Island, FL

Enjoy Florida living in this beautifully maintained pool home situated on a spacious corner lot in an established neighborhood. From the moment you arrive, you'll appreciate the inviting layout designed for both everyday comfort and effortless entertaining. The open living spaces flow seamlessly to the private screened lanai, sparkling pool, and outdoor retreat--perfect for relaxing evenings, weekend gatherings, or enjoying the Florida sunshine year-round. The kitchen offers abundant cabinetry, granite countertops, stainless appliances, and a breakfast bar overlooking the main living area. The spacious primary suite provides a peaceful escape with generous closet space and ensuite bath. A cozy fireplace adds warmth and charm to the living room, while multiple access points to the outdoor living spaces create an airy indoor-outdoor feel. Conveniently located near shopping, dining, parks, & everyday amenities, this home offers the perfect blend of comfort, space, and Florida lifestyle

1842 Harbor Island Drive, Fleming Island

Listing courtesy of NEXTHOME ENDLESS SUMMER.

Selling Office: .

$399,400

4 Beds ⋅ 2 Baths ⋅ 2138688 MLS

Enjoy waterfront living in this beautifully updated 4-bedroom, 2-bath home featuring peaceful water views and modern upgrades throughout. The heart of the home showcases granite countertops, stainless steel appliances, luxury vinyl plank flooring, and updated bathrooms designed for both style and comfort. A professionally screened lanai provides the perfect space to relax, entertain, or enjoy your morning coffee overlooking the water. Recent improvements include a new roof (2023), new HVAC system (2024), and a Level 2 EV charger, offering peace of mind and energy-conscious convenience. The washer and dryer are included, making this home truly move-in ready. Located in a desirable community with low HOA fees and no CDD fees, residents enjoy convenient access to the 8-mile paved Black Creek Trail, top-rated schools, shopping, dining, parks, golf courses, and NAS Jacksonville. Combining modern updates, scenic waterfront views, and an exceptional location.

1671 Dockside Drive, Fleming Island

Listing courtesy of UNITED REAL ESTATE GALLERY.

$360,000

4 Beds ⋅ 2 Baths ⋅ 2129950 MLS

Experience tranquility in this beautifully updated 4BR/2BA brick home in the sought-after Harbor Island community. This turn-key retreat features a BRAND NEW ROOF and FULLY PAID SOLAR PANELS, offering monthly energy savings. Step inside to 1,758 sq ft of modern living with luxury laminate wood floors and an open-concept kitchen boasting granite countertops/ wood block counter, and SS Frigidaire appliances. Nestled on a quiet cul-de-sac, your private backyard oasis overlooks a serene pond and protected preserve—perfect for birdwatching and peaceful evenings. Updated bathrooms, ceiling fans in all rooms, and a neutral, elegant palette make this move-in ready. Enjoy the best of Fleming Island living in this updated beauty!

1301 Portside Drive, Fleming Island

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$395,000

4 Beds ⋅ 2 Baths ⋅ 2124685 MLS

BUYER BONUS $5,000 toward buyer closing costs, rate buy down, you decide, with acceptable offer at closing. Affordable POOL Fleming Island home in Harbor Island with low HOA and no CDD fees! Fresh interior paint and newly painted kitchen cabinets! Tucked away on a quiet cul-de-sac, this beautiful pool home offers the perfect blend of privacy and comfort. Step inside to find an open floor plan filled with natural light, perfect for both everyday living and entertaining. Your backyard oasis awaits! Enjoy endless summer days in the sparkling in-ground salt system pool, surrounded by a private fenced yard that's perfect for family fun, cookouts and gatherings with friends. Bonus, enclosed 14 x 12 all season room with its own climate controlled unit, not included in the square footage, for flex space to enjoy. Fully fenced back yard, the cul-de-sac setting provides added peace and minimal traffic, while the convenient location keeps you close to shopping, dining, and top-rated schools. Easy commute to NAS Jax, Jacksonville beaches. Don't miss your chance to own this slice of Florida paradise - schedule your private showing today!

