Timberwoods Estates Homes with Pool

Timberwoods Estates Homes with Pool

Welcome to Timberwoods Estates, an enchanting subdivision nestled in the heart of Wildwood, Florida, in beautiful Sumter County. This serene community offers a perfect blend of nature and modern living, making it an ideal place for families and individuals seeking a tranquil lifestyle without sacrificing convenience.

Timberwoods Estates is characterized by its lush landscapes, friendly neighbors, and a strong sense of community. The winding streets are lined with charming homes, each exuding its unique character while maintaining a cohesive aesthetic. One of the standout features of this subdivision is the availability of homes with private pools, allowing residents to enjoy the Florida sunshine and warm weather year-round. Imagine spending lazy afternoons lounging by your pool, hosting barbecues, or enjoying evening swims under the stars—Timberwoods Estates makes this dream a reality.

Beyond the comforts of home, residents of Timberwoods Estates have access to a variety of local amenities. The nearby Wildwood city center offers shopping, dining, and recreational options, ensuring that everything you need is just a short drive away. Nature enthusiasts will also appreciate the proximity to beautiful parks and nature trails, perfect for hiking, biking, or simply enjoying the great outdoors.

Whether you’re looking for a family home or a peaceful retreat, Timberwoods Estates in Wildwood, FL, is a community that promises a fulfilling lifestyle. Explore the possibilities today and discover your dream home with a pool in this idyllic subdivision!

Newest Timberwoods Estates Homes with Pool

$214,000
2 Beds ⋅ 2 Baths ⋅ G5116367 MLS
Virtually Staged. Gorgeous 2-Bedroom, 2-Bath Home with Exceptional Upgrades & Canal Views Welcome home to this gorgeous, meticulously maintained 2-bedroom, 2-bath residence offering nearly 1,600 square feet of beautifully appointed living space.. This home is truly in absolute, move-in-ready condition and showcases quality craftsmanship and upgrades throughout. The spacious interior features soaring high ceilings, brand-new laminate flooring, and a stunning kitchen complete with gorgeous corian countertops and stainless-steel appliances. The entire home is sheetrocked, with 3/4-inch crown molding throughout, raised two-panel interior doors, and elegant 3-inch trim that adds a beautiful finishing touch. Additional quality features include double-pane, impact-resistant windows, marble window sills, and deluxe window treatments. The home also boasts plywood subflooring throughout, providing an exceptional foundation beneath the beautiful new flooring. Enjoy Florida living at its finest from both the front and rear lanais, where you can relax and take in the gorgeous, peaceful views of the canal and surrounding wooded areas. The outdoor spaces are perfect for morning coffee, entertaining, or simply enjoying the tranquil scenery. The property also includes a large exterior storage shed with a washer and dryer, providing abundant storage and convenience. An RO and golf certificate are included, adding even more value to this exceptional home. From the immaculate interior to the serene outdoor setting and extensive list of upgrades, this home offers the perfect combination of comfort, elegance, quality, and Florida lifestyle living. This is a must-see property that truly stands apart! The community is absolutely gorgeous with countless amenities, which include: large swimming pool with hot tub, 18 hole championship golf course, driving range and putting greens, shuffleboard, tennis, pickle ball, fitness center, library, billiards room, softball field. What more can you ask for? This is a beautiful home in a beautiful community. You won't be disappointed!!!

