Homes for Sale Near Lakeview Middle in Winter Garden - 73 homes

Remarks: Short Sale. Don't miss this beautifully updated 2-bedroom, 2-bathroom townhouse offering the perfect blend of comfort, convenience, and unbeatable location. Tucked away in a quiet community, this home is just minutes from all the charm and excitement of downtown Winter Garden, known for its boutique shopping, top-rated restaurants, farmers market, splash pad, and the scenic West Orange Trail. Inside, you'll find a thoughtfully updated interior offering easy, low-maintenance living. Perfect for first-time buyers, downsizers, or investors looking for a move-in ready property in one of Central Florida's most sought-after towns. With its prime location close to shopping, dining, parks, and major roadways, this townhouse offers an unbeatable opportunity to enjoy the best of downtown Winter Garden living without the downtown price tag. Schedule your showing today!

Listing is courtesy of: REAL BROKER, LLC (407-922-8986)

Listing Agent: Denise Pellegrino (352-978-9720)

Remarks: Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: Under contract-accepting backup offers. Welcome to this exceptional 4-bedroom, 4-bath residence with a private office, expansive loft, and 2,831 square feet of beautifully designed living space in the highly sought-after McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. Perfectly positioned on a private corner end lot, this stunning home is complemented by a welcoming front porch and showcases timeless architecture, upscale designer finishes, and exceptional attention to detail. Step inside to discover soaring ceilings, abundant natural light, and beautiful white oak luxury vinyl plank flooring throughout the main living areas. A private office just off the foyer provides the ideal work-from-home space or flex room, while custom window treatments, plantation shutters, designer wallpaper, elegant accent walls, and custom built-ins create a warm yet sophisticated atmosphere. At the heart of the home, the gourmet chef's kitchen features custom cabinetry with upgraded hardware, quartz countertops, an oversized island with designer pendant lighting, a gas cooktop, custom vent hood, built-in wall oven, decorative tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room, where custom built-ins create the perfect gathering space for entertaining or relaxing. The thoughtfully designed floor plan includes a private first-floor guest suite with a full bath, ideal for guests or multigenerational living. Upstairs, an expansive loft offers flexible living space perfect for a media room, game room, or second family room. The luxurious primary suite is privately situated away from the secondary bedrooms and offers tray ceilings, designer accent walls, a spacious walk-in closet, and a spa-inspired en-suite bath featuring dual quartz vanities, a soaking garden tub, and a separate walk-in shower. Two additional upstairs bedrooms each feature walk-in closets, with one offering its own private en-suite bath, while another full bath serves the remaining bedroom and loft. Even the laundry room has been elevated with designer wallpaper, quartz folding countertops, and an included washer and dryer. Outside, the private corner homesite enhances both curb appeal and privacy, offering additional green space and a peaceful setting to enjoy the Florida lifestyle. Living in Oakland Park means embracing one of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market. With convenient access to Florida's Turnpike, SR-429, downtown Orlando, and Central Florida's world-famous attractions, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Erica Sadelfeld (407-427-0398)

Remarks: Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with modern finishes. Inside, you'll find a functional layout with inside laundry, a warm and welcoming atmosphere, and a newer air-conditioning system for added peace of mind. Enjoy quiet mornings or relaxing evenings from the desired front and rear porches overlooking the fully fenced yard, ideal for entertaining, pets or simply enjoying the Florida lifestyle. The oversized double carport and extended driveway provide abundant parking, while the exterior storage room within the carport offers exceptional flexibility for hobbies, tools, golf cart accessories or additional storage needs. Homes with this level of charm, character and accessibility rarely become available in downtown Winter Garden. Combining an unbeatable location, oversized corner lot and the convenience of golf cart living just near everything Plant Street has to offer, this is a special opportunity to own a piece of one of Central Florida's beloved historic communities.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Michael Mitchell, Jr (352-768-1712)