1608 Dockside Drive, Fleming Island

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$450,000

5 Beds ⋅ 4 Baths ⋅ 2114777 MLS

This ALL brick 5 bedroom 3.5 bath home with views of the pond is perfect for you! Completely updated, this spacious floor plan offers a formal sitting area, dining room, living room with fireplace, and a HUGE air conditioned back porch. The primary bedroom has vaulted ceilings, access to the back porch, and a large bathroom that includes a walk-in shower and separate tub. The 5th bedroom, at the front of the house, would make a great office or playroom. Tile runs throughout the house, no carpet anywhere. Updates to the home include NEW roof and gutters, NEW AC for porch, REMODELED primary bathroom, REMODLED kitchen, NEW flooring in all bathrooms and kitchen, NEW lighting fixtures, NEW stainless steel dishwasher, microwave and stove. FRESH interior paint and decorative paint at fireplace. All of this, plus your own mature fruit trees in your yard. The Harbor Island neighborhood has a very low yearly HOA and is conveniently located to all Fleming Island has to offer.

1634 Dockside Drive, Fleming Island

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

Selling Office: .

$309,900

4 Beds ⋅ 2 Baths ⋅ 2110223 MLS

JUST LISTED in Harbor Island community of Fleming Island! BUYER INCENTIVE: SELLER PAYING up to 2% of purchase price towards Buyer's closing costs! (with approved offer, must be written into contract). Great home on the cul-de-sac with brick front, neutral colors throughout including Vinyl Plank Flooring throughout much of it's open floor plan. Large covered patio - great for entertaining friends or family! Home is clean and ready for the next owners - don't miss this one. CALL YOUR AGENT TODAY!

1207 Stern Way, Fleming Island

Listing courtesy of RE/MAX SPECIALISTS.

Selling Office: .

$350,000

3 Beds ⋅ 2 Baths ⋅ 2101014 MLS

Nestled in the highly sought-after Fleming Island area, this charming and lightly lived-in 3-bedroom, 2-bathroom home offers an inviting open floor plan and versatile living spaces perfect for any lifestyle.The heart of this home is the family room, which seamlessly flows into the updated kitchen boasting granite counters and ample space for entertaining! Imagine cozy evenings by the gas log fireplace, enjoying stunning views of the expansive screened lanai and the beautifully landscaped, fenced-in backyard - an ideal setting for outdoor entertaining or peaceful relaxation. Designed for privacy, this home features a desirable split bedroom plan. The spacious owner's suite is a true retreat, boasting two closets and a private bath with a separate shower. For added flexibility, a separate living room and dining room provide excellent opportunities for conversion into a dedicated office, playroom, or flex space to suit your needs.

1835 Harbor Island Drive, Fleming Island

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$310,000

4 Beds ⋅ 2 Baths ⋅ 2098274 MLS

COME GET READY FOR SCHOOL WITH THIS LOVELY OPEN CONCEPT 4 BEDROOM HOME, enter onto luxury vinyl flooring with open bright living room which leads to spacious tiled eat in kitchen, quartz counters, all appliances included, nice breakfast bar overlooks cozy family room with tile fireplace, big backyard for the kids and dogs to play, good sized primary suite with luxury bathroom , garden tub, double sinks on marble counters separate shower, split bedrooms, ceiling fans, 2 car garage with washer dryer closet. HVAC transferable warranty. LOCATION LOCATION! TOP RATED SCHOOLS, EASY ACCESS FOR SHOPPING, DINING, FISHING, BOAT RAMPS, BIKING, HIKING AND YOUR JOB! WELCOME HOME ON FLEMING ISLAND!

1317 Portside Drive, Fleming Island

Listing courtesy of IAD FLORIDA LLC.

Selling Office: .

$336,200

4 Beds ⋅ 2 Baths ⋅ 2097767 MLS

Multiple Offers received. Seller is asking for Highest and Best by 5 P.M. on 07/14/25. Well-maintained and full of warmth, this home offers an entertainer's dream backyard—complete with an extended paver patio, built-in fire pit with seating, lush landscaping, and a large fully fenced yard with a shed. Inside, you'll find a cozy living room with a gas fireplace, beautiful wood flooring, tile in all bedrooms (no carpet!), and a bright, open layout. The kitchen features stainless appliances and great storage, while the Florida room adds extra living space year-round. Located in the heart of Fleming Island with no CDD fees!

