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$550,000
3 Beds 2 Baths Fries Winter Garden SubDv. 34787 Zip Code
Located in the heart of Historic Downtown Winter Garden…golf cart district! Walkable to amazing restaurants, boutiques, breweries, splash pad, Saturday Farmer’s Market or one of the many specialty events held throughout the year! This darling 1930’s craftsman bungalow had a complete restoration in 2017 and is still in mint condition! All the vintage charm without all the headaches! Spaces were thoughtfully reconfigured, new energy efficient windows were installed, a tankless gas hot water heater, electrical updates including a new panel and plumbing update from cast iron to PVC. Also, NEW HVAC in 2025! Now, let’s take a tour! Imagine a nostalgic brick walk way leads to the prettiest shade of vintage blue door, tidy landscaping and crisp wood work frame the picture. As the door opens, your eyes are drawn upward to the sparkling chandelier casting prismatic light across the vaulted ceilings. Raising the ceilings was part of the restoration and such a good choice! The natural light in the home is also quite nice. This space would be great as a family room or formal sitting area. Double doors open to a sunroom/ private office that would also make a fantastic playroom. The kitchen update included new appliances, including a gas range! Attractive gray shaker wood cabinets & white quartz countertops seem timeless, not trendy in this historic style. Another nice feature is having the kitchen and eating area in the center of the home, not closed off like many homes of this era. A stackable washer and dryer is also centrally located making laundry a breeze! The great room stretches across the back of the house with a bay window and wood beam accents. A spacious and relaxing place to admire the lush fenced backyard, tree canopy and fun macramé swing. The authentic vintage shed, paver patio and large level yard is the perfect back drop for BBQ’s and parties! At night, you’ll love the bistro lighting that gives the entire space a glow! After a fun evening of entertaining, retire to one of the three cozy bedrooms. Ensuite and spare baths are both ones you’d “PIN” as favorites with stunning tile work, ornate mirrors and funky shabby chic vanities! Little fact…The center bedroom lost the closet in the remodel, however there’s room for an armoire or space saving Ikea closet! Winter Garden is a suburb of Orlando that embraces modern luxuries with old world charm. A place to put roots down and stay forever!

315 S Boyd Street, Winter Garden

$1,575,000
4 Beds 4 Baths Oakland Pk Un 7 South 112/136 Lot 175 SubDv. 34787 Zip Code
Welcome to 1096 Riverway Drive, a fully custom home built by RCB Homes, currently under construction in the award-winning community of Oakland Park. Scheduled for completion in December 2025, this home spans 4,000 square feet of thoughtfully designed living space. Set on a picturesque tree-lined street, the home’s inviting curb appeal is enhanced by a large wrap-around front porch, a long ribbon driveway, and architectural details that reflect Oakland Park’s charm and character. Inside, the open-concept floor plan has been designed for comfort and entertaining. The main level features a chef’s kitchen that includes premium appliances, custom wood cabinetry, quartz countertops, and a fully equipped hidden Butler’s Pantry. The Butler’s Pantry includes both upper and lower wood cabinetry, expansive countertops, and space for a secondary refrigerator. The kitchen overlooks the great room, which is anchored by a large fireplace. Adjacent to the kitchen is the dining room, which features vaulted ceilings and unique wood beam accents. The living and dining areas flow seamlessly to the outdoor lanai and pool house, which are situated courtyard style around the yard space that is dedicated for a future private pool. The downstairs also features the laundry room, access to the garage, a powder bathroom for guests, and a dedicated office with a closet. In addition, the main level boasts the incredible primary suite, complete with large windows, ceilings accents and an oversized en-suite. The en-suite includes a large vanity with dual sinks, an oversized walk-in shower with custom tile details, and a large walk-in closet that will be completed with built-ins. Going upstairs, the staircase will be completed with open railing, and the top of the stairs welcomes you into the generous loft. The loft has large windows overlooking the front yard of the home, letting in an immense amount of natural light. The loft is accompanied by three additional bedrooms. One bedroom features its own en-suite, and the other two guest bedrooms are positioned with a Jack and Jill bathroom in between. The pool house provides additional versatility, great for a game room, home gym or an additional home office. Every inch of this home reflects RCB Homes’ signature craftsmanship and attention to detail. Residents of Oakland Park enjoy access to two resort-style pools, scenic parks, and miles of walking and biking trails, including direct access to the West Orange Trail. Oakland Park is also golf cart friendly, as well as a close distance to Downtown Winter Garden/Plant Street. Completion expected December 2025. Ready to experience the best of Winter Garden living? Schedule your private tour today!

1096 Riverway Drive, Winter Garden

$659,990
4 Beds 3 Baths Tuscany SubDv. 34787 Zip Code
Beautifully updated POOL home in the desirable Tuscany community! Major updates include a new water heater (2020), whole house re-plumed (2021), new saltwater pool/spa with panoramic screen (2022), and new HVAC (2024). Pool features include Heat pump/chiller combo, iAquaLink (an intelligent pool control-turn on filter, lights, spa through app), auto fill/auto drain, bubbler, and Eco pool feature (circulation). Kitchen features quartz counters, 42” cabinets, stone backsplash, and stainless appliances, opening to a cozy family room with fireplace and French doors to the pool. Enjoy a private primary suite with pool access and a luxurious bath. Additional highlights include crown molding, 10-ft ceilings, bamboo/slate/travertine flooring, smart thermostat, and a fully fenced backyard. Excellent location near the West Orange Trail, downtown Winter Garden, and SR 429. This home truly shines!