Remarks: Virtually Staged. Built by the owner with uncompromising construction standards, this Winter Garden masterpiece delivers the kind of quality and engineering you simply don’t find in today’s market. And with the seller just reducing the price, this luxury home is now an even more exceptional opportunity. Concrete structural design, hurricane-rated engineering, impact windows, full foam insulation, fiber-cement siding, and an Ipe hardwood porch set the tone for durability and refinement. Inside, natural light pours across level-5 walls, rich wood flooring, crown molding, and custom shutters—creating a warm, polished, magazine-worthy aesthetic. The open living and chef’s kitchen are built for elevated living: gas range, pot filler, handcrafted cabinetry, and a dramatic retractable pocket door that dissolves the boundary between indoors and out. The resort-style back porch is a showpiece—pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, and a half bath—perfect for hosting unforgettable evenings. The primary suite is pure indulgence, featuring a spa-inspired bath with dual shower heads, soaking tub, digital controls, a custom closet, and a private concrete safe room. A butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring elevate everyday convenience. Upstairs, the bonus/game room and oversized balcony create a luxe hangout zone. Storage is abundant with walk-in closets throughout. And the finished two-story garage loft—pre-plumbed and air-conditioned—offers endless possibilities: in-law suite, golf simulator lounge, gym, office, or creative studio. Outside, curated landscaping, gas lanterns, an architectural driveway, and a heated concrete hot tub with Wi-Fi controls complete the experience. All just moments from Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre. A rare blend of craftsmanship, luxury, and location—now at an even more compelling price.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Lora King (407-947-7653)

Remarks: Exceptional Downtown Winter Garden Investment Opportunity! Located in one of the most desirable areas of Downtown Winter Garden, this property presents an outstanding opportunity to build your dream home or complete a substantial renovation in an area where redevelopment continues to thrive. The existing 1924 home is approximately 912 square feet with 2 bedrooms and 1 bathroom and is being sold AS-IS, with the value primarily in the location and land. Public records indicate a 5,024-square-foot lot zoned R. Enjoy the unmatched lifestyle that Downtown Winter Garden is known for, with convenient access to Plant Street's award-winning restaurants, boutique shopping, the weekly Farmers Market, Crooked Can Brewing Company, live entertainment, and the West Orange Trail. Whether you're a builder, investor, or buyer looking to create a custom home in one of Central Florida's most sought-after downtown districts, this is a rare opportunity to secure a property with tremendous potential in a location where new construction and beautifully renovated homes continue to command premium values. Don't miss your chance to invest in the future of Downtown Winter Garden!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Corey Cannon (407-615-0215)

Remarks: This beautifully updated 3 bedroom, 1 bathroom home offers modern comfort at an unbeatable value. With 814 sq ft of living space, it features a brand-new roof, newer A/C, fresh interior and exterior paint, a fully remodeled kitchen with a new fridge, and brand new remodeled bathrooms—giving you peace of mind and a move-in ready lifestyle. Located in the heart of Winter Garden, this home is close to shops, dining, and entertainment, all while being tucked into a welcoming neighborhood. Whether you’re a first-time buyer, downsizing, or looking for an investment property, this gem checks all the boxes. Don’t miss this rare opportunity to own a beautifully renovated home in one of Central Florida’s most sought-after communities—for less than $300K! **All measurements must be verified by the buyer.** FHA buyers are welcome!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Christopher Sukhram (407-558-8460)

