Homes for Sale in Naples, FL Between $500,000 to $550,000

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Welcome to your dedicated resource for Homes for Sale Between $500,000 to $550,000 in Naples, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Naples, FL agents, The Fortune Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $500,000 to $550,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Naples, FL Homes for Sale Between $500,000 to $550,000

$525,000

2 Beds ⋅ 2 Baths ⋅ 226036617 MLS

Move right in and start enjoying the Naples lifestyle! Offered turnkey furnished and beautifully updated, this Capri villa in the sought-after gated community of Island Walk is ready for its next owners. Light, inviting interiors feature luxury plank flooring, a beautifully renovated kitchen with quartz countertops, stainless steel appliances, and updated cabinetry, along with two tastefully remodeled bathrooms featuring frameless glass showers and stylish finishes. The open, spacious layout is designed for comfortable everyday living and flows seamlessly to the west-facing lanai, a private, serene oasis where you can unwind, entertain, and enjoy beautiful Naples sunsets. Additional highlights include custom closet systems, central vacuum, a hurricane-rated front door, and a newer roof (2021). Island Walk is known for its picturesque lakes, charming bridges, lush tropical landscaping, and miles of scenic walking and biking paths that wind throughout the community. At the heart of it all is the vibrant Town Center, complete with resort and lap pools, a fitness center, tennis, pickleball, bocce, an on-site restaurant, and everyday conveniences including a post office, gas station, car wash, and salon. Add in an active social calendar, a prime North Naples location close to shopping, dining, and beautiful Gulf beaches, and it's easy to see why Island Walk remains one of the area's most sought-after communities. This move-in-ready villa offers the perfect opportunity to embrace the Naples lifestyle, whether as a seasonal retreat or a year-round residence. Beyond the home, it's the Island Walk lifestyle that makes this community so special! Known for its picturesque lakes, charming bridges, and miles of walking and biking paths, Island Walk offers resort-style amenities and an active social atmosphere. Residents enjoy a vibrant Town Center with resort and lap pools, fitness center, tennis, pickleball, bocce, an on-site restaurant, and everyday conveniences including a post office, gas station, car wash, and salon. Conveniently located near Naples' shopping, dining, and beautiful Gulf beaches, this turnkey villa offers the opportunity to move right in and start enjoying your own version of everyday luxury.

5781 Drummond WAY, Naples

$549,000

2 Beds ⋅ 2 Baths ⋅ 226038979 MLS

Western sunset views, peaceful pond vistas, and added privacy, this Winding Cypress villa offers a setting that’s truly special! Beautifully upgraded, this unfurnished 2 Bedroom + Den residence enjoys desirable western exposure overlooking a picturesque pond, complemented by private green space adjacent to the property, creating a serene and tranquil retreat. Inside, an inviting open floor plan showcases builder-installed upgrades, elegant porcelain tile, granite countertops, and a stylish kitchen featuring stainless steel appliances and decorative backsplash. The spacious den offers flexibility as a third bedroom or home office. Additional highlights include California Closets throughout, plantation shutters, and a two-car garage. Enjoy the best of resort-style living with an on-site restaurant and bar, pools, fitness center, pickleball, tennis, bocce, and scenic nature trails with bird-watching overlooks. Ideally located between downtown Naples and Marco Island, this exceptional villa combines privacy and beautiful surroundings. Come for the views and stay for the lifestyle. Fall in love with everything Winding Cypress has to offer! Seller is a licensed FL Realtor.

7591 Jacaranda LN, Naples

$525,000

2 Beds ⋅ 2 Baths ⋅ 226038192 MLS ⋅ Glencove BLDG.

Enjoy lots of sunshine and volume ceilings in this open floor plan condo in Pelican Bay. This condo offers an enclosed, private stairway to the second-floor residence. The great room and dining room are open to one another giving the residence a spacious feeling. The bedrooms each have an en-suite bath so that the split bedrooms function like a dual main bedroom floorplan. The kitchen is light, bright and well-maintained with a pantry cabinet for those who cook. Both bedrooms are graciously sized with ample closet space and space for a sitting area/desk and include plantation shutters for privacy. This unit offers a glass enclosed Florida room which acts as additional living space for a den/family room or extra guests. The laundry is in unit, and there is additional storage outside the unit near the entrance. All this in the premier community of Pelican Bay, which offers all members the use of its 2 beach restaurants, tennis pavilion, fitness center, kayaking, biking, walking paths and of course beach access! This unit is located in Glencove, which is just a short stroll the beach tram, and minutes from Waterside Shops, The Artis, Mercato and many of the great places that Naples has to offer.

