Homes for Sale Near West Orange High in Winter Garden - 94 homes

Remarks: One or more photo(s) has been virtually staged. NEW ROOF (2025) ~ TWO NEW A/C UNITS (2024) ~ and a NEW WATER HEATER (2024) headline this exceptional LAKEFRONT ESTATE on Black Lake, where recent RENOVATIONS and thoughtful design have transformed the home into a must see retreat designed to impress! Ideally situated behind the gates of Bay Isle in Winter Garden, this remarkable home is the cherry on top of 6.44 ACRES surrounded by lush mature trees and sweeping LAKE VIEWS, creating a peaceful personal oasis just minutes from everything. A paver driveway and COURTYARD ENTRANCE invite you into the residence, complemented by a split 3-car garage and beautiful architectural details that set the tone for what awaits inside. Spanning OVER 4,000 SQ FT of curated living space, the home blends timeless craftsmanship with a fresh, modern edge. Sleek PORCELAIN TILE and rich WOOD FLOORS flow throughout, while intricate DESIGN WORK and CUSTOM BUILT-INS add character and sophistication from floor to ceiling. Designed with both everyday living and entertaining in mind, the layout offers MULTIPLE LIVING AREAS & FLEX SPACES, and formal living and dining rooms, all positioned to maximize NATURAL LIGHT and capture the home’s breathtaking water views. Walls of windows pull the outdoors in, creating a light-filled atmosphere that highlights the beauty of the surrounding landscape! At the heart of the home, the GOURMET KITCHEN delivers everything a home chef could want and more. Outfitted with a gas range, gas oven, waterfall island, dual pantries for abundant storage, and a rare Doyon Etuve Proofer, the space is as functional as it is impressive, easily supporting everything from quiet dinners to large gatherings. Your MAIN FLOOR OWNER’S SUITE is a true retreat with tranquil views of Black Lake, a sitting area, a dedicated dressing space, and a beautifully designed modern en-suite bath that feels straight out of a home magazine. Throughout the rest of the home, additional bedrooms and flexible spaces offer endless possibilities for guests, offices, hobbies, or creative pursuits. Step outside and the lake lifestyle truly comes to life. MULTIPLE OUTDOOR LIVING SPACES invite you to relax, entertain, or simply take in the scenery, while the PRIVATE DOCK on Black Lake makes it easy to bring your boat and enjoy everything lakefront living has to offer. Despite the sense of seclusion, this home remains incredibly convenient to daily life. Shopping, dining, and major roadways including SR-429 are just minutes away, placing you close to Winter Garden’s vibrant charm, area attractions, and world-famous theme parks. Elegance personified, this extraordinary home delivers the privacy, style, and space you have been searching for. Bring your boat, embrace the lake life, and discover the lifestyle waiting for you in Bay Isle!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. One or more photos have been Virtually Staged. I'm excited to share details about a well-appointed executive home in the highly sought-after Deerfield Place Subdivision. This rare and spacious residence features 5 bedrooms and 4 bathrooms, encompassing over 3,400 square feet. The downstairs area includes a bedroom and full bath, a formal dining room, a formal sitting room, and a generous family area. The home also boasts beautiful wood laminate flooring throughout, an oversized kitchen, and a huge upstairs bonus room. The private, expansive master suite offers a comfortable sitting area and an oversized, spa-like bath, providing ample space for relaxation. Recent upgrades to the home include a new roof in 2020, a new refrigerator, and new laminate flooring in both the dining room and formal living area. The location is truly exceptional, offering convenient access to the Winter Garden Village Shopping District and the charming Winter Garden Downtown area. Please note that room sizes are approximate. This is truly a wonderful area to call home.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Barry Stephens (407-547-6500)

