Apartments for Rent Near Dillard Street Elemin Winter Garden - 3 rentals

Remarks: Imagine starting your mornings beneath towering oak trees in the heart of the Winter Garden Historic District, where life moves just a little slower and neighbors still wave as they pass by in their golf carts. Tucked away on a quiet dead-end street in the sought-after Winter Garden Golf Cart District, this spectacular rental offers a rare opportunity to live in one of the most beloved pockets of town—on a street where homes seldom become available for rent. Set on a massive lot with an incredible backyard oasis, the property is surrounded by lush landscaping and mature fruit trees, creating a private retreat that feels worlds away while still being just minutes from the vibrant heart of downtown. Inside, the solid block home welcomes you with timeless charm, featuring pristine terrazzo floors and a dramatic wood-burning fireplace that anchors the spacious family room—perfect for cozy evenings or gathering with friends. The home offers generous living spaces with large formal living and dining rooms, ideal for entertaining or simply spreading out and enjoying the comfort of home. Step outside to an enormous covered and screened rear porch where you can relax with your morning coffee, host weekend barbecues, or unwind as the Florida breeze moves through the trees and across the expansive backyard. Beyond the main home, the property continues to impress with a full two-car garage, plus a separate backyard workshop complete with power and A/C—perfect for hobbies, projects, or additional workspace. A large secured wrap-around covered storage shed provides even more room for tools, equipment, or recreational gear. Living here means embracing the lifestyle that has made Winter Garden one of Central Florida’s most desirable communities. Just a quick golf cart ride away, you’ll find the brick-lined charm of Plant Street, where local restaurants, boutiques, and entertainment create a lively small-town atmosphere. Spend evenings enjoying live music and craft beer at Crooked Can Brewing Company, or start your Saturdays exploring the famous Winter Garden Farmers Market, consistently ranked among the best in the region. With year-round events, incredible dining, unique shops, and the charm of historic downtown just minutes away, this home offers more than a place to live—it offers a lifestyle. Opportunities like this rarely come along in the Historic District. Schedule your showing today and start living the authentic Winter Garden life.

Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)

Listing Agent: Joshua Brown (407-936-5344)

Remarks: LAWN CARE, PEST CONTROL & HVAC MAINTENANCE INCLUDED!Welcome to the established community of FULLERS CROSSING in Winter Garden! Located within the highly sought after golf cart district and just 10 MINUTES from Downtown Winter Garden, this beautifully maintained 4-bedroom, 2-bath home offers the ultimate lifestyle with easy access to Plant Street, where you can enjoy local favorites like the Crooked Can Brewery Food Hall, the Winter Garden Farmers Market, boutique shopping, dining, and year-round community events. This spacious home features a functional split floorplan offering both privacy and flexibility, along with a dedicated den or study that can easily be used as a 5TH BEDROOM, home office, or flex space. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, custom cabinetry, and ample storage space, all overlooking the main living areas. The primary suite is a true retreat, complete with an oversized walk-in closet and a fully remodeled, spa-like bathroom featuring a custom walk-in shower with five showerheads, creating an oasis experience right at home. This home features no carpet throughout, making for easy maintenance, with wood flooring in all bedrooms for a clean and modern feel. Step outside to enjoy a spacious, fully fenced backyard with no rear neighbors, providing added privacy and the perfect setting for entertaining or relaxing. This home offers the perfect combination of space, location, and low maintenance living. Schedule your private showing today!

Listing is courtesy of: SUNDIAL REAL ESTATE LLC (407-601-2200)

Listing Agent: Michael Salazar (407-692-5614)

Remarks: One or more photo(s) has been virtually staged. Available April 10th, 2026, Welcome to 391 Floral Drive, a beautifully remodeled 3-bedroom, 2-bathroom home in the heart of Winter Garden’s highly sought-after Golf Cart District. This stunning 2022 renovation combines modern elegance with cozy charm, offering 1,728 sq. ft. of thoughtfully designed living space. Step inside to discover an open-concept layout featuring luxury vinyl plank flooring, a chef’s kitchen with sleek stainless steel appliances, a spacious island, and stylish new cabinetry—perfect for entertaining! The primary suite boasts a spa-like en-suite bath with gorgeous new tile, modern vanities, and a serene ambiance. But the real showstopper? The resort-style backyard! A brand-new heated pool, screened-in porch, and a paver patio create the ultimate private oasis—ideal for relaxing or hosting friends year-round. With a new roof, updated AC, electric fireplace and prime location just blocks from Downtown Winter Garden’s restaurants, farmers markets, and festivals, this home offers both style and convenience. Plus, enjoy easy access to Lake Apopka’s scenic beauty at nearby Newton Park. Don’t miss this rare gem—schedule your private tour today! All residents are enrolled in the Resident Benefits Package (RBP) for $59.00/month which includes liability insurance, credit building to help boost the resident's credit score with timely rent payments, up to $1M Identity Theft Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, HVAC filters, and much more! More details upon application. This property offers an option of a security deposit-free lease using Obligos billing authorization technology for qualified tenants. Non-refundable application fee of $80 per person above the age of 18 years of age. One time admin fee of $295 for approved application.

Listing is courtesy of: CANI PROPERTY MANAGEMENT (321-280-9065)

Listing Agent: Jeremy Porter (321-280-9065)