1674 Victoria Way, Winter Garden

$210,000
2 Beds 2 Baths Townhomes Winter Garden SubDv. 34787 Zip Code
Vaulted ceilings in the great room & kitchen, along with a skylight make this 2 bedroom 2 bathroom condominium Light, Bright & Inviting. Located in a quiet community this end-unit is move-in ready and can be available for quick closing and occupancy. New paint throughout. Kitchen has new kitchen cabinet doors, stainless steel appliances & newer (2022) Dishwasher. Screened patio is larger than most in the community & has a small storage closet. The master bedroom features a walk-in-closet and private full bathroom. 2 assigned parking spots, community swimming pool, exterior maintenance and landscaping are included in the monthly HOA fee. This community is near charming downtown Winter Garden known for it's Farmer's Market, restaurants, shopping, access to the West Orange Trail, minutes from baseball fields and pickleball courts, and convenient to Hwy 50, the Florida Turnpike, and SR 429.

355 Douglas Way Unit 53, Winter Garden

$545,000
4 Beds 3 Baths Covington Chase SubDv. 34787 Zip Code
**HISTORIC DOWNTOWN WINTER GARDEN -- GOLF CART DISTRICT -- WEST ORANGE TRAIL** **OVERSIZED PRIVATE LOT** **FOUR BEDROOMS -- THREE FULL BATHROOMS** **NEWER HVAC - 2024 + NEWER WATER HEATER -- 2021** **HARDWOOD FLOORING** **FULLY FENCED YARD -- COVERED & SCREENED PATIO LANAI** Welcome to this beautiful move-in ready home located in downtown Winter Garden's highly desired Covington Chase neighborhood! Experience the best of both worlds -- the LOCATION right within downtown & the golf cart district…with the PEACE OF MIND that comes with a newer home. Starting with great curb appeal, this home sits on a special oversized lot with plenty of space between homes…no need to touch your neighbor’s house with this one. Fantastic & flexible floor plan features FOUR bedrooms on a three-way split plan and THREE full bathrooms...all on ONE STORY. This is an ENERGY STAR CERTIFIED home with special features including R-30 insulation & Low-E double pane insulated windows. The large open living space welcomes with newer HARDWOOD FLOORING, lots of NATURAL LIGHT throughout and a beautiful spacious kitchen which is the heart of this home. All appliances convey including washer & dryer. RECENT UPGRADES & UPDATES: HVAC -- 2024. Water Heater -- 2020. Exterior Paint -- 2021. Hardwood Flooring -- 2021. Luxury Carpet (Bedrooms) -- 2021. Interior Paint. New Toilets. Garage Epoxy & Shelving. Custom Window Moldings. Rain Gutters. Private Mailbox. Security System. Termite Bond. LIVE the Florida lifestyle outdoors…ENJOY peace & privacy in the beautiful fully-fenced backyard complete with a covered & screened patio lanai. Plenty of space for your outdoor dreams & plans. This community features a fantastic pool, playground and park area all for a very LOW HOA fee...in addition, the West Orange Trail runs RIGHT THROUGH the center of the community around the corner from the home! It is also ZONED for GOLF CART use throughout Downtown Winter Garden. HUGE weekly farmer's market, annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks and recreation...come JOIN THE FUN! Also conveniently located just minutes from the Winter Garden Village shopping center and just one minute from HWY 429. WELCOME HOME!

446 Millwood Place, Winter Garden

$469,000
3 Beds 2 Baths Island Pointe Sub SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Active Under Contract - accepting back up offers. Welcome to this spacious 3-bedroom, 2-bath home with a 2-car garage, ideally situated in the highly desirable golf cart district of downtown Winter Garden. Step inside to discover a split bedroom floor plan with vaulted ceilings and a cozy living room with fireplace, seamlessly connected to the dining area—creating a warm, inviting space for gatherings. The chef-inspired kitchen serves as the heart of the home, featuring quartz countertops, stainless steel appliances, an eat-in breakfast bar, and ample cabinetry for storage and style. Enjoy the convenience of an indoor laundry room with a sink and extra storage. The primary suite offers comfort and privacy with a generous walk-in closet and a spa-like ensuite bath, while two additional bedrooms and a full bath with dual linen closets provide plenty of space for family or guests. Relax or entertain in the expansive Florida room overlooking the manicured backyard—perfect for morning coffee or evening gatherings. Additional highlights include luxury vinyl flooring in wet areas and new carpet in the bedrooms for added comfort. Perfectly located just a five-minute bike or golf cart ride from Historic Downtown Winter Garden, this home offers easy access to local shops, restaurants, the Saturday farmers market, Lake Apopka parks, and the West Orange Trail. With a low HOA and endless possibilities for personalization, this property combines comfort, convenience, and the coveted Winter Garden lifestyle. Don’t miss your chance to call this charming home yours—schedule your private showing today!