Remarks: Gorgeous pool home in Cypress Reserve featuring a private office, loft/game room, theater room, and over 4,100 sq ft with a 3-car garage. This stunning 4-bedroom, 3.5-bath residence offers thoughtfully designed living space that blends elegance, comfort, and functionality—delivering an exceptional lifestyle in one of Winter Garden’s most sought-after communities. From the moment you enter, soaring 20-foot ceilings, expansive windows, and an abundance of natural light greet you. A grand staircase and balcony create a striking focal point, anchoring the open-concept living area. The entry features formal living and dining spaces, along with a private office with French doors—ideal for working from home. At the heart of the home is a beautifully appointed gourmet kitchen, designed for both everyday living and entertaining. Highlights include a gas cooktop, built-in convection oven and microwave, pot filler, elegant backsplash, oversized center island, and extended cabinetry with ample storage—all overlooking the main living area and pool. The spacious primary suite is conveniently located on the main floor and features tray ceilings and a versatile sitting area—ideal for a secondary office, fitness space, or private retreat. The oversized custom walk-in closet is a standout, while the luxurious primary bath offers a large walk-in shower with a rain shower head, dual vanities, a soaking tub, and abundant cabinetry. Upstairs, you’ll find a generous loft, a dedicated media/theater room, and three additional bedrooms, including a Jack-and-Jill layout with walk-in closets. The flexible floor plan offers endless possibilities, with the loft or media room easily convertible into an additional bedroom. Step outside to your backyard retreat featuring a screened-in, heated saltwater pool with sun shelf, an expansive paver patio, and plenty of space for outdoor entertaining or relaxing in the Florida sunshine. With HOA green space behind the home, you’ll enjoy a more open feel and peaceful views. Additional highlights include 8-foot doors and high ceilings throughout, a tankless water heater, a spacious laundry room with utility sink and storage, oversized under-stair storage, and beautiful curb appeal with low-maintenance landscaping. Ideally located within walking distance to highly rated SunRidge Elementary and Middle School, and just minutes from downtown Winter Garden, Winter Garden Village, SR 429, Florida’s Turnpike, I-4, Downtown Orlando, Orlando International Airport, and nearby attractions including Walt Disney World. Outdoor enthusiasts will love the proximity to the West Orange Trail and Tucker Ranch Recreation and Nature Complex, offering over 300 acres of scenic trails, green space, and outdoor recreation. Residents of Cypress Reserve also enjoy a community pool and playground with a low HOA. This exceptional home truly has it all—luxury, space, versatility, and an unbeatable location. Schedule your private showing today!

Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)

Listing Agent: Deb Schroeder (407-234-2256)

Remarks: You'll fall in love with this ONE STORY, Beautiful and Comfortable Winter Garden POOL home Featuring 4 Bedrooms, 2.5 Bathrooms, and Approximately 2200 Sf of Living Space! The saltwater pool is fairly new, added in 2020, with Pebbletech surface and screen enclosure, just off the covered Lanai. Inside the fenced back yard is also a large pavers area for relaxing at your firepit. The home has amazing amenities: 18" Ceramic tile floors in the living areas, Laminate Wood flooring in all bedrooms, Mosaic Inlays, and French Doors to the Formal Dining Room (currently used as an office) and also to the Formal Living room or Den. The Gourmet Kitchen is a focal point that includes Custom Fans, Pendant Lighting, and Volume Ceilings and comes complete with All Stainless Steel Appliances (Smart Refrigerator, Under Counter Microwave), a Gas Range, Wall-mount pot filler, Granite Countertops, 42" Wood Cabinets, Huge Center Island, Decorative Backsplash, and Large Eat-in area with Bench Seating. The Family Room open to the Kitchen is accented with Natural Stacked Stone, Wall Sconces, A Napoleon Wall electric Fireplace and more. AT&T is currently installing Fiber in the neighborhood, i.e., bandwidth to get 1G will be low priced and provide amazing internet connections! This great home is located less than a mile from West Orange High School and walking distance to YMCA. Enjoy the nearby Winter Garden Village shopping and restaurants. Easy commute via the Turnpike and Toll Roads to Downtown Orlando, Disney, Universal, and Orlando airport. Call to see it today!

