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$4,090,000
5 Beds ⋅ 7 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Welcome to this stunning 2021-built home in one of Sarasota's most iconic and picturesque historic neighborhoods, Cherokee Park. Offering luxurious living with thoughtful design, this spacious residence of over 6000 square feet features a desirable first-floor primary suite with a decadent bathroom with soaking tub, oversized marble shower, and access to the covered porch for your morning coffee. The gourmet kitchen is equipped with Wolf and Subzero appliances, marble countertops, a walk-in pantry, oversized island for food prep or casual dining, and sweeping views of the pool and lush backyard. A dedicated dining room provides an elegant setting for formal entertaining. The family room is centrally located for optimal entertaining and boasts a gas fireplace, marble detail, and custom built-ins. The sophisticated den offers custom cabinetry and is ideal for a home office or a sitting room. Upstairs, you'll find four additional bedrooms, each offering ample space and walk-in closet storage, complemented by three full bathrooms. There is a large exercise room / flex space on the 2nd floor which includes counter space and an undercounter refrigerator and relaxation area. The third floor includes a movie room. The first floor laundry room boasts a custom mudroom with shoe cubbies and a built-in desk, conveniently located off the four-car garage. The private guest suite includes a kitchenette, separate laundry, and elevator access, making it ideal for extended family, a live-in nanny or au pair, or visiting guests. This home features beautiful oak flooring throughout, adding warmth and elegance to every room. Impeccable attention to detail is evident in every corner and the rooms are filled with abundant natural light. Step outside to your own private resort-style retreat, complete with a fully equipped outdoor kitchen and bar area, perfect for alfresco dining and entertaining under the Florida sky. Enjoy quiet evenings on the back porch overlooking the heated pool and fenced yard with newly installed and maintenance-free turf grass. Built with steel-reinforced framing and durable Hardie board siding this home offers superior structural integrity, is built to the latest hurricane codes and is not in a flood zone. Perfect for multigenerational living or hosting guests, this home combines modern elegance with practicality. Co-listing agent is the owner.

1686 North Drive, Sarasota
$3,950,000
4 Beds ⋅ 5 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Nestled along Cherokee Drive in the prestigious Cherokee Park neighborhood, this residence enjoys a premier setting on one of Sarasota’s most sought-after streets, renowned for its graceful oak canopy and classic west-of-the-trail charm. This residence embodies the perfect balance of modern architecture, natural materials, and tranquil privacy. Designed by award-winning architect Guy Peterson and constructed by master builder Pat Ball, the home delivers a rare combination of architectural pedigree and enduring craftsmanship. Positioned on a gracious, estate-sized parcel surrounded by lush greenery, the home’s U-shaped floor plan wraps around its showpiece, a 45-foot crystal-clear pool with integrated spa, creating a seamless indoor–outdoor living experience that defines the Sarasota lifestyle. Outside, the stone pathway leading to the custom mahogany front door sets a striking geometric tone. Inside, board-on-board architectural molded concrete accent walls, Santos Mahogany wood floors, and cypress-accent ceilings strike a natural harmony with the home’s sleek, modern lines. Floor-to-ceiling impact-rated Marvin windows flood the interior with light, framing tranquil views of the pool and landscape from nearly every room. The wide-open living and dining area, anchored by a wood-burning fireplace, sets the tone for elegant yet effortless entertaining. The chef’s kitchen features Wolf and Sub-Zero appliances, extensive custom maple cabinetry, and a seamless connection to both indoor and outdoor dining spaces. In the west wing, the expansive primary suite serves as a private retreat with walls of glass overlooking the grounds, complemented by an adjacent executive office for work-from-home convenience. The east wing hosts two en-suite guest bedrooms, each with sliding glass doors opening directly to the pool. A detached guest cabana offers a complete living area, kitchenette, and en-suite bedroom that is ideal for visitors, extended stays, or use as a private art studio or executive home office. Located within Cherokee Park, one of Sarasota’s most established and beloved neighborhoods, this home offers walking distance to Southside Elementary, minutes to Southside Village and downtown Sarasota, and easy access to Siesta Key Beach, just five streets away. The community is known for its family-friendly gatherings, tree-lined streets, and timeless Sarasota character.