601 Robin Lane, Wildwood
$124,900
2 Beds ⋅ 2 Baths ⋅ G5115784 MLS
Start enjoying the Florida lifestyle in this inviting 2-bedroom, 2-bath home designed for comfortable, low-maintenance living. The open floor plan creates a bright and welcoming space that's perfect for entertaining friends or simply relaxing at home. One of the home's standout features is the spacious screened front lanai—the ideal spot to enjoy your morning coffee, visit with neighbors, or unwind while taking in Florida's beautiful weather year-round. The kitchen is thoughtfully designed to maximize efficiency, offering everything you need within easy reach while remaining open to the living and dining areas, so you're always part of the conversation when entertaining. Both bedrooms are comfortably sized, providing plenty of room for overnight guests, hobbies, or a home office. Two full bathrooms add convenience and privacy for you and your visitors. Outside, you'll find a large carport with ample parking and a generously sized storage shed with direct access to the laundry room. The extra storage space is perfect for tools, seasonal decorations, golf gear, bicycles, or all the extras that make Florida living so enjoyable. Whether you're searching for a full-time residence or a seasonal getaway, this home offers the comfort, convenience, and easygoing lifestyle you've been looking for. Just move in, relax, and start enjoying everything your Florida retirement community has to give. The community is absolutely gorgeous with countless amenities, which include: large swimming pool with hot tub, 18 hole championship golf course, driving range and putting greens, shuffleboard, tennis, pickle ball, fitness center, library, billiards room, softball field, and a 5 star restaurant and lounge. What more can you ask for? This is a beautiful home in a beautiful community. You won't be disappointed!!!

413 S Timber Trail, Wildwood
$89,900
2 Beds ⋅ 2 Baths ⋅ G5114722 MLS
Nestled in the beautiful and activity-rich Continental Country Club, this AWESOME 2-bedroom, 2-bath home offers an open, spacious floor plan and an unbeatable location near the back gate for quick access to Hwy 44, 175, the Turnpike, The Villages, shopping, dining, and more. Inside, you'll find exceptional storage throughout with abundant cabinets, countertops, and closets-including an impressive four closets in the primary bedroom-along with roomy, well-laid-out bathrooms ready for your personal touch. The home features convenient inside laundry, a welcoming front sidewalk, a bight Florida room, covered carport, and a large storage shed perfect for tools, hobbies, or golf gear. This property is priced right and presents a fantastic opportunity to bring your updating ideas and make it truly yours. A Resident owner Certificate conveys with the home, providing lower HOA fees and full access to Continental's outstanding amenities including a resort-style pool, fitness center, clubhouse, fishing, crafts, woodworking, softball, golf, and countless activities designed for an active Florida lifestyle.

103 N Timber Trail, Wildwood
$128,500
2 Beds ⋅ 2 Baths ⋅ G5113301 MLS
- This fabulous 2-bedroom, 2-bath home is truly ready for you, beautifully updated and tastefully remodeled to give you the most comfort, style, and easy Florida living. Inside, you’ll find abundant storage, generous cabinetry, Walkin closets, and a flowing floor plan that makes the home feel open and inviting from the moment you step in. The charming front screen room is perfect for morning coffee or evening relaxation, and the home sits proudly on a huge corner lot near the back gate—giving you quick, convenient access to The Village of Fenney, Sawgrass, Middleton, Chitty Chatty, Brownwood Square, the new Super Walmart, and so many other local attractions. This home is nestled in a very active gated golf community offering endless activities, beautiful nature walks, fishing, swimming, and plenty of fun at the popular Oaks Restaurant and Lounge. Continental Country Club is truly wonderful place to enjoy time with family and friends and to embrace your retirement in beautiful, sunny Florida—come experience the lifestyle and make this home yours!! (more pictures to come)

101 Cypress Road, Wildwood
$159,000
2 Beds ⋅ 2 Baths ⋅ G5113244 MLS
PRICE DROP! BEAUTIFULLY RENOVATED HOME ON LAND NEAR THE VILLAGES! Welcome to this fully updated 2-bedroom, 2-bath home offering modern comfort, stylish finishes, and an unbeatable location just minutes from The Villages. Completely refreshed throughout, this move-in-ready property features a bright and inviting floor plan with all-new interior updates, fresh finishes, and brand-new appliances included. The spacious kitchen provides plenty of cabinet space and flows seamlessly into the dining area, creating the perfect space for everyday living and entertaining. Both bedrooms are generously sized, while the two full bathrooms have been thoughtfully updated for a clean, modern feel. Ample storage can be found throughout the home. Outside, enjoy the convenience of a deep covered carport, utility shed, and a peaceful setting on a desirable street within a welcoming golf community. Located just moments from shopping, restaurants, medical facilities, entertainment, and all the amenities The Villages has to give, you'll enjoy both convenience and a relaxed Florida lifestyle. With easy access to major highways and the Florida Turnpike, commuting is simple and efficient. No to mention, all the Villages activities are accessible and only a short golf car ride away! For outdoor enthusiasts, Serenity Pond is just a short stroll away, offering a tranquil spot for catch-and-release fishing and enjoying nature. Don't miss your chance to own this beautifully renovated home in a prime location. Schedule your private showing today!