Listing is courtesy of: WATSON REALTY CORP (407-298-8800)

Listing Agent: Lois Ann Cox, Pa (407-666-8452)

Remarks: Welcome to beautiful Winter Garden. Check out this exceptional 5-bedroom, 3-bathroom home is located in a gated community that blends comfort with a friendly neighborhood atmosphere. Thoughtfully designed, the home features four bedrooms upstairs and a flexible downstairs bedroom ideal for guests or a home office. The spacious primary suite serves as a private escape, complete with a soaking tub, separate shower, and ample room to relax. Upstairs, two expansive loft areas provide endless possibilities—perfect for a home gym, media room, play space, or additional living area. The main level boasts formal living and dining rooms, along with a large family room that opens through sliding doors to a private pool retreat with two paved seating areas, ideal for entertaining or unwinding. An open floor plan, elegant dual-entry wooden staircase, and stainless steel appliances add to the home’s appeal. Offering generous space, charming details, and a peaceful yet convenient location, this home captures the best of Florida living—schedule your showing before it’s gone.

Listing is courtesy of: HP GLOBAL REALTY LLC (407-925-6780)

Listing Agent: Heron Patel (407-925-6780)

Remarks: One Photo has been virtually staged with furniture. You found it!! Beauty in Winter Garden! Sought after location near downtown Winter Garden! This Windtree 2/2 condo on the 2nd floor has been totally & BEAUTIFULLY REMODELED in 2026 as follows! BRAND New Wood laminate flooring in living room & bedrooms. Kitchen has BRAND NEW farmhouse porcelain sink with floating butcher block shelves, shaker moss cabinets with brushed gold handles and faucet & exquisite quartz counter tops with marble herringbone backsplash. BRAND NEW Frigidaire stainless steel appliances. 3k in upgrades for recessed lighting. BRAND NEW Frigidaire Stackable washer & dryer with convenient according door being installed as well! Unit has own private storage under stairs (approx. 4X9 perfect for bicycles etc.) Community Pool & basketball court. Easy access to 408,429, FL. Turnpike, Disney, Universal and downtown Orlando.

Listing is courtesy of: WATSON REALTY CORP (407-298-8800)

Listing Agent: Rick Evans, Ii (407-538-9295)

Remarks: Enchanting newly built home in Avalon Ridge with a private pool, located in one of the most desirable areas of Winter Garden. This beautiful residence has been thoughtfully designed and features 4 bedrooms with carpet flooring, 3 full bathrooms, and a perfect blend of modern space, functionality, and elegant finishes. The living area features sliding glass doors that open to the outdoor space and private pool, creating the perfect setting for entertainment and relaxation. The spacious living room flows seamlessly into a large kitchen equipped with modern cabinetry, stainless steel appliances, elegant countertops, and a generous center island. The primary suite offers a spacious bathroom with dual sinks, a large walk-in closet, and a comfortable walk-in shower. The three additional bedrooms provide plenty of space for family members or guests. The three-car garage offers ample room for vehicles, storage, or even a workspace. Ideally located in a rapidly growing area, just minutes from major highways, shopping centers, restaurants, and top-rated schools. Don't miss this opportunity—schedule your showing today!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Jennifer Olmeda (407-547-9242)

