Waterside Village Real Estate

Waterside Village Real Estate

Welcome to Waterside Village, a hidden gem nestled in the heart of Sarasota County, Florida. This picturesque subdivision offers a harmonious blend of serene living and vibrant community life, making it the perfect place for families, retirees, and anyone looking to enjoy the best of Florida’s coastal lifestyle.

Waterside Village is renowned for its stunning natural beauty, featuring lush landscapes, tranquil waterways, and an array of recreational opportunities. Residents can take advantage of scenic walking trails, perfect for morning strolls or evening jogs, while the nearby lakes provide a serene backdrop for kayaking, fishing, or simply unwinding in nature. The community is thoughtfully designed, with well-maintained homes that reflect a variety of architectural styles, ensuring there’s something for everyone.

One of the standout features of Waterside Village is its strong sense of community. Neighbors become friends here, with regular events and gatherings that foster connections among residents. From seasonal celebrations to casual get-togethers at the community clubhouse, there’s always something happening to bring people together.

Conveniently located, Waterside Village offers easy access to some of Sarasota’s most popular attractions. Enjoy the stunning beaches of Siesta Key, indulge in shopping and dining at local boutiques and restaurants, or explore the vibrant arts scene that Sarasota is known for. With top-rated schools and essential amenities just a stone’s throw away, you’ll find everything you need right at your fingertips.

In Waterside Village, you’re not just buying a home; you’re investing in a lifestyle filled with warmth, community, and endless possibilities. Come discover your new beginning in this enchanting Florida paradise!

Newest Listings in Waterside Village

$305,000
3 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to Waterside Village, a community of just 48 homes that offers a peaceful setting while keeping you close to everything Winter Haven has. This move-in ready 3-bedroom, 2-bath home offers an open floor plan, spacious kitchen with a large walk-in pantry, and a backyard designed for entertaining. Enjoy the screened-in lanai, pool deck, and above-ground pool with a recently replaced liner, all within a fully fenced yard complete with a storage shed. Conveniently located near shopping, restaurants, grocery stores, and LEGOLAND, you'll love having everything you need just minutes away.

144 Waterside Circle, Winter Haven
$359,900
2 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 34240 Zip Code
Welcome to Avanti at Waterside, where modern, maintenance-free living is paired with one of Sarasota’s most desirable lifestyle destinations. Located just minutes from Waterside Place, you’ll enjoy easy access to waterfront dining, boutique shopping, community events, farmers markets, live entertainment, and scenic walking paths in the heart of Lakewood Ranch’s Waterside district. This beautifully maintained home with a versatile flex room offers an open-concept floor plan designed for both everyday comfort and easy entertaining. The flex room provides the perfect space for a home office, den, hobby room, or guest retreat. Hurricane-impact windows provide added peace of mind, storm protection, energy efficiency, and noise reduction. Enjoy Florida living year-round from the screened rear lanai and private fenced outdoor space, a rare feature in the community. Additional highlights include a Taexx® in-wall pest defense system, an epoxy-coated garage floor, and maintenance-free living with lawn care included. Whether you’re looking for a full-time residence or a seasonal retreat, this move-in ready home offers the perfect combination of comfort, convenience, and low-maintenance living in sought-after Avanti at Waterside.