1960 Harbor Island Drive, Fleming Island

Listing courtesy of HERRON REAL ESTATE LLC.

Selling Office: .

$335,000

4 Beds ⋅ 2 Baths ⋅ 2092365 MLS

Come enjoy this lovely well maintained 4 bedroom beauty. Upon entering, the formal dining room is to your right. you then flow seamlessly to the open great room with a bar off to the the left for those informal family gatherings. Prepare your meals and be included in this open concept. Serve brunch in the breakfast nook. Great room goes out to an open patio with an oversized lot for the area. Total parcel size is .43 of an acre. Home as a 2 car garage with extra expanded driveway to park additional cars. Both bathrooms have been updated.

1203 Stern Way, Fleming Island

Listing courtesy of I ON REAL ESTATE & INVESTMENTS.

Selling Office: .

$347,600

3 Beds ⋅ 2 Baths ⋅ 2088420 MLS

Welcome to 1275 Pirates Cove in the heart of Fleming Island. This well-maintained 3-bedroom, 2-bath brick home offers comfort and function with thoughtful upgrades throughout. The fully fenced backyard features mature trees, and a spacious screened sunroom—perfect for year-round enjoyment. Inside, the home boasts vaulted ceilings, a wood-burning fireplace, and a bright kitchen with stainless steel appliances and ample cabinet space. The primary suite includes dual sinks and a walk-in hydrotherapy tub installed in 2022. The secondary bedrooms are spacious and share a full bath. Recent updates include a 2023 HVAC system, 2021 water heater, and 2011 architectural shingle roof. Located in a quiet, established neighborhood with no CDD fees and close to top-rated Clay County schools, shopping, and dining. This home combines indoor comfort with outdoor living and is move-in ready. Don't miss your chance to own this Fleming Island gem.

1275 Pirates Cove Lane, Fleming Island

Listing courtesy of REALTY ONE GROUP ELEVATE.

Selling Office: .

$339,000

3 Beds ⋅ 2 Baths ⋅ 2088123 MLS

Move-in ready and full of charm, this 3-bedroom, 2-bath home offers 1,512 sq ft of open-concept living in the highly sought-after Harbor Island neighborhood of Fleming Island. Situated on a quiet dead-end street, this beautifully maintained property rests on a 0.195-acre lot with lush landscaping, a full sprinkler system, and great curb appeal. Inside, you'll find a bright and spacious layout featuring hardwood floors throughout, a large primary suite with an ensuite bath, and a desirable split-bedroom floor plan that offers privacy. The formal dining room adds versatility—it's perfect for entertaining, but also ideal as a home office or easily converted into a fourth bedroom. Built in 1998 and well-maintained over the years, this home features recent updates including a brand-new HVAC system (2024) and a newer roof (2012). You'll also enjoy a roomy 2-car garage and a convenient indoor laundry area that makes everyday living a breeze. Zoned for top-rated schools and close to shopping, dining, and parksthis home checks every box for comfort, convenience, and value. Don't miss your chance to live in one of Fleming Island's most desirable communities!

1940 Harbor Island Drive, Fleming Island

Listing courtesy of FREEDOM REALTY GROUP LLC.

Selling Office: .

$343,000

5 Beds ⋅ 4 Baths ⋅ 2082875 MLS

Discover the potential in this charming brick home, nestled in the peaceful Harbor Island neighborhood. Priced to reflect its need for TLC, this 2,572 sq. ft. home offers an exciting chance for someone to bring their vision to life and create their dream home. A recent appraisal in its current condition valued the property at $455,000, making this a remarkable opportunity to renovate and add value. The well-designed open floor plan features formal living and dining areas flowing into a great room with a cozy fireplace and wood-look tile flooring throughout the main living areas and bedrooms. The spacious kitchen, complete with a breakfast nook and included appliances, awaits your personal touch. The primary bedroom is a true retreat with vaulted ceilings, patio access, a generous walk-in closet, & a tub with a separate shower. The split floor plan includes three additional bedrooms—one with a private en-suite—plus a fifth versatile room ideal as an office or extra bedroom. Enjoy relaxing in the sunroom with peaceful pond views or tending to the fruit trees in the backyard. Additional features include a side-entry garage and conveyed washer and dryer. Don't miss this fantastic chance to own and transform a Harbor Island gem!