Remarks: On a quiet street, under Canopy of oak trees, residents enter the community’s gated entrance into a secluded community of 49 luxury homes. Situated on a corner lot the SANIBEL model home aka “The Castle” that won the Excel Award for THE BEST MODEL IN FLORIDA. It is a 4BR/ 4.5 Ba/ 3-car garage. This beauty comes with large entertainment areas inside and out. On the 1st floor you’ll find : Wine Cellar, Jr. Owner’s Suite, Flex/Office & a Guest Bath. Magnificent Chef’s kitchen, at the heart of the house, and features 42” cabinetry with second-tier upper lighted hutch stack for oven space. The cabinet-front door to the pantry eloquently blends with the cabinetry of the entire kitchen. 2nd Floor, the Owner’s Suite master bedroom w/balcony access. Also on this level is a large gathering room, 2 more bedrooms w/en-suite baths & large laundry room. Stunning Oasis backyard with a resort style salt-water pool & spa with a summer kitchen under a covered pergola. Built in surround sound In and outside. Just a few minutes from Plant St. Winter Garden Downtown, Winter Garden Village Shopping, Disney World, and toll road access to Downtown Orlando. This is a true Owner’s retreat.

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

Listing Agent: Christian Ngoie (407-705-7525)

Remarks: PRIME Winter Garden location off Hardwood Marsh and Avalon! It’s not often a home hugs you when you walk through the door, the hint of warmth through the window and the enveloping feeling of home. A true place of stillness that is so hard to find nowadays. The Hawthorne model is really the perfect floor plan! With space for everyone still managing to embody an inviting coziness with over 3,500 sq ft of living space for you, your family…an unexpected guest! A quaint entry with 2 areas for an office, formal living opens up to a 2-story ceiling in the family room with adjacent kitchen! A large island has seating and room for a full size dining table in the breakfast nook! An abundance of windows and sliding glass doors reveal a lovely view of the tropical foliage. Enjoy cooking while watching movies keeping everyone together! The thoughtful design gives ample prep space and tons of cabinet storage! This perfect entertaining area spills into the oversized screened lanai that can be enjoyed year round with an array of fruit trees and a natural privacy from the mature landscape. The primary suite is on the first floor ensuring you can enjoy this home even into your golden years! A relaxing escape with back yard views, ensuite bath with large soaking tub, shower, dual vanities and 2 walk-in closets! Again, storage is not an issue in this home! On the second floor, stairs lead to a huge loft/bonus room that peers over the family room with a half wall that aids in noise reduction. Want a more open feel? Check out Etsy’s decorative railings to personalize your loft! Built-in character ensures many creative ways to utilize the space! This upstairs is “cart wheel” worthy and the options are endless! The bedrooms are spread apart giving every occupant their own area! A centrally located study/art nook even has an opening to the downstairs so you never miss the words "dinner's ready"! This fantastic layout allows you to fulfill your every wish for not only a beautiful, but organized space! No more trying to make things work, because it all fits! They say #1 rule in buying real estate is LOCATION & this community of well manicured lawns ensures your biggest investment is a good one! You can still find that hometown feel you see in movies, with the weekly Farmer's Market in Historic Downtown, soccer and baseball fields bustling on Saturday mornings! Monthly and seasonal events are also abundant and so fun! Pop over to Epic or Disney for the afternoon or enjoy delicacies from around the world at Epcot! All just a short drive from home! The house across the street recently sold for 870k!

Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)

Listing Agent: Autumn Makin (352-455-0044)

