Homes for Sale Near West Orange High in Winter Garden - 168 homes

Remarks: Looking for a move-in ready home in Winter Garden with modern upgrades, an ideal location, and a true sense of community? Welcome to this beautifully maintained 3-bedroom, 3-bathroom home in the highly desirable Oakland Park neighborhood. Designed for today's lifestyle, this home features a bright open-concept floor plan, abundant natural light, spacious living areas, and a functional layout that's perfect for both everyday living and entertaining. Premium upgrades include gas appliances, elegant plantation shutters, and stylish finishes throughout, offering a turnkey, low-maintenance home you can enjoy from day one. Located in one of Winter Garden's most sought-after golf cart communities, Oakland Park offers resort-style amenities, scenic trails, parks, green spaces, and top-rated schools, creating the perfect setting for an active, connected lifestyle. Just minutes from Historic Downtown Winter Garden, you'll have easy access to the nationally recognized farmers market, local restaurants, boutique shopping, coffee shops, seasonal festivals, live entertainment, and the West Orange Trail. Whether you're searching for a close knit neighborhood, a home near downtown Winter Garden, or a community with exceptional amenities, this property checks every box. Don't miss this opportunity to own a beautifully upgraded home in one of Central Florida's most desirable communities.

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

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

Remarks: Under contract-accepting backup offers. Price Improvement! Seller says Sell it! Offering $5,000 Buyers Incentive at closing. Welcome to established Regency Oaks subdivision in Stonecrest, in the heart of Winter Garden! Situated on a desirable corner lot, this screened-in POOL home offers an incredibly flexible floor plan designed to fit today's lifestyle. Listed as a 3-bedroom home, it also features a spacious flex room overlooking the pool and backyard, along with a separate oversized bonus room that can easily serve as an additional bedroom, home office, media room, playroom, fitness studio, guest retreat, or additional living space. The split-bedroom layout provides privacy, while the primary suite features a walk-in closet, garden tub, and separate shower. Fresh interior paint and updated laminate flooring enhance the home's inviting feel. Step outside to your private backyard oasis complete with a sparkling pool, mature shade trees, a side yard for gardening and a pool safety fence—creating the perfect setting for entertaining or relaxing while enjoying Florida's indoor-outdoor lifestyle. Recent improvements include a new roof (2023), 2017 air handler, 2018 A/C condenser, and a recently serviced irrigation system for added peace of mind. Residents of Regency Oaks enjoy low monthly HOA fees and outstanding community amenities including scenic walking trails around a picturesque pond with benches, a clubhouse, community pool, and two neighborhood parks/playgrounds. Ideally located walking distance of Winter Garden Village at The Grove and just minutes from Historic Downtown Winter Garden, the West Orange Trail, major highways, shopping, dining, entertainment, top rated schools and Central Florida's world-famous attractions. Orlando International Airport and Florida's east coast beaches are both approximately an hour away.

Listing is courtesy of: METRO CITY REALTY (407-237-3331)

Listing Agent: Beatrice Miranda (407-592-4448)

Remarks: Under contract-accepting backup offers. Luxury At its Finest. This Beautiful Immaculate Open Concept 4 bedrooms, 4 baths residence featuring a spacious loft with a full bath. Loft on 2 nd Floor can potentially be used as a 5th bedroom. Ideal for guests retreat, home office, media lounge, media room or additional entertainment for the entire family. The Amazing Gourmet Chefs kitchen with under cabinet lighting Gas stove, double oven showcases an extra large extended island perfect for entertaining. Complemented by elegant finishes. Open concept living spaces and exceptional comfort throughout the home in its entirety. French Doors gives access to the resort style pool with 4 therapy jets, bubblers on the sun shelf, custom hand rail with multi led lights with a Wet Edge Pool Interior. Elegant Pavers. The Pool is 3 ft on the shallow end and 6 ft on the deep end and measures 15 x 31. This home is taken care with lots of Pride and Tender Loving care. This home sits on a corner Lot with lots of privacy for all entertainment and relaxation. Garage has overhead racks for extra storage. This is a very small community that is peaceful and tranquil for great evening walks. By Appointment Only. Thank You.