1041 Sadie Lane, Winter Garden

$532,000
4 Beds 2 Baths Stoneybrook West Ut 04 48 48 SubDv. 34787 Zip Code
Welcome to this well-loved 4-bedroom 2-bathroom home in the desirable golf community of STONEYBROOK WEST! With UPDATED KITCHEN AND BATHROOMS and a split floor plan, this home offers comfort, space, and flexibility for everyday living. The primary suite features two walk-in closets and opens to a EXTENDED SCREENED IN PORCH with custom tile, ceiling fans, and a doggy door that leads to a tiled grilling area—perfect for outdoor entertaining! The second bathroom also opens to the porch, adding to the home’s easy indoor-outdoor flow. A formal living room offers a great option for a HOME OFFICE, playroom, or flex space. Additional highlights include a 2025 PAVER DRIVEWAY and a fully fenced backyard backing to conservation providing privacy and peaceful views. ROOF 2018 HVAC 2018 and BRAND NEW WATER HEATER!!! Lovingly maintained and full of charm, this home is ready for its next chapter—come make it yours!

2656 Slagrove Court, Winter Garden

$600,000
4 Beds 3 Baths Longleaf At Oakland SubDv. 34787 Zip Code
*** Back on the market after being temporarily off while the Seller moved (~45 days).*** NEW PRICE *** MOTIVATED *** Stunning former MODEL HOME on a premium CORNER lot (FENCING is allowed)– loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful upgrades throughout, offering both comfort and style. Step inside to discover a bright, open floor plan featuring elegant luxury plank flooring and oversized tile. The ACCENT WALLS add depth and sophistication, while motorized shades and custom lighting fixtures bring both convenience and ambiance. Motorized shades offer effortless control of natural light and privacy at the touch of a button! The gourmet kitchen is a chef’s dream, complete with QUARTZ countertops, stainless steel appliances, under and over cabinet lighting, pull out cabinet organizers, elegant tile backsplash, a touchless faucet, and a large island perfect for entertaining. The home is also pre-wired with SURROUND SOUND, creating an immersive experience for movie nights or background music throughout the home. Downstairs is complete with a dining area, a bedroom/office (no closet), half bath, and a screened-in patio with collapsible sliding glass doors and motorized shades for added privacy. Upstairs you’ll find the PRIMARY SUITE with spa-like bath, a loft, two additional bedrooms, one full bath with a tub/shower combination, and a laundry room with a utility sink and folding table. The primary suite is generous in size and features a tray ceiling, crown molding, dual sinks, stone counters, an oversized shower, linen closet, and a walk-in closet with custom shelving. The loft is the perfect place to feature a second living area, or you can turn it into a play area for the little ones. This home is the perfect blend of luxury, functionality, and location. The 2-car garage has ample room for storage and includes a paver driveway, epoxy flooring, and is EV -ready for your electric car.  You’ll find a large open field to enjoy your morning walks with your furry friends across from the home. The community features a waterfront pool, parks, and playgrounds. If you’re feeling up for an adventure, the 22 mile long WEST ORANGE TRAIL is across the street from the entrance of the neighborhood and takes you into the highly sought after area of downtown Winter Garden where you can enjoy rooftop dining, charming boutiques, and a lively Farmers Market. You can also enjoy close proximity to the Oakland Town Center, Oakland Nature Preserve, Speer Park's playgrounds, tennis & pickleball courts, basketball courts, picnic areas, & the Healthy West Orange Arts & Heritage Center. Enjoy the tranquility of this peaceful neighborhood, with easy access to the Turnpike, East-West Expressway, 429, grocery shopping, theme parks, and golf courses, this home offers a lifestyle of unparalleled beauty and convenience. Embrace the enchanting OAKLAND-WINTER GARDEN lifestyle and make this exquisite residence your next place to live!

2606 Bobcat Chase Boulevard, Oakland

$530,000
3 Beds 2 Baths Covington Park A B D E F G & J SubDv. 34787 Zip Code
Welcome to the GOLF CART district of WINTER GARDEN! This STUNNING home was the former Ryan MODEL HOME located in Covington Park. Upon arrival you will notice the SHOW STOPPER LANDSCAPING which provides the most desirable CURB APPEAL. Step inside and you will find a very well maintained home that provides a SPACIOUS open floor plan. The kitchen has plenty of GRANITE counter space, tiled backsplash, closet pantry, beautiful cherry cabinets, and a breakfast bar. You will LOVE the open floor concept with being in the kitchen and never missing a thing with full view of the family room. There you will find sliding glass doors that lead to your screened lanai and extra added privacy with your FULLY VINYL FENCED backyard which is also large enough to build a pool. Enjoy family dinners in your formal dining room, and there is also a den/study adorned with french doors, or could be used as a formal living room or any flex space that fits your needs. Laundry will never be a hassle having your inside laundry room. This split bedroom plan offers convenience and privacy with 2 additional spacious rooms and guest bath which would also make a great pool bath. The community offers a pool, playground, West Orange Trail, and park. Enoy the downtown Winter Garden golf cart life with all the shops, dining, splash pad, annual events, and the AWARD WINNING FARMERS MARKET EVERY SATURDAY!!! This is the PERFECT neighborhood so schedule your showing today!!!

714 Parkmont Place, Winter Garden

$560,000
3 Beds 2 Baths Traditions Sub SubDv. 34787 Zip Code
Welcome Home! Beautifully updated in the heart of Winter Garden’s Golf Cart District! Upon entering you will find vaulted ceilings, engineered hardwood, open floor plan with split bedrooms, stunning upgrades, and custom built-ins. Kitchen features quartz counters, custom soft-close cabinets, farmhouse sink, large island overlooking the living area, pendant lighting, and stainless steel appliances. The fully fenced backyard boasts pavers, pergola, and a finished shed with electric, insulation, internet, mini split (2025), and more, perfect for an office or studio. Mini split in garage (2025) included. HVAC (2018), Roof (2017), smart garage door, and recessed lighting. Located just steps from the West Orange Trail, award-winning farmers market, local dining, shopping, and more in Historic Downtown. Easy access to major highways makes commuting a breeze. Don’t miss this incredible location and lifestyle!

