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Homes for Sale with a Pool in 34104, Naples, FL

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Welcome to your dedicated resource for homes for sale with a pool in 34104, 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 34104, 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 with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in 34104, Naples, FL

$640,000
3 Beds ⋅ 2 Baths ⋅ 226027113 MLS
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to this beautifully updated single-family home in the highly sought-after Berkshire Lakes community of Naples, Florida. Perfectly positioned on a premium corner lot within a quiet cul-de-sac, this 3-bedroom, 2-bath residence offers 2,085 square feet of thoughtfully designed living space. This home stands out with a metal roof installed in 2023 with a transferable lifetime warranty, providing exceptional durability, storm protection, and long-term peace of mind—an increasingly valuable feature for Florida homeowners. Inside, you’ll find updated flooring throughout, high vaulted ceilings that enhance the sense of space and natural light, and a modernized kitchen featuring stylish finishes and new appliances installed in 2022. The well-defined layout offers distinct living and dining areas, creating a comfortable flow for both everyday living and entertaining, while the updated guest bathroom adds to the home’s appeal. Step outside to your private outdoor retreat complete with a pool and hot tub, perfect for relaxing or hosting guests year-round. Electric hurricane shutters offer added convenience and protection, making storm preparation simple and efficient. With low HOA fees and a prime Naples location close to shopping, dining, and Gulf beaches, this home delivers exceptional value in one of the area’s most established and desirable communities.

6630 Middlesex PL, Naples
$1,100,000
4 Beds ⋅ 226026942 MLS
UPDATED FOUR-UNIT INVESTMENT OPPORTUNITY – NEVER FLOODED! Rare opportunity to own two adjacent duplexes totaling four 1-bedroom, 1-bath residences in a highly desirable central Naples location. Offering proven rental history, private on-site parking, and strong income potential, this property is well suited for investors seeking immediate cash flow with long-term appreciation. Several units have been thoughtfully updated with herringbone-pattern tile flooring, quartz countertops, modern cabinetry, stainless steel appliances, renovated bathrooms, new windows, energy-efficient mini-split A/C systems, and on-demand water heaters. Select units also feature private screened lanais, adding desirable outdoor living space for tenants. The buildings have been well maintained, with roofs replaced in 2006 and reported to be in good condition. Additional opportunities remain to further enhance rental income and overall value. Ideally located just minutes from Downtown Naples, Fifth Avenue South, Naples' world-famous beaches, Celebration Park, Publix, shopping, dining, pickleball courts, and major conveniences, the property benefits from consistent tenant demand in one of Southwest Florida's most sought-after rental markets. Whether you're expanding your investment portfolio, completing a 1031 exchange, or seeking a well-located multi-family asset with immediate income and future upside, this is a rare opportunity in the heart of Naples.

3365 Estey AVE, Naples
$239,000
2 Beds ⋅ 2 Baths ⋅ 226026815 MLS ⋅ Granada Lakes BLDG.
TURNKEY and fully furnished! This rarely available 2 bedroom + den, 2-bathroom lakefront condo in the gated community of Granada Lakes has been recently refreshed and is entirely move-in ready for an owner-occupant, seasonal buyer, or investor. Enjoy direct lake views from every single room in the home, as well as from the private screened balcony. The open floor plan features an in-unit washer and dryer, a fully equipped kitchen, and a primary suite with a custom-shelved walk-in closet. One of the guest bedrooms is currently configured as a dedicated home office, complete with a workstation and dual monitors. This property is situated in a non-flood zone with no pending special assessments. Granada Lakes is a pet-friendly community offering excellent amenities, including two swimming pools, a hot tub, a fitness center, tennis courts, and community lake fishing. The location offers unmatched daily convenience. You are directly across the street from Publix, Aldi, Starbucks, and Five Guys, and just one street away from Calusa Park Elementary School. World-class dining in Downtown Naples and pristine

