Wellington, FL Real Estate | Wellington, FL Waterfront Homes for Sale

This beautifully upgraded home offers a perfect blend of style, functionality, and modern convenience. When entering the home, you cannot miss the dramatic high ceiling and the elegant plank tile flooring continued throughout the main living areas. Step into the gathering room and delight in the welcoming lake view straight ahead! The sliding glass doors open fully and pocket to enjoy the indoor/outdoor living this home provides. The home's layout is enhanced by custom touches, including wood beams and built-in shelving in the office/den, crown molding, as well as custom closets throughout for exceptional storage. The primary bathroom has been completely remodeled with thoughtful design and high-end finishes while the guest bath kept its footprint but was refreshed with new shower door, shower floor, fixtures and lighting. Enjoy Florida living outdoors with an extended patio with built-in grill, quartz countertop, remote phantom screens, and a fully fenced backyard. Imagine beginning and ending each day enjoying the water view and temperate weather. The extensive landscaping and outdoor lighting provide great curb appeal and evening ambiance. Fully replaced windows & doors with hurricane impact in August 2026 for peace of mind, protection and energy efficiency. Hobbyists will be excited to see the garage, which includes a workbench and lots of cabinets for tools or other supplies. Additionally, the garage has an extended depth, and the driveway has been widened to accommodate additional parking when necessary. The Castellina community provides a gated and manned entry, clubhouse with fitness center, heated pool, tennis courts and pickleball. The quarterly fee also includes lawn maintenance and sprinkler care. This home has been meticulously maintained and thoughtfully enhanced- truly move in ready and designed for comfortable Florida living. The best homes are the ones that stay relevant no matter what season of life you are in. Here, there's room to settle in, stretch out, and make new memories along the way. Whatever the future brings, this home offers a strong and welcoming foundation for every chapter still ahead.

3704 Siena Circle, Wellington

$420,000

3 Beds ⋅ 2 Baths ⋅ B26069897 MLS

Welcome to Mayfair a highly sought after 55+ gated community situated in the heart of Wellington. This spacious 2nd floor coach home features 3 bedrooms, 2 full baths, and 1 car garage. Step inside to a bright, open layout with a screened balcony overlooking a tranquil pond. Amenities include a clubhouse, fitness center, and heated pool. Mayfair requires at least one resident to be 55+, with no occupant under 19. Two pets are permitted per household. New roofs and fresh exterior paint. Centrally located within walking distance of shopping, restaurants, Wellington Amphitheater, Community Center, and Village Hall. Minutes from WEF Showgrounds. Unit is Available fully furnished with all furnishings; bring your toothbrush! Room measurements have been estimated and should be verified.

2144 Wingate Bend, Wellington

$388,750

3 Beds ⋅ 2 Baths ⋅ B26023542 MLS

Located in the highly sought-after gated community of Mayfair on Lake Wellington, this waterfront first-floor coach home offers 3 bedrooms, 2 baths, and a 1-car garage with a spacious and desirable 3-way split bedroom floor plan—perfect for privacy when family and guests are visiting. The kitchen features new kitchen cabinets. The primary suite is generously sized and features a large walk-in closet, additional wall closet, linen closet, dual sink vanity, oversized Roman soaking tub, and a separate walk-in shower for added convenience. The home also offers an eat-in kitchen with a pass-through window to the dining area, an interior laundry room, and exterior storage space. The unit comes with full accordion hurricane shutters. Enjoy peaceful water views from this well-positioned unit while adding your own personal touches and updates to make it shine again. Mayfair on Lake Wellington is a gated 55+ community offering wonderful amenities including a clubhouse with kitchen, fitness center, heated swimming pool, and social activities. Conveniently located in the heart of Wellington, residents enjoy being within walking distance to the Wellington Senior Center, Wellington Amphitheater, shopping, restaurants, and community events. Fantastic opportunity to create your perfect Florida retreat! NEW AC and interior paint August 2026, roof was replaced in 2024 as well as exterior painting.

2149 Wingate Bend, Wellington

$334,990

2 Beds ⋅ R11166269 MLS

Waterfront living in the heart of Wellington. This beautifully maintained townhome features a brand new 2025 roof, two spacious primary suites, tranquil canal views and spectacular sunset evenings. Enjoy the private patio area or upstairs balcony while watching the sunset. This delightful townhome offers an unbeatable location close to world class equestrian events, shopping, dining and top rated schools. Minutes to Wellington International. Experience the best of Wellington in this warm and inviting home perfect for seasonal visitors, equestrian enthusiasts or year round living.