139 Faulkner Street, Winter Garden

$440,000
3 Beds 2 Baths Covington Chase Ph 2a SubDv. 34787 Zip Code
Stunning 3-bedroom, 2-bath home located in the heart of downtown Winter Garden’s Golf Cart District. This well-maintained property features wood floors in the living room, tile in the dining and kitchen areas, and ceiling fans in every room. The spacious master suite can be converted into two rooms and offers private access to the screened lanai. Enjoy a fully fenced backyard with vinyl fencing, multiple fruit trees, garden space, and beautiful landscaping. Located in Covington Chase/Covington Park, which offers a community pool and playground. Just a short golf cart ride to Plant Street’s shops, restaurants, coffee shops, bars, farmers market, Winter Garden Theatre, splash pad, and Crooked Can Brewery. Close to the West Orange Trail, the new Orlando General Hospital clinic, and City Hall. This move-in ready home offers the perfect combination of comfort, community, and location!

434 Millwood Place, Winter Garden

$800,000
5 Beds 3 Baths Cambridge Crossing Ph 02 43/147 SubDv. 34787 Zip Code
Introducing an exceptional opportunity to reside in Windermere Crossing, Winter Gardens premier gated community. First time being offered by original owners this home reflects years of thoughtful care and meticulous upkeep. You'll love the privacy this oversized conservation homesite with mature landscaping provides. Upon entering you'll feel the grand spaces with high ceilings and natural light. This versatile floor plan offers 4 bedroom split plan on first level plus flex room ideal for multi-generational living or guest accommodations. Spacious second level bonus room provides flexible family options. The primary suite is a sanctuary of comfort, complemented by an ensuite bathroom with separate vanities, soaking tub and separate shower with dual walk-in closets. Direct access from the primary suite, family and secondary bedroom to the patio and pool area enhances the indoor-outdoor living experience. Kitchen located off the family room provides a center island with 42" Cabinets, solid surface counters, decorative backsplash, work space desk with full Stainless appliance package. Enjoy the peaceful views from the breakfast nook. Step outside to discover a private pool surrounded by extensive pavers with lush tropical landscaping, creating a tranquil retreat to soak up the Florida sunshine. Recent upgrades provide peace of mind, including a new roof (2017), Trane HVAC systems (2017 & 2018). Engineered Hardwood floors and tile throughout the first level make cleaning a breeze. This home has storage galore with custom built-ins including a Murphy bed! Located across the street from A-rated Lake Whitney Elementary this residence is also just minutes from shopping, dining, entertainment, and major highways (429, 408, Turnpike). Parents will love the cul-de-sac location too. Perfect for keeping an eye on the little ones for outdoor play space with no traffic! Experience the perfect blend of luxury, privacy, and convenience. Make this your new place to call home!

1061 Spring Mill Drive, Winter Garden

$535,000
2 Beds 2 Baths Island Pointe Sub SubDv. 34787 Zip Code
CUSTOM SALTWATER POOL HOME ON HALF-ACRE LOT WITH PRIVATE GARDEN OASIS! Set on a spacious treed lot backing up to conservation land—with no rear neighbors—this Winter Garden home offers the perfect blend of privacy and charm. Even better, it’s only a five-minute bike ride to Historic Downtown Winter Garden and has a low HOA. The outdoor space is truly the showstopper: a saltwater pool framed by lush greenery, winding garden paths, a wooden Adirondack swing, and hidden sitting areas. Nearly 1,000 sq. ft. of covered and screened porch space expands the living area outdoors, ideal for entertaining, a man cave, or flexible bonus space. Inside, the home features Brazilian solid-wood floors, custom cabinetry, granite counters, a stone backsplash, built-in oven/microwave, and display cabinets with under-cabinet lighting. The great room stuns with cathedral beamed ceilings, a gas fireplace, and floor-to-ceiling windows that overlook the gardens. The primary suite includes vaulted ceilings, a bay window, dual closets, and a spa-style bath with double vanities, garden tub, and separate shower. A secondary bedroom is large enough to serve as a second master. Additional details include wide interior doorways for accessibility, plaster walls, a leaded-glass entry, double-pane insulated windows, and a 16-SEER A/C. The roof, replaced in 2020, is now just about 5 years old, offering peace of mind for years to come. A transferable termite bond, thoughtful design, and prime location make this home a standout in Winter Garden.

975 Sadie Lane, Winter Garden

$410,000
3 Beds 2 Baths Regal Pointe Ph 02 47/133 SubDv. 34787 Zip Code
Live the Winter Garden lifestyle in this beautifully maintained home with lakefront living in a quiet community, just minutes from downtown Winter Garden! Enjoy a fenced backyard right on the lake, perfect for morning coffee, evening sunsets, or weekend BBQs. The screened patio with vinyl panels offers year-round comfort. Located in a beautiful deed-restricted community with a sparkling pond and a fountain that lights up at night, this home also boasts a very low HOA. You’ll be just minutes from downtown Winter Garden and Winter Garden Village, giving you quick access to shopping, dining, and entertainment — whether by car, bike, or even golf cart! Plus, you’re within 25 minutes of Orlando’s theme parks, airport, and downtown Orlando. Furniture may also be negotiated for a very reasonable fee, making this home move-in ready!