1634 Dockside Drive, Fleming Island

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$320,000

3 Beds ⋅ 2 Baths ⋅ 2078981 MLS

Discover this charming and affordably priced 3-bedroom, 2-bath home in desirable Fleming Island! Featuring an open floor plan with a split bedroom layout, this home offers both space and privacy. Recent updates include a new roof and fresh paint in 2024, ensuring a move-in-ready experience. Enjoy outdoor living in the large screened patio overlooking the fenced backyard, perfect for relaxing or entertaining. Plus, plenty of storage in the 2-car garage. Conveniently located near shopping, dining, and top-rated schools, this home is a fantastic opportunity. Don't miss out—schedule your showing today!

1367 Keel Court, Fleming Island

Listing courtesy of ALLISON JAMES ESTATES AND HOMES FLORIDA.

Selling Office: .

$315,000

4 Beds ⋅ 2 Baths ⋅ 2046828 MLS

Nestled in the heart of Fleming Island, this charming brick home exudes serene living, tucked away in a quiet, tree-lined neighborhood. Situated just five minutes from the bustling CR 220 corridor, offering a range of upscale shopping centers, dining options, entertainment venues, and medical facilities. As you step inside, you'll be greeted by soaring 10-foot vaulted ceilings and a spacious, open floor plan bathed in natural light. The modern kitchen is equipped with gleaming black granite countertops, stainless steel appliances, a breakfast bar, pantry, and attractive pendant lighting. Adjacent to the kitchen is a cozy breakfast nook and a formal dining room —perfect for casual meals with family or entertaining. The primary ensuite features vaulted ceilings, a generous walk-in closet, dual vanity sinks, and a luxurious tiled shower. Three additional bedrooms and a bathroom offers plenty of space for family or guests. Step into the fully enclosed Florida room offering a versatile Space for year-round enjoyment with the perfect view of your backyard oasis. The oversized, fenced yard is a nature lover's dream, filled with mature trees, bushes, and flowers that provide both shade and privacy. Directly off the Florida room is a concrete patio, ideal for summer barbecues. This home is a must-see for anyone seeking the laid-back Florida lifestyle in one of Fleming Island's most desirable locations!

1775 Dockside Drive, Fleming Island

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$467,000

4 Beds ⋅ 2 Baths ⋅ 2038089 MLS

Stunning custom renovated pool home in highly sought after Fleming Island. Home exemplifies attention to detail rarely found in this market. Incredible upgrades displayed, from cabinet door hardware to detailed trim work and feature walls. Floor to ceiling next level renovations featuring Riad zellige fireplace tile with handcrafted mantel,all new designer lighting throughout, arched pocket door, and more. The custom kitchen features an oversized island with TONS of storage, quartz countertops, docking drawer, builtin pantry with sliding drawers, one of a kind vent hood, under cabinet lighting, pot filler, and specialty backsplash. The beautiful antique dutch door welcomes you into your showcase laundry room, where the task of laundry is finally(almost) enjoyable :) All this, while friends and family enjoy lounging in the screened lania or poolside. Minutes from Doctors Lake Marina and NAS Jax. Your new home is waiting for you!

1410 Starboard Court, Fleming Island

Listing courtesy of UNITED REAL ESTATE GALLERY.

Selling Office: .

$425,000

4 Beds ⋅ 2 Baths ⋅ 2027758 MLS

Make a splash this summer with this beautiful 4/2 pool home in Harbor Island. Featuring a recently updated kitchen with all stainless-steel appliances, 42-inch cabinets, and soft close drawers. An inground pool with a fully fenced, beautifully landscaped back yard ready for the first pool party of the year. You will find additional space in the Florida Room that can be accessed through the home or from outside near the pool. The owner's bathroom was recently updated with a separate shower, garden tub and double vanity. Bring your hammock and enjoy all that Fleming Island has to offer!

1371 Keel Court, Fleming Island

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Selling Office: .

