Cherokee Park Homes with No Deed Restriction Community Extras

Cherokee Park Homes with No Deed Restriction Community Extras

Welcome to Cherokee Park, a hidden gem nestled in the heart of Winter Park, Florida. This charming subdivision is perfect for those seeking a peaceful suburban lifestyle without the constraints of deed restrictions. Imagine living in a vibrant community where your creativity and individuality can flourish, free from the limitations often imposed by traditional neighborhood guidelines.

Cherokee Park boasts a diverse array of homes, each with its unique character and charm. From cozy single-family residences to modern designs, there’s something to suit every taste and lifestyle. The spacious lots provide ample room for outdoor activities, gardening, or even expanding your dream home. With no deed restrictions, homeowners have the freedom to personalize their properties, whether that means adding a pool, creating a garden oasis, or parking an RV.

The location of Cherokee Park is simply unbeatable. You’ll find yourself just moments away from Winter Park’s renowned dining, shopping, and cultural attractions. The picturesque parks and scenic lakes offer endless opportunities for outdoor adventures, while the vibrant downtown area is perfect for enjoying art festivals and local markets. Families will appreciate the access to top-rated schools and community resources, making Cherokee Park an ideal place to settle down.

Join the welcoming community of Cherokee Park and experience the perfect blend of tranquility and convenience. With its charming homes, beautiful surroundings, and the freedom to express your personal style, this subdivision is truly a place where dreams can take root and flourish. Don’t miss your chance to call Cherokee Park home!

Newest Cherokee Park Homes with No Deed Restriction Community Extras

$245,000
4 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 32117 Zip Code
Welcome to this single-story, block-construction home in Holly Hill offering 4 bedrooms, 2 full bathrooms and 1,116 square feet of living space. The property sits on a 0.19-acre lot and features tile flooring, central air conditioning, public water and sewer, an attached garage and additional covered carport parking. The practical floor plan provides flexible space for everyday living, guests or a home office. Conveniently located near shopping, dining and major roadways, this home is ready for its next owner. Schedule your private showing today!

Holly Hill
$2,300,000
3 Beds ⋅ 4 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and a rare opportunity to create a home tailored to your vision. Surrounded by a lush, expansive yard with ample room for a pool, the property offers exceptional flexibility for its next owner. Enjoy the home's timeless character as it is, or take advantage of the opportunity to create your dream home in one of Sarasota's most established neighborhoods. Inside, a light-filled, open floor plan is complemented by beautiful wood floors and an inviting sense of warmth throughout. The main level features a comfortable guest bedroom with an adjacent full bath, as well as a spacious en-suite primary bedroom, offering the ease and convenience of first-floor living. Upstairs, a private en-suite retreat is filled with character, featuring charming dormer windows, built-in window seats, and extensive storage. Adding to the property's remarkable potential is a recently approved variance along the side of the lot, providing an additional 10 feet of buildable envelope and expanding the possibilities for a future renovation, addition, or new residence. Ideally situated West of the Trail, this exceptional property places you close to top-rated schools, Sarasota Memorial Hospital, the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and vibrant downtown Sarasota. With its coveted location, generous homesite, and unique development potential, this Cherokee Park property presents an extraordinary opportunity to create something truly special.

1585 South Drive, Sarasota
$2,690,000
3 Beds ⋅ 2 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Rarely available in Cherokee Park, widely regarded as one of Sarasota’s most desirable West of Trail neighborhoods, 1722 North Drive presents an extraordinary opportunity on a remarkably oversized 150-by-150-foot homesite with an impressive 150 feet of street frontage. Significantly larger and more generously proportioned than many properties in the neighborhood, the square parcel offers the scale, symmetry, and flexibility increasingly difficult to find in Sarasota’s most established luxury enclaves. Cherokee Park is distinguished by its quiet, tree-lined streets and an architectural landscape where beautifully restored historic residences sit alongside prominent new custom homes designed and built by some of Sarasota’s most respected architects and builders. Within that setting, this property stands apart. Mature, century-old oak trees frame the perimeter, creating a park-like canopy of privacy, shade, and character while leaving the heart of the lot remarkably open. The combination of its ideal square configuration, substantial street presence, and undisturbed tree canopy creates a compelling canvas for a future luxury residence, with room to build a custom home, pool, outdoor living areas, and landscaped grounds without overwhelming the site. The existing home is charming, comfortable, and move-in ready, giving its next owner the flexibility to enjoy the property immediately, renovate over time, or hold it while designing a future custom residence. Recent improvements include a new air-conditioning system, hot water heater, sewer line, and resurfaced pool, all completed in 2024. A separate bonus space offers an ideal setting for a work-from-home office, art studio, gym, or creative retreat. Located just moments from Southside Elementary School and close to Southside Village, downtown Sarasota, the bayfront, and Sarasota Memorial Hospital, 1722 North Drive combines one of the city’s most coveted residential settings with the dimensions and character of a truly distinctive homesite. Whether enjoyed as it stands today or reimagined as a significant new estate, this is a rare opportunity to secure an unusually substantial parcel and lasting value in the heart of Cherokee Park.

1722 North Drive, Sarasota
$1,549,000
4 Beds ⋅ 5 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Less than 4 miles to Siesta Key Beach and under 3 miles to Downtown Sarasota, this newly built 4-bed modern home in Sarasota delivers luxury living, investment flexibility, and an exceptional West of the Trail location. Built in 2024, this contemporary residence offers approximately 2,900 square feet with 4 bedrooms+ den and 4.5 baths, featuring open-concept living spaces, clean modern design, energy-efficient construction, and seamless indoor-outdoor flow ideal for entertaining. Located within Sarasota city limits with 7-night minimum rental potential, this property is an outstanding opportunity for both investors and end users seeking a luxury lifestyle close to Downtown Sarasota, Southside Village, Sarasota Memorial Hospital, and Siesta Key Beach. Room for a future pool. Located within the coveted Southside school district.

1734 Wisconsin Lane, Sarasota
$2,000,000
Cherokee Park SubDv. ⋅ 34239 Zip Code
This exceptional 100X200 lot in historic Cherokee Park awaits your dream home, with Fergeson Brothers as the designated design and construction company; this west-of-the-trail neighborhood is located on Sarasota Bay in the City of Sarasota; The adjoining lot is also available.

1749 Cherokee Drive, Sarasota
$6,950,000
4 Beds ⋅ 4 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Dreaming of breathtaking sunsets? This property is for you! A one of a kind bayfront lot located in highly sought-after Cherokee Park, West of Trail. Located in "X" flood zone this property offers unobstructed panoramic views of Sarasota Bay. The stunning vistas of Ringling Bridge, Siesta Key and downtown are truly mesmerizing. Boating enthusiasts will appreciate the brand-new dock with a 16,000lb lift and direct access to Sarasota's exceptional boating waters. Enjoy the home as it is or take advantage of this rare opportunity to build a custom waterfront estate on this magnificent property. Offered at $6,990,000, do not miss your chance to own one of Sarasota's finest waterfront locations.

1504 S Lodge Drive, Sarasota
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