Homes for Sale with a Pool in Lakeland, FL

4 Beds ⋅ 2 Baths ⋅ Oaks Of Lakeland The SubDv.

Virtually Staged. Welcome to 928 Timbergreen Drive in Lakeland—a beautifully updated home that perfectly blends classic comfort with modern functional living. Featuring fresh paint completed this month, this light-filled residence features an open floor plan designed to maximize space and natural light. At the heart of the home is a spacious kitchen with an expansive layout, ample counter space, a bright eat-in area, and stainless appliances. The kitchen flows seamlessly into a grand living room highlighted by soaring cathedral ceilings and a magnificent stone wood-burning fireplace. The home offers 4 generously sized bedrooms with large reach-in closets enclosed by clean bi-fold doors. The primary suite serves as a private retreat with a walk-in closet and an en-suite bathroom. Step outside to enjoy an expansive screened lanai overlooking a private, fenced half-acre lot showcasing a massive in-ground pool—an absolute paradise for entertaining under mature oak trees. The property also features a spacious 2-car garage with ample space to park your boat. Located on a quiet cul-de-sac, this move-in ready home is a must-see!

928 Timbergreen Drive, Lakeland

$564,500

4 Beds ⋅ 2 Baths ⋅ Magnolia Chase SubDv.

Welcome to 2349 Chesterfield Circle — a stunning South Lakeland pool home tucked inside the rarely available Magnolia Chase subdivision off Crews Lake Drive. From the moment you arrive, this home stands out with its lush, established landscaping, beautiful palms, and private tropical feel that makes the property feel like its own secluded retreat. Inside, this 4 BEDROOM, 2 BATHROOM home offers an impressive 2,588 square feet of living space with soaring 10-foot ceilings, extensive crown molding, tall baseboards, and elegant trim details around the windows. The spacious kitchen features beautiful granite countertops, warm wood cabinetry, and plenty of room for gathering, entertaining, and everyday living. The backyard is where this home truly becomes unforgettable. Step outside to a resort-style pool area finished with elegant pavers, a covered patio, a spa/hot tub, and mature tropical landscaping that creates privacy and a true Florida oasis. Whether you are hosting friends, relaxing after a long day, or enjoying quiet weekends at home, this outdoor space is designed to be enjoyed. Major updates add even more peace of mind, including a roof replaced in late 2024 and an AC system that is only a few years young. Ideally located in South Lakeland near George Jenkins High School, shopping, dining, and just moments from the 551-acre Lakeland Highlands Scrub preserve with scenic trails and natural Florida beauty, this home offers the space, setting, and lifestyle buyers are looking for. Homes in Magnolia Chase do not come available often. Schedule your private showing and come experience why this one is so special before the opportunity is gone. This property also has the option of an assumable loan at 5.24%. Please call for more details.

2349 Chesterfield Circle, Lakeland

$300,000

3 Beds ⋅ 2 Baths ⋅ Honeytree East SubDv.

Welcome home to this well-maintained and charming 3-bedroom, 2-bathroom residence with a BRAND NEW ROOF installed June 2026, ideally located in Lakeland, just minutes from Southeastern University, Grove Park Publix, shopping, dining, and everyday conveniences. Offering a functional and inviting layout, this move-in ready home features spacious living areas, luxury vinyl flooring throughout all of the home, a cozy fireplace, and an updated kitchen with a pantry, stainless steel appliances, and plenty of cabinet and counter space. Two additional bedrooms provide room for family, guests, a home office, or hobbies. Step outside the sliding glass doors from the living room to the lanai and enjoy your own backyard retreat. The screened lanai features a relaxing spa that stays with the home, creating the perfect place to unwind after a long day. The fully fenced backyard offers plenty of space for entertaining, pets, gardening, or outdoor activities, and even includes an above-ground pool for enjoying Florida's sunshine. Additional highlights include a one-car garage, updated finishes, and a convenient location near Southeastern University, Grove Park Publix, downtown Lakeland, medical facilities, and major commuter routes. Whether you're looking for your first home, a primary residence, or an investment opportunity in a growing area of Lakeland, this property is one you won't want to miss. Schedule your private showing today and discover everything 1309 Cinnamon Way W has to offer, including the spa that stays!

1309 Cinnamon Way W, Lakeland

$1,040,000

4 Beds ⋅ 3 Baths ⋅ Estates At Cypress Trace SubDv.

Under Construction. Located in the gated community of Estates at Cypress Trace, this exceptional new construction home offers the perfect blend of luxury, privacy, and convenience. Nestled in North Lakeland, this exclusive neighborhood provides a peaceful retreat while remaining just minutes from I-4, making travel to Tampa and Orlando effortless. The Abigail floor plan offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 bathrooms, a 3-car garage, and a spacious open-concept layout. A standout feature is the oversized fourth bedroom, designed to function as a game room, media room, playroom, guest suite, or flexible living space to fit your family's needs. Inside, soaring 12-foot ceilings, LVP flooring, custom cabinetry, quartz countertops, and designer finishes create a clean, timeless aesthetic. The gourmet kitchen features Frigidaire appliances, a large center island, and an impressive super pantry complete with custom wood shelving and additional quartz workspace. The great room is anchored by a floor-to-ceiling cultured stone fireplace wall featuring a 60-inch electric fireplace with log set, remote control, and custom cedar mantel. Designed for Florida living, the expansive screened lanai serves as a true extension of the home. The custom 30' x 13' saltwater pool is fully enclosed within the lanai and features a PebbleTec finish, LED lighting, splash shelf.