161 Santa Clara DR Unit 10, Naples
$205,000
2 Beds ⋅ 2 Baths ⋅ 226026132 MLS ⋅ Windjammer Village Of Naples BLDG.
One or more photo(s) has been virtually staged, AI generated or rendered. Recently Updated Corner Lot Home in Windjammer Village of Naples! Discover the perfect blend of comfort, convenience, and value in this beautifully refreshed two-bedroom, two-bath home located on a desirable corner lot in the gated 55+ community of Windjammer Village of Naples. Recent improvements include fresh interior and exterior paint, laminate flooring throughout the living, dining, and kitchen areas, plus a refreshed kitchen featuring updated countertops, sink, and backsplash. The open floor plan creates a bright and inviting space that's ready for your personal style. The dining area is highlighted by beautiful bay windows, offering the perfect spot to enjoy gorgeous evening sunsets. Just beyond, the enclosed lanai features its own dedicated air-conditioning unit, creating a comfortable year-round living space ideal for relaxing, entertaining, or pursuing your favorite hobbies. Situated on a corner lot, this home offers the added benefit of additional parking, along with an attached storage shed providing plenty of room for tools, seasonal décor, bicycles, or beach gear. The washer and dryer are conveniently located inside the home. Many of the listing photos have been virtually staged to help you envision the possibilities while showcasing the spacious layout. With the home presented as a blank canvas, you'll have the opportunity to create a space that truly reflects your own style and taste. Windjammer Village is a gated community offering an active lifestyle with low association fees and an outstanding Naples location. You'll be just minutes from shopping, dining, and approximately 15 minutes from the renowned restaurants of Fifth Avenue South and the beautiful Gulf beaches. Whether you're looking for a seasonal retreat or a full-time Florida residence, this move-in-ready home is ready for you to make it your own.

95 Oceans BLVD, Naples
$249,000
2 Beds ⋅ 2 Baths ⋅ 226023668 MLS ⋅ Country Haven BLDG.
Offered turnkey and overlooking the golf course, this second floor two bedroom, two bath residence brings easy living to Country Haven inside Countryside Golf and Country Club. Arrive with a suitcase. The furnishings convey, so the home is ready for season the day you close. A bright, open plan connects the living and dining rooms to a screened lanai that frames a green, private outlook over the course. The eat in kitchen offers a pantry, a sunny breakfast nook, and a pass through that keeps the cook in the conversation. The Master Suite sits privately apart with an ensuite shower bath and a walk in closet, while the guest bedroom and bath give visitors their own space. Assigned covered parking sits steps away. Countryside recently completed a $15 million renovation, with an expanded clubhouse, a new resort style pool, dining, tennis, and pickleball, gated and minutes from downtown Naples, Fifth Avenue South, and the beaches.

7380 Saint Ives WAY Unit 1202, Naples
$314,700
3 Beds ⋅ 2 Baths ⋅ 226025926 MLS ⋅ Blue Heron BLDG.
Beautifully maintained 3-bedroom, 2-bath condo offering tranquil lake views and an ideal blend of comfort and convenience. The recently updated kitchen features KitchenAid stainless steel appliances, modern finishes, and ample cabinet space. Hurricane-impact windows provide added peace of mind and energy efficiency. Other recent updates include paint, new screens and updated bathrooms. The primary closet and laundry room had custom shelving added providing organization. The bright, open living, dining and lanai areas flow seamlessly to the scenic lake view, creating a relaxing atmosphere for everyday living or entertaining. Additional features include covered parking and community pool. Conveniently located just a short drive from downtown, shopping, dining, and the area's beautiful beaches. There is a county park just 2 miles away offering recreational activities. This move-in-ready condo is perfect as a full-time residence, seasonal getaway, or investment opportunity.