1608 Shaker Circle Circle, Wellington

$15,975,000

3 Beds ⋅ 3 Baths ⋅ B26044879 MLS

Offered for the first time in over 16 years, this premier estate in the heart of Grand Prix Village is one of Wellington's most admired equestrian properties. Designed by a true horseman to the highest standards, the farm seamlessly blends elegance, functionality, and privacy in a setting that is both stately and inviting. At the center of the property sits a beautifully designed 22-stall barn with two wide, airy aisles, complemented by thoughtfully appointed owner's and staff quarters. Every detail reflects quality craftsmanship and a deep understanding of the sport. The equestrian amenities are exceptional, highlighted by a 170' x 240' arena, ideal for top-level training and competition preparation. Additional features include a horse walker and nine well-maintained paddocks, round pen and sand track around the arena offering both convenience and optimal care for the horses. Perfectly positioned only a short hack to both major Wellington International show grounds, This special property allows riders to move effortlessly between venues while enjoying the tranquility of a private farm. Always admired and rarely available, this is a truly rare opportunity to own a standout farm in one of the most sought-after equestrian communities in the world.

3454 Grand Prix Farms Drive, Wellington

$4,299,000

4 Beds ⋅ 3 Baths ⋅ B26028993 MLS

Set behind dual gated entrances and perfectly positioned in the heart of Wellington's premier equestrian community, this exceptional turnkey 5-acre farm is the ultimate blend of luxury lifestyle and elite equestrian functionality — offered fully equipped and ready just in time for season. Designed for effortless indoor-outdoor living, the beautifully appointed 4-bedroom, 3-bath residence plus den features a desirable split-bedroom floor plan, chef's kitchen with Thermidor appliances, and expansive covered and screened entertaining spaces centered around a custom pizza oven for unforgettable evenings under the stars. The 2019-built 12-stall barn was thoughtfully designed with both horse and rider in mind, offering a stylish studio lounge, tack room, feed room, four covered wash stalls with fans, and extensive additional storage complete with electric, water, RV hookups, and storage container. At the center of the farm, the professionally engineered 175' x 110' arena boasts oversized irrigation jets and significant recent upgrades, including extensive drainage improvements, an $18,000 custom drain system, and precision laser grading for exceptional footing and performance. The ring can easily be expanded to accommodate a regulation dressage arena or larger. Six lush irrigated paddocks, hacking access to the breathtaking 365-acre preserve, direct connection to Wellington's bridle paths, and close proximity to WEF create the ultimate equestrian lifestyle package. And the best part, the sunsets are to die for! Nothing but preserve land for miles and miles! DISCLAIMER: All information provided to you regarding this Property has been obtained from third parties such as the Multiple Listing Service, public records and other sources. The Sellers, Realtor and Broker make no representation as to the accuracy of this information. Buyers should perform their own due diligence regarding this Property before executing a Contract for Sale and Purchase for this Property.

2587 Skipiks Way, Wellington

$1,495,000

6 Beds ⋅ B26047907 MLS

Welcome to this exceptional waterfront residence in the prestigious Olympia community of Wellington, Florida. This two-story single-family home showcases 5,716 square feet of refined living space, featuring six generously appointed bedrooms and seven bathrooms to accommodate an active lifestyle. The flooring has just been updated throughout, and a custom kitchen with custom pantry anchors the main level. The thoughtfully designed floor plan spans two levels, offering flexibility for various living arrangements and entertaining. Outside, a heated pool sits just off the covered patio. With a two-car garage for convenient parking and vehicle storage, this waterfront property provides the perfect blend of sophisticated living and direct water access.

2816 Pillsbury Way, Wellington

$9,995,000

12 Beds ⋅ B26002820 MLS

Enjoy the best of both worlds on this exceptional 10+-acre equestrian property, ideally located just minutes from Global and WEF while offering the tranquility of Wellington's farm life. This property combines top-tier equestrian amenities with luxurious living, providing everything needed for you and your horses. The 26-stall center-aisle barn is the standout feature of this property, equipped with 6 wash stalls, 2 tack rooms, a feed room, and a lounge. A separate building offers even more versatility, with a second lounge, 2 bathrooms, an oversized laundry room, and 2 spacious 2-bedroom, 1-bathroom apartments. Additionally, a huge storage area provides ample space for hay, shavings, tractors, golf carts, jumps, and farm equipment. Other equestrian facilities include 2 all weather arenas a large grass riding field, a 6-horse covered hotwalker, and 15 paddocks, all designed to support training, turn-out, and leisure riding. The property features two beautiful homes. The original 4-bedroom, 3-bathroom single-story home has been recently remodeled throughout, offering wood and tile floors, a beautiful kitchen with all new appliances, and a screened-in patio with a heated pool and jacuzzi for relaxing. The second residence is a newly constructed 2-story, 4-bedroom, 3-bathroom home with modern finishes, ideal for a property manager or staff. Privacy and convenience are essential, with 1 private entrance for the original home and 2 separate entrances for the barn, allowing easy access. The estate is surrounded by lush landscaping, including a clusia hedge and tropical palms, offering both beauty and privacy. Recent updates include brand-new roofs on all structures, a new water filtration system and newer AC units throughout. This property offers the ideal blend of luxury, functionality, and location, making it the perfect place to live, train, and enjoy the equestrian lifestyle. List of improvements with current owner -Replaced ALL the roofs on all structures (barn, house, storage building) -Added an oversized arena approximately 150' x 250' -Replaced the footing in both arenas (ESI) -Added a 6 horse hotwalker -Added an additional 8 stalls and refaced all stalls -Added one additional tackroom and 2 additional wash stalls -Added paddocks (total of 15) -Replaced the AC units and Hot water heaters -Added an additional septic system -Added a new well -Replaced the water system servicing the house and barn -Completely updated/remodeled the original house -Built a brand new two story 4 bedroom 3 bath house -Updated the 2 staff apartments both 2 bedroom 1 bath -Added a laundry room for the barn -Added a second lounge with a full bathroom -Added a 3rd automatic gate off 57th Place -Replaced the pool heater, screening around the pool and leveled the pavers -Added a Clusia hedge along the front and side of the property for additional privacy -Added a coved viewing deck along the larger arena