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Tracy Hampstead (407-803-3137)

Remarks: Under contract-accepting backup offers. SHOW STOPPER! Welcome to 15587 Hamlin Blossom - in the highly sought-after gated community of HICKORY HAMMOCK. A rare find, this Ashford model by M/I Homes is one of only six Ashford floor plans built in the community. Every detail of the 1860 sq. ft has been thoughtfully designed and meticulously cared-for, creating a TURNKEY experience unlike any other. Start off on your paver driveway and enjoy the handpicked lush new landscaping and welcoming porch-sitting area where you can immediately enjoy the outdoor Florida lifestyle. NEW EXTERIOR PAINT. Once inside you are greeted with perfection. NEW luxury vinyl flooring in each bedroom. NO CARPETS throughout the entire SINGLE STORY home. A foyer that immediately impresses with crafted lighting fixtures and perfectly placed decor. SPLIT FLOOR PLAN creates privacy for the two bedrooms and bath in the front of the home. Double vanity with UPGRADED lighting and hardware to elevate the bathroom space. The OPEN FLOORPLAN and dining room/living room combo is perfect for entertaining guests. Create the ideal ambiance with your ALEXA-enabled recessed lighting. A chef’s dream kitchen with BRAND NEW refrigerator, NEW dishwasher, and NEW garbage disposal. The primary suite is perfectly appointed with classic upgrades and reading nook. The HIGHLIGHT of the home is the wraparound paver patio with outdoor living/dining room space and OUTDOOR KITCHEN all under a screen enclosure overlooking a fully fenced, newly landscaped outdoor and garden area. Other upgrades include NEW washer/dryer, NEW HVAC components, NEW TESLA charging station. Hickory Hammock is a special enclave of Winter Garden that overlooks John’s Lake. Residents enjoy water views, private fishing pier, tennis courts, beach volleyball courts, nature trails, resort-sized swimming pool, fitness center, clubhouse, and nature trails. Located in the heart of Winter Garden and Horizon West, this home is approximately 5 minutes from SR 429, 10 minutes from Hamlin Town Center, 10 minutes from Downtown Winter Garden, and approximately 25 minutes from Walt Disney World. Residents enjoy convenient access to shopping, dining, entertainment, top-rated schools, major employment centers, and everything that makes Winter Garden one of Central Florida's most desirable places to live. Contact list agent for full list of upgrades AND seller’s complete maintenance schedule/records. Homes this well cared for do not come on the market often. See it for yourself today!

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Michelle Zimmerman (732-616-6019)

Remarks: Welcome to this beautifully maintained end-unit townhome in the highly sought-after Hickory Hammock at Johns Lake! Filled with natural light from additional windows and offering extra green space rarely found with townhome living, this move-in-ready home combines comfort, style, and an unbeatable Winter Garden location. The open-concept floor plan features a spacious great room, dining area, and a well-appointed kitchen with granite countertops, stainless steel appliances, and abundant cabinet space—perfect for everyday living and entertaining. Upstairs, the private primary suite provides a relaxing retreat, while two additional bedrooms and an upstairs laundry room offer comfort and convenience for family and guests. Enjoy peaceful mornings or relaxing evenings on the covered patio overlooking lush green space. Hickory Hammock is a gated, virtual guard community surrounded by Johns Lake, Lake Burnett, and Lake Claire, offering resort-style amenities including a community pool, clubhouse, fitness center, tennis courts, sand volleyball, dog park, playgrounds, parks, and a community fishing pier. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, SR-429, the Florida Turnpike, top-rated schools, shopping, dining, and Central Florida's world-famous attractions, this home offers the perfect blend of convenience and lifestyle. Don't miss this exceptional opportunity—schedule your private showing today!

Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)

Listing Agent: Corey Smallman (407-744-2765)

Remarks: Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

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

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

Remarks: Virtually Staged. Fabulous 5 bedroom, 4 bath pool home lovingly cared for by the original owners. Situated near the end of a cul-de-sac on an almost ½-acre lot with a fully fenced backyard in the gated community of Wintermere Pointe! A long driveway provides ample parking and leads to the OVERSIZED 3-CAR GARAGE, which was extended an additional 4 feet during construction to provide exceptional storage space. Inside, this spacious and thoughtfully designed home features tile flooring throughout the main living areas downstairs, wood laminate flooring in the family room, and brand new carpet on the staircase and in the upstairs 5th bedroom. The desirable 3-way split bedroom floor plan provides wonderful privacy for family and guests. Featuring loads of storage throughout, including an oversized under-stair storage closet in the back hall, a generously sized linen closet in the alcove between Bedrooms 2 and 3, and an additional storage closet in the laundry room. The primary suite is privately located on one side of the home and features French doors opening to the lanai and pool, two walk in closets and a beautifully UPDATED primary bath with new flooring, separate vanities that offer plenty of storage, quartz countertops, a renovated shower with glass surround and updated showerhead plus a private water closet with a new commode. All commodes throughout home have been replaced with "comfort height" commodes. At the heart of the home is the spacious kitchen offering abundant cabinetry, granite countertops and LG stainless appliances (Bosch dishwasher) replaced in 2022. The kitchen opens to the family room w/surround sound, creating a comfortable and inviting space for everyday living and entertaining. Upstairs, the huge 5th bedroom offers incredible flexibility with two walk in closets and a private bathroom - perfect for guests, multigenerational living, a bonus room or private retreat. Outdoor living is exceptional! A huge Florida room was added across the back of the home, providing additional all-season living and entertaining space beyond the screened pool and lanai. The expansive, fully fenced backyard and almost ½-acre homesite provide plenty of room to enjoy the Florida lifestyle. MAJOR UPDATES INCLUDE: ALL NEW energy-efficient windows (June 2023) and doors (2024), Water softener (February 2024), Water heater (September 2023), garage door opener (2021), Roof (May 2017) and HVAC (September 2015) with annual maintenance service. AC ducts were inspected with boots resealed to drywall and collars in June 2019, then professionally cleaned and inspected in March 2024. Annual septic service, including draining and filter cleaning, was completed in January 2026, and the dryer vent was cleaned in April 2026. The transferable termite bond renews in November 2026. Additional improvements include replacement of the sprinkler meter including the majority of electrical sprinkler valves, gutter cleaning and sealing and installation of Gutter Guards in March 2025, along with replacement of two electrical valves at the pool pump. THE LOCATION IS FANTASTIC! Just 5 minutes to Winter Garden Village for abundant shopping and dining, including the new Seasons 52 coming soon. Approximately 10 minutes to charming Downtown Winter Garden with its popular restaurants, shops and Saturday Farmers Market and approximately 16 minutes to Disney! Zoned for highly rated Lake Whitney Elementary, SunRidge Middle, and West Orange High School. This home is truly a special opportunity!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Sherri Palmer (407-718-0412)

Remarks: Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.

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

Listing Agent: Christopher Bessette (407-292-5400)

Remarks: PREMIUM CONSERVATION LOT offering privacy and natural beauty, with a GREEN SPACE on the right side of the home and a park with sitting benches and sidewalks located across the street. Discover exceptional value and picturesque Florida living in this beautifully appointed 4-bedroom, 2.5-bath home offering 2931 square feet of thoughtfully designed living space. Enjoy tranquil views of the Lake Burnett inlet from the screened lanai. Inside, a bright open-concept floor plan showcases tile flooring throughout the first floor, luxury vinyl plank flooring upstairs, crown molding, custom window casings, a designer feature wall in the dining room, and elegant finishes throughout. The spacious kitchen is the heart of the home, featuring 42-inch cabinetry, stainless steel appliances, a walk-in pantry, a kitchen island, and seamless flow into the great room and dining areas—perfect for entertaining and everyday living. A flex room / office on the first floor, provides ideal additional living area or work-from-home space. Upstairs, the game room offers even more flexibility. Double doors lead to the spacious primary suite, featuring a charming window bench seat, large walk-in closet, dual vanities, soaking tub, walk-in shower, and private water closet. Generously sized secondary bedrooms provide ample space, with two bedrooms featuring walk-in closets. Step outside to the fully fenced backyard with aluminum fencing and dual side gates, where peaceful conservation views create the perfect backdrop for relaxing or entertaining. Additional upgrades include fresh exterior paint, a new water heater, new dishwasher, newer washer and dryer, gutters with premium leaf protection, and pre-wiring for a security system. Residents of Hickory Hammock enjoy resort-style amenities including a clubhouse, pool, fitness center, tennis courts, sand volleyball courts, fishing pier, playground, walking trails, community parks, and golf cart-friendly streets. Conveniently located just 10 minutes from the 429, connecting you to the Turnpike and I-4. A quick 10 minutes to the Winter Garden Village and Downtown Winter Garden, you'll enjoy easy access to boutique shopping, restaurants, coffee shops, Plant Street Market, and the popular Saturday Farmers Market. Now offered at an exceptional value, this home presents an outstanding opportunity to enjoy the Florida lifestyle you've been dreaming of. Schedule your private showing today. WELCOME HOME!

Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)

Listing Agent: Janelle Conway (407-595-0009)

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.

Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)

Listing Agent: Xiaoli Lin (561-385-7610)

Remarks: Under contract-accepting backup offers. Nestled in the highly coveted Courtlea Oaks community, within Winter Garden’s sought-after golf cart district, this beautifully updated home offers the perfect blend of timeless charm and modern luxury. Enjoy the lifestyle that has made historic downtown Winter Garden one of Central Florida’s most beloved destinations—just minutes away you’ll find award-winning restaurants, boutique shopping, the renowned Saturday Farmers Market, live entertainment, festivals, and miles of the West Orange Trail. Situated on an oversized .33-acre homesite, this exceptional residence offers 2,765 square feet with three bedrooms, two-and-a-half baths, and thoughtfully designed living spaces filled with architectural character. From the moment you enter, you’ll be welcomed by soaring ceilings, rich hardwood flooring, custom board-and-batten millwork, crown molding, and a stunning two-story foyer that creates an unforgettable first impression. At the heart of the home is a beautifully renovated kitchen featuring custom white cabinetry, a center island, farmhouse sink, professional-style gas range with pot filler, stainless steel appliances, and generous workspace—perfectly designed for both everyday living and effortless entertaining. The kitchen flows seamlessly into the spacious family room and sun-filled dining area overlooking the backyard oasis. Upstairs, the expansive loft provides exceptional flexibility as a media room, home office, fitness space, or could easily accommodate a fourth bedroom. The secondary bedrooms are generously sized, including one with a charming custom-built window desk. The beautifully updated bathrooms continue the home’s timeless design with quality finishes throughout. Step outside to your own private retreat featuring a sparkling pool, expansive brick paver deck, lush landscaping, and plenty of room for entertaining or simply relaxing under the Florida sun. Homes in Courtlea Oaks are rarely available. Combining an exceptional location, beautiful updates, timeless architecture, and one of Winter Garden’s most desirable lifestyles, this is a home you’ll be proud to call your own.

Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)

Listing Agent: Jennifer Coon (321-948-8056)

Remarks: Welcome to this beautifully maintained unfurnished 2-story townhouse located in the gated community of Daniels Landing. Surrounded by attractive landscaping, this charming 2-bedroom, 3-bath home offers a spacious and functional layout designed for comfortable living. Step inside to find a freshly repainted interior, high ceilings, laminate flooring, and an open-concept floor plan that seamlessly connects the combined living and dining areas, creating an inviting space for both relaxing and entertaining. The kitchen is equipped with stainless steel appliances and offers ample cabinet and counter space for everyday convenience. Upstairs, the spacious primary suite features a private ensuite bath, providing a peaceful retreat at the end of the day. Additional highlights include a 2-car garage and a private enclosed courtyard with vinyl fencing—perfect for outdoor dining, entertaining, or enjoying your own quiet outdoor space. Located in the desirable gated community of Daniels Landing, this home combines comfort, style, and convenience in one exceptional property.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Gillian Redman (863-521-7329)