Remarks: One or more photo(s) has been virtually staged. One or more photos are virtually staged. Location. Luxury. Architectural character. Welcome to The Sanibel, affectionately known as “The Castle,” an award-winning home just minutes from the charm and energy of Historic Downtown Winter Garden. This stunning residence blends timeless Italian-inspired architecture with modern comforts, creating a home that feels both elegant and inviting. From the moment you arrive, the home makes a memorable first impression with its arched wood double doors, custom soffit lighting, and classic concrete tile roof. Step inside and you’re greeted by soaring ceilings, detailed beams, and crown molding that add warmth and sophistication to the open-concept living spaces—perfect for both everyday living and entertaining. The gourmet kitchen is designed to impress, featuring premium KitchenAid appliances, a natural gas cooktop, built-in refrigerator, 42” custom cabinetry, a hidden walk-in pantry, and a reverse osmosis water system. Whether hosting guests or enjoying a quiet night at home, this kitchen is the heart of it all. The first floor offers exceptional flexibility with a private office and a Junior Owner’s Suite—ideal for guests or multi-generational living. Upstairs, the primary suite becomes your personal retreat with a unique round spa-inspired bathroom, oversized walk-in closet, wet bar, and access to a private balcony. Two additional en-suite bedrooms, a loft, and an upstairs laundry room complete the second level. Step outside and enjoy multiple spaces designed for relaxing and entertaining, including Trex-decked balconies, a summer kitchen, and a peaceful fountain feature. Additional highlights include surround sound wiring, a whole-home generator, and thoughtful upgrades throughout the home. Beyond the property itself, the location truly sets this home apart. You’re just minutes from Downtown Winter Garden’s award-winning farmers market, vibrant restaurants, charming boutiques, scenic parks, and top-rated schools—with easy access to major highways for commuting throughout Central Florida. Recognized as Florida’s Best Model Home by the SEBC Excel Awards, The Sanibel offers a rare opportunity to own a home that combines architectural distinction, luxury features, and an unbeatable Winter Garden lifestyle. Note: One image includes a virtually added pool to illustrate potential backyard possibilities.

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

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Under contract-accepting backup offers. Welcome to this charming and beautifully updated 3-bedroom, 2-bath bungalow located minutes from the heart of highly desirable Winter Garden! This move-in ready home offers the perfect blend of character, comfort, and modern upgrades—including a brand-new roof for peace of mind. Step inside to discover a warm and inviting layout with stylish updates throughout, creating a light and airy feel that’s perfect for both everyday living and entertaining. The cozy bungalow design offers functionality and charm, making it an ideal primary residence, second home, or investment opportunity. Living in Winter Garden means enjoying one of Central Florida’s most sought-after communities, known for its historic downtown, vibrant lifestyle, and strong sense of community. Just minutes away, you’ll find the award-winning Winter Garden Farmers Market, held every Saturday and featuring over 100 vendors, live music, and a lively, family-friendly atmosphere . Stroll along the charming brick-lined streets of downtown, filled with boutique shops, local dining, and cultural attractions. Don’t miss your opportunity to own this adorable, updated bungalow in one of Central Florida’s most beloved communities—schedule your private showing today!

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

Listing Agent: Tara Heard (407-637-4634)

Remarks: Short Sale. 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: Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Step into the Imperial by Pulte Homes, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom home with a 2-car garage offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring 42” soft-close cabinetry, striking quartz countertops and decorative tile backsplash. Whirlpool stainless steel appliances, including a built-in natural gas cooktop and a refrigerator, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, enhancing the flow of indoor-outdoor living. The first floor also offers a convenient powder room, perfect for guests. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and a bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room with utility sink simplifies everyday tasks. Beautiful wood-look luxury vinyl plank flooring is found throughout the main living areas of the first-floor, at the stair case, and first floor bedroom, while plush, stain-resistant Shaw carpet can be found throughout the upstairs bedrooms and loft, and tile complements the bathrooms and laundry room. Designer-curated finishes elevate every corner of this home, including pendant light pre-wire and under cabinet lighting in the kitchen, brushed nickel plumbing fixtures and hardware, 2” faux wood blinds, and Whirlpool washer and dryer enhance the home's style and comfort. This home is equipped with a smart thermostat, smart doorbell, and LED downlights, ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!

Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)

Listing Agent: Adrienne Escott (407-250-9131)

Remarks: THE BEST OF AVALON RIDGE. FULLY UPGRADED. DESIGNER-CURATED. UNMATCHED. Welcome to one of the most exceptional residences in Avalon Ridge, a 2024-built estate that sets the standard for luxury living. Offered at $2,200,000, this is not just another home in the neighborhood, it is the benchmark: the most upgraded, most refined, and most thoughtfully designed. Spanning a grand two-story layout, this residence offers 6 bedrooms, 5 full baths, and 2 half baths, seamlessly blending modern sophistication with elevated functionality. From the moment you enter, you’re met with striking architectural presence, enhanced by custom high-end carpentry, bespoke built-ins, designer vanities, and fully customized walk-in closets; every inch curated with intention. The home is grounded by premium upgraded flooring throughout and anchored by a true gourmet kitchen, a showpiece space designed for both everyday living and elevated entertaining. Flowing effortlessly into expansive open-concept living areas, this home was built to impress and perform. The main-level primary suite is a private sanctuary, featuring a spa-inspired bath, dual vanities, and an oversized custom closet. Floor-to-ceiling sliding glass doors flood the home with natural light and open to a generous backyard, complete with approved plans for a future resort-style pool, offering the opportunity to create a true private oasis. Upstairs, the lifestyle continues with a spacious loft featuring a built-in wet bar, perfect for entertaining or unwinding. Four additional bedrooms include a well-designed Jack-and-Jill layout, while a dedicated bonus/media room provides flexibility for a theater, game room, or lounge. ADDITIONAL HIGHLIGHTS INCLUDE: Dual laundry rooms (both levels for ultimate convenience) * Two EV charging stations * Designer lighting and custom window treatments throughout * Extensive built-ins and upgraded finishes that convey. For those seeking a fully turnkey experience, select designer furnishings may be available under a separate agreement, making this one of the most compelling move-in-ready opportunities in Winter Garden. This is more than a home, it’s the crown jewel of Avalon Ridge. A rare opportunity to own the best-renovated, best-designed, and best-presented property in the community.

Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)

Listing Agent: Dianna Desboyaux (407-920-4601)

Remarks: Under contract-accepting backup offers. Welcome to this fantastic, move-in ready, 4-bedroom, 2.5-bathroom, two-story home with a two-car garage. Enter the foyer leading directly into the open-concept living room and kitchen. The kitchen is functional and stylish, featuring laminate countertops, an island, and stainless steel appliances. Conveniently located off the kitchen are the laundry room, a half bathroom, and access to the two-car garage. All four bedrooms are located on the second level, with the primary suite situated at the rear of the home for privacy. A small flex space upstairs is perfect for a reading nook or a small office area. The primary bedroom features a walk-in closet and an attached ensuite with dual sinks and a tub/shower combo. Schedule your showings today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under contract-accepting backup offers. *Ask about a lender provided credit up to $12,500 on this home!* Welcome to 327 S Lakeview Ave, a rare opportunity in the heart of the golf cart district in Downtown Winter Garden. Built in 2014 and tastefully updated, this move-in ready property offers the perfect blend of character, comfort, and flexibility with no HOA. This unique property features a 2-bedroom, 2-bath main home plus a detached 1-bedroom, 1-bath guest cottage, ideal for buyers seeking a multi-generational home, income-producing property, or a home with an in-law suite. Situated on an oversized, fenced corner lot, the property is enhanced by lush, mature landscaping and a charming mini vineyard with sweet muscadine grapevines perfect for homegrown wine or fresh snacking. Inside, the main residence offers a desirable split floor plan with bright, open living spaces and abundant natural light. The inviting living room features a cozy fireplace perfect for relaxing evenings or entertaining guests. The spacious kitchen flows seamlessly into the main living area and is equipped with a gas range, making it ideal for home chefs. The private primary suite is tucked away, creating a peaceful retreat, while the secondary bedroom offers comfort and privacy for guests or family. The detached guest cottage features its own private entrance, making it ideal for rental income, a home office, or private accommodations for extended family. Step outside to the covered back patio, accessible from both the living area and primary suite perfect for entertaining and relaxing. Pre-plumbed with natural gas you can create your dream summer kitchen. The fully fenced backyard and garden space provide both privacy and room to enjoy Florida outdoor living. Located just blocks from the West Orange Trail, Plant Street Market, and the award-winning Winter Garden Farmers Market, you’ll enjoy walkable access to top-rated restaurants, coffee shops, boutiques, and year-round community events. Whether you're searching for a primary residence with rental income potential, a flexible investment property, or a home with a guest house in Winter Garden, this property offers unmatched versatility in one of Central Florida’s most sought-after locations. Don’t miss your chance to own a home near Downtown Winter Garden with income potential and no HOA, schedule your private showing today.

