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COOPER & SEWELL ADD - O6427252 - 211 N HIGHLAND AVE, WINTER GARDEN, FL 34787 Just Added on 07/22/2026 11:13AM
$2,150 | Single Family Home | 2 beds | 1.0 baths | 1 gar
Welcome to this delightful 2-bedroom, 1-bathroom cottage located in the Historic District of Winter Garden. Just two blocks from Plant Street, you'll enjoy easy walking access to local restaurants, coffee shops, and boutique shopping. This home features beautiful hardwood flooring throughout, with tile in the kitchen and bathroom for added durability and style. Off the main living area is a spacious flex room—perfect for a home office, playroom, or additional living space to suit your needs. The kitchen has ample cabinet space. Please note the fireplace is non working, decoration only. The property includes a detached one-car garage off the kitchen, connected to the home by a covered walkway, with washer and dryer hooks ups, offering both convenience and charm. The large front and backyard are shaded by mature trees, creating a serene and inviting outdoor space. Don’t miss the opportunity to make this unique home yours! *RentSpree applications will not be accepted. Residents are enrolled in the Resident Benefits Package (RBP) for $39.95/month. More details upon application.
Listing is courtesy of: WATSON REALTY CORP
ENCORE/OVATION PH 4A - O6427186 - 12743 BRODLOVE LN, WINTER GARDEN, FL 34787 Just Added on 07/21/2026 11:47PM
$3,300 | Single Family Home | 4 beds | 3.5 baths | 2 gar
This beautiful 4-bedroom, 3.5-bath home for rent in the highly desirable area of Winter Garden offers a perfect blend of comfort, space, and style. Featuring a 2-car alley-load garage in the back and a welcoming front porch, this home boasts an impressive 2-story foyer and a private downstairs bedroom with a full bath—ideal for guests, in-laws, or a home office. The open-concept layout seamlessly connects the family room, kitchen, and dining area, all filled with natural light from large windows. Enjoy the Florida lifestyle on the angled covered lanai accessed through sliding glass doors. Wood-look tile flows throughout the first floor, which also includes a convenient powder bath near the garage entrance. Upstairs, a spacious loft offers a perfect spot for relaxing or entertaining, along with three more bedrooms, including a private owner’s suite located at the back of the home for added privacy.
Listing is courtesy of: ROBERT SLACK LLC
OSPREY RANCH-PH 1 - O6426960 - 12560 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 1 Day on yellowkey
$3,500 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Welcome to your single-family home in the highly sought-after community of Osprey Ranch! Located in the heart of charming Winter Garden, this beautiful 4-bedroom, 3-bath residence with a 2-car garage offers the perfect blend of comfort, convenience, and community — an ideal place to raise a family. Enjoy living just minutes from world-class theme parks, top-rated local schools, major roadways, dining, shopping, parks, and vibrant farmers' markets. Families will appreciate the excellent educational opportunities nearby, making this location truly special. Inside, you'll find a spacious, gourmet-style kitchen with a large center island, flowing into the open-concept dining area and expansive family room — perfect for entertaining and everyday living. The first floor features a comfortable bedroom with a walk-in closet and a full bathroom, offering flexibility for guests or multi-generational living. Upstairs, the privately located owner’s suite includes a beautiful bathroom with dual sinks and a generous walk-in closet, creating a relaxing retreat. Step outside to enjoy your open-air patio — ideal for weekend barbecues, or relax on the welcoming front porch after a long day. Don't miss the opportunity to live in one of Winter Garden’s most desirable neighborhoods! Schedule your private tour today and experience the perfect place to call home.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE
SILVERLEAF RESERVE AT HAMLIN - WINTER GARDEN, FL 34787 1 Day on yellowkey
$2,950 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Energy-Efficient Home in Silverleaf Reserve Winter Garden! This spacious Hurston model features an open-concept layout with a stunning kitchen, complete with a large island overlooking the dining area and family room-perfect for entertaining and everyday living. The upstairs loft offers flexible space to fit your lifestyle, whether as a home office, playroom, or media room. Located in the desirable Silverleaf Reserve community, you'll enjoy easy access to top-rated schools, dining, shopping, and entertainment in the heart of Winter Garden. Built with innovative energy-efficient features, this home helps reduce utility costs while providing year-round comfort and peace of mind.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY
WATERLEIGH PH 5 - O6426380 - 11170 HOLLOW BAY DR, WINTER GARDEN, FL 34787 1 Day on yellowkey
$3,600 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Beautiful Clearden Floor Plan in the Highly Desirable Waterleigh Community! Welcome to this beautifully maintained 4-bedroom, 3.5-bathroom home located in the sought-after Waterleigh community in Winter Garden. Designed for both comfort and functionality, this spacious two-story home features an open-concept layout perfect for everyday living and entertaining. The first floor offers a private guest suite with a full bathroom, ideal for visitors, multigenerational living, or a home office. The gourmet kitchen showcases stainless steel appliances, quartz countertops, abundant cabinet space, and a large island overlooking the spacious dining and family room, creating the perfect space to gather with family and friends. Upstairs, the generous primary suite features a spacious walk-in closet and an en-suite bathroom with dual vanities. Two additional bedrooms, a full bathroom, a versatile loft, and a conveniently located laundry room complete the second floor. Additional features include a two-car attached garage, central air conditioning, and plenty of storage throughout. Residents of Waterleigh enjoy an exceptional resort-style lifestyle with multiple swimming pools, two clubhouse amenity centers, fitness centers, dog parks, playgrounds, mini-golf, beach volleyball courts, sports fields, walking trails, scenic lakes, and beautifully maintained green spaces. Waterleigh offers an exceptional lifestyle with the added convenience of having both an elementary school and a middle school located within the community, making it an ideal place for families. Residents also enjoy easy access to Publix, Hamlin Town Center, shopping, dining, medical facilities, and Walt Disney World.
WATERLEIGH - O6426062 - 17823 ADRIFT RD, WINTER GARDEN, FL 34787 2 Days on yellowkey
$3,450 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Beautifully renovated 4-bedroom home located in one of the area’s most desirable communities. This bright and inviting residence features abundant natural light, modern finishes, spacious living areas, and a functional floor plan ideal for everyday living and entertaining. The private backyard overlooks a peaceful green space, offering extra privacy and a relaxing setting with no immediate rear neighbors. Conveniently located near the community clubhouse and within walking distance of Water Spring Elementary and Water Spring Middle School, this home provides an exceptional combination of comfort, convenience, and lifestyle. Residents enjoy access to a wide variety of resort-style amenities, including a community pool, clubhouse, playgrounds, recreational areas, walking trails, and beautifully maintained common spaces. Move-in ready and ideally situated near schools, shopping, dining, major roads, and everything the area has to offer. A wonderful opportunity to live in a highly sought-after community!
ANNIE L BERRY SUB - G5115261 - 205 S WOODLAND ST, WINTER GARDEN, FL 34787 4 Days on yellowkey
$3,850 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Virtually Staged. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom, 2500 sq ft ranch-style home, ideally located within a 5-minute walk to historic downtown Winter Garden in the heart of the Golf Cart District. Situated on a spacious corner lot, this home blends classic charm, thoughtful upgrades, and everyday functionality—perfect for families, snowbirds, or anyone seeking a relaxed yet connected lifestyle. Step inside to an open and airy floor plan featuring wood flooring in the main living areas and tile in the kitchen and bathrooms. The generously sized kitchen serves as the heart of the home, offering abundant counter space, ample storage, and natural light—ideal for cooking, entertaining, or casual dining. The fully fenced backyard provides privacy and space for outdoor living, pets, or play. A rare find, the 2-car garage includes a pass-through rear door that opens to an additional parking pad—perfect for a trailer, golf cart, or extra vehicle. You’ll also find a small air-conditioned room inside the garage, ideal for a home office, workout space, hobby room, or climate-controlled storage. Located in one of Winter Garden’s most desirable areas, you’re just a quick walk from local shops, yoga studios, restaurants, the farmers market, and community events. With no HOA and a layout built for both comfort and convenience, this home offers a unique opportunity to enjoy both peace and a vibrant, walkable lifestyle. Flexible Lease Term. Perfect if you are Building a home in Winter Garden. Yard care included.