Remarks: Perfectly positioned on a quiet cul-de-sac in the sought-after Oakland Hills community near historic downtown Winter Garden. This FULLY FURNISHED and thoughtfully designed custom home on a single level, combines timeless modern farmhouse architecture with today's finest technology and craftsmanship. Curb appeal abounds with a classic mix of Hardie board siding and brick, anchored by a large, shaded front porch glowing with authentic gas lanterns from New Orleans — a true farmhouse welcome. When evening arrives, intentional landscape lighting accentuates the lush grounds and craftsmanship evident in every corner. Inside, the statement grand great room makes an unforgettable first impression with soaring 22+ foot ceilings, exposed beams, and dormer windows that fill the room with natural sunlight from morning to evening. Throughout the home, ten-foot ceilings, custom moldings and baseboards, LBU lighting with LED bulbs, and natural hardwood floors (in all but the media room) keep the ambiance light and welcoming. The heart of this custom residence is a true chef's kitchen: Monogram appliances, two oversized islands, a 36" gas range, paired with Moen and Kohler fixtures, all wrapped in custom Wellborn cabinetry with soft-close doors and drawers. A back second kitchen — the ultimate working pantry — adds double ovens, a microwave, a commercial Keurig, and abundant storage for effortless entertaining. Just off the main living space, a warm and welcoming library/office with custom-built bookcases and Zoom room offers a quiet retreat. The generous primary suite is a luxurious escape, complete with a spa-inspired bathroom centered around an oversized Kohler clawfoot tub. Two additional guest suites offer king beds and ensuite baths with double vanities, while a thoughfully designed bunk room with its own private bath means every guest feels right at home. Movie nights reach a new level in the dedicated media room with a 4K projector and Atmos surround sound. Outdoor living takes center stage on the expansive covered lanai, where a fully equipped summer kitchen with 36" Coyote natural gas grill, exhaust vent, steel doors, and retractable screen — makes alfresco entertaining effortless. Beyond, a private backyard with a heated pool and natural gas fire pit invites year-round gatherings that won't be forgotten. Enjoy smart home living at it's best with a Crestron home automation system, WattBox® UPS battery, Uniview Turret security cameras monitored by Future Home Integration, plus whole-home Wi-Fi with service options from Spectrum or Quantum. Custom closets, two laundry rooms, and an oversized three-car garage with an incredible amount of extra storage. Oakland Hills is an exclusive enclave of just 17 custom homes, minutes from the West Orange Trail, downtown Winter Garden, and Winter Garden Village. Perfectly positioned with easy access to the Turnpike, SR 429, and SR 408, it makes commuting, theme park visits, and airport runs a breeze. Schedule your private tour today and experience everything this meticulous one-of-a-kind home has to offer!

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Julie Bettosini, Pa (321-689-9594)

Remarks: 131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three-story home offers 3 bedrooms, 3.5 bathrooms, and 1,906 square feet of heated living space. Each bedroom features its own en-suite bathroom, providing privacy and comfort for all. This home includes an elevator that conveniently connects the first and second floors along with an oversized rear-entry two-car garage, a small balcony, and a convenient in-unit laundry closet. Inside, the open-concept main level boasts a gourmet kitchen with stainless steel appliances, a large island, and ample cabinetry. Premium finishes throughout include wood-look tile flooring, crown molding, and plantation shutters. The primary suite offers generous closet space and a spa-inspired bath with dual vanities, a soaker tub, and a walk-in shower. Thoughtful design and quality craftsmanship combine with a prime location just steps from downtown Winter Garden’s restaurants, shops, and the Plant Street Market, making this property an exceptional opportunity to enjoy upscale living in one of the area’s most sought-after neighborhoods.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: Welcome home to this beautiful 4-bedroom, 2-bathroom single-family residence located in the heart of Winter Garden! Spanning 2,199 square feet of living space, this home features a highly desirable split floor plan with soaring volume ceilings that create an open and airy atmosphere. The spacious layout includes a welcoming living area, laminate flooring in the bedrooms, and an attached 2-car garage. Step outside to your private, screened-in patio overlooking an expansive 8.125-square-foot lot, offering plenty of space for outdoor entertaining or relaxation. Nestled in a quiet neighborhood, this property offers unbeatable convenience. Enjoy fast access to SR 429, the Florida Turnpike, and charming historic downtown Winter Garden. Don't miss the opportunity to own a piece of this highly sought-after community—schedule your private tour today!