Remarks: You will find comfort, convenience and flexibility with this lovely well maintained 3 bedroom 2 1/2 bath townhome located in Stoneybrook West. With Ceramic tile in the kitchen and bathrooms, the owner replaced all carpet with laminate wood flooring. The en suite primary bathroom was beautifully updated in 2025 with attention to upgrades like a double vanity quartz countertop and soft closed drawers. The Primary suite has two walk in closets and new energy efficient windows. The second bedroom boasts a walk in closet as well. From the cozy screened back patio, it’s a quick walk to the community playground and pool. This quiet family friendly community is within walking distance of all your shopping needs and also just a short drive to Winter Garden Village and charming Historic Downtown Winter Garden. There you’ll find the West Orange Trail for biking, running or a simple stroll after dining at some of the area’s finest restaurants. Adding to your peace of mind, the roof was replaced in 2023 along with repainting of the exterior of the properties in the community. The HVAC was replaced in April 2021. The exterior was upgraded to a 3 ton in August 2019 and maintained annually. Schedule your showing and make this turnkey townhouse your home.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Jodene Chase (407-616-5634)

Remarks: Under contract-accepting backup offers. Welcome to Southern Pines in the heart of Winter Garden! This clean and well-maintained 1-bedroom, 1-bath upstairs condo offers bright, open living with a rare combination of features you won’t often find in the community. Positioned on the upper level, the home enjoys enhanced privacy and abundant natural light with windows on both sides of the building, creating an airy and inviting atmosphere throughout the open-concept living and dining area. The kitchen flows seamlessly into the main living space and features granite countertops, ample storage, and all appliances convey with the sale — making this home truly move-in ready. Enjoy peaceful views overlooking the community tennis courts and resort-style pool. Downstairs, the attached 1-car garage and generous under-stair storage closet provide exceptional storage space — a true rarity within the neighborhood. Enjoy maintenance-free living, with HOA fees covering lawn care, cable, internet and water. Spend your weekends exploring Winter Garden Village, just 1.5 miles away, or immerse yourself in the charm of historic Downtown Winter Garden, filled with cozy cafés, boutique shops, farmers markets, and more. Outdoor enthusiasts will appreciate easy access to the West Orange Trail, perfect for biking, jogging, or leisurely strolls. Commuting is effortless with quick connections to the Florida Turnpike, SR 408, and SR 429. The gated Southern Pines community offers impressive amenities, with the pool, hot tub, and clubhouse located across the street. Additional features include a covered playground, movie theater, game room, office space, outdoor kitchen with grills, tennis court, indoor basketball and racquetball courts, sand volleyball, and even a car wash station. Don’t miss your opportunity to own in one of Winter Garden’s most convenient and amenity-rich communities. Schedule your showing today.

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

Listing Agent: Anna Gay Hunter (407-446-9878)

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: Tucked inside a sought-after gated community, this beautifully designed 4-bedroom, 4-bath home offers the perfect blend of comfort, elegance, and everyday livability. From the moment you arrive, you’ll appreciate the sense of privacy, space, and thoughtful design that make this home truly special. With formal living and dining rooms, a private office/study, and a spacious bonus room with a full bath, there is room for everyone to live, work, gather, and unwind. At the heart of the home, the centrally located kitchen brings everything together, opening naturally to the main living areas and creating an ideal setting for both entertaining and daily life. Appointed with granite countertops, a center island, double ovens, and a pantry, it is as functional as it is inviting. Beautiful crown molding, decorative wall details, and tile flooring throughout the main living spaces add warmth and character, while the bedroom spaces offer comfort and privacy. The primary suite is a peaceful retreat, privately positioned and complete with two walk-in closets, dual vanities, a soaking tub, and a separate shower. Secondary bedrooms are thoughtfully arranged, including a Jack-and-Jill bath, while the bonus room provides flexible space for guests, a media room, a playroom, or multi-generational living. Step outside and enjoy your own private Florida oasis. The screened saltwater pool, convenient pool bath, and expansive paver deck with both covered and open-air areas create the perfect backdrop for quiet mornings, weekend gatherings, and year-round outdoor living. Backing to a green area, the setting feels peaceful and private, offering a rare sense of escape while still being close to everything. Located near Winter Garden Village, Highway 429, top-rated schools, shopping, and dining, this exceptional home offers not just a place to live, but a lifestyle to love. Make sure to check out the 3D tour and Virtual tours.