7822 Great Heron WAY Unit 201, Naples
$342,900
3 Beds ⋅ 2 Baths ⋅ 226026405 MLS ⋅ Sherwood BLDG.
MOTIVATED SELLER- PRICE REDUCTION!! Welcome to Sherwood – Naples Living at Its Best Discover comfort, convenience, and resort-style living in this beautifully maintained 1st-floor end unit coach home in the highly desirable Sherwood community! This 3-bedroom, 2-bath home offers over 1,600 sq. ft. of living space with an open-concept design perfect for everyday living and entertaining. A HOME YOU'LL LOVE The open living and dining areas create a warm and inviting atmosphere. The well-appointed kitchen features abundant cabinetry, granite countertops, upper cabinet lighting, a breakfast area, and plenty of functionality for everyday living. Additional highlights include tile flooring throughout, interior rooms painted within the past two years, a fully updated guest bathroom (2024), a new AC unit (2025), and a new garage door motor (2026). The spacious primary suite offers a walk-in closet, a private en-suite bath with dual vanity cabinet, and a walk-in shower. Two additional bedrooms provide flexibility for family, guests, or a home office. COMFORT & CONVENIENCE Enjoy the ease of first-floor living with an attached garage (no stairs), easy access, and added privacy on your screened lanai—complete with tile flooring. RESORT-STYLE AMENITIES Sherwood residents enjoy access to a wealth of amenities, including 12 acres of picturesque lakes, two pools, a tennis court, four pickleball courts, a fitness room, and a clubhouse with a gathering room and kitchen—perfect for social events and activities. A COMMUNITY THAT HAS IT ALL Sherwood is a pet-friendly community (up to 2 pets) with six neighborhood associations and a master association that maintains our beautiful common areas. Low condo fees include internet, cable, water, garbage, and outdoor pest control for worry-free living. PRIME NAPLES LOCATION Ideally located just off Radio Road, this home is only a short drive to the stunning white sand beaches of Naples and approximately eight miles from Downtown Naples, with close proximity to historic Naples, Tin City, the airport, premier shopping, dining, and easy access to I-75. Whether you're looking for a seasonal retreat or a full-time residence, this move-in ready home offers the perfect blend of comfort, convenience, and the Florida lifestyle. Don't miss your opportunity to own a slice of paradise—schedule a showing today!

517 Robin Hood CIR Unit 101, Naples
$449,800
3 Beds ⋅ 3 Baths ⋅ 226026106 MLS
UPDATED HOME WITH FULLY FENCED BACKYARD - BRAND NEW ROOF & LOW HOA FEES! Welcome to this move-in-ready home in the desirable Leawood Lakes community, offering over 2,000 square feet and ONE OF THE LARGEST FLOOR PLANS in the neighborhood. With 3 bedrooms and 3 full bathrooms, this spacious residence provides a versatile layout that's ideal for families, multigenerational living, or as an investment opportunity. Major improvements include a BRAND-NEW ROOF (2026), NEW LVP FLOORING IN ALL BEDROOMS (NO CARPET!), NEW INTERIOR PAINT, and NEW LANDSCAPING, giving the home a fresh, modern feel inside and out. Featuring TWO PRIMARY SUITES —one on the first floor and another on the second—this home is perfectly designed for those seeking flexibility and privacy. The first-floor primary suite includes a spacious bedroom, private bathroom, walk-in closet, and a versatile den/kitchenette area with its own private access to the backyard. Upstairs you’ll find the second primary suite, an additional bedroom, two full bathrooms, and an open-concept living, dining, and kitchen area. A private balcony off the upstairs living area features stairs leading directly to the backyard, creating a seamless indoor-outdoor living experience. Step outside to enjoy a spacious, fully fenced backyard with upgraded landscaping, offering plenty of room for pets, outdoor entertaining, gardening, or future enhancements. Additional highlights include a 1-CAR GARAGE, PAVER DRIVEWAY, generous storage, and a functional floor plan designed for comfortable everyday living. Residents of Leawood Lakes enjoy a beautifully maintained community with LOW HOA FEES and access to a community pool, all while being conveniently located JUST MINUTES FROM DOWNTOWN NAPLES, 5th Avenue South, Naples' white-sand beaches, shopping, dining, and only about 6 minutes to I-75, providing easy access throughout Southwest Florida. With an unbeatable Naples location and exceptional versatility, don't miss this exceptional opportunity to own one of the largest homes in Leawood Lakes! FREE ONE-YEAR AMERICAN HOME SHIELD HOME WARRANTY INCLUDED! THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER, INQUIRE FOR MORE DETAILS** (Renderings that showcase furniture have been virtually staged)