116 Cypress Road, Wildwood
$119,900
2 Beds ⋅ 2 Baths ⋅ G5110061 MLS
ANOTHER PRICE IMPROVEMENT!!! Welcome to this charming home offering nearly 1,300 square feet of comfortable living space, thoughtfully designed with an open floor plan perfect for both everyday living and entertaining. The spacious layout features a bright and airy living room and dining room combination, seamlessly flowing into a large, open kitchen with plenty of room for cooking, gathering, and storage. In addition to the main living areas, you’ll find a separate family room—ideal for relaxing, a home office, or a media space. The home sits on an oversized lot, providing exceptional privacy and plenty of outdoor space to enjoy. The entire outside of the home was recently painted. Recent updates add peace of mind and modern appeal, including a brand-new air conditioning system installed in February 2026 and a new water heater in March 2026. All the flooring was installed in 2024. The home also features new front windows, a new sliding glass door, newer appliances throughout. An oversized carport offers ample covered parking and additional storage space. With its combination of updates, space, and privacy, this home is a fantastic opportunity you won’t want to miss.The community is absolutely gorgeous with countless amenities, which include: large swimming pool with hot tub, 18 hole championship golf course, driving range and putting greens, shuffleboard, tennis, pickle ball, fitness center, library, billiards room, softball field, and a 5 star restaurant and lounge. What more can you ask for? This is a beautiful home in a beautiful community. You won't be disappointed!!!

108 N Timber Trail, Wildwood
$84,900
2 Beds ⋅ 2 Baths ⋅ O6392964 MLS
By far the best value in Continental Country Club, located minutes from the Villages! This clean, functional, move-in ready home offers a fantastic opportunity to enjoy everything the retired lifestyle is known for—golf, recreation, entertainment, and an active 55+ community. While the home could benefit from some cosmetic updates, the price simply can’t be beat, making it the perfect opportunity to add your own personal touches and build instant value. The seller is also offering a $1,000 closing cost credit for buyers who close within 30 days of contract. Inside, you’ll find a spacious and inviting layout with a bright living room that flows into an air-conditioned Florida Room, creating additional space for relaxing or entertaining year-round. The main living areas feature luxury vinyl plank flooring, offering a clean, modern, and low-maintenance feel. The kitchen includes a convenient breakfast bar, while the dining area features a built-in hutch for extra storage and display. The primary suite offers a large walk-in closet and an en-suite bath with a walk-in shower. An attached workshop and carport add extra convenience and functionality. Living in Continental Country Club means enjoying a true resort-style lifestyle with access to an impressive list of amenities including an 18-hole championship golf course, clubhouse with restaurant and lounge, pool, tennis and pickleball courts, fitness center, library, billiards room, arts and crafts studios, a woodcrafter’s shop, and shuffleboard courts. Residents also enjoy access to Lake Okahumpka for boating, fishing from the dock, and on-site boat storage. The community is conveniently located just five minutes from The Villages with easy access to shopping, dining, entertainment, and medical services, and near I-75 and the Florida Turnpike, placing Orlando about an hour away and Tampa or Daytona Beach roughly 90 minutes away. Buyers must be 55+ with a minimum 700 credit score and complete a community application and credit check. This is an incredible opportunity to enjoy the Florida lifestyle in a well-maintained home with endless potential.

415 S Timber Trail, Wildwood
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