Timberwoods Estates Homes with Deed Restrictions Community Features

Timberwoods Estates Homes with Deed Restrictions Community Features

Welcome to Timberwoods Estates, a serene subdivision nestled in the heart of Wildwood, Florida, within the charming Sumter County. This picturesque community is designed for those who appreciate the beauty of nature while enjoying the comforts of modern living. Timberwoods Estates offers a unique blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat.

In Timberwoods Estates, you’ll find a collection of beautifully crafted homes, each reflecting the community’s commitment to quality and aesthetics. The homes are thoughtfully designed with deed restrictions in place, ensuring that the neighborhood maintains its charm and appeal. This means you can enjoy a cohesive and well-kept environment where pride of ownership is evident in every residence.

The community features an array of amenities that enhance the lifestyle of its residents. You can take leisurely strolls along well-maintained sidewalks, enjoy picnics in the lush green spaces, or engage with friendly neighbors at community gatherings. Timberwoods Estates is also conveniently located near local shopping, dining, and recreational opportunities, making it easy to enjoy everything Wildwood has to offer.

With its ideal location, beautiful homes, and a welcoming atmosphere, Timberwoods Estates is more than just a place to live; it’s a community where memories are made, and friendships flourish. Discover the charm of Timberwoods Estates—where your dream home awaits amidst the natural beauty of Florida. Come and experience the lifestyle you’ve always dreamed of!

Newest Timberwoods Estates Homes with Deed Restrictions Community Features

3 Beds ⋅ 2 Baths ⋅ OM731187 MLS

Welcome to 705 Oak Blvd, a spacious TURNKEY 3-bedroom, 2-bath home offering 1,680 sq. ft. of comfortable living in the sought-after Continental Country Club, a gated 55+ golf community just minutes from The Villages. Situated on a beautifully landscaped .22-acre lot, this inviting home features vaulted ceilings, a bright and spacious living area, inside laundry, and a well-equipped kitchen with appliances included. Enjoy Florida living from the enclosed porch, while the attached 2-car garage provides exceptional parking and storage—a feature not commonly found among many homes in the community. Continental Country Club offers an impressive active-adult lifestyle with a clubhouse, community pool, fitness center, dog park, tennis courts, restaurant, golf-cart-friendly streets, and an 18-hole championship golf course. The monthly association fee also includes cable TV, internet, trash, and grounds maintenance. Whether you're searching for a full-time residence or a seasonal Florida retreat, this move-in-ready home delivers the space, convenience, amenities, and lifestyle you've been looking for.

705 Oak Boulevard, Wildwood

2 Beds ⋅ 4 Baths ⋅ G5116950 MLS

Step into this exquisite waterfront sanctuary in Continental Country Club, where refined living meets serene natural beauty in a residence designed for comfort, sophistication, and effortless Florida living. This luxury-styled 2-bedroom, 2-bath home unfolds with an elegant, well-crafted floor plan that captures peaceful water views from the moment you enter. The family room becomes a private retreat overlooking the deck and pond—your front-row seat to the fountain, shimmering water, and daily wildlife. It’s the perfect setting for savoring your morning coffee or unwinding with an evening beverage while entertaining guests in style. The open kitchen offers lanai seating, barstools, and generous counter space, flowing seamlessly into a grand living room ideal for upscale gatherings. The primary suite is a calming haven with abundant closets, a beautifully appointed bath, and fresh paint throughout that enhances the home’s polished, high-end feel. Guests will enjoy their own luxurious retreat with an oversized bedroom and bath, plus inside laundry discreetly tucked behind custom barn doors for added charm and convenience. Downstairs, discover a full bonus living level—complete with an additional bedroom—perfect for hosting guests or transforming into a craft studio, workshop, or private lounge. The garage with full door access leads to a well-designed driveway framed by manicured landscaping and custom wood shutters that elevate the home’s curb appeal. Out back, a substantial dock invites you to embrace waterfront living at its finest—relaxing, fishing, or simply enjoying the peaceful setting. This exceptional property includes the Resident Owner Certificate, is priced for immediate interest, and delivers a rare blend of luxury, comfort and Florida Lifestyle. You'll want to call your agent quickly - THIS IS THE ONE!!

802 Oak Boulevard, Wildwood

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

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

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

2 Beds ⋅ 2 Baths ⋅ G5113244 MLS

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, with a BRAND NEW HVAC system and NEW ROOF, 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

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

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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