$375,000

3 Beds ⋅ 2 Baths ⋅ 2009993 MLS

Gorgeous Harbor Island home nestled on a quiet cul de sac location with a peaceful lake view. Private rear yard and patio perfect for entertaining. Great cul de sac to live on. Excellent Fleming Island location close to shopping and lifestyle amenities A rated schools. Under a mile from Doctors Lake Marina to keep your boat to enjoy Doctors Lake and the St Johns River. Boat to a Jags game. 4 Miles S of I295. Freshly redone with new paint, appliances, fixtures and flooring. Transferable Termite bond. Homes like this one dont last long in Fleming Island. Some pics have been virtually staged marked VS.. Under $164 a sq ft is an amazing price for Clay county

1401 Starboard Court, Fleming Island

Listing courtesy of RE/MAX SPECIALISTS.

Selling Office: .

$439,000

4 Beds ⋅ 2 Baths ⋅ 1240148 MLS

Hot New Listing! Solid Brick home on a lush, pristine, corner lot nestled in a quiet, established Fleming Island neighborhood with low fees just minutes away to shopping, dining, parks and NAS. Gorgeous floors throughout this stunning, spacious home enhance the layout and semi open floorplan with private master bedroom and en suite. Bonus features such as; custom crown, new fans and lighting along with a generous screened in patio for lazy weekend mornings when you say yes to that extra cup of coffee. Nearly new AC means you can easily stay home and keep cool while you unpack. Private backyard with plenty of room for a pool, spa or even both. Is this your new address? Take a tour and find out!

1905 Harbor Island Drive, Fleming Island

Listing courtesy of REALTY ONE GROUP ELEVATE.

Selling Office: .

$400,000

4 Beds ⋅ 2 Baths ⋅ 1240879 MLS

Welcome to 1516 Wayward Wind Lane in beautiful Fleming Island, Florida! This charming 3-bedroom, 2-bathroom home is the epitome of comfort and convenience. Nestled in a serene neighborhood, this property offers a spacious open floor plan, perfect for entertaining guests. The modern kitchen features stainless steel appliances and granite countertops, making meal preparation a delight. Step outside to a large backyard, ideal for relaxing or hosting outdoor gatherings. Located close to top-rated schools, shopping centers, and parks, this home also has a roof that is 3 years old and a brand new HVAc as of 8/2 Also there is a storage shed and building with power and garage door out back for a work shop. Call today for your private viewing.

1516 Wayward Wind Lane, Fleming Island

Listing courtesy of KELLER WILLIAMS FIRST COAST REALTY.

Selling Office: .

$327,000

3 Beds ⋅ 2 Baths ⋅ 1233106 MLS

This turn-key 3 bed, 2 bath home is ready for you to make it yours! Features include hardwood flooring throughout the living room. Tile can be found in all wet areas & bamboo flooring can be found in the dining room & all bedrooms. As you enter the home to the left you will find the kitchen which features, stainless steel appliances & laminate countertops. To the right of the entryway, you will find the formal dining room. The living room features a wood burning fireplace & access to the backyard. To the right of the living room, you will find the primary suite which features a garden tub, separate shower area, & a walk in closet. To the left of the living room, you will find both guest beds & the guest bath. Outback you will find a screened porch, patio area, & the fully fenced in yard.

1647 Dockside Drive, Fleming Island

Listing courtesy of WATSON REALTY CORP.

Selling Office: .

$440,000

3 Beds ⋅ 2 Baths ⋅ 1229101 MLS

**SELLER OFFERING $10K TO BUY DOWN RATE** Welcome to Fleming Island's finest gem! This meticulously maintained all-brick home exudes elegance and offers a luxurious living experience. With 3 bedrooms, 2 bathrooms, and a multitude of impressive upgrades, this residence is a true showstopper. As you step inside, you'll immediately notice the impeccable care this home has received. From the completely renovated kitchen, designed to create an open floor concept, to the updated bathrooms, every detail has been thoughtfully considered. The new wood-like tile floors add a touch of sophistication, while the brand new appliances elevate the culinary experience to new heights. New ceiling fans, added recess lighting and so much more.

1662 Dockside Drive, Fleming Island

Listing courtesy of HERRON REAL ESTATE LLC.

Selling Office: .

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