Listing is courtesy of: LISA REALTY PARTNERS
LAKESIDE AT HAMLIN - O6426255 - 5043 LAKE HAMLIN TRL, WINTER GARDEN, FL 34787 5 Days on yellowkey
$3,200 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Welcome to this well maintained two Story 2023 built 4 Bedroom/ 3 Full bath covered lanai home in the LAKESIDE AT HAMLIN tucked away in the heart of Winter Garden**Open concept kitchen overlooking the living area, dining room, and Covered Porch**Entertaining is a breeze, as this single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage**Stainless Steel Appliances** Master Bedroom has an en suite bathroom with a double vanity, Spacious Shower space as well as a Spacious Walk-in closet** On the First floor one Spacious bedroom and full bathroom, perfect for guests or a home office**This home features a space to fit all your needs. Plenty of storage with laundry room**All Appliances plus Washer & Dryer**2 Car Garage**Great location in the heart of Winter Garden, Close to Highways, Shopping, Restaurants, Walt Disney World, Winter Garden Village**Ready to move in 9/1/26.
Listing is courtesy of: C I REALTY
- O6425756 - 15349 SHONAN GOLD DR, WINTER GARDEN, FL 34787 5 Days on yellowkey
Welcome to this beautifully maintained 4-bedroom, 3-bathroom single-story home offering 2,204 square feet of thoughtfully designed living space in the highly desirable Hamlin Reserve community of Winter Garden. This open-concept home features a spacious great room, a separate dining area, and a gourmet kitchen complete with quartz countertops, a large waterfall island, 42-inch cabinetry, stainless steel appliances, and a gas range—perfect for both everyday living and entertaining. The split-bedroom floor plan provides privacy, while the generous primary suite offers a walk-in closet, dual vanities, and a frameless glass shower. High ceilings, abundant natural light, and stylish finishes create a bright and welcoming atmosphere throughout. Enjoy relaxing on the covered lanai or take advantage of the community amenities, including a resort-style pool, clubhouse, parks, playgrounds, and scenic walking trails. Conveniently located in the heart of Horizon West, you’re just minutes from Hamlin Town Center, shopping, dining, entertainment, SR-429, Orlando Health Horizon West Hospital, and top-rated Orange County schools. Rent includes lawn care and HOA fees. This is a wonderful opportunity to enjoy low-maintenance living in one of Winter Garden’s most sought-after communities.
Listing is courtesy of: RE/MAX PRIME PROPERTIES
WATERLEIGH PH 3B 3C & 3D - S5153831 - 15537 MANGO ISLE ST, WINTER GARDEN, FL 34787 6 Days on yellowkey
$3,800 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Like-new 4-bedroom, 3-bath single-family home in desirable Waterleigh at Horizon West. Bright, open floor plan filled with natural light, featuring a formal dining room that flows into a spacious kitchen and living area—perfect for entertaining. One bedroom and full bath downstairs is an ideal space for guests or multigenerational living. Upstairs includes three additional bedrooms plus a versatile loft, perfect as a second living area, game room, or office. Enjoy a paved driveway, covered lanai, nicely sized backyard, and included washer and dryer. Located in a resort-style community near Hamlin Town Center, FL-429, Winter Garden Village, and just minutes to Disney. Zoned for highly rated schools. Move-in ready and beautifully maintained. The nearby Winter Garden Village provides a more modern shopping experience with over 100 retailers. Community features clubhouses, three pools, fitness center, playgrounds, walking trails, dog parks, and more. Move-in ready and beautifully maintained.
Listing is courtesy of: FLORIDA HOMES REALTY & MORTGAGE
WATERLEIGH PH 3B 3C & 3D - O6425890 - 16856 OAKBORO ST, WINTER GARDEN, FL 34787 6 Days on yellowkey
$2,800 | Single Family Home | 3 beds | 2.0 baths | 2 gar
AVAILABLE NOW – Beautiful 3-bedroom home with a fenced backyard, located in the sought-after Waterleigh community. Enjoy an open-concept layout featuring a stylish kitchen with Samsung stainless steel appliances, a walk-in pantry, and a large island—perfect for entertaining. The kitchen flows seamlessly into a spacious family room, ideal for modern living. Brick pavers highlight both the driveway and the covered lanai, where you can relax and take in views of the Magic Kingdom fireworks from your own backyard! Waterleigh offers resort-style amenities including two stunning clubhouses, multiple pools, a miniature putting green, three fitness centers, and tennis courts—all just minutes from Disney in Winter Garden/Horizons West. Note: No representations or warranties are made regarding school districts or school assignments. Please verify independently.
Listing is courtesy of: EMPIRE NETWORK REALTY