Naples

$525,000

4 Beds ⋅ 3 Baths ⋅ 226038743 MLS

Welcome to this stunning NEW CONSTRUCTION home featuring modern design, beautiful finishes, and endless possibilities! The main residence offers 3BD, PLUS a den and 2 full bathrooms along with a separate 1BD / 1BA in-law suite with its own private entrance, ideal for multigenerational living, guests, or potential rental income! Step inside to a bright, open layout featuring gorgeous tile flooring throughout, recessed lighting, sleek white cabinetry, and stylish black accents. The beautifully designed bathrooms feature floor-to-ceiling black marble-look tile, modern vanities, and glass-enclosed showers. The primary bathroom includes a double vanity with elegant vessel sinks. Enjoy a spacious backyard with a covered patio, perfect for relaxing or entertaining. An added bonus is the approximately 20-foot-wide side access, providing convenient entry to the backyard for trucks, RVs, boats, trailers, and other recreational vehicles, subject to local regulations. Whether you're looking for a beautiful new home, extra living space, or potential income-producing opportunities, this property offers the perfect combination of style, space, and flexibility.

4284 72nd AVE NE, Naples

$545,000

3 Beds ⋅ 2 Baths ⋅ 226038833 MLS

Exceptional opportunity in Golden Gate Estates featuring 2.27 acres of private land with endless possibilities. This spacious 3-bedroom, 2-bath residence offers the acreage and flexibility today’s buyers desire, with ample room for a pool, guest house, detached workshop, RV and boat parking, or a custom outdoor retreat. To add even more value, the seller is offering a credit at closing—ask for details. Enjoy the freedom of no HOA restrictions, versatile land use, and estate-style living, all while being conveniently located near shopping, dining, schools, and major roadways. A rare blend of space, privacy, and location that’s becoming increasingly difficult to find.

2772 38th AVE SE, Naples

$519,000

2 Beds ⋅ 2 Baths ⋅ 226038495 MLS

Discover an exceptional opportunity to enjoy the coveted Eagle Creek Country Club lifestyle at 91 Cypress View Drive, where timeless charm, effortless comfort, and an outstanding South Naples location come together. This inviting, tastefully furnished 2-bedroom, 2-bath residence offers approximately 1,665 square feet of thoughtfully designed living space, enhanced by soaring ceilings, skylights, elegant French doors, and a charming bay window room with a queen sized murphy bed that welcomes an abundance of natural light. A desirable split-bedroom floor plan provides privacy and comfort, creating an ideal setting for both everyday living and hosting guests. Perfectly positioned within walking distance of the golf practice range and clubhouse, this residence offers convenient access to the amenities and experiences that make Eagle Creek so desirable. Nestled within an intimate, gated country club community, Eagle Creek offers an exceptional array of amenities, including championship golf, tennis, bocce, swimming, fitness facilities, and clubhouse dining. From mornings on the fairways to leisurely afternoons by the pool and evenings spent with friends, every day presents an opportunity to embrace the best of country club living. Ideally located in South Naples, Eagle Creek provides convenient access to pristine Gulf beaches, upscale shopping, exceptional dining, and the vibrant destinations of downtown Naples and Marco Island. Whether envisioned as a year-round residence or an elegant seasonal escape, 91 Cypress View Drive presents a wonderful opportunity to experience the beauty, recreation, and welcoming atmosphere of Eagle Creek Country Club, with immediate golf membership available.

91 Cypress View DR Unit C77, Naples

$550,000

2 Beds ⋅ 2 Baths ⋅ 226038138 MLS

An exceptional waterfront opportunity in Naples’ vibrant Bayshore Arts District! Offering 50 feet of frontage on Haldeman Creek, this property combines a peaceful natural setting with boating access to Naples Bay and the Gulf of Mexico beneath the Bayshore Drive bridge. Remodeled 2-bedroom, 2-bathroom home is offered fully furnished and provides a comfortable place to enjoy today, while the waterfront homesite presents an exciting opportunity for future new construction. Enjoy the existing home as a coastal getaway or envision a custom residence designed to maximize the water views and outdoor living. A private dock adds to the appeal for boating and fishing enthusiasts. Approximately a quarter-mile walk to Celebration Park and close to Rebecca’s Wine Bar, Seventh South Bar, local shops, and restaurants, this location places you in the heart of Bayshore’s arts and dining scene—only 2 miles from 5th Avenue South and Naples’ beautiful beaches. With its waterfront setting and redevelopment potential, this property offers a compelling opportunity to create your vision in one of Naples’ most distinctive neighborhoods.

