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Countryside Naples Florida Homes for Sale

Naples Florida Real Estate

Countryside Naples Real Estate

Homes For Sale9$619K - $829K
Condos For Sale9$239K - $359K
Sold ( Past 6 Months )22$219K - $769K
Last updated at 9:25pm 12/04/2025

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$829,000
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Countryside

200 Saint James Way, Naples, FL 34104

Homes - 2,128 ft² / 2,534 ft² - 2 Car Garage

3 Bed / 3 Baths / Pool

Built 1991
Countryside Naples Homes for Sale: Live the Dream in Countryside Golf & Country Club! One of Naples’ premier gated communities with a rare blend of privacy, luxury, and convenient coastal living. Nestled on a tranquil lakeside lot with lush vegetation and calusia hedges that buffer the pool and entertaining area for extra seclusion, this impeccably maintained three bedroom, three bath, single-family home offers a sublime sanctuary with panoramic water views, high-volume ceilings throughout every room, and a durable metal roof that promises years of worry-free living. Step inside to discover an expansive open floor plan accentuated by soaring ceilings, walls of natural light, and a seamless flow to the outdoors. The living spaces are ideal for entertaining or quiet relaxation alike. Outside your rear lanai, the lake fountain (that illuminates in the evening) is nothing short of serene - a perfect setting for morning coffee or evening sunset reflections. This home has been lovingly cared for, with attention to detail evident in every corner. The magic of this address extends far beyond your doorstep. Living at Countryside means enjoying a lifestyle few communities can match. Over the past few years, the club has undergone a sweeping transformation: the 18-hole Arthur Hills / Kipp Schulties course was thoughtfully renovated, and the 21,000-square-foot clubhouse was fully refurbished both inside and out. The revamped amenities include indoor and alfresco dining, bars both inside and on the terrace, a resort-style pool with outdoor tiki dining, wellness center and full social calendar. There is no food minimum requirement at the clubhouse, a rare find in country-club living. Countryside is a bundled golf community. The dues structure is known to be among the most affordable in Southwest Florida. And then there’s Naples itself — a city beloved for its sugar-sand beaches, world-class dining, art galleries, championship golf, and vibrant cultural scene. Imagine beach afternoons, strolling elegant Fifth Avenue (just minutes away), and returning home to this private haven. This home is ideally located for proximity to Downtown 5th Avenue, grocery stores, pharmacies, high-end dining and entertainment. You won’t compromise on convenience: you’re just a short drive from the Gulf, I-75, Marco Island, and all the best of Collier County while enjoying a retreat-like residence behind the gates. This is more than just a home - it’s a lifestyle. A place where privacy, elegance, and the very best of Naples converge.



$799,000
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Countryside

421 Countryside Dr, Naples, FL 34104

Homes - 1,514 ft² / 2,382 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 1989
Countryside Naples Homes for Sale: Golf Included! Step into this completely reimagined three-bedroom, two bath home showcasing Coastal Farmhouse elegance and modern luxury throughout. Every detail has been thoughtfully curated—from the brand-new designer kitchen and spa-inspired baths to the stylish flooring, lighting, and finishes. The expansive lanai opens to a new saltwater pool with sun-shelf, surrounded by a paver patio, walk and driveway and outdoor kitchen- creating a seamless indoor-outdoor flow for entertaining or relaxing. All new hurricane rated windows and doors. Located in Countryside Golf & Country Club the best community value in Naples now boasting a $14 million renovation, residents enjoy resort-style amenities including a championship golf course, clubhouse, tennis, pickleball, wellness center, five star dining, and more. Golf membership is included—with no waiting list! This home offers the perfect combination of timeless style, comfort, and community living in one of Naples’ most sought-after golf destinations. Walk to the club or the back gate and stroll 5 minutes to Starbucks, Publix, Walgreens, Banks & Restaurants. Minutes to our sugar sand beaches, I75 , Marco Island and the upscale shops & restaurants of Downtown Naples. Some images may have been digitally enhanced.