8110 Cypress Woods Avenue, Lakeland

$290,000

3 Beds ⋅ 2 Baths ⋅ Silver Lakes Rep SubDv.

Welcome to this well-maintained 3-bedroom, 2-bath home located in the highly desirable 55+ Silver Lakes community! Offering comfort, convenience, and beautiful lake views, this home is designed for easy Florida living. Step inside to find updated vinyl flooring in the dining room, recessed lighting in the kitchen, and a spacious layout perfect for everydayw living and entertaining. The home features a natural gas stove, central heating system, and water heater, providing efficiency and added peace of mind. During power outages, residents can continue using many essential natural gas-powered appliances, an invaluable feature during storm season. Technology and convenience are seamlessly integrated throughout the home. The refrigerator and washer is Wi-Fi enabled, allowing smart connectivity and remote monitoring. The garage door opener is also Wi-Fi compatible and includes a battery backup system, enabling operation of the garage door even during a power outage. Additional updates include a refrigerator, washer, and microwave that are only two years old, helping reduce future maintenance concerns. Enjoy tranquil lake views from the backyard, creating the perfect setting for relaxing mornings and peaceful evenings. Silver Lakes offers an active lifestyle with exceptional amenities, including a clubhouse, swimming pool, sauna, billiard room, and a variety of community activities. The low HOA fee of just $235 per month includes lawn service, irrigation, basic cable, and internet, allowing for truly low-maintenance living. Don't miss this opportunity to own a move-in-ready home with modern conveniences, energy-efficient natural gas features, and beautiful water views in one of the area's most sought-after active adult communities. Schedule your private showing today!

2258 Silver Re Drive, Lakeland

$235,000

3 Beds ⋅ 3 Baths ⋅ Autumnwood Grove SubDv.

Welcome home to this beautifully move-in ready maintained 3-bedroom, 2.5-bath townhome located in the highly sought-after Autumn wood Grove community in South Lakeland. Designed for comfort and convenience, this spacious residence features an open-concept layout that seamlessly connects the living, dining, and kitchen areas, creating the perfect space for everyday living and entertaining. Natural light fills the home's inviting interior, while the thoughtfully designed floor plan provides both functionality and privacy. Upstairs, the spacious primary suite serves as a relaxing retreat with a private en-suite bath and generous closet space. Two additional bedrooms provide versatility for family, guests, or a dedicated home office. Step outside to your private patio and enjoy a peaceful setting ideal for morning coffee or unwinding at the end of the day. Residents of Autumnwood Grove enjoy gated access, community amenities, and a prime location just minutes from shopping, dining, medical facilities, schools, and the Polk Parkway for convenient access throughout Central Florida. Whether you're searching for your first home, a low-maintenance lifestyle, or a smart investment opportunity, this move-in-ready townhome combines comfort, location, and value in one exceptional package. Schedule your private showing today!

4086 Winding Vine, Lakeland

$256,900

3 Beds ⋅ 3 Baths ⋅ Hampton Hills South Ph 03 SubDv.

This beautiful 3-bedroom, 2-bathroom townhome offers the perfect combination of comfort, convenience, and low-maintenance living. Featuring a spacious and functional floor plan, this home is ideal for first-time homebuyers, growing families, downsizers, or investors looking for a great opportunity in a desirable Lakeland location. Enjoy being just minutes from shopping, dining, schools, medical facilities, and everyday conveniences. Located near Lakeland Square Mall and major highways, including I-4, commuting to Tampa, Orlando, and surrounding areas is quick and easy. The home offers comfortable living spaces, ample natural light, and a welcoming atmosphere perfect for relaxing or entertaining. Whether you're looking for your primary residence or an investment property, this townhome checks all the boxes. Don't miss your opportunity to own a well-located home in one of Lakeland's growing communities. Schedule your private showing today.

3740 Woodbury Hill Loop, Lakeland

$199,900

2 Beds ⋅ 2 Baths ⋅ Colonnades Ph 02 SubDv.

Set at the back of The Colonnades on a corner lot, this one gives you more room around you and less traffic going by. Off the single-car carport, a covered screen room and a storage-and-workshop area add space for slow mornings outside and the projects you finally have time for. Inside is a comfortable 2 bed, 2 bath that's clearly well loved and maintained, with the big-ticket items already handled: new roof (2025), new water heater (2025), and HVAC serviced (2025). The $197/month HOA covers your lawn, cable, and internet, with the gated 55+ community's clubhouse, pool, and fitness center included. Less to take care of, more to enjoy. Worth seeing in person.