Listing is courtesy of: MARTI PURDY PROPERTIES INC (407-614-6177)

Listing Agent: Marti Purdy (407-761-0848)

Remarks: Under contract-accepting backup offers. ***Seller to offer up to $17,000 toward buyer's closing cost & or rate buy down.*** There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving as the heartbeat that connects residents to both nature and one another. At 931 Kylee Alley, this lifestyle is fully realized. Positioned on a prominent corner lot, this David Weekley Stoneybrook residence showcases timeless architecture with a clean, sophisticated presence. One of the greatest luxuries here is the ease of ownership. The homeowners' association provides full landscaping maintenance, allowing the property to remain in pristine condition without demanding your time. Your weekends are yours to enjoy, not manage. Inside, the home immediately impresses with intentional sightlines and natural light. Built in 2022, the design feels both current and enduring. Soaring ceilings and expansive windows, complemented by custom plantation shutters, create a bright yet grounded atmosphere. The gourmet kitchen anchors the home, featuring an oversized island with sleek, solid surface countertops that serve as the perfect setting for gathering, entertaining, or everyday living. The floor plan is designed for both connection and privacy. The main level offers a flexible and refined space that can function as a guest suite or executive-style home office. Upstairs, the private quarters provide a peaceful retreat. The primary suite is expansive and serene, complete with a spa-inspired bath designed for relaxation at the end of the day. Living here means immediate access to the West Orange Trail and the best of Winter Garden. Bike to Plant Street, enjoy the Saturday Farmers Market, or simply take in the charm of one of Central Florida’s most sought-after destinations. Within Oakland Park, residents enjoy resort-style amenities, including multiple pools, a clubhouse, and a dog park, all contributing to a true lock-and-leave lifestyle. From an investment perspective, this property stands out. It offers an exceptional price per square foot for Oakland Park, with pricing thoughtfully adjusted to reflect the opportunity for upstairs flooring customization. In a community where demand continues to outpace supply, especially for newer construction on premium corner lots, this home represents both immediate value and long-term upside. 931 Kylee Alley is more than a home. It is a strategic acquisition within one of Winter Garden’s most desirable communities.

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

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

Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 1950 Pantheon Drive, a charming 3-bedroom, 2-bath home located in the desirable Alexander Ridge community of Winter Garden. Offering 1,769 square feet of living space, this thoughtfully designed split-bedroom floor plan provides comfort, privacy, and easy everyday living. From the moment you arrive, the home makes a welcoming first impression with a bright exterior, paver driveway, covered entryway, mature landscaping, and a large front tree that adds shade and curb appeal. Inside, the open living, kitchen, and dining areas create a functional flow for relaxing, gathering, and entertaining. The living room features warm engineered wood flooring, neutral tones, and natural light from multiple windows, creating a bright and inviting main living space. The kitchen overlooks the living area and features granite countertops, warm wood cabinetry, stainless steel appliances, pendant lighting, recessed lighting, a breakfast bar, a center island, a deep kitchen sink, and a modern pull-down faucet.  Just beyond the kitchen, the dining area provides a dedicated space for meals while remaining connected to the heart of the home. The private primary suite offers neutral tones and direct access to the ensuite bathroom. The primary bath features dual sinks, granite countertops, warm wood cabinetry, upgraded lighting, a walk-in shower with a glass enclosure, a separate soaking tub, and direct access to the walk-in closet. The walk-in closet also includes convenient door access to the laundry room, adding a smart everyday function. Bedrooms 2 and 3 are located on the opposite side of the home and share a spacious second bathroom. Recent updates include HVAC replaced in August 2024, PAID OFF Solar Panels in 2018, ROOF installed in 2023. The solar system is paid off, helping create an energy-efficient home with low-cost utilities. Alexander Ridge offers inviting community amenities, including a resort-style pool with paver decking, lounge areas, a covered pavilion, playground, open green space, and beautifully maintained common areas surrounded by mature landscaping and palm trees. This Winter Garden home blends comfort, function, efficiency, and community living in one inviting package.