Listing is courtesy of: ACTION PLUS REALTY SERVICES (407-905-5774)

Listing Agent: Luis Bello (321-436-9099)

Remarks: Virtually Staged. Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully updated residence showcases more than $500,000 in improvements, creating a move-in-ready experience for the next owner. From the moment you arrive, you'll appreciate the extensive upgrades throughout the home, including porcelain tile throughout the main living areas on the first floor, engineered white oak hardwood flooring throughout the second level, a custom wood and iron staircase, upgraded cabinetry, quartz countertops, designer finishes, and a beautifully appointed kitchen featuring premium KitchenAid appliances, a gas cooktop, and custom soft-close cabinetry. Designed for both everyday living and entertaining, the backyard is a true showpiece. Enjoy a resort-style saltwater pool and spa, gas-heated for year-round enjoyment, expansive outdoor living areas, and a fully equipped summer kitchen featuring premium Blaze appliances. Electric screens allow you to enjoy outdoor dining and entertaining comfortably while taking in the peaceful lakefront setting and stunning sunset views. Boating enthusiasts will appreciate the private dock complete with a 5,000-pound boat lift, offering direct access to Lake Apopka, one of Florida's largest lakes. With more than 30,000 acres of open water to explore, the lake offers endless opportunities for boating, fishing, watersports, and unforgettable sunset cruises. Known for its trophy bass fishing, abundant wildlife, and expansive waterfront views, Lake Apopka provides a rare opportunity to enjoy true lakefront living with the freedom and space that few Central Florida lakes can offer. This property delivers the waterfront lifestyle Florida is known for. Additional highlights include a convenient first-floor bedroom, a second-floor laundry room, solar panels that will be paid off at closing, natural gas service, a Culligan water filtration system, dual pool pumps, and city sewer, a significant advantage for a waterfront property. Ideally located just minutes from Downtown Winter Garden, shopping, dining, and major roadways, this exceptional lakefront residence offers the perfect balance of luxury, recreation, and everyday convenience.

Listing is courtesy of: ALIGN REAL ESTATE LLC (305-389-2922)

Listing Agent: Tiffany Pantozzi (407-955-9716)

Remarks: Under contract-accepting backup offers. Back on the market! Mediterranean Elegance Meets Lakeside Luxury on John's Lake! Welcome to your own private paradise, nestled in the exclusive, small gated waterfront enclave of John’s Cove. Step inside this gorgeous, custom-built estate and be instantly captivated by soaring 25-30 foot vaulted ceilings, a dramatic winding staircase, elegant Roman-style arches and columns and abundant natural light. In this spectacular 4-bedroom, 4.5-bath pool home you'll enjoy breathtaking views of the pristine, spring-fed John’s Lake from almost every room, delivering all the scenic beauty without the hassle, upkeep, or worries of lakefront maintenance! A formal dining room and formal living room, both with soaring ceilings, adorn each side of the grand staircase. The heart of the home is a gourmet kitchen featuring brand-new stone tile backsplash, granite countertops, abundant wood cabinetry with crown molding, and two islands, both with sinks and bar seating. The chef of the family will appreciate the newer stainless steel appliances, 5-burner gas cooktop with a pot filler and convenient “prep” sink in addition to a separate double-bowl sink. Enjoy sipping coffee while watching the sun rise through the trees, over the water in the cozy breakfast nook, which perfectly frames your gorgeous pool and lake views. The kitchen overlooks the spacious family room anchored by a custom mantel gas fireplace with French doors to the outdoor kitchen. The luxurious first-floor primary suite is a true retreat, offering tranquil views with private access to the outdoor pool patio. It features his-and-her walk-in closets—one uniquely doubling as a highly secure panic/safe room with a steel door and 12-inch concrete walls! The en-suite spa bath features an oversized tub, a circular walk-in shower, and dual vanities. A versatile fourth bedroom downstairs is conveniently located across a full bath, and provides excellent additional living space that can easily transition into a home office, den, or flex room. Upstairs, you will find two generously sized bedrooms—including a private suite with its own full bathroom—both boasting access to a second-floor balcony with sweeping treetop lake views. A splendid column-clad catwalk leads to the stadium-seating theatre room (which can easily serve as an additional home office or den) and a full hallway bath complete the second floor. Step outside to your spectacular outdoor oasis. The expansive screened patio encloses a resort-style heated pool and spa (built in 2017) complete with a sun shelf, fountain, and elegant pavered decking. Entertain with ease at the outdoor summer kitchen featuring a built-in grill, countertop space, and a mini-fridge. This home has a fresh coat of exterior paint, newer AC, new water heater, and direct lake access is just steps away via the private community boat ramp. Water enthusiasts will love the easy access for recreational boating, skiing, tubing, and sport fishing on this sprawling 2,500-acre lake that feels like a chain of lakes. You CAN have it all in this fabulous Florida oasis that feels miles away from it all, yet is just minutes from the Turnpike, SR 429, SR 408, downtown Winter Garden, as well as the best shopping, dining and entertainment in all of Central Florida!