4918 Pleasant Hollow Trail, Lakeland

$375,000

2 Beds ⋅ 2 Baths ⋅ Lake James Ph 01 SubDv.

Welcome to this beautifully crafted custom home by Ernie White, located in a desirable gated 55+ community in North Lakeland. Offering over 2,000 square feet of thoughtfully designed living space, this residence features 2 spacious bedrooms and 2 full bathrooms, with a study and an open, inviting layout ideal for both everyday living and entertaining. Inside, you’ll find a blend of wood and tile flooring throughout, creating a warm yet low-maintenance environment. The generous living areas flow seamlessly, while large windows provide natural light and a comfortable atmosphere. You can also enjoy an expansive bonus area that can be used as a sitting room, office or hobby area. This home also has plenty of storage options. Enjoy a truly carefree lifestyle with HOA fees that include lawn care, cable, internet and use of all amenities. The community itself is quiet, beautifully maintained, and rich in amenities, featuring a clubhouse, fitness center, and sparkling pool—perfect for socializing or relaxing. If you’re looking for quality construction, comfort, and an active yet peaceful community, this exceptional home is a must-see. Act quickly--this home is priced to sell and ready for its next owner.

2356 Lake James Way, Lakeland

$130,000

2 Beds ⋅ 2 Baths ⋅ Lakeside Village 01 Condo SubDv.

** $10K PRICE REDUCTION as of 7/22/2026!** POOL-VIEW CONDO IN A WATERFRONT 55+ COMMUNITY! Bring your decorating ideas and make this spacious second-floor, 2-bedroom, 2-bath condominium your own. Unit A-208 offers a comfortable living and dining area, a generously sized primary bedroom, two full bathrooms, abundant storage, an in-unit laundry area and an enclosed Florida room overlooking the community pool. The galley-style kitchen provides plenty of cabinetry and counter space, while the flexible floor plan offers excellent potential for seasonal or year-round living. This home is ready for updated flooring and personal touches, giving the next owner an opportunity to choose the finishes and style they prefer rather than paying a premium for someone else’s renovations. Lakeside Village is an established 55+ community located on Lake Parker and features a community pool, clubhouse, shuffleboard and a peaceful waterfront deck where residents can relax and enjoy Florida lakefront living. Conveniently located near shopping, restaurants, medical facilities and everything Winter Haven has to offer. Priced with the updates in mind—come see the space, the pool view and the possibilities!

1130 N Lake Parker Avenue Unit A208, Lakeland

$169,900

2 Beds ⋅ 2 Baths ⋅ Kimberlea Condo 06 Ph 01 SubDv.

Welcome to maintenance-free living in the highly sought-after Kimberlea community! This spacious 2-bedroom, 2-bath condominium offers approximately 1,605 square feet of thoughtfully designed living space featuring soaring vaulted ceilings, abundant natural light, a freshly painted interior, and an open-concept layout ideal for both everyday living and entertaining. The desirable split-bedroom floor plan provides privacy and flexibility, while the oversized primary suite features two walk-in closets and a private en-suite bath. In addition to the generous living and dining areas, you'll appreciate the versatile Florida room—perfect as a home office, hobby space, reading nook, or additional sitting area. An interior laundry area, ample storage, and assigned covered carport parking add to the home's convenience. Enjoy a truly carefree lifestyle with an HOA that covers the roof, exterior maintenance, water, trash, lawn care, community pool, tennis courts, and beautifully maintained grounds. Whether relaxing on your private patio or enjoying the community amenities, Kimberlea offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally located in South Lakeland, you'll be just minutes from shopping, dining, parks, downtown Lakeland, Lakeland Linder International Airport, and the new Orlando Health Lakeland Highlands Hospital campus featuring Watson Clinic services. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this well-maintained, move-in-ready condo offers exceptional value in one of Lakeland's most established and desirable communities.

2025 Sylvester Road Unit MM4, Lakeland

$345,000

4 Beds ⋅ 2 Baths ⋅ Riverstone Ph 2 SubDv.

Welcome to this beautiful home in the sought after Riverstone Community. This 4-bedroom, 2-bathroom, split floor plan is a gorgeous open concept home that is minutes away from Sun and Fun yearly event. The kitchen has a walk-in, built out pantry to store food and bakeware. The Stainless steel appliances, granite countertops, and prep island are any chef's dream. The sink faucet has been replaced so that cleaning up is efficient. The 2-car garage has been epoxied so that everything stays looking like new. The beautiful primary bathroom has been updated to include a tiled shower with a glass door. The bathroom linen closet and primary walk-in closet have been customized to keep life organized. The screened in porch with the lake view is as stunning as the sunsets that can be viewed every night. The house is located on the bend so traffic is minimal. The community offers 2 pools, community center, walking trails, dog park,, and fitness stations. The home is located a short drive from the I-4 and SR60 that lead to Orlando, Tampa, and all the fun spots in Florida. Lakeland is home to many head quarters including Publix, Geico, Carrier, and many more. Please schedule a viewing before this gem is gone.

5853 Arlington River Drive, Lakeland

Homes for Sale with a Pool in Lakeland, FL

All Homes for Sale with a Pool in Lakeland, FL

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