1739 Cherokee Drive, Sarasota
$3,881,000
4 Beds ⋅ 5 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Priced to sell. Recipient of eleven awards, including Residential Design and Build Design Excellence and Home of the Year by SRQ Magazine, this exceptional residence is the result of a thoughtful collaboration between Jonathan Parks Architect and Michael A. Gilkey Inc landscape designer. Located in one of Sarasota’s oldest and most established neighborhoods, the home seamlessly blends a traditional 1920s architectural vocabulary with a modern appreciation for simplicity and precision. The result is a sophisticated four-bedroom residence with a British Colonial sensibility—elegant, timeless, and thoughtfully designed for today’s lifestyle. Set on an unusually large 20,000-square-foot lot and located outside of any flood zone, the property offers a rare sense of space and privacy. An artistic pool and a series of designated outdoor living areas, framed by curated garden vignettes, complete this tranquil retreat. The striking foyer welcomes you with understated elegance, gleaming wood floors, and an immediate sense of refinement. Walls of glass define the main living spaces, filling the interior with natural light and highlighting the fireplace as a focal point. While the classic elements of a traditional home remain—stucco exterior, white roof, and ironwork details—the overall aesthetic is contemporary and quietly confident. Large windows and an open floor plan are designed to maximize light and create a seamless connection to the outdoors. A spacious screened patio offers an inviting setting for both relaxation and al fresco dining. Mature Mahoe trees, native to South Africa, line the exterior and rise gracefully to the level of the home’s high windows, enhancing privacy and serenity. The primary suite occupies its own private wing on the first floor, complete with a secluded courtyard, while an ensuite guest bedroom and office balance the opposite wing. Upstairs, two additional ensuite bedrooms each enjoy private balconies overlooking the lush grounds. Throughout the home, a Zen-like sense of peace and tranquility prevails—a true sanctuary of thoughtful design and quiet luxury.

1729 Cherokee Drive, Sarasota
$3,350,000
4 Beds ⋅ 5 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Welcome to this rarely available Cape Cod–style residence, comprised of a masterfully renovated main house and separate luxe guest house poised on an expansive 20,000 sq. ft. lot in Sarasota’s prestigious Cherokee Park. Elevated 23 feet above sea level and nestled on a wide, tree-lined street in the coveted West of Trail district—within the top-rated Southside school zone—this 4-bedroom, 3 full/2 half bath +office private compound blends timeless architecture with designer-curated sophistication. A stately front porch framed by lush landscaping and classic brick walkway introduces the home with understated grandeur. Handcrafted, glass-inlaid iron double doors open to a refined foyer where natural light, elegant millwork, and soaring 10-foot ceilings set the tone for the bespoke interiors beyond. Inside, original hardwood floors, designer lighting by Arteriors, Eichholtz, and Kelly Wearstler, and high-end finishes selected by Chelsea Dunbar of Blu Interiors create a sense of warmth and refinement throughout. The quartz-clad chef’s kitchen is as functional as it is beautiful, featuring a Wolf natural gas range, KitchenAid French-door refrigerator, ample pantry space, and custom cabinetry—perfectly suited for both intimate dining and entertaining. Anchored by a wood-burning fireplace, the main living and dining spaces flow seamlessly outdoors to an inviting Pennsylvania bluestone patio, low-maintenance Astroturf lawn, and wrap-around Brazilian teak deck—an idyllic setting for year-round enjoyment. The serene first floor primary suite is a private retreat showcasing three custom-designed walk-in closets and a spa-inspired bath with marble finishes, dual vanities, heated towel bar, and a zero-entry shower with body sprays. Ascend the custom staircase to find 2 tailored guest retreats with spa-like bath, each offering serene views and thoughtfully appointed details for ultimate comfort and privacy. Throughout the home, custom wallcoverings by Phillip Jeffries, Scalamandré, and Élitis add layers of texture and artistry, while upgraded systems—including a surround sound system, six climate zones, and multiple laundry areas—enhance everyday comfort. Resort-style living continues outdoors with a 9-foot-deep pool framed by classic Bevolo gas lanterns and an extraordinary luxury guest house built in 2016. This refined space includes an entertaining area with custom built-ins, full bar, refrigerator drawers, Scotsman icemaker, private guest suite, 1.5 baths, gym, and an outdoor teak shower. The fully equipped outdoor kitchen features a natural gas Lynx grill, XL Green Egg, quartzite prep counters, and a covered gazebo ideal for al fresco dining. All impact doors and windows, cedar shake roof, and Hardie Board siding add to the beauty and durability of the home. Completing this exceptional estate is an oversized 2.5-car detached garage and secure, fully fenced grounds with electric fence. Enjoy tree-lined streets with sidewalks and a true sense of community, all just a short stroll or golf cart ride to Southside Village where residents enjoy boutique shops, Morton’s Gourmet Market, cafés, and top-rated restaurants, and minutes from downtown Sarasota and Siesta Key Beach. This is refined Gulf Coast living—where timeless architecture meets effortless luxury in one of Sarasota’s most treasured neighborhoods.

