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

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: Under contract-accepting backup offers. Welcome to one of Winter Garden's most coveted addresses — nestled in the heart of the Golf Cart District, this beautifully appointed Oakland Park home delivers the Florida lifestyle you've been waiting for. With 4 bedrooms, 3.5 bathrooms, and 3,012 square feet of thoughtfully designed living space, this 2013-built corner lot residence blends everyday comfort with elevated finishes at every turn. Step inside to soaring vaulted ceilings in the family room that create an immediate sense of volume and light. Rich wood flooring flows through the downstairs living areas, complemented by clean ceramic tile and plush carpet in the bedrooms — a seamless combination of warmth and function. The open layout is designed for real living, whether it's a quiet evening in or hosting the people you love most. Outside, brick pavers set the tone for an outdoor living experience that's genuinely special. A large covered back patio creates the perfect setting for morning coffee or evening entertaining, while a classic breezeway connects the home to the garage with both style and practicality. But it's the location that truly sets this home apart. Oakland Park is one of Central Florida's most sought-after communities — complete with two resort-style pools, a beautifully appointed clubhouse, and a dedicated dog park. Step outside your door and hop on your golf cart to access the iconic West Orange Trail, or cruise just minutes into the heart of Downtown Winter Garden, where Plant Street Market, award-winning restaurants, rooftop bars, and a thriving local food scene await. This is the rare home where community, convenience, and character all converge.

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

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

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: Experience the Best of Downtown Winter Garden Living!!! Perfectly positioned in the highly sought-after Heritage at Plant Street, this exceptional corner-unit townhome offers the ultimate blend of luxury, convenience, and low-maintenance living—all within Winter Garden's coveted Golf Cart District and with direct access to the acclaimed West Orange Trail. Built in 2018 by M/I Homes and lovingly maintained by its original owners, this beautifully upgraded 3-bedroom, 2.5-bath residence with a 2-car epoxy-finished garage showcases thoughtful design, premium finishes, and one of the community's most desirable locations. The HOA covers exterior maintenance—including the roof and landscaping—so you can enjoy a carefree lifestyle. The coveted corner location offers abundant natural light, added privacy, a grassy side yard perfect for pets or play, and guest parking just steps from the front door. Inside, the popular Windham II floor plan features soaring ceilings, an open layout, and a bright flex room ideal for a home office, playroom, or second living area. The designer kitchen impresses with GE Profile slate appliances, a natural gas cooktop, stacked convection wall oven and microwave, 42-inch cabinetry, Silestone countertops, tile backsplash, under-cabinet LED lighting, and an oversized island with breakfast seating. It opens seamlessly to the dining area and great room, where corner windows fill the space with natural light. Large-format ceramic tile runs throughout the first floor. A spacious laundry room with a full-size washer and gas dryer, plus oversized under-stair storage, adds everyday convenience. Upstairs, the private owner's suite features a walk-in closet and an elegant bath with a dual Silestone vanity and a tiled walk-in shower with seamless glass enclosure. Two additional bedrooms share a stylish full bath with coordinating finishes. French doors with built-in blinds lead to your private screened brick-paver courtyard with covered and open seating areas overlooking the grassy side yard. The rear-entry garage includes screened sliders that create a refreshing cross breeze into the courtyard. Additional upgrades include ENERGY STAR® Low-E windows, energy-efficient HVAC, whole-home water softener and conditioner, under-sink instant hot water, premium whisper-quiet ceiling fans with remotes, faux wood blinds, and a timeless neutral interior palette. The townhome was used as a second/vacation home so can be sold fully furnished!!! Residents enjoy a community pool and dog park, all just minutes from the award-winning restaurants, boutiques, breweries, farmers market, and year-round events of historic Downtown Winter Garden. Rarely does a corner-unit home of this caliber become available. Enjoy designer upgrades, abundant natural light, and true lock-and-leave convenience in one of Central Florida's most desirable downtown communities. Hop on your golf cart, explore the West Orange Trail, and experience the vibrant Winter Garden lifestyle.

Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)

Listing Agent: Mark Hide (407-832-7332)

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: Price Reduction! Owner says SELL!! Welcome home to this tastefully renovated 2/2 second floor condo located in the sweet spot of bustling Winter Garden Florida USA. Just about everything was updated in 2024 to include the kitchen with beautiful stainless appliances, granite countertops, cabinetry & lighting. The owner has spent in excess of $60,000 on these renovations. Fresh paint throughout. New laminate flooring & baseboards in 2025, there is no carpet. The split bedroom layout is perfect for privacy while the primary bedroom is spacious with a walk in closet and ensuite bathroom. The 2nd bedroom includes a custom built closet and shelving providing ample storage options. The 2nd bathroom is adjacent to the 2nd bedroom. The washer and dryer hookups are located just off the kitchen providing easy access. This unit is conveniently located near the center of the community, just steps from the clubhouse, pool and mail areas. It also includes 2 designated parking spots just outside the unit. Windtree Gardens is situated in a fabulous area of Winter Garden providing quick access to all major roadways including the turnpike, 408 and 429. It is also just minutes from Historic Downtown Winter Garden including all that Plant Street has available, boutique shops, outdoor dining, Award Winning Farmer's Market, the very popular West Orange Trail and splashpad for the little ones. Also just a short drive to Winter Garden Village at Fowler Grove with numerous dining and retail options. Bonus..there is a Starbucks near the entrance to the community. This unit is ideal for a starter home, a second home or an investment property. Schedule your showing soon as this one is sure to fly off the shelf.