6499 Silverstar Drive, Sarasota
$855,000
2 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 34240 Zip Code
Virtually Staged. Welcome to 8100 Slipway Dr, Sarasota, FL 34240, where luxury, comfort, and peace of mind come together in one exceptional Florida home. Nestled in Waterside – Lakehouse Cove community, this beautifully upgraded residence offers the perfect blend of modern elegance and everyday functionality. Step inside and experience an open, light-filled floor plan enhanced by custom lighting that creates a warm, sophisticated ambiance throughout. The gourmet kitchen and living spaces flow seamlessly, making this home ideal for entertaining or relaxed Florida living. Retreat to your private outdoor oasis featuring a heated pool and spa, perfect for year-round enjoyment. Whether hosting guests or enjoying a quiet evening under the stars, this space delivers the ultimate Florida lifestyle. A versatile bonus office or den provides the perfect space for working from home, a quiet retreat, or even a flex room to suit your lifestyle needs. This home is thoughtfully equipped with hurricane impact doors and windows, providing security and energy efficiency. A whole house Generac generator ensures uninterrupted comfort, giving you confidence and convenience during any season. The spacious 3-car garage offers ample room for vehicles, storage, and even a golf cart, adding both convenience and flexibility to your daily living. The custom-designed primary closet adds a touch of luxury and organization to your daily routine, while every detail of this home reflects quality craftsmanship and attention to detail. Located in Sarasota, FL, near Lakewood Ranch, top-rated schools, shopping, dining, and Gulf Coast beaches, this property is ideal for buyers seeking a luxury home in Sarasota, a pool home in Sarasota FL, or a move-in-ready Florida dream home. Do not miss this opportunity to own a stunning Sarasota pool home with premium upgrades in one of the area’s most sought-after locations.

8100 Slipway Drive, Sarasota
$1,950,000
4 Beds ⋅ 4 Baths ⋅ Waterside Village SubDv. ⋅ 34240 Zip Code
In sought-after Wild Blue at Lakewood Ranch, this newly completed, professionally designed residence offers an exceptional blend of modern elegance, privacy and effortless Florida living. Built in 2025, this four-bedroom, 3.5-bath plus office home spans over 2,800 square feet and is ideally on a private homesite with serene wooded views, creating a tranquil and refined retreat. From the moment you arrive, the home’s clean architectural lines and sophisticated finishes set the tone for what lies within. Inside, an open-concept floor plan is filled with natural light, highlighting soaring ceilings, designer details and a seamless flow between living spaces, ideal for everyday comfort and elevated entertaining. At the heart of the home, the chef’s kitchen is thoughtfully designed with sleek quartz countertops, custom wood cabinetry, premium KitchenAid appliances, and an expansive island that anchors the space while offering function and style. The adjoining great room opens effortlessly through expansive sliding glass doors to the outdoor living area, creating an indoor-outdoor lifestyle experience. The primary suite is a private sanctuary, offering peaceful views, dual walk-in closets, and a spa-inspired bath featuring a freestanding soaking tub, glass-enclosed shower, and refined finishes. Each additional bedroom is generously sized with beautiful baths, providing comfort and privacy for family and guests alike. A spacious private office, accessed through elegant double doors, offers an environment for working from home or creating a quiet retreat. Generously sized and thoughtfully positioned, this space blends functionality with refined design, complementing the home’s sophisticated aesthetic. Go outside to your custom-designed outdoor oasis, where luxury living comes to life. The expansive covered lanai is anchored by a stunning outdoor fireplace, creating a warm and inviting focal point for evening gatherings. A resort-style pool and spa are enhanced by elegant water features, including tranquil fountains that add visual beauty and a soothing ambiance. The outdoor kitchen and multiple seating areas complete this private retreat, all set against lush landscaping and a serene natural backdrop, ideal for entertaining or unwinding in complete privacy. Residents of Wild Blue enjoy an amenity-rich lifestyle with access to tennis and pickleball courts, a fitness center, scenic recreational and biking trails, and opportunities for outdoor recreation including fishing and water access, all within one of Lakewood Ranch’s exciting and upscale new communities. This move-in-ready home offers the rare opportunity to enjoy new construction without the wait, where thoughtful design, high-end finishes and an exceptional setting come together to create an elevated living experience.