1774 Cherokee Drive, Sarasota
$2,300,000
3 Beds ⋅ 4 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Welcome to 1585 South Drive, a timeless cottage-style residence in the beloved West of Trail community of Cherokee Park. Thoughtfully updated and rich with character, this home seamlessly blends historic charm with modern comfort. Refinished white oak floors, abundant natural light, stylish finishes, and a gracious, contemporary layout make it truly move-in ready. Elevated more than 10 feet above sea level yet just three houses from the bay, the home enjoys both beauty and peace of mind on a corner lot at the quiet end of the street. From the inviting brick front porch, step into a foyer with custom board-and-batten detailing. To the right, a generous living room encourages gathering; to the left, a versatile office, den, or sitting room is tucked behind sliding doors for a quieter retreat. Expansive windows frame leafy views and bathe the interiors in light. At the heart of the home, the oversized kitchen impresses with a large central island, abundant counter space, walk-in pantry, wet bar, and KitchenAid appliances. The adjoining dining room opens to the backyard and screened porch, creating seamless indoor-outdoor living. The primary suite is privately situated on the main level, offering a spacious walk-in closet, serene ensuite bath, and direct screened porch access. Nearby, a second bedroom with its own hall bath serves perfectly as a guest suite, children’s room, or home office. Upstairs, a private retreat includes a large bedroom with dormer windows, built-in window seats, an ensuite bath, and extensive storage. Additional highlights include a recently remodeled marble powder room, a well-equipped laundry room, an irrigation well, and an attached two-car garage. The generously sized lot offers ample room for a pool, guest house, or future expansion. Sarasota's West of Trail neighborhoods are coveted for their proximity to Sarasota Memorial Hospital, downtown, and the sugar white sands of Siesta Key. Cherokee Park is perhaps the most prized of these, celebrated for its stately homes, wide tree-lined streets with sidewalks, walkability to Southside Village and Southside Elementary, and cherished traditions — from bustling Halloweens to twinkling luminaries and carriage rides at the holidays. While the surrounding streets boast their share of impressive new construction, this well-proportioned and well-preserved original stands apart for its enduring charm, turnkey livability, and exceptional value. Designer furnishings by Pecky Interiors are optionally available.