3201 Sabal CT, Naples

$500,000

2 Beds ⋅ 2 Baths ⋅ 226037877 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. In the sought-after Naples Reserve community, this freshly painted residence offers a desirable combination of comfortable living, flexible space and an extended lanai with western exposure for sunset views. Featuring two bedrooms, two full baths, a versatile den and a two-car garage with a lockable storage closet, the thoughtfully designed floor plan provides inviting spaces for everyday living and entertaining, with room to personalize the outdoor setting to suit your lifestyle. Inside, abundant natural light enhances the freshly painted interiors, while tile flooring throughout the main living areas and carpeting in the bedrooms create a practical balance of style and comfort. Recessed lighting adds a clean, contemporary touch. The kitchen features stainless steel appliances, quartz countertops, a tile backsplash and a central island that offers additional workspace and a natural gathering point. A breakfast bar provides casual seating, while the open dining and living areas create an easy flow for hosting family and friends. Sliding glass doors extend the living space onto the expanded lanai, creating an inviting setting for outdoor relaxation and dining. The western exposure provides the opportunity to enjoy colorful evening skies as the sun sets. The yard also offers room for a future pool, allowing buyers to envision an outdoor retreat tailored to their preferences. Manual shutters provide storm protection, while a newly installed whole-home water filtration system offers an additional upgrade for everyday comfort and convenience. The primary suite features his-and-hers walk-in closets and custom mirrors, while the en-suite bath is appointed with dual sinks and a spacious glass-enclosed shower. A second bedroom and full bath accommodate guests and the separate den offers flexibility for a home office, reading room or additional living space. Naples Reserve elevates the everyday with an impressive collection of resort-inspired amenities centered around a lakefront clubhouse. Residents enjoy a resort-style pool, fitness center, tennis and pickleball courts, bocce, basketball and a tiki bar and café. Waterfront recreation includes access to a private beach, boat ramp, Kontiki Island, electric boats, paddleboards and kayaks. Miles of paths, two dog parks and a one-mile rowing lane further expand the opportunities for outdoor enjoyment. Combining a functional floor plan, an extended sunset-facing lanai, convenient lockable garage storage and an extensive array of community amenities, this residence offers a relaxed Southwest Florida lifestyle with opportunities to enjoy indoor comfort and outdoor recreation in Naples Reserve.

14943 Edgewater CIR, Naples

$520,000

3 Beds ⋅ 2 Baths ⋅ 226038340 MLS

Enjoy the ease of Florida living in this beautifully maintained, Serenity floor plan single family villa, ideally situated on a corner lot in the gated, amenity-rich community of Winding Cypress. Being offered turnkey furnished, this thoughtfully designed residence has three bedrooms, two baths, and an inviting open-concept design, while combining comfortable living with effortless indoor-outdoor enjoyment. Tile flooring throughout, granite countertops, tile backsplash, and stainless-steel appliances create a timeless, welcoming kitchen. New AC in 2021. Plantation shutters throughout and a freshly painted interior add to the appeal, while the extended screened lanai provides a relaxing outdoor retreat overlooking a peaceful, landscaped view. A newly added privacy hedge (2025) enhances the setting, creating an ideal space to enjoy morning coffee or unwind at the end of the day. Impact-resistant doors and windows, hurricane fabric screens for the lanai, and an attached two-car garage offer added convenience and peace of mind. Winding Cypress, a natural gas community carefully designed around preserved natural beauty, is known for its active, social lifestyle and impressive amenities. Residents enjoy a welcoming clubhouse, heated resort-style pool and spa, poolside dining at the Shady Palm, fitness center, library, and community gathering rooms. Pickleball, tennis, and bocce courts offer opportunities to stay active, while two dog parks, a community garden, and scenic walking and nature trails invite residents to enjoy the outdoors. Whether seeking a seasonal retreat or a year-round residence, this residence offers an appealing combination of comfort, convenience, and the vibrant Winding Cypress lifestyle, conveniently close to everything Naples has to offer.

7098 Live Oak DR, Naples

$529,900

3 Beds ⋅ 2 Baths ⋅ 226037816 MLS

MODERN UPDATES, A PEACEFUL SETTING & HOA FEES OF JUST $59 PER MONTH! This beautifully renovated 3-bedroom, 2-bathroom home with a 2-car garage offers a combination of style, comfort, and investment potential in Naples’ Orange Tree community. With a tenant in place through April 2027, this property is an attractive opportunity for investors or buyers planning for future personal use. Sale subject to the existing lease. Situated on a quiet cul-de-sac, this home features a bright, open layout and modern finishes throughout. The peaceful backyard offers a welcoming retreat for morning coffee, outdoor dining, and relaxing evenings under the Florida sky. Orange Tree combines a peaceful residential setting with amenities for an active Florida lifestyle, including a community pool, clubhouse, tennis courts, fishing pier, park, and playground. Shopping, dining, and schools are nearby.