434 Leawood CIR, Naples
$1,549,000
4 Beds ⋅ 3 Baths ⋅ 226026100 MLS
Discover the perfect blend of coastal luxury, convenience, and exceptional indoor-outdoor living in this remarkable Naples residence. Thoughtfully designed for both everyday comfort and effortless entertaining, this spacious home offers an abundance of room for family and guests while embracing the very best of the Southwest Florida lifestyle. Perfectly positioned in the highly desirable waterfront community of Avion Park along the Gordon River, this property provides convenient boating access to Naples Bay, the Gulf of Mexico, and beyond—making it an ideal retreat for boating enthusiasts. Spend your days cruising the waterways, enjoying waterfront dining, or exploring the endless coastal destinations just minutes from your dock. Just steps away, the Gordon River Greenway and Baker Park offer miles of scenic walking and biking trails, kayaking, community events, and beautiful green spaces to enjoy year-round. Located only minutes from Naples' award-winning beaches, upscale shopping, fine dining, and vibrant downtown attractions, this home combines an exceptional location with an unmatched lifestyle. Whether you're searching for a year-round residence, a seasonal escape, or the perfect home for entertaining, this property presents a rare opportunity to enjoy one of Naples' most coveted waterfront settings. Confidential sales are welcomed. Non-Disclosure Agreements (NDAs) are available upon request to ensure a discreet and private transaction.

1680 Avion PL, Naples
$339,900
2 Beds ⋅ 2 Baths ⋅ 226025908 MLS ⋅ Sherwood BLDG.
Motivated Sellers. Gorgeous, newly renovated second floor unit. Vaulted ceilings, open kitchen with views of the preserve from the lanai. Meticulously maintained, custom cabinetry, New impact windows & sliders, modern, light and airy, ready to be enjoyed by the new owners. *Dogs welcome! One or Two Dogs allowed with a 100lb combined weight limit. Have a pick-up truck...? That's ok too! Lots of wonderful amenities come with this beautiful home. Easy access to downtown Naples and I75.

225 Robin Hood CIR Unit 203, Naples
$489,900
3 Beds ⋅ 2 Baths ⋅ 226024377 MLS
Experience the best of Naples living in this beautifully renovated 3-bedroom, 2-bath end-unit villa, featuring the largest floor plan in the gated Villas of Whittenberg. Ideally located just inside the controlled-access entrance, this home offers an open, spacious layout with soaring vaulted ceilings, abundant natural light, and spectacular long lake views from the oversized screened and enclosed lanai. Designed for both comfort and style, the interior showcases tile flooring throughout, a fully remodeled kitchen with abundant cabinetry, updated bathrooms with modern finishes, and a spacious two-car garage complete with built-in cabinetry, a convenient kitchenette, and an extended driveway with parking for up to four additional vehicles. Major improvements provide peace of mind, including a new roof (2018), updated 2.5-ton HVAC system, and a leased solar panel system that may be transferred to the new owner, offering the potential for long-term energy savings. Residents enjoy outstanding amenities, including a community clubhouse, swimming pool, and fitness center, all while benefiting from one of the lowest HOA fees in the area. The community is pet-friendly, allowing up to two pets. Perfectly situated just 10 minutes from Downtown Naples and the Gulf's white-sand beaches, this exceptional home is also minutes from top-rated schools, shopping, dining, medical facilities, and I-75. Move-in ready, beautifully upgraded, and offering an unbeatable combination of space, location, lake views, and value—this is a rare opportunity you won't want to miss.

5205 Whitten DR Unit 57, Naples
$495,000
2 Beds ⋅ 2 Baths ⋅ 226025417 MLS
Cheerful Pool Home on a Large Corner Lot! Not 10 minutes from Naples most famous beaches, this pool home offers 2 bedrooms and a large den with an oversized 2-car garage, open floor plan, generator, metal roof, granite in kitchens and baths, and storm protection. The spacious great room concept home offers so much! Stretch out for a nap by your solar-heated swimming pool! Other upgrades include a white energy-efficient metal roof (2013) and a tankless water heater. Warm and welcoming with a peek of a lake view from the pool lanai with an undercover outdoor patio area. Lovely Maplewood just east of Livingston and 10 minutes from beaches and 5th Ave., affordable association fees make this the perfect place to begin your new adventure in Naples, FL.

295 Stanhope CIR, 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.