Listing is courtesy of: GILKEY REAL ESTATE (407-712-3111)

Listing Agent: Laura Romot (407-361-1771)

Remarks: Discover this move-in ready 3-bedroom, 2-bathroom CBS construction home in Winter Garden, FL, nestled in the highly sought-after Park Avenue Estates community. Just minutes from downtown Winter Garden, award-winning dining, shopping, and the popular farmers market, this home offers the perfect mix of charm and convenience. Featuring a newer roof, a low HOA, and access to a community pool, you’ll enjoy a relaxed lifestyle in one of Central Florida’s most vibrant neighborhoods. The nearby West Orange Trail is perfect for biking, morning runs, or evening strolls surrounded by Florida’s natural beauty. This move-in ready home places you close to everything, from boutiques and restaurants to top-rated Winter Garden schools. Whether you’re enjoying local amenities or simply relaxing at home, this property provides the ideal opportunity to experience the best of Winter Garden living.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Christian Dyas (407-375-7368)

Remarks: Welcome to 1743 Fullers Oak Loop in Winter Garden, an incredible POOL home built in 2017, featuring high ceilings, functional split floor plan, expansive lanai with outdoor speakers, screened pool, and peaceful greenspace views. Freshly professionally painted inside and out in 2026, this move-in-ready property also includes paid-off solar panels for energy savings. The layout offers flexible living spaces, open gathering areas, a spacious primary suite retreat, and large secondary bedrooms designed for comfortable everyday living and entertaining. The kitchen features a breakfast bar, ample cabinetry, closet pantry, double ovens, and stainless steel appliances while overlooking the family room and pool area. The serene backyard view can be enjoyed from the kitchen, family room, and primary bedroom, creating a seamless indoor-outdoor feel throughout the main living spaces. Additional features include an interior laundry room with a utility sink and built-in cabinetry, 3-car garage, and large paver driveway. This small community has just one entrance, and the HOA also includes cable and internet, adding everyday value and convenience. Just steps away, enjoy direct access to the West Orange Trail for biking, walking, exercise, and more, along with a nearby dog park and The Backyard, a fun outdoor dining option. The trail also leads into Historic downtown Winter Garden, offering local shopping, dining, breweries, the popular Farmer’s Market, and year-round community events. Conveniently located near major roadways, shopping, restaurants, airports, theme parks, and parks, this home combines location, functionality, and outdoor living in one of Central Florida’s most desirable communities. Schedule your private showing today.

Listing is courtesy of: EXIT GLOBAL REALTY (407-725-7180)

Listing Agent: Stacy Wilson (407-970-7892)

Remarks: Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden. Blending modern updates with timeless charm, this move-in-ready residence offers stylish finishes, functional living spaces, and a convenient location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright, refreshed interior featuring contemporary flooring, recessed lighting, updated fixtures, and an open, inviting atmosphere. The fully remodeled kitchen showcases elegant white shaker cabinetry, sleek countertops, stainless steel appliances, and modern hardware, creating a clean and sophisticated space for everyday living and entertaining. The renovated bathrooms feature designer-inspired finishes, including a spacious walk-in shower with stunning marble-look tile, upgraded fixtures, and a modern vanity. Thoughtful updates throughout the home provide a fresh, cohesive look while maintaining comfort and functionality. Outside, enjoy a spacious lot shaded by mature trees, offering room for outdoor entertaining, gardening, pets, or future expansion. Fresh exterior improvements and landscaping enhance the home's curb appeal, while the absence of HOA restrictions provides added flexibility and freedom. Conveniently located near shopping, dining, parks, the West Orange Trail, major highways, and all that Downtown Winter Garden has to offer, this turnkey property presents an exceptional opportunity for homeowners and investors alike. Don't miss your chance to own a beautifully updated home in one of Central Florida's most sought-after communities.