307 Grand Royal Circle, Winter Garden

$537,000
4 Beds 3 Baths Johns Landing Ph 02 48 138 SubDv. 34787 Zip Code
Welcome to your dream home in the highly sought-after Johns Landing community! This immaculate 4-bedroom, 3-bathroom residence offers a perfect blend of elegance, comfort, and convenience—nestled in the heart of charming Oakland, FL. From the moment you step inside, you’ll be greeted by soaring ceilings, abundant natural light, and an open-concept layout ideal for both entertaining and everyday living. This home has been meticulously maintained-- with fresh exterior paint, 2 nest thermostats, engineered hardwood flooring, electric water heater 2024, upgrades to bathrooms, new roof in 2021 and more! The chef’s kitchen boasts granite countertops, stainless steel appliances, and a spacious island, seamlessly flowing into the family room and dining area. The private owner’s suite features a spa-like bathroom with dual vanities, a soaking tub, and a walk-in shower. Step outside to your covered lanai and enjoy peaceful views of your beautifully landscaped yard—perfect for morning coffee or evening gatherings. Beyond the comfort of home, you’ll love the location! Just minutes from Walt Disney World Resort, Universal Orlando Resort, SeaWorld, and Orlando’s world-class dining, shopping, and entertainment and the famous Downtown Winter Garden area. Outdoor enthusiasts will appreciate easy access to the West Orange Trail for biking and walking, as well as nearby Lake Apopka for boating and fishing. With close proximity to major highways, commuting to Downtown Orlando or Orlando International Airport is a breeze. The neighborhood features 2 pickleball courts, tennis court and playground as we well as community boat ramp to John's Lake. Don’t miss this rare opportunity to own a slice of Florida paradise—schedule your private tour today!

326 Largovista Drive, Oakland

$479,900
3 Beds 2 Baths Tuscany Ph 02 SubDv. 34787 Zip Code
Golf cart district * motivated seller * Beautiful single-story home is nestled in a serene cul-de-sac in the heart of downtown Winter Garden. It is just an 8-minute drive to downtown Winter Garden, 5 minutes away from Publix, 10 minutes to Walmart, 14 minutes to target in winter garden village, easy access to SR-429 and Florida turnpike, offering exceptional convenience. This cozy 3-bedroom, 2-bathroom and an office can be an easy 4th bedroom. Modern single-story home provides 2,035 square feet of comfort and style. Fully renovated in 2022, featuring no carpeting throughout with dual offices, the kitchen has been updated with refinished cabinets and stainless steel appliances. Additionally, the roof and air conditioning were replaced in 2020, making it an ideal choice for buyers seeking a quick-move-in home!

1672 Malcolm Pointe Drive, Winter Garden

$515,000
3 Beds 3 Baths Latham Park North SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained one-owner home in the highly sought-after Latham Park community of Winter Garden, ideally located just minutes from Hamlin, top-rated schools, and the 429 expressway. Built in 2018, this charming Celebration-style home offers the perfect blend of modern design, comfort, and convenience. From the covered front porch, enjoy nightly views of the Disney fireworks, or unwind on the spacious covered lanai overlooking your peaceful backyard. Inside, the home boasts a bright, open layout with neutral laminate flooring throughout the main level and cozy Shaw stain-resistant carpet upstairs. The heart of the home is the gourmet kitchen, featuring 42" white cabinetry, sleek white quartz countertops, a large island with modern black fixtures, and Whirlpool stainless steel appliances, including a gas range, refrigerator, microwave, and dishwasher. Upstairs, you'll find all bedrooms, including the spacious primary suite with an ensuite bathroom offering dual sinks, a walk-in shower, and a large walk-in closet. The convenient second-floor laundry room comes complete with a gas washer and dryer. Additional features include: Gas furnace and tankless gas water heater, community pool, fire pit, playground, clubhouse, and 1,000-ft nature preserve boardwalk Perfectly situated near Hamlin Groves Town Center, you'll have easy access to shopping, dining, a luxury movie theater, and the Orlando Health Hospital. And with Disney just 15 minutes away, you'll enjoy the magic from the comfort of your own home.

14214 Shocklach Drive, Winter Garden

$660,000
3 Beds 2 Baths Woodbridge On Green SubDv. 34787 Zip Code
First time on the market! This one-owner Custom St. Andrews Model pool home has been meticulously maintained and showcases a blend of modern design and timeless style. From the moment you arrive, the curb appeal stands out with a paver driveway and sidewalk framed by reinforced concrete borders, a manicured lawn, elegant topiary plantings, and trimmed box hedges. A custom front door complements the updated garage door with mid-century flair. In the backyard, you’ll enjoy tranquil views of the large pond and fountain, framed by Rubellini palms and lush, tasteful landscaping. Step inside to find an inviting formal dining room and a versatile living room, currently used as an office. Volume ceilings and a striking three-sided gas fireplace create warmth and character, while the spacious family room opens seamlessly to the lanai and sparkling screened pool—perfect for entertaining. The bright kitchen features light cabinetry, a subway tile backsplash, stainless steel appliances, and a cozy breakfast nook with views of the pool and backyard. The popular split-bedroom layout offers privacy for all. The primary suite, located just off the kitchen, boasts a sitting area ideal for reading or relaxing, with direct access to the pool and serene backyard views. The ensuite bath includes a large walk-in shower, deep soaking tub, dual sinks with a vanity area, and a walk-in closet with custom built-ins and stylish accent doors. Two additional bedrooms on the opposite side of the home share a full bath and linen storage, while one guest room at the front of the home offers extra privacy. The homes water lines have been updated and replaced to current 2025 code with Warranty This community makes maintenance easy with HOA-provided lawn care (mowing, trimming, fertilization, and hedge work), irrigation, and exterior house painting every nine years. Residents also enjoy access to a dedicated storage lot for boats or RVs, high-speed fiber optic service, and a prime location adjacent to the private West Orange County Country Club. With unbeatable amenities, thoughtful details throughout, and a rare first-time offering, this home truly has it all. Schedule your private tour today!