5656 South Shore Boulevard, Wellington

$1,750,000

5 Beds ⋅ B26062027 MLS

Palm Beach Elegance in the Heart of Wellington FL! Step into timeless elegance in this extraordinary Olympia estate & gated home. A private gated courtyard welcomes you into a grand foyer with 22' ceilings, exquisite custom millwork, coffered ceilings, designer lighting, and an elegant coastal-inspired design filled with natural light throughout. A true entertainer's dream with a large open kitchen, center island, 2 pantries, double ovens, 3 sinks & custom cabinetry. This magnificent home has 5 spacious bedrooms with ensuites, 6 full bathrooms, 1 elegant powder room, a private den, and an expansive loft perfect for a media/game room, office, or play area. Enjoy an expansive premium lake lot with magnificent natural preserve views and space to build your own custom pool & outdoor area. Expansive walls of glass illuminate the gracious living areas while showcasing tranquil garden views, creating a seamless connection between indoor and outdoor living. The luxurious primary suite is a private sanctuary featuring intricate ceiling details, a spacious sitting area, and a spa-inspired bath with a dramatic soaking tub beneath a skylight, dual vanities, and 2 separate showers. Throughout the home, exceptional architectural details, and timeless finishes reflect an uncompromising commitment to quality and design. Offering an unparalleled blend of elegance, comfort, and enduring style, this remarkable residence captures the essence of a true Palm Beach-inspired estate in the heart of Wellington—a rare opportunity to own one of the area's most distinguished homes. Thoughtfully designed with upscale features for effortless living, including community-maintained lawn care and sprinkler system, whole-home stereo system hookup, motorized electric shades, and a front-door intercom system—all adding to the home's comfort, convenience, and sophisticated lifestyle.

2311 Stotesbury Way, Wellington

$1,350,000

3 Beds ⋅ 3 Baths ⋅ B26021675 MLS

Beautifully maintained 3-bedroom, 3-bath home in the highly sought-after Shady Oaks community of Palm Beach Polo & Country Club. This home features an open-concept layout that flows well, along with a private pool and peaceful views overlooking the Dunes preserve, offering both privacy and a serene setting. The kitchen was updated in 2022 and opens to the main living areas, creating a bright and comfortable feel throughout. Ideally located near Wellington's equestrian venues, dining, and shopping, residents also enjoy access to pickleball, tennis, walking trails, and a fitness center- perfect for both everyday living and entertaining. A great opportunity to own in one of Wellington's premier communities.

2920 Twin Oaks Way, Wellington

$1,700,000

3 Beds ⋅ 3 Baths ⋅ B26042048 MLS

Wake up in this elegantly renovated villa tucked within the most sought after community in Wellington, and take an inspirational morning walk through the private and protected 300+ acre nature preserve right outside your backyard. Bathed in natural light and framed by lush new landscaping, this residence exudes effortless sophistication. Enjoy the assurance of a new roof, water heater, pool, and beautifully refreshed interiors offering both comfort and style. Offered fully furnished for a seamless move-in, this turnkey retreat is perfect for relaxing poolside or entertaining after a day at the show grounds, courts, or golf course. Ideally located just minutes from PBI, Downtown West Palm Beach, and the island of Palm Beach—your seasonal retreat awaits you.

2951 Twin Oaks Way, Wellington

$1,350,000

5 Beds ⋅ R11139220 MLS

Resort-Style South Florida Living • 5BR • 4.5BA • Office • Den • Pool • Lakefront • Cul-de-Sac • Full Impact Windows Discover true South Florida luxury living in this beautifully upgraded 5-bedroom, 4.5-bath home located in Wellington's premier resort-style community, Olympia. Surrounded by stately royal palm trees and tropical landscaping, this home offers elegance, comfort, and secure peace of mind with full impact windows throughout. ✨ Property Highlights 5 Bedrooms/den/office 4.5 Bathrooms - Spacious and beautifully appointed Dedicated Office - Perfect for working from home Private Den/Sitting Room - Ideal for a lounge area, playroom, or reading retreat Grand Main-Level French Doors - Walkout access creating a seamless indoor-outdoor flow Furniture and draperies are exclu

2904 Payson Way, Wellington

Wellington, FL Waterfront Homes for Sale

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