Winterplace Homes for Sale

Winterplace Homes for Sale

Welcome to Winterplace, a charming subdivision nestled in the heart of Delray Beach, Palm Beach County, FL. This vibrant community offers a perfect blend of tranquility and convenience, making it an ideal place to call home.

Winterplace is known for its picturesque streets lined with beautiful homes that exude Southern charm. Residents here enjoy a close-knit community atmosphere and a range of amenities, including well-maintained parks, walking trails, and community events.

If you are looking for homes for sale in Winterplace, you are in luck! True to its reputation, Winterplace offers a diverse selection of properties to suit every lifestyle and budget. From cozy single-family homes to spacious estates, there is something for everyone in this sought-after neighborhood.

Living in Winterplace means having easy access to all that Delray Beach has to offer. From pristine beaches and top-rated restaurants to boutique shops and cultural attractions, the area provides endless opportunities for entertainment and relaxation.

Whether you are a first-time homebuyer, a growing family, or a retiree looking for a peaceful retreat, Winterplace has something for everyone. Come and discover the magic of this wonderful community and find your dream home in Winterplace, Delray Beach.

Newest Winterplace Homes for Sale

5 Beds ⋅ 4 Baths ⋅ B26054609 MLS ⋅ The Colony BLDG.

RARE COURTYARD HOME WITH PRIVATE POOL AND DETACHED GUEST HOUSE! This unique Delray Beach residence features a 4-bedroom, 2-bath main house with over 2,694 square feet of flexible living space, plus a 1-bedroom, 1-bath GUEST HOUSE. Enjoy a courtyard pool, private backyard with a beautiful mango tree, and space to create your own oasis. The gated community has a LOW $315 HOA FEE and offers a fitness center, heated pool, hot tub, card room, playground, and basketball court. A two-car garage and driveway provide ample parking. Some photos are virtually staged. Video available upon request. Information is deemed reliable but not guaranteed. Buyer to verify all measurements, features, permits, zoning, and material facts. Information provided is deemed reliable but not guaranteed and is subject to errors, omissions, or changes without notice. All measurements, features, and specifications are approximate. Buyer is solely responsible for independently verifying all information, including square footage, lot size, room dimensions, permits, zoning, and any other material facts prior to purchase.

4831 S Classical Boulevard, Delray Beach

3 Beds ⋅ 4 Baths ⋅ B26045302 MLS ⋅ The Colony BLDG.

Nestled within the gated community of The Colony at Delray Beach, just approximately 10 minutes from the famed Atlantic Avenue, this spacious and light-filled residence offers an exceptional blend of comfort, privacy, and everyday convenience. Soaring two-story ceilings and expansive windows fill the home with natural light, creating an inviting sense of openness throughout. Designed with both functionality and flexibility in mind, the residence offers approximately 3,000 square feet of living space, featuring a desirable first-floor primary suite, additional guest bedrooms, a loft, three-and-a-half baths, and a two-car garage. The generously sized kitchen overlooks the family room, creating a seamless setting for daily living and entertaining alike. Privately positioned with lush greenery beyond, the screened patio provides a tranquil outdoor retreat with no immediate rear neighbors. Residents of The Colony enjoy a low HOA and access to an impressive collection of amenities, including a gated entrance, resort-style pool, fitness center, basketball court, playground, and community events throughout the year.

4858 S Classical Boulevard, Delray Beach

4 Beds ⋅ 3 Baths ⋅ B26033971 MLS ⋅ Colony At Delray Bch BLDG.

BRAND NEW ROOF TO BE INSTALLED PRIOR TO CLOSING. Gated Colony at Delray Beach offers resort-style amenities — clubhouse, fitness center, lakeside pool with sundeck & cabanas, basketball court, and playground. This elegant 4BD/2.5BA + flex room Mediterranean home with 2-car garage delivers soaring vaulted ceilings, arched doorways, and large-format tile throughout. Chef's kitchen with granite countertops and center island opens to the family room. Formal dining room with dramatic iron chandelier. Private pool oasis with lush tropical landscaping. Minutes from Atlantic Ave, dining, boutiques, and pristine beaches. Furniture negotiable. Live the South Florida lifestyle you deserve!