14014 Fairway Willow Lane, Winter Garden

$960,000
4 Beds 4 Baths Cypress Reserve Ph 1 SubDv. 34787 Zip Code
Gorgeous pool home in the highly desirable Cypress Reserve community! 4 bedroom, 3.5 bath with a sprawling 4000 sf and 3 car garage. Inside you will be greeted by tall soaring ceilings, tall windows with lots of natural light, and a spacious open floorpan with the staircase and balcony anchored in the center of the room serving as an elegant focal point. The entry has a formal dining area to the left and an office with French doors to the right. The stunning kitchen is a chef's dream and is the center of attention for entertaining and gatherings. Enjoy cooking your favorite meals in the magazine worthy kitchen with premium stainless steel appliances, gas stove, beautiful white cabinets, butler's pantry, granite countertops, modern backsplash, and a large island. You will notice the architectural details including arched walkways, tray ceilings, 8 foot doors and wood vinyl floors. Entertain family and friends in the large living area while overlooking the serene pool and conservation view. Retreat to the primary bedroom on the first floor with plenty of space for a sitting area, with duel walk in closets, and a beautiful en suite with a garden tub, large shower and duel vanities. On the second floor you will find the other 3 large spacious bedrooms and a huge loft space that is perfect for a game room or home theater. The loft has a bathroom and another room that can be used for an additional home office/flex space or home gym. The guest bath offers duel sinks and a private tub/shower combo. This home is surrounded by conservation land, no construction is allowed in front of or behind this home, so you will always have a tranquil and clear view outside your windows. Throw a barbecue and float around in the salt water pool with waterfall features and a gorgeous view of nature. Energy efficiency with a solar system that is owned outright, Ecobee smart thermostat, tankless water heater, whole home water system and fresh interior paint. In walking distance to Sunridge Elementary and Middle Schools. Close to downtown Winter Garden with all of its great dining options and conveniently located close to the 429 and Florida's Turnpike. Schedule your showing today for this stunning Winter Garden home and make it yours today!

13881 Jomatt Loop, Winter Garden

$1,370,000
5 Beds 6 Baths Hickory Hammock Ph 1d SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Come see this beautiful property in the Hickory Hammock gated neighborhood in Winter Garden. The stunning pool and spa features fire bowls, jetted arching water, surround sound outdoor system, digital light package, water sun deck, and sunken seating area. Elegance meets everyday comfort, offering nearly half an acre of beautifully manicured space, a large driveway, and 3-car garage, one of which is air-conditioned, making it perfect for that special car or workshop; all setting the tone for the stunning features found inside. The foyer greets you with soaring ceilings, modern light fixtures, and gorgeous wooden handrails, along with a convenient half bathroom and a formal dining room, perfect for hosting special occasions. The kitchen is a chef’s dream with two islands, stainless steel appliances, glass-front cabinetry, chic design features, a wine fridge, and a breakfast bar that makes preparing meals of any size feel effortless. A large sunny dining area nearby is ideal for quick family meals, while the open layout connecting the kitchen, dinette, and living room looks out over the pool area ensuring you never miss a moment with your loved ones. A custom home office on the first floor includes an en suite bath that doubles as a pool bathroom with direct lanai access. All-new flooring was installed throughout the home in 2020, with tile downstairs and wet areas, and solid white oak hardwood upstairs. Upstairs lies all of the bedrooms, ensuring optimal privacy when hosting guests, as well as a bonus loft space with half bath and nearby laundry room. The versatile loft upstairs provides an area for anything that suits your family's needs, while the upstairs laundry room with a sink adds convenience and practicality. The spacious primary suite offers a relaxing retreat with a tray ceiling, private balcony, abundant natural light, and a custom walk-in closet organization system. The primary en suite bathroom exudes luxury and features a dual sink vanity and a large walk-in shower with dual shower heads. Additional bedrooms upstairs are equally inviting, with ample storage and natural light, as well as a Jack-and-Jill bathroom with dual sinks. Back downstairs, spend your days in your own private resort with a screened-in lanai featuring a sparkling saltwater pool & spa, and a covered patio area, perfect for al fresco dining and lounging in the warm Florida sunshine. Take a dip in the resort-style pool, soak up the sun on the patio or enjoy a summer BBQ; the options for fun & relaxation in this beautiful outdoor space are truly limitless! The spacious fenced backyard allows four legged friends and little ones to roam freely with peace of mind. This gated community enhances your lifestyle with amenities such as a dog park, tennis courts, fitness center, playground, pool, and golf-cart-friendly streets so you never have to go too far for some family fun. Located near FL-429 and the Florida Turnpike, this home makes commuting a breeze and keeps you close to lakes, nature trails, and parks so you can truly enjoy Central Florida's natural beauty. You’ll also enjoy top-rated schools and nearby shopping and dining at Winter Garden Village and downtown Winter Garden. With Disney just 20 minutes away, Universal Studios and downtown Orlando within 25 minutes, and the airport only 30 minutes away, this home provides the very best of the Central Florida lifestyle. Don't miss out on this stunning home, schedule your private showing TODAY!