$759,900
Decrease*
$40K
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Countryside

522 Countryside Dr, Naples, FL 34104

Homes - 1,869 ft² / 2,261 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 1990
Countryside Naples Homes for Sale: Wake up to the beautiful sunrise over the lake and the first hole in this beautiful and spacious single family home at the Countryside Golf and Country Club, where a new multi million dollar resort is open and filled with activities and an awesome Florida lifestyle. This well appointed home has the perfect location, on the golf course and within walking distance of the new clubhouse, pickleball, tennis, bocce outdoor concerts and so much more With two large bedrooms and a den which can serve as a 3rd bedroom, this home has an open kitchen with an island and granite countertops, and a breakfast area complete with bay window and comfortable seating. The primary bedroom is large and overlooks the inground pool and the golf course, and the primary bath is beautifully tiled and updated. In the middle of the home off of the living room is a large den with bookcases and a pull out sofa for guests, and further down the hall is the second bedroom and the guest bathroom, all complete with furnishings. A separate dining room is off of the kitchen and a bonus Florida room was added to the original design to provide more living and entertaining space. Plantation shutters adorn every impact window and the air conditioner and water heater are both in perfect operating order. There is something for everyone at Countryside....great food, outdoor concerts, game nights, karaoke, field trips, an attended fitness center with a variety of classes to choose from, music, weekly dances, theme nights, celebrations of all kinds, a speaker series book club, and social gatherings along with golf, tennis, pickleball and bocce. Add to this your proximity to great shopping, major highways, fine dining and the glorious Gulf of Mexico, we mean it when we say that 'it doesn't get any better than this!!"



$739,900
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Countryside

401 Countryside Dr, Naples, FL 34104

Homes - 2,487 ft² / 2,487 ft² - 2 Car Garage

3 Bed / 3 Baths

Built 1988
Countryside Naples Homes for Sale: WOW!! WHAT A HOME! Walk right in to this bright, modern, and totally renovated 3 bedroom, 3 bath home home at the newly remodeled Countryside Golf and Country Club. With full golf privileges built into the sale of this home, this home boasts an expanded living area with an open concept kitchen, a large living room/dining room combination and a large and bright bonus family room with space for great entertaining and comfortable living. In addition to the 3 bedrooms, there is an additional work/hobby, storage room off of the family room. Luxurious vinyl plank flooring is offered throughout, and an additional walk-in pantry/combination laundry room with extra cabinetry is off of the kitchen. The large kitchen island with granite countertops seats 4 , while quartz countertops complete the rest of the kitchen counter space. This home is located on a preserve for extra privacy and has a generator that remains with the home to keep you safe and comfortable during a storm. I addition to county water, this home has a well which waters the yard on a regular basis. Countryside has just completed a two year renovation project where resort like amenities and activities will keep all residents connected and involved. Golf tennis pickleball, cards, outdoor concerts, field trips, karaoke, Binga, Name that Tune, lecture series, book club, an attended fitness center and so much more. Add to this proximity to the highways, great shopping, fine dining, Fifth Avenue, and the glorious Gulf of Mexico, it really doesn't get any better than this. Nestled on a preserve with trees and privacy, this home also has a full generator that comes with the home. Along with county water, this home also has a well which waters the back yard regularly with lawn nutrients.



$739,000
Decrease*
$50K
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Countryside

581 Country Walk Ct, Naples, FL 34104

Homes - 1,743 ft² / 2,199 ft² - 2 Car Garage

4 Bed / 2 Baths / Pool

Built 1987
Countryside Naples Homes for Sale: Looking for a nicely updated pool home with bundled golf and one of the best locations in Countryside? This beautifully updated four-bedroom, two-bath residence is directly across the street from the newly renovated clubhouse, offering unmatched convenience to golf, tennis, dining and all the club’s resort-style amenities. On a quiet cul-de-sac with private garden views and desirable western exposure, this light-filled home is move-in ready and ideal for year-round or seasonal living. Go inside to cathedral ceilings and luxurious vinyl plank flooring throughout, creating a modern and cohesive flow. The open kitchen features white shaker-style cabinetry, quartz countertops, bar seating, recessed lighting and high-end appliances, including a range with hood, under-counter microwave, refrigerator/freezer and dishwasher. The kitchen features a cozy breakfast nook by three windows, filling the space with natural light and charming garden views. The open layout flows seamlessly into the spacious living room, which opens through glass sliders to the screened lanai, ideal for enjoying private garden views and peaceful western sunsets. The outdoor living area is wonderful for entertaining, with a covered space featuring dual ceiling fans and a sparkling pool for enjoying Florida’s warm weather in comfort and style. The owner’s suite offers a peaceful retreat with a spacious flex area for a reading nook, home office or private lounge. It also features a walk-in closet with built-in shelving and a spa-inspired en-suite bath with a dual quartz vanity and a walk-in shower adorned with large porcelain tile. One guest bedroom overlooks the lanai, while two additional guest rooms share a beautifully appointed bath with a frameless glass walk-in shower. Countryside Golf & Country Club offers full golf membership with this home and an incredible social lifestyle, all just minutes from Naples white sandy beaches, shopping, dining and major roadways. With a freshly completed clubhouse renovation that includes indoor and outdoor dining, a resort-style pool, tennis, pickleball, fitness center and an active social calendar, this is your opportunity to live the ultimate Naples golf lifestyle in a prime location.