1585 South Drive, Sarasota
$1,850,000
4 Beds ⋅ 4 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
Historic Cherokee Park: This prime, “West of the Trail” property with oak-lined boulevard streets and decorative light posts is located near Southside Village. At 20 feet elevation, this property has NO HISTORY OF FLOODING. There is a low annual HOA and no CDD’s. Situated on a picturesque lot, this home with a guest house boasts privacy and tranquility; surrounded by mature landscaping that provides a serene oasis. Both the main house and guest house have brand new roofs with certified GAF 25-year warranties. The main house has three bedrooms with two and a half baths, while the guest house has one full bath and kitchenette; totaling 3,227 square feet. Entering the home through the gated flagstone courtyard, you will find the openness of the home with authentic Saltillo tile flooring. The master bath has travertine flooring, dual sinks on a granite countertop, an open travertine shower and a tub. The guest bath flooring has custom multicolor tiles; embracing the “vintage” feel. The kitchen has granite countertops with stainless steel appliances, including a French door refrigerator/freezer (2022), and combination microwave/air fryer/convection oven with a Bluetooth-communicating combination range/oven/convection oven (11/2023.) The guest house flooring is wood looking wide ceramic tile. Three wood burning fireplaces, (two in the main house and one in the guest house), have been restored and are fully functional. Ample storage space includes a large walk-in closet with built-ins in the master bedroom and four cedar closets. No need for gutter cleaning, as both houses have Leaf Filter screens that come with a lifetime warranty. The multi-zone irrigation system is controlled by an automated clock and recently converted to metered city water (5/2025) due to the original surface well going dry due to drought. In the tranquil backyard, the large brick paver patio features an arbor and a fountain. Prior to Hurricane Milton on October 9, 2024, there were cascading bougainvillea on the arbor which had to be pruned back. Along the fenced and stucco wall back yard perimeter, there were traveler’s palms and white birds of paradise that further obstructed views to surrounding properties and gave the backyard a more private, tropical feel. An additional bonus is the yard’s double gate that backs up to Harmony Lane for tree trimming and construction access. A new custom front door with glass insets and updated hardware was installed in 1/2025. The proximity of this home to downtown and the world renowned Siesta Key beaches makes it the perfect base for enjoying all that Sarasota has to offer. The holiday parties and social gatherings promote a sense of community. Don't miss the opportunity to own this exceptional property, where prime location, a spacious lot, and unparalleled privacy come together to create a truly magnificent living experience.

1713 North Drive, Sarasota
$1,637,500
3 Beds ⋅ 3 Baths ⋅ Cherokee Park SubDv. ⋅ 34239 Zip Code
One or more photo(s) has been virtually staged. Welcome to 1616 North Drive, Fourth in from the Bay in Coveted CHEROKEE PARK. EXCELLENT LOCATION to Build a New Home or Renovate the Existing Home on this Spacious 100' x 150' (15,000 Sq. Ft.) Lot. Boundary and Tree Survey Available upon Request. Walk Right Down the Sidewalk to Southside Elementary School. Over 2,800 Sq. Ft. of Living Area Including 3 Bedrooms, 2.5 Baths and a Family Room with Cathedral Ceilings and Wood Burning Fireplace. The house has been well maintained by the original owner. High ceilings with crown molding in living and dining rooms. Large Eat-in-Kitchen with Breakfast Nook overlooks the serene backyard with slumbering oaks and Staghorn Ferns. Bonus room could be a 4th bedroom, Nanny's quarters, a home office, gym or a playroom for little ones. 8' x 8' Workshop and extra storage off the garage. Sprinkler system with separate water meter. Wood deck off back porch has been removed. CHEROKEE PARK is a picturesque neighborhood known for it's beautiful oak-tree lined streets and offers a family-friendly atmosphere. There is an active Voluntary Homeowners Assn that organizes neighborhood social events during holidays and throughout the year. CONVENIENTLY LOCATED close to the beach, Southside Elementary School, Sarasota Memorial Hospital, Downtown Sarasota, and the shops and restaurants in Southside Village, this home offers a wonderful opportunity to ENJOY THE BEST OF SARASOTA LIVING.

1616 North Drive, Sarasota
$275,000
4 Beds ⋅ 4 Baths ⋅ Cherokee Park SubDv. ⋅ 32117 Zip Code
Welcome to this spacious home offering just under 3,000 sq ft of comfortable living! With 4 bedrooms, 2 full baths, and 2 half baths, there's room for everyone. The inviting living room features a charming wood-burning fireplace, while the kitchen opens to a generous dining area—perfect for entertaining. Enjoy the natural light in the bright bonus room, play games in the expansive recreation room, and take advantage of the convenient indoor laundry and abundant storage. Situated on a corner lot, the property also includes an above-ground pool—ready to be filled and enjoyed all summer long! Don't forget the spacious front porch, perfect for sipping sweet tea and enjoying peaceful evenings. All information taken from the tax record, and while deemed reliable, cannot be guaranteed. Realtor is Related to the Seller.

600 10th Street, Daytona Beach