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Short Sale. SHORT SALE APPROVED READY TO CLOSE AND MOVE-IN READY and quietly positioned within a well-established Winter Garden community, this updated 2-bedroom, 2-bath condo offers a NEW ROOF, and an easy, comfortable lifestyle in one of Central Florida’s most desirable areas. Approaching the home, you’ll appreciate the tucked-away cul-de-sac location with paved private streets and sidewalks that create a calm, residential feel. Step inside through the front entrance and you’re immediately welcomed into a bright, open living space where natural light enhances the clean layout and efficient use of square footage. The living room feels inviting and functional, offering enough space to relax, entertain, or simply enjoy a quiet evening at home. Continuing through the home, the upgraded kitchen with GRANITE counter tops, anchors the main living area with modern appliances, ample cabinetry, and practical counter space. Its open connection to the living room allows for easy conversation while cooking, hosting, or enjoying everyday routines, making the space feel connected and intentional. The primary bedroom is set apart as a comfortable retreat, featuring brand-new carpeting and a private en-suite bathroom. The bathroom has been thoughtfully renovated with updated finishes that feel fresh and clean without excess. The secondary bedroom is well-sized and flexible, ideal for guests, a home office, or additional living space, with a second fully updated bathroom conveniently nearby. Throughout the condo, the layout flows efficiently from room to room, offering smart storage, comfortable proportions, and a low-maintenance design well suited for full-time living or long-term ownership. Assigned parking adds convenience, while the community’s shared amenities—including a COMMUNITY POOL—enhance the overall lifestyle. Located just minutes from downtown Winter Garden, residents enjoy close proximity to local shops, dining, farmers markets, and the West Orange Trail. Easy access to major highways makes commuting throughout Central Florida simple, whether heading toward downtown Orlando, major employment centers, or nearby attractions. This location is ideal for buyers exploring Orlando homes for sale or those planning an Orlando relocation home in a walkable, community-oriented area. While not intended as a short-term rental investment, this Winter Garden property represents a strong opportunity within the Central Florida real estate market for buyers seeking comfort, location, and value. Contact us today for a private tour or more details on this exceptional opportunity.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Simi Lakhani (407-408-7393)

Remarks: Large Price Improvement. Downstair location, peace and ease with this updated 2/2 FIRST FLOOR condo in Winter Garden. You will love this condo placement in the rear of the community near the pond with fountain, community pool, rentable clubhouse, basketball courts and NO STAIRS. Enjoy the private setting while sitting on your screened porch with your favorite book or beverage and the frequent visits from the neighborhood ducks. The condo has been updated to include the cabinets, counters, updated bathrooms and tile floors throughout. Move in ready so just grab your things and come on. What's Nearby? ANYTHING you could need or want. Only 1.5 miles from downtown Winter Garden, 2.5 miles to Winter Garden Village, 15 miles to Walt Disney World® and other theme parks, 24 miles to MCO Orlando's International Airport/Brightline highspeed passenger train and just over an hour to dip your toes in salty water and sand on Florida's World Famous Beach in Daytona. Downstair units with perfect location do not come around often so book your private tour today and ask your REALTOR for the video walk through link.

Listing is courtesy of: BONJORN REAL ESTATE (352-394-2112)

Listing Agent: Mendy Bacon (407-383-7213)