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

Listing Agent: Ryan Leitter (321-684-9699)

Remarks: Meticulously updated and move-in ready, this stunning residence is located in the highly sought-after gated community of Waterside in Winter Garden. Designed with both luxury and functionality in mind, the home features a desirable first-floor primary suite boasting an expansive en-suite bath with dual sinks and two custom-organized walk-in closets. The main level also includes a guest bedroom with its own full bath, a private office/den, and a convenient powder room. The second floor is an entertainer's dream, offering a massive loft, a Jack-and-Jill suite, and an additional bedroom with a private full bath. Significant upgrades abound, including new dual AC units (2024), rich hardwood flooring (2019), and a modern electric fireplace. Premium features include plantation shutters, custom shelving in the pantry and primary closets, a whole-house water purification system, and noise-blocking insulation for ultimate serenity. Outdoor and tech upgrades feature an extended driveway and an installed Tesla charger. Residents enjoy resort-style amenities including a community pool, fitness center, and clubhouse. Perfectly situated on a prime lot, you are minutes from Winter Garden Village, major highways, and premier shopping and dining. This could be your perfect dream home—schedule your private tour today!

Listing is courtesy of: ONE STOP SERVICE REALTY INC (407-739-3196)

Listing Agent: Ye Kang (321-279-1059)

Remarks: Under contract-accepting backup offers. Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Candace Cassidy (407-529-8630)

Remarks: Beautiful 2-bedroom, 2-bathroom condo just under 1,300 sq ft in one of the most desirable areas of Winter Garden. Both bedrooms feature large walk-in closets, and the layout is exceptionally well designed, making the home feel spacious and comfortable. The unit COMES WITH A 1-CAR GARAGE, a rare and valuable feature. All appliances are BRAND NEW, including refrigerator, microwave, stove, and dishwasher. A washer and dryer are also included. The flooring has been completely renovated to elegant wood flooring throughout. The main living area offers a separate flex space that is PERFECT for a home office or a kids’ play area. Conveniently located next to the community car wash, with resort-style amenities that include an amazing clubhouse, pool area with barbecue grills, fully equipped gym, tennis courts, basketball courts, and more.

Listing is courtesy of: JOHN SILVA REALTY & ASSOCIATES (407-420-7908)

Listing Agent: John Silva (407-420-7908)

Remarks: Welcome to The Orchard, a tidy gated community of townhomes in sought-after Winter Garden. This residence blends modern comfort with low-maintenance living, offering a bright, open layout that feels inviting from the moment you step inside. Thoughtful upgrades elevate every space—stylish flooring, fresh finishes, and a contemporary color palette create a clean, move-in-ready atmosphere. The kitchen serves as the heart of the home, featuring new appliances, fine cabinetry, sleek countertops, and a functional layout ideal for everyday living. The open-concept living and dining areas flow seamlessly to a private outdoor space, perfect for morning coffee or unwinding at the end of the day. Upstairs, spacious bedrooms provide comfort and flexibility, while the primary suite offers a peaceful retreat with generous closet space and an updated en-suite bath. A dedicated laundry area and attached garage add convenience to the home’s thoughtful design. Residents of The Orchard enjoy gated security, a tranquil pool area and playground, and a prime Winter Garden location just minutes from shopping, dining, top-rated schools, and the charm of downtown Winter Garden. Tastefully updated, well-maintained, and ideally located—this townhome is the perfect blend of style and convenience.

Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)

Listing Agent: Drew Ross (407-383-6497)