15956 Citrus Knoll Drive, Winter Garden

$645,000
4 Beds 3 Baths Johns Landing Ph 01 44/47 SubDv. 34787 Zip Code
Discover this fantastic 4-bedroom, 3-bathroom home located at 829 Cura Ct in beautiful Oakland, Florida. This property offers an incredible ********SOLOR energy system installed in 2021 that's completely PAID IN FULL********, meaning you can enjoy virtually no electric bills. The home features attractive laminate flooring throughout and has been well-maintained with recent updates. The standout feature is the custom kitchen built in 2023, showcasing beautiful wood cabinets and modern stainless steel appliances that create a perfect blend of style and functionality. The roof was replaced in 2018, along with the AC system, pool heater, and pump. Additional improvements include a new hybrid water heater in 2021, a whole house filtration system in 2021, and a brand new electric panel in 2025. Step outside to your private backyard oasis featuring a swimming pool perfect for relaxing or entertaining guests. The community offers access to a boat dock on Johns Lake, ideal for water skiing and other recreational activities. Location is everything, and this home delivers. You're just minutes away from charming downtown Winter Garden, offering dining, shopping, and entertainment options. The Oakland Nature Preserve is nearby for outdoor enthusiasts, and convenient amenities like grocery stores are easily accessible. This energy-efficient home combines modern updates with comfortable living spaces. The open floor plan and well-appointed bedrooms make it perfect for families or anyone seeking a peaceful retreat. With all the recent improvements including the stunning new kitchen and the solar system already in place, you'll move into a home that's ready to enjoy without additional major expenses. Don't miss this opportunity to own a beautifully updated home in a desirable Oakland location with lake community amenities.

829 Cura Court, Oakland

$560,000
3 Beds 2 Baths King Bay SubDv. 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to your downtown Winter Garden dream. This updated three-bedroom, two-bath pool home sits right in the golf cart district, just minutes from Plant Street Market, Crooked Can Brewery, and the Saturday Farmers Market. Picture weekend strolls with a coffee in hand, dinner with friends at your favorite local spot, and nights catching live music at the Garden Theatre. Inside, the vibe is comfy-chic with a newer roof, fresh paint inside and out, and a brand-new irrigation system so you can chill instead of worry. The kitchen was remodeled in 2022 with modern finishes that make cooking or hosting feel effortless. Step out back to your own little resort: a sparkling pool with a new heater that keeps the Florida sunshine going all year. Whether it’s summer BBQs, neighbor hangouts, or quiet poolside evenings, this backyard is pure main-character energy. You’ll also love the minimal HOA and the easy access to Orlando, the airport, and the beaches. But nothing beats coming home to that small-town Winter Garden charm. If you’ve been dreaming of a place that feels like a vacation every day, this is the one. Everything you love is just a golf cart ride away. Would you like me to make it slightly shorter so it fits cleanly in a listing flyer or Instagram caption too?

312 N Park Avenue, Winter Garden

$482,500
3 Beds 2 Baths Oak Park At Winter Garden SubDv. 34787 Zip Code
Discover this beautifully updated 3-bedroom, 2-bathroom home in Winter Garden, FL, offering a desirable split floor plan and exceptional use of space. Recent upgrades include remodeled bathrooms, new sink and kitchen countertops, fresh exterior paint, newer roof, newer HVAC, and no carpet for easy maintenance. Just blocks from downtown Winter Garden’s dining, shopping, and award-winning farmers market. Located in the sought-after Golf Cart District, this home offers the perfect blend of charm and convenience with a low HOA. Hop on the West Orange Trail minutes from your doorstep, perfect for a morning run or bike ride or afternoon stroll enjoying the beautiful Florida scenery West Orange County has to offer. Whether you’re relaxing at home, exploring local boutiques and restaurants, or cruising to the farmers market on your golf cart, this move-in ready property puts you in the heart of one of Central Florida’s most vibrant communities.