Listing is courtesy of: EXP REALTY LLC (407-641-2808)

Listing Agent: Todd Schroth, Pa (407-641-2808)

Remarks: Virtually Staged. Welcome home to 921 Bending Oak Trail in highly sought-after, downtown, golf cart district of Winter Garden! This spacious 4-bedroom, 2.5-bath home is perfectly situated on a private oversized corner lot with serene pond views, offering both privacy and a peaceful backdrop. The thoughtfully designed layout features a first-floor primary suite and convenient downstairs laundry room. The main living areas showcase updated modern, stone-like tile flooring, while the kitchen offers a large walk-in pantry that extends under the staircase for exceptional storage. The spacious Living Room and covered patio are wired for a surround sound system and have beautiful water views from the windows and paver patio. Upstairs, you’ll find generously sized secondary bedrooms, including one with an oversized walk-in closet, along with a large loft ideal for a home office, playroom, or flex space, all featuring engineered hardwood flooring. Enjoy outdoor living with a spacious entertaining area and the added benefit of a rear-entry garage accessed through a private, owners-only alleyway where you can also enter the home without climbing any stairs. Major updates include a roof replacement in 2025, making this home as practical as it is beautiful. Lastly, the location is incredible, the neighborhood is extremely well maintained, offering a tranquil walking community around Brandy Lake and duck filled ponds, a sparkling community pool, entertaining pavilion, community greenspace, and perfect playground for the little ones.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Claire Sims, Llc (203-767-8109)

Remarks: Virtually Staged. Welcome to 14779 McClane Road! Set behind the gates of Oxford Chase, this one of a kind Mattamy home stands apart from anything else in the community. Five bedrooms, four baths, and 3,118 square feet of genuinely upgraded living on a lot that simply cannot be replicated. At the heart of it is a custom designed kitchen any chef would love to call their own. A dramatic waterfall edge stone island seats four beneath designer glass pendants, surrounded by crisp white cabinetry, a deep stainless farmhouse apron sink, a gas cooktop beneath a vented stainless chimney hood, and a full stainless double wall oven. It opens directly into the great room and flows to a formal dining room crowned by a tray ceiling, bay window, and cascading crystal chandelier. Large stone look tile runs continuously through every common area with no transitions and no compromises. The attention to detail carries throughout. Every bathroom features tile taken floor to ceiling in the shower surrounds, accented by a custom glass mosaic inlay band. The first floor primary offers privacy and generous proportions, while a main floor laundry room adds a deep storage closet, the kind of everyday storage that makes a home genuinely functional. Upstairs is where this floor plan gets extremely special. A spacious loft paired with its own full bathroom creates a genuine second living quarters, not a bonus room with a powder bath down the hall. Aging parents get real independence. Young adults returning home get privacy and dignity. An au pair, a long term guest, or a live in caregiver has a complete suite of their own. It is the kind of true multi generational layout families search for and rarely find. An oversized 3 car garage with an extra deep bay handles the vehicles, the workshop, and everything in between. Step outside and the setting speaks for itself. An oversized covered lanai opens onto a wide, open lawn with no rear neighbors and no homes across the way. The protected retention area means that openness is permanent, not a temporary view waiting to be built out. The yard is already pre wired for a pool, so your private resort is ready whenever you are. A walking trail sits just a short stroll from your door. And nearly every night, you can finish dinner on the lanai and watch Disney's fireworks light up the sky, visible from multiple vantage points throughout the home. The location may be the quietest luxury of all. SunRidge Elementary and SunRidge Middle are an easy walk from your front door. AdventHealth Winter Garden sits roughly five minutes away. Minutes in the other direction, the new $31 million Tucker Ranch wellness complex is bringing a teaching farm, botanical gardens, retreat center, and fitness trail system, joining the existing 200 acre nature preserve on Johns Lake with its kayak launch and miles of trails. Plant Street's restaurants and award winning Farmers Market, Winter Garden Village, and quick access to the 429 are all close at hand, with Orlando International Airport about 30 minutes out. Homes in Oxford Chase rarely come available, and lots like this one almost never do. Seller offering a $1,000 paint allowance and a $500 cleaning allowance to buyer at closing. Schedule your private showing today!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Ryan Persaud (646-404-3085)