$724,900
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Countryside

229 Countryside Dr, Naples, FL 34104

Homes - 1,563 ft² / 1,811 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 1992
Countryside Naples Homes for Sale: The time is now to make this single family residence your new abode! It can be your year round residence, winter home, or make it an investment property as it is currently. This home has everything conveniently located and shows well. There are three bedrooms, two bathrooms, formal dining area and a comfortable living area to relax in. The kitchen area features ample newer cabinetry, appliances, granite countertop with a breakfast bar for two. All windows and patio doors have been updated to impact glass for hurricane protection. The patio area is set up for socializing, dining, swimming, sun bathing, in an area lush with greenery around the pool cage. The primary bedroom is set back by the pool with its own bathroom and walk in closets. This well-maintained home is in the best private member owned golf community in the vicinity. The clubhouse just reopened with the most attractive lounge, dining areas, in addition to outdoor dining and firepit areas. The outdoor pool cafe/bar and resort pool are now open. By late December there will be pickleball courts added by the tennis and bocce courts. For the golfers there is a putting green, driving range, and of course the 18-hole golf course along with various leagues you as a golf member can join. This course went through an update in 2019 and is enjoyed by everyone! Don’t want to forget the city amenities which are extensive, theaters, playhouses, restaurants, and the beautiful Gulf of Mexico!! The Buyer assumes the assessment going forward for the resort pool, outdoor dining amongst other enhancements at $293.85 per quarter until 5/1/2033. This renovation was extensive and took approximately 2 years. We are all so grateful the construction days are behind us, and we get to return to indoor club dining and holidays celebrated with our neighbors and friends.



$700,000
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Countryside

161 Saint James Way, Naples, FL 34104

Homes - 1,575 ft² / 1,975 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool / Spa

Built 1990
Countryside Naples Homes for Sale: Welcome to this light and bright home in the highly desirable community of Countryside! This beautifully maintained residence features tile flooring throughout the main living areas and soaring vaulted ceilings that create an open, airy ambiance. The spacious kitchen offers a large center island, eat-in dining space, and extended built-in counters with cabinetry that seamlessly connect to the living area—ideal for entertaining or casual gatherings. Step outside to your private tropical retreat, where the expansive screened lanai invites you to relax and enjoy the sparkling pool, soothing spa, and a covered sitting area perfect for dining al fresco. The outdoor space has been thoughtfully updated with a new pool heater (2023), new pool pump (2024), and a newly screened pool cage (2023) for worry-free enjoyment. Inside, all 3 bedrooms showcase rich wood flooring, while the primary suite offers a dual vanity and a generous walk-in shower. This home also features hurricane impact windows and hurricane shades (2024), providing peace of mind and energy efficiency. Additional highlights include a new A/C (2022), new electrical panel (2023), tile roof, two-car garage, and beautifully landscaped grounds that enhance the home’s curb appeal. Countryside is a gated, private membership community offering resort-style amenities including a clubhouse, golf course, restaurant, fitness center with attended staff, bocce, pickleball, putting green, sauna, community pool and spa, and more. Ideally located just minutes from downtown Naples, white-sand Gulf beaches, shopping, dining, and entertainment, this home perfectly combines the comfort of private living with convenient access to everything Southwest Florida has to offer.