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

Listing Agent: Jeff Dodds (407-937-9521)

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)

Remarks: Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor and another upstairs, making it ideal for multigenerational living, extended guests, or added privacy. Step inside to soaring high ceilings and an open-concept floor plan filled with natural light. The heart of the home is the gourmet gas kitchen, featuring 42-inch cabinetry, elegant quartz countertops, a large center island, built-in convection oven, stainless steel appliances and premium finishes throughout. A dedicated beverage station with a separate bar refrigerator provides the perfect space for entertaining guests. Upstairs, you'll find an expansive loft that offers endless possibilities as a media room, game room, home office, or additional living space. Outside, enjoy your own private backyard retreat complete with a sparkling pool, ideal for relaxing or hosting family and friends year-round. The garage is equipped with overhead storage shelving, providing ample space to keep seasonal items and equipment neatly organized. With its spacious layout, upscale finishes, abundant storage, and exceptional amenities, this beautifully maintained home is truly move-in ready and offers the perfect combination of elegance, functionality, and Florida living at its finest. This community features a pool pool, nature trails, playground, dog park, and private dock. Conveniently located near shopping, dining, main highway and more.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: PRICE IMPROVEMENT! Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the interiors are bright and inviting. Recent enhancements include new exterior paint (2026), a tankless water heater (2026), and a added ensuite bathroom (2026) making two primary suites on the second floor. Generous storage is thoughtfully integrated with expansive closet space, while a whole-home water softener and purification system, including an under-sink filter, ensures elevated everyday comfort. At the heart of the home, the gourmet kitchen is both functional and beautifully appointed, featuring dual sinks, a dedicated prep island, and upgraded soft-close cabinetry. The oversized three-car garage provides ample room for vehicles, storage, or recreational needs. Outdoors, the lifestyle truly unfolds. A recently resurfaced covered boat dock—complete with lift, lighting, fan, and sink—offers direct access to one of Florida’s largest spring-fed lakes, part of the Harris Chain and extending to the St. Johns River and Atlantic Ocean. The expansive grounds are enriched by mature, fruit-bearing trees including mango, avocado, star fruit, and citrus, creating a lush, private retreat. Surrounded by natural beauty, the property attracts an impressive array of wildlife. Unforgettable sunrises and sunsets can be enjoyed from multiple vantage points, including the living spaces, patio, dock, and three north-facing bedrooms with water views. This is a home that seamlessly balances elegance and ease—offering a rare opportunity to experience serene waterfront living in one of Winter Garden’s most iconic settings.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: Virtually Staged. Welcome to ISLAND POINTE, one of Winter Garden’s most desirable communities, ideally located in the area's sought-after GOLF COURSE DISTRICT, just minutes from Historic Downtown Winter Garden and the vibrant Plant Street corridor. Here, you can embrace the true Florida lifestyle—hop on your golf cart and enjoy easy access to award-winning restaurants, boutique shopping, breweries, the famous Winter Garden Farmers Market, and year-round community events. This beautifully maintained CUSTOM BUILT home offers nearly 3,000 square feet of thoughtfully designed living space, featuring 4 spacious bedrooms, 3 full bathrooms, a DEDICATED OFFICE, and a highly functional open floor plan perfect for today's lifestyle. From the moment you enter, you'll appreciate the architectural character of the elegant rounded corners, soaring living spaces, and abundant natural light. Designed with both privacy and functionality in mind, the home features a highly desirable three-way split bedroom floor plan, making it ideal for families, guests, multigenerational living, or those who work from home. The dedicated office provides the perfect remote workspace while maintaining separation from the bedroom wings. At the heart of the home is a chef-inspired kitchen designed for entertaining, featuring an OVERSIZED BREAKFAST BAR, DOUBLE PANTRIES, abundant cabinetry, and generous prep space. The kitchen flows seamlessly into the main living area, where a stunning three-panel pocket sliding glass door opens the home to the outdoors, creating the ultimate indoor-outdoor Florida lifestyle. The spacious primary suite serves as a private retreat, while the secondary bedrooms are thoughtfully positioned throughout the home for maximum comfort and privacy. Outside you will find your private backyard retreat, complete with a covered lanai and a convenient outdoor shower, perfect after gardening, outdoor activities, or future pool days. The FULLY FENCED backyard offers plenty of room to design and build the custom pool of your dreams, while still leaving ample space for outdoor entertaining, pets, play areas, or gardening. Major updates include ROOF(2019) WATER HEATER(2021) and two HVAC systems, ensuring comfort and efficiency throughout the home. Car enthusiasts will love the OVERSIZED DRIVEWAY with a 2-car garage and extended space specifically designed to accommodate a golf cart or even just extra storage making it easy to take advantage of Winter Garden's golf-cart-friendly lifestyle. Combining a prime location, flexible floor plan, major system updates, and room to create your own backyard oasis, this home offers an exceptional opportunity in one of Winter Garden's most sought-after neighborhoods. Schedule your private showing today.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Nicole Dege (443-404-9293)