4889 N Classical Boulevard, Delray Beach

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Jill Stone

As a leading force in the luxury real estate market, Jill Stone is dedicated to elevating the client experience through unparalleled service and unwavering integrity. With a proven track record as a top-producing Sales Agent & Team Coach, she understands that successful real estate transactions are built on trust, transparency, and strong relationships. Through her experience working in dual markets in her over decade long career, Jill holds an in-depth knowledge of the South Florida luxury market, expertly guiding clients through the nuances of high-end properties and matching lifestyles with locations. Her approach combines strategic marketing insights with a personalized touch, ensuring each client feels valued and informed throughout their journey. Jill’s relationship with Illustrated Properties includes the incredible partnership with Forbes Global Properties, Leading Real Estate Companies of the World, and Luxury Portfolio. Additionally, her affiliation with Nexus Sports and Entertainment—a premier relocation network for professional athletes—allows her to expertly cater to the unique needs of clients in the Sports and Entertainment sectors, providing them with tailored solutions, relocation packages, and insights to navigate the market with confidence. Driven by her commitment to ethical practices, Jill prioritizes the needs of clients above all else, fostering lasting connections that extend beyond the closing table. With her expertise, clients can confidently navigate the complex world of luxury real estate, knowing they have a dedicated advocate by their side.

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David J. Thompson

Born and raised in the scenic expanse of upstate New York, David Thompson’s journey from a young archaeologist to a leader in luxury real estate reads like a tapestry of ambition, innovation, and service. Armed with a Bachelor of Arts degree in Anthropology with a concentration in Archaeology from the State University of New York at Cortland, David began his career unearthing the stories of civilizations past. Yet, his talents soon propelled him into a realm of modern engineering, where he contributed to landmark projects at Lockwood Greene, an international engineering firm in Manhattan. Among his notable contributions were projects tied to the George Washington Bridge, Merck Pharmaceuticals, the United States Postal Service, and Newark International Airport, each a testament to his precision and vision. In 2002, David embraced a new chapter in South Florida, bringing his multifaceted expertise to the dynamic world of political consulting and online marketing. As Executive Vice President and Partner at a prominent firm, he harnessed the emerging power of digital media to shape the outcomes of pivotal political campaigns. His innovative strategies were instrumental during the Tea Party wave of 2008, and his expertise became indispensable in gubernatorial, U.S. Senate, and presidential election cycles. Revered as a thought leader, his influence extended to national organizations and Fortune 500 corporations, cementing his reputation as a trusted advisor in high-stakes arenas. Today, David channels his diverse professional journey into co-founding the Stone Thompson Luxury Group at Illustrated Properties, an elite real estate team based in Jupiter, Florida. As a leader of the brokerage’s Sports & Entertainment division, he continues to merge precision, vision, and innovation, elevating his clients’ experiences in the luxury market. Beyond his professional achievements, David’s life is imbued with a profound commitment to faith and service. A devout Catholic, he has served on the boards of numerous faith-based organizations and has been a cornerstone of leadership within the Jupiter Palm Beach chapter of Legatus, where he served as President for five terms and was named Southeast Region President of the Year in 2022. He is also a founding board member of the Priestly Fraternity of St. Peter (FSSP) Provincial Advisory Council and the Young Catholic Professionals Palm Beach chapter. As a Commissioner for Planning & Zoning for the Town of Jupiter, he continues to play a pivotal role in shaping the community he calls home. In 2024, David and his wife, Andrea, were invested as Dame and Knight of the Equestrian Order of the Holy Sepulchre of Jerusalem, a reflection of their enduring dedication to faith and charitable service. Married for 16 years, the Thompsons share their home with their two rescue dogs: Lola Maria, a spirited Miniature Pinscher, and Otto von Benedictus, a noble Doberman Pinscher. David Thompson’s story is one of relentless curiosity, dynamic leadership, and an unwavering commitment to the values that anchor his life. From unearthing the past to building a future defined by service and excellence, his legacy is one of inspiration and enduring impact.

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