$675,000
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Countryside

241 Saint James Way, Naples, FL 34104

Homes - 1,699 ft² / 1,766 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 1990
Countryside Naples Homes for Sale: Debuting this GOLF INCLUDED pool home in Countryside Golf and Country Club where Resort Style Amenities meet everyday comfort at the most affordable price in Naples. This TURN KEY 2-bedroom plus den, 2-bath open-concept home showcases a designer kitchen with updated finishes and a seamless flow into the spacious dining and living area, all highlighted by rich Travertine flooring. Step into the enclosed glass Florida room, perfect for relaxing or entertaining year-round, and enjoy tranquil views of the preserve beyond. The outdoor paver-lined lanai with a private screened-in cage offers complete privacy — a peaceful retreat surrounded by lush tropical landscaping. Additional highlights include Split bedroom layout for privacy. Expansive primary suite with walk-in closet. 2-car garage with ample storage Countryside’s newly (2025) reimagined 14 million dollar clubhouse, wellness center, tennis, bocce, pickleball, and championship golf, this move-in-ready home offers no waiting for golf membership — just bring your clubs and start living the Naples lifestyle you deserve. Walk out the back gate and stroll 5 minutes to Starbucks, Publix, Walgreens, Banks & Restaurants. Minutes to our sugar sand beaches, I75 , Marco Island and the upscale shops & restaurants of Downtown Naples Select photos may include virtually enhancements for presentation only.



$619,000
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Countryside

157 Saint James Way, Naples, FL 34104

Homes - 1,595 ft² / 1,957 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 1992
Countryside Naples Homes for Sale: GOLF INCLUDED! This turnkey 3-bedroom, 2-bath golf & pool home located in Countryside Golf & Country Club, a nationally recognized top -5 financially sound club which just unveiled its $14 million resort-style renovation. Fees are the LOWEST IN NAPLES. Golf included the Arthur Hills redesigned 18 hole course, driving range, putting greens, Har-True Tennis Courts, Bocce, state-of-the-art wellness center, social events and debuting this fall brand-new pickleball facilities — all designed for the ultimate in resort-style living. Close today and golf tomorrow! This home offers a spacious layout with a beautiful outdoor living space, perfect for entertaining around the pool. Each of the 3 BR features its own walk in closet- two in the owners ensuite. Upgraded with a newer metal roof (2018), A/C (2023), complete re-ductwork, pool pump and pool heater. This home is move-in ready and fully equipped for investment, seasonal or full-time living. Walk out the back gate and stroll 5 minutes to Starbucks, Publix, Walgreens, Banks & Restaurants. Minutes to our sugar sand beaches, I75 , Marco Island and the upscale shops & restaurants of Downtown Naples. This is an incredible affordable opportunity to enjoy golf, luxury, and lifestyle in one of Naples’ best values!



$769,000
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Countryside

509 Countryside Dr, Naples, FL 34104

Homes - 2,210 ft² / 2,210 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 1988
Countryside Naples Homes Under Contract: GOLF INCLUDED at Countryside Golf & Country Club, where resort-style living meets timeless elegance. This three bedroom, two bath pool home debuts with a formal living and combined dining space, eat-in kitchen, spacious den/family space that flows into the Florida room. Professionally decorated and landscaped this home offers the perfect blend of comfort, style and access to one of Naples’ most vibrant private communities. Recently, Countryside completed a $14 million renovation, elevating the club to a resort style experience with spectacular new amenities — from championship Arthur Hills Designed 18 hole golf course tennis, to bocce, pickleball, fitness and a full calendar of social events. This is a rare opportunity with no waiting for golf membership — step right into the active Naples lifestyle without delay. The home is thoughtfully curated both inside and out. Open living spaces flow seamlessly to the screened lanai and sparkling pool. Countryside Golf & Country Club is known for its welcoming atmosphere and exceptional value. Walk out the back gate and stroll 5 minutes to Starbucks, Publix, Walgreens, Banks & Restaurants. Minutes to our sugar sand beaches, I75 , Marco Island and the upscale shops & restaurants of Downtown Naples. Truly an unbeatable location just minutes from Naples’ white-sand beaches and world-class shopping and dining.