653 Stevelynn Circle, Winter Garden

$867,500
4 Beds 3 Baths West Lake Hancock Estates SubDv. 34787 Zip Code
Welcome to this extensively upgraded, smart-enabled Pool and Spa one-story home featuring a 3-car garage and a long list of modern improvements both inside and out. Nestled in the Luxury Overlook at the Hamlin community, zoned for top-rated schools, and less than 15 minutes to the back entrance of Walt Disney World. Inside, the kitchen and laundry room were fully remodeled in 2025. Chef’s dream kitchen features a premium double wall oven with versatile top oven (can be converted into 2 separate cooking compartments) giving you three independent cooking zones in one appliance; In addition you have the full-size oven and range, giving you four cooking areas to prepare multiple dishes at once, perfect for hosting holidays, dinner parties, or just making weeknight meals a breeze. There’s also dedicated Coffee water lines and a spacious custom-built pantry with rotating storage. The laundry room includes an all-in-one smart washer/dryer, custom cabinetry with slide-out hampers, and a mop closet. Thoughtful interior upgrades are found throughout: a motorized shade for the sliding glass door, a custom hallway game/coat closet, a Jack & Jill bath with new tile and shower, redesigned guest closets—including one with a built-in desk perfect for working or studying from home—and a custom primary closet with added lighting, drawers, mirrors, and shelving. The primary bathroom is equipped with convenient USB outlets, including one dedicated for accessories. The oversized garage offers space for 3 cars and ample storage, including pull-down stairs to attic, featuring Tesla EV and golf cart charging outlets, ceiling-mounted storage, and additional laundry hookups for an additional washer and dryer. Major systems provide peace of mind, HVAC replaced in 2023 with TRANE, pool equipment updated within the last two years, gas pool/spa heater 2025, new garage door openers, tracks, exterior access panels, and the exterior painted 2022. Technology upgrades include hard-wired Quantum fiber internet, an Eero Wi-Fi mesh system with three access points, smart light bulbs, motion sensors, USB outlets, smart smoke/carbon monoxide detectors (all new), and multiple ethernet ports throughout. In-ceiling speakers inside and outside, 5 exterior security cameras (expandable to 8), and an ADT security system with door and window sensors complete the package. Step outside to your private oasis with an oversized pool and spa, artificial turf around the screened lanai, soffit lighting, smart pool controls, custom outdoor cabinetry with water line and filtration system set up for fridge/ice maker and coffee maker, and the lanai is set-up to keep you comfortable year-round with hard-wired additional fans and heaters. The fenced yard, complete with gated access and dog run area completes this incredible outdoor living space. The community features resort-style amenities, including a dock, boat ramp, clubhouse, gym, dog park, playgrounds, and scenic walking trails. Minutes from the Hamlin Town Center, the new hotspot in Horizon West, where you can enjoy shopping, unique restaurants, a brewery, and entertainment, including the luxury Cinepolis and PopStroke. Explore the community's walking trails on foot, by bike, or by running, or take a golf cart ride! These trails lead directly to the Town Center, making it easy to navigate and enjoy everything this vibrant area has to offer. Schedule your appointment to tour today!

7779 Minutemen Loop, Winter Garden

$1,570,500
3 Beds 4 Baths 34787 Zip Code
A Rare Slice of Serenity in the Heart of Horizons West — 5526 Tiny Road Almost five acres in the middle of one of Central Florida's most sought-after communities isn't just rare — it's nearly impossible to find. While the rest of Horizons West builds closer together, 5526 Tiny Road sits on almost five rolling, private acres surrounded by open sky, a private pond, and natural Florida landscape — all within walking distance of community trails, top-rated schools, and the brand-new Orange County Library currently under construction just steps away. This is the property buyers spend years waiting for. The freedom of acreage. The convenience of community. No HOA. No compromise. The custom-built 2007 estate offers 2,400 square feet of thoughtfully designed living space — three bedrooms, a spacious loft, and 2.5 bathrooms inside, plus a half bath in the oversized 3.5-car garage built for the enthusiast, the workshop, the toys, or all three. The open-concept layout is filled with natural light, anchored by a gourmet kitchen and flowing living spaces designed for both everyday comfort and effortless entertaining. Step outside and the property truly comes alive. A front gazebo attached to the home frames sweeping views across the acreage. The screened rear lanai overlooks a nature preserve. Sunrises and sunsets paint the elevated ridge in a way that no subdivision lot can replicate. Wild turkeys, native birds, and open Florida sky are your neighbors. Just a short ride to Hamlin Town Center, Disney World, SR-429, and everything Horizons West continues to build around you — including planned road enhancements to Tiny Road itself, with landscaped medians and expanded sidewalks that will further elevate the entrance to this property. Properties like this don't come back to market. Once it's gone, it's gone — because there is nothing left to build like it here. 3 Bed | Loft | 2.5 Bath + Garage Half Bath | 3.5-Car Garage | Almost 5 Acres | No HOA | Custom 2007 Build | Private Pond | Horizons West / Independence-Summerport

5526 Tiny Road, Winter Garden

$780,000
4 Beds 4 Baths Cypress Reserve SubDv. 34787 Zip Code
*Click the link for 3-D Tour* Welcome to this beautifully maintained 4-bedroom, 3.5-bath pool home in the heart of Winter Garden, built in 2017 and offering the perfect blend of comfort, privacy, and convenience. Nestled on a conservation lot with no rear neighbors, this home features a spacious screened-in saltwater pool with a freestanding hot tub and covered seating area, ideal for outdoor living. Inside, enjoy an open floor plan with vaulted ceilings, abundant natural light, and a chef's kitchen complete with gas range, breakfast bar, under-cabinet lighting, and custom pantry storage. The first floor features all tile, while the second floor has brand-new carpet throughout, including a large loft perfect for a game room, office, or play space. Upstairs, two bedrooms share a full bath, while a separate fourth bedroom includes its own ensuite. Storage is maximized with custom-built systems in every closet and pantry, plus overhead garage storage and built-ins in the laundry room. The three-car side-entry garage adds extra curb appeal and functionality. Located in the community of Cypress Reserve which features a pool and playground and is just steps from Sunridge Elementary and Middle Schools, this home is minutes from historic downtown Winter Garden and a mile from from the Tucker Ranch Park and Nature Preserve with a new Wellness Park being completed next year. This community also offers an easy commute to theme parks and the airport via access to major roadways to enjoy all that Central Florida has to offer.

13857 Jomatt Loop, Winter Garden