8352 Sea Glass Court, Sarasota
$249,900
2 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 34292 Zip Code
LOOK...PRICE IMPROVEMENT!! Welcome to Waterside Village! A beautiful community is just minutes away from downtown Venice with a variety of restaurants and shopping. This tastefully updated ground-floor unit offers serene nature views right from your backyard. Relax in your enclosed lanai while enjoying peaceful water views and watching local birds in their natural habitat. Inside, the home features new luxury vinyl plank flooring throughout (2025), new granite countertops, sink, and disposal (2025), and a freshly painted interior, creating a bright and inviting space. Major updates include a new HVAC unit and water heater (2025), providing added comfort and peace of mind. The kitchen includes a charming sunny breakfast nook—perfect for starting your day—while the open-concept living and dining area creates an ideal space for entertaining or relaxing with friends and family. You’ll also appreciate the extra storage space, including a convenient outdoor shed that’s perfect for beach chairs, bikes, and outdoor gear. You will be minutes away from local beaches. Waterside Village amenities include a clubhouse, swimming pool, tennis courts, and pickleball courts, offering plenty of opportunities to stay active and social. Don’t miss your chance to own this move-in-ready gem in a beautiful community. Schedule your showing today before it’s gone!

204 Silver Lake Drive Unit 102, Venice
$229,000
2 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 34285 Zip Code
Welcome to 841 Waterside Dr. #206, a spacious and well-designed 2-bedroom, 2-bath condo with a den/study offering approximately 1,300 square feet of comfortable living space and tranquil Curry Creek views. END-UNIT! This thoughtfully designed split floor plan places the guest bedroom and den at the front of the residence, while the private primary suite is tucked away at the rear, featuring vaulted ceilings, a generous walk-in closet, and a large ensuite bath. The open living and dining area is bright and inviting with vaulted ceilings, and the condo is being offered unfurnished, providing the perfect opportunity to make it your own. Enjoy relaxing on the screened lanai, complete with a convenient laundry closet, plus additional storage located by the carport. As a resident of Waterside Village, you’ll enjoy access to the Waterside Village pool, along with full use of all Bird Bay Village amenities, including a junior Olympic pool, tennis and pickleball courts, fitness center, and over 40 active clubs. The maintenance fee covers exterior maintenance and insurance, grounds maintenance, recreational facilities, pool maintenance, management, pest control, sewer, water, and trash, allowing for truly low-maintenance living. Ideally located less than five minutes to Historic Downtown Venice and area beaches, with the Legacy Trail right outside the community entrance—this is the carefree Florida lifestyle you’ve been waiting for, where every day feels like a getaway.

841 Waterside Drive Unit 206, Venice
$3,849,900
4 Beds ⋅ 5 Baths ⋅ Waterside Village SubDv. ⋅ 34240 Zip Code
Experience elevated waterfront living in The Wild Blue Showcase Home by John Cannon Homes, a stunning, custom-designed residence located in the exclusive Wild Blue at Waterside in Lakewood Ranch. Situated on a spacious homesite, this 3,782 sq. ft. home offers 4 bedrooms, 5 bathrooms, a private casita, and a versatile bonus room. A thoughtfully crafted floor plan blends sophisticated design with effortless livability—from the chef-inspired kitchen with an oversized island and walk-in pantry to the expansive great room and luxurious owner’s suite with a spa-like bath. Outdoor living takes center stage with a generously sized lanai, ideal for relaxing, entertaining, or enjoying Florida’s year-round sunshine. In addition, Wild Blue offers a vibrant, amenity-rich lifestyle with 6 tennis courts, 8 pickleball courts, basketball court, event lawn, dog parks, shaded pavilions, lakeside trails, a kayak launch, children’s playground, and outdoor fitness areas. Just beyond, residents also enjoy convenient access to Midway Sports Complex, featuring 13 acres of open green space, athletic fields, and community gathering areas. Whether you're exploring boardwalks through natural wetlands or enjoying a lakeside picnic, The Wild Blue Showcase Home by John Cannon Homes is your gateway to luxury living with an active, connected lifestyle in one of Southwest Florida’s premier master-planned communities. Wild Blue offers luxury living in the heart of Lakewood Ranch with exceptional amenities for all ages. The new clubhouse (under construction) will feature concierge service, private theater, fitness center, golf simulator, billiards room, and two resort-style pools, plus a future full-service restaurant and patio bar. Ideally located near UTC, Waterside Place, and top dining and shopping, Wild Blue delivers an elevated lifestyle in a premier LWR community.

1018 Blue Shell Loop, Sarasota
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