687 Grove DR, Naples

$510,000

4 Beds ⋅ 3 Baths ⋅ 226038117 MLS

Your private pool retreat awaits in Verona Walk. This four-bedroom, three-bath DiVosta townhome combines solid poured-concrete construction, approximately $50,000 in improvements, and resort-style living. A private screened courtyard features a heated pool with lighting and a safety fence—an inviting setting for morning coffee, alfresco dining and relaxed entertaining. Inside, continuous vinyl flooring throughout offers a cohesive, carpet-free finish. Plantation shutters, upgraded countertops, a subway tile kitchen backsplash, and LG appliances complement a breakfast bar with pendant lighting. An updated bathroom, primary-bedroom barn doors and remote-controlled ceiling fans throughout installed in 2020 add comfort and character. Additional features include a 2021 mold-protection and Air Flo enhancements, a 2019 water heater, new garbage disposal 2023. Accordion hurricane shutters and a motorized hurricane-protection door in the primary bedroom. The epoxy-finished two-car garage offers rear-alley access and partial plywood attic flooring for additional storage. Decorative rock landscaping accents the driveway, while a welcoming front porch provides another spot to unwind. Weber grill, lanai bench and pub table with two swivel chairs are included; additional furniture is negotiable. Gated Verona Walk offers pickleball, tennis, a fitness center, resort-style pool, gelato café, scenic walking and biking paths, a post office and an on-site gas station. Discover space, privacy and your own poolside escape in this inviting Naples home. Schedule your private showing today!

8069 Chianti LN, Naples

$549,000

3 Beds ⋅ 2 Baths ⋅ 226038364 MLS ⋅ Cherry Oaks BLDG.

Sunset first. Everything else second. There's something about a western exposure over water that never gets old. From the screened lanai, the view stretches across the lake to the golf course beyond, with the setting sun providing a different show every evening. And unlike a view you only appreciate from one room, this one becomes part of how you live. Welcome to Cherry Oaks at Fiddler's Creek. This first-floor coach home gives you single-family living without the upkeep: 2,408 square feet, a three-bedroom-plus-den floor plan, two full baths, and a two-car garage attached right to the residence. Bring your suitcase and start enjoying Naples. Inside, the layout is open, bright, and comfortable. Oversized sliders pull the lake view straight into the living area, and finishing touches like plantation shutters, crown molding, and designer lighting give every room a polished feel. The kitchen is built for everyday living and entertaining, with granite countertops, soft-close cabinetry, a gas cooktop, tile backsplash, GE Profile stainless steel appliances, and a casual dining area. The primary suite is a retreat of its own, two walk-in closets with custom built-ins, dual vanities, a separate makeup vanity, soaking tub, and oversized walk-in shower. Two guest bedrooms provide comfortable accommodations for family and friends, while the den offers a dedicated space for a home office, reading room, or media room. The beautifully renovated guest bathroom brings an unexpected touch of luxury with Brazilian Cristallo quartzite, a walk-in shower, shiplap detailing, and updated lighting. The improvements extend well beyond the finishes. Storm Smart impact windows, updated lanai sliders, no-see-um screening, a whole-home HVAC replacement, and a tankless water heater are among the investments already made. The lanai received new porcelain tile in 2025, and both guest bedrooms have updated flooring. Even the garage has been thoughtfully finished with epoxy flooring, cabinetry, and slat-wall storage. Beyond your front door, Fiddler's Creek offers a lifestyle that's difficult to duplicate. Recent community enhancements include a refreshed resort-style pool with waterfalls and slides, an upgraded Gator Grille, and 10 new pickleball courts. The renovated clubhouse features a fitness center, six Har-Tru tennis courts, a hot tub, sauna, and steam room. Golf is never required, but it's there when you want it. An optional membership opens up the championship course, the new golf clubhouse, the marina, and a private beach club, and there's currently no wait to join. The sunset views draw you in. The space, condition, furnishings, and Fiddler's Creek lifestyle make it easy to stay.

8951 Cherry Oaks TRL Unit 101, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.

Homes for Sale in Naples, FL Between $500,000 to $550,000

All Naples, FL Homes for Sale Between $500,000 to $550,000

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Own In Naples - Patti Fortune at Downing-Frye Realty, Inc.

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