Remarks: Welcome to Historic Winter Garden, Florida. NO HOA! Where small-town charm, community, and modern living come together, and you keep more of what's yours with no HOA fees. Built in 2023, this beautifully designed 4-bedroom, 2-bath home with a 1-car garage offers the perfect blend of contemporary comfort and timeless neighborhood character. Start your mornings on the inviting front porch, the ideal spot for coffee, fresh air, and easy neighborhood conversations. Step inside to an open-concept layout that feels bright, spacious, and instantly welcoming, whether you're hosting friends or enjoying a quiet evening in. The modern kitchen impresses with granite countertops, sleek cabinetry, and a generous workspace that flows seamlessly into the main living areas. Laminate flooring throughout the main living spaces adds a clean, low-maintenance finish. Beyond your front door, downtown Winter Garden is just minutes away, a historic district one of Central Florida's most beloved. Spend your weekends at the popular Saturday Farmers Market, dining at local restaurants ranging from cozy cafés to fine-dining establishments, or soaking up the seasonal festivals and community events that give this area its unmistakable energy. Newer construction. Modern finishes. A welcoming, active community. And no HOA. This Winter Garden gem checks every box, so don't miss your chance to make it yours.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Nicole Mickle (407-353-0826)

Remarks: Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and location. Built in 2018, the home features a bright, open-concept floor plan with spacious living areas, a modern kitchen, and plenty of room for both everyday living and entertaining. Step outside and enjoy all the amenities that make Oakland Trails so special, including a resort-style community pool and playground. Outdoor enthusiasts will love being just minutes from the renowned West Orange Trail, offering miles of scenic paths for walking, running, and biking through some of Central Florida’s most beautiful landscapes. Conveniently located near historic downtown Winter Garden, shopping, dining, and major roadways, this home combines small-town charm with everyday convenience. Whether you're relaxing at the pool, exploring the nearby trail system, or enjoying all that the area has to offer, this property delivers the Florida lifestyle you've been looking for.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Brynn Allen (407-617-8963)

Remarks: Under contract-accepting backup offers. PARADE of HOMES-OAKLAND PARK! Experience refined Florida living in the heart of Winter Garden, where timeless architecture, thoughtful design, & an unbeatable location come together in this exceptional custom-built residence. Situated on an expansive corner lot (~1/4 acre) overlooking one of the community’s most beloved PARKS, this four-bedroom (w/ room for a 5th & office), four-bath luxury HEATED POOL home offers privacy, space, & picturesque views. You’re moments from stunning sunsets, a walk by the LAKE, multiple parks & playgrounds, the community clubhouse, & direct access to the scenic WEST ORANGE TRAIL— a 22-mile paved trail ideal for biking, jogging, & casual strolls. From the moment you arrive, the stunning brick-accented front porch sets the tone, offering a welcoming space to relax while enjoying tranquil park views. Inside, rich wood flooring flows throughout the main living areas, complementing the home’s elevated finishes, such as crown molding, wainscoting, trim work, & custom built-ins. The chef’s kitchen is a true showpiece. Outfitted with premium Thermador & JennAir appliances, QUARTZITE counters, custom cabinetry, designer fixtures, a walk-in pantry, & spacious gathering space, this kitchen was designed for both everyday living & elegant entertaining. The adjacent dining & living areas are bathed in natural light, enhanced by multiple French doors that frame panoramic views of the pool and backyard retreat. The indoor-outdoor connection is simply spectacular. Step outside to your private oasis featuring a sparkling resort-style pool (runs with an ozonator) with travertine decking, generous covered lanai, & an outdoor kitchen equipped with a mini fridge & 48 inch griddle. Each of the four bedrooms is generously sized, offering comfort & versatility for family & guests. One generously sized bedroom is downstairs, which has access to the pool & park through French doors. The primary suite serves as a luxurious retreat with a spa-like bath & dual closets, while all four baths (three en-suite) are thoughtfully designed with quality finishes (marble upstairs, quartzite downstairs). Need an elevator? There's space for the addition! A well-appointed MUDROOM adds everyday convenience & organization, seamlessly blending practicality with style. Additional FEATURES: whole house water filtration system, in-ceiling speakers in the living room, the lanai by the pool, & front porch, tankless water heaters, hard wired cameras inside/out, ample storage, landscape lighting, Cat 6 wiring w/ WiFi access points, & an OVERSIZED garage (~2 1/2). Just a short GOLF CART ride away, you’ll find the charm & vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, community connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks. Custom built POOL homes are RARE to market in Oakland Park. Make this DREAM home your reality today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Ashley Boyd (321-209-5540)