$743,000
Sold Price:
$725,000
Sold Date:
07/10/2025
View Details

Countryside

450 Countryside Dr, Naples, FL 34104

Homes - 2,103 ft² / 2,501 ft² - 2 Car Garage

3+Den / 3 Baths / Pool

Built 1990
Countryside Naples Homes: Welcome to this beautifully maintained and freshly painted home located in the prestigious Countryside Golf & Country Club of Naples, Florida. This spacious residence offers 3 bedrooms, 3 bathrooms, and a generous layout perfect for comfortable living and entertaining. Situated on an expansive lot with breathtaking views of the golf course and serene water features, this home provides the ideal backdrop for relaxation and outdoor enjoyment. Vaulted ceilings throughout enhance the sense of space, while large windows allow natural light to flood the interior. Step outside to your private oasis, complete with a heated pool—perfect for year-round enjoyment. Whether you're lounging by the pool or enjoying the scenic views, this home offers the perfect combination of luxury and tranquility. As part of the exclusive Countryside Golf & Country Club, a private golf membership is included, allowing you to enjoy world-class amenities and an active lifestyle. In addition, a spectacular new clubhouse featuring a restaurant, outdoor café, bar, and pool will be completed shortly, offering even more luxury and convenience at your doorstep. Don’t miss the opportunity to own this stunning property in one of Naples' most desirable communities.



$742,000
Sold Price:
$700,000
Sold Date:
08/22/2025
View Details

Countryside

221 Saint James Way, Naples, FL 34104

Homes - 1,619 ft² / 2,023 ft² - 2 Car Garage

3 Bed / 2 Baths / Pool

Built 1989
Countryside Naples Homes: Dreaming of bundled golf and tranquil lake views from your own private pool? This nicely updated three-bedroom, two-bath home in Countryside Golf & Country Club has it all, including full golf membership and western exposure for stunning sunsets. Go inside to soaring cathedral ceilings with recessed lighting and luxurious vinyl plank flooring that runs seamlessly throughout the home. The new kitchen showcases white shaker-style cabinetry, quartz countertops with a dramatic waterfall edge, a spacious four-seater center island and high-end stainless steel appliances. Natural light floods the adjacent, open-concept dining and living areas from two glass sliders, creating a seamless indoor-outdoor connection ideal for entertaining. The screened lanai features a spacious covered area for sitting and dining, a pool wrapped in travertine flooring, and private lake views for unwinding and hosting guests. The owner’s suite is a relaxing retreat with private lanai access, a walk-in closet with custom built-ins, and a spa-like en-suite bath featuring dual quartz vanities, a walk-in shower with floor-to-ceiling tile, bench, niche and frameless glass enclosure. Two guest bedrooms with charming bay windows share a beautifully finished bath with a frameless glass walk-in shower. A well-appointed laundry room includes a washer and dryer, overhead cabinetry and a large storage closet with built-in shelving. Countryside offers a newly renovated clubhouse experience coming in July, with resort-style pool, outdoor dining, a circular bar, fire pits, tiki bar and casual social spaces. Residents also enjoy tennis, pickleball, fitness center with attendant, cards, concerts, field trips, themed events and more. With proximity to Naples white sand beaches, 5th Avenue South and the Gulf, this home offers the best of Naples lifestyle.



$560,000
Sold Price:
$540,000
Sold Date:
06/11/2025
View Details

Countryside

417 Countryside Dr, Naples, FL 34104

Homes - 1,641 ft² / 2,094 ft² - 2 Car Garage

2+Den / 2 Baths / Pool

Built 1988
Countryside Naples Homes: Welcome to your private retreat in the heart of Naples! This beautifully maintained 2-bedroom + den, 2 bathroom single-family pool home is located in the highly sought-after Countryside Golf & Country Club and includes a DEEDED BUNDLED GOLF MEMBERSHIP. Inside, you'll find a bright and open layout featuring vaulted ceilings, fresh paint, and brand-new LED can lighting throughout. The spacious eat-in kitchen flows seamlessly into the living area and opens to a screened-in lanai with peaceful preserve views — perfect for entertaining or relaxing by your private pool. The primary suite offers direct access to the lanai, a large walk-in closet, and an en-suite bathroom complete with dual sinks, a soaking tub, and a separate shower. The flexible den with French doors is ideal as a home office, guest space, or reading room. Countryside is a gated, active golf community with outstanding amenities including an 18-hole golf course, full-service clubhouse with dining, tennis and bocce courts, fitness center, and a full calendar of social events. Located just 6.5 miles (15 minutes) from Downtown Naples, 14 miles (25 minutes) from Marco Island, and 7 miles (15 minutes) to the Gulf beaches, this home offers the perfect blend of privacy, comfort, and access to the best of Southwest Florida. Don’t miss this opportunity to enjoy year-round resort-style living in one of Naples’ most desirable bundled golf communities.




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