Homes for Sale Near West Orange High in Winter Garden - 114 homes

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: 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: 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. *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: 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: 2/1 Excellent

Listing is courtesy of: HOMESMART (407-476-0451)

Listing Agent: Maria Lloret (407-929-1994)

Remarks: Twinwaters ** Former MODEL home built with BEAUTIFUL UPGRADES ** 3 car garage ** Heated POOL & SPA HOME ** Upgraded pool automation NEW 2024 Aqualink control unit, NEW pool pump versa flow 2025, new pool heater 2021, NEW pool salt cell and perfect space for entertaining under the giant +/-40x12 lanai featuring an outdoor kitchen w/gas grill and refrig** Prime CULDESAC location on dead end st across from green space with HOA community pool and play area a short walk ** +/-14x19 beautiful primary bedroom ensuite w french doors leading to the pool & outdoor living space ** Some upgr incl: solar panel system (paid off) for pool, wood tile all main rooms and bathrooms, 8' 2 panel square interior doors, 10' ceilings, crown molding, surround sound 5.0 Polk audio surround ceiling speakers & subwoofer in all the main rooms, quartz counters in the master and kitchen ** Primary bath offers a free standing soaking tub, dual vanities, sinks, a heated bidet, spacious walkin shower & huge walk in closet with custom shelving ** Sonos system upgr receiver 2021 ** Perfect set up for inlaw or guest suite at the end of the main hall with 2 bedrooms, walk in closets and a full bathroom with access to the outdoor living area -Just add a door for a private separate space ** Another possible guest suite is the 1 bedroom and full bath right off the foyer for a guest area ** The main living space offers a lovely inviting open floor plan featuring a family room with sliding glass doors to the pool area and cafe space w beautiful stone accent wall ** The kitchen features upgraded white cabinetry with roll out shelves 2020, white quartz counters, above & under cabinet lighting, an expansive breakfast bar, a separate kitchen island making it a perfect spot to gather ** Built in Kitchenaid built in convection oven, cooktop & Kitchenaid exhaust fan make it enjoyable for cooking ** 2 pantries including a butlers pantry w quartz counters, white cabinets with rollout shelves 2023, a wine chiller Kitchenaid refrig & wine rack plus a separate walk in closet pantry with built in shelving ** Fantastic floor plan with a den/study off foyer or use as another bdrm, then a guest or inlaw suite across the hall & 2 additional bedrooms at the end of the hallway with a 3rd full bath ** Electric heat and hot water heater **Propane gas pool heater and gas grill **Whole house water softener treatment system 2020 & security system main control panel just replaced *All rm measurements are from the Meritage builder flr plan and are approximate. Buyers to verify measurements. Seller did not use the solar panel pool heater system ** The following convey: Wine chiller Kitchenaid refrig in butlers pantry, water softener, Sonos system upgraded 2021 and receiver replaced 2021, security system and 4 exterior cameras 2021, refrig and grill on the outdoor kit., solar panels for the pool heater, all pool equipment, pool heater, metal overhead racks in the garage and attached wall racks **Not conveying: Kit ice maker machine, cable box and Roku not incl.

Listing is courtesy of: INDEPENDENCE REALTY GROUP LLC (407-408-6662)

Listing Agent: Andrew Philippone (407-408-6662)

Remarks: Presenting this exquisite modern residence standing alone without neighbors in either side or rear in a neighborhood of almost 150 homes showcasing souring ceilings, designer finishes, and an open-concept living space bathed in natural light. A gourmet kitchen that anchors the home, while expansive glass doors reveal a resort-style screened pool and outdoor lounge. Architecture, luxurious details inside all bathrooms and kitchen, and seamless indoor-outdoor living create an exceptional retreat for refined entertaining. An amazingly fancy electric chimney gives the living room area warmth and elegance. AC units are of high efficiency with hotel fragrance throughout the entire home. COME AND SEE IT SOON! AC units is 3 years. New roof to be installed.

Listing is courtesy of: PAULINO GLOBAL REAL ESTATE (407-455-1981)

Listing Agent: Andrea Paulino (813-753-6110)

Remarks: Public on Zillow / Realtor

Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)

Listing Agent: Saijun Gong (407-775-8533)

Remarks: Welcome to this stunning architectural masterpiece nestled in the heart of Twinwaters, one of Winter Garden’s most sought-after communities. This elegant two-story home seamlessly blends sophistication and comfort, offering over 3,600 square feet of beautifully designed living space. Step through the grand entryway to find soaring ceilings, expansive windows that fill the home with natural light, and designer finishes that exude contemporary luxury. The gourmet chef’s kitchen is a true showpiece—featuring 42” custom cabinetry, gleaming quartz countertops, a massive entertainment island, stainless steel appliances, and a walk-in pantry, perfect for culinary enthusiasts and family gatherings alike. The open-concept great room flows effortlessly into a spacious dining area and covered lanai, ideal for both indoor and outdoor entertaining. Upstairs, the luxurious primary suite offers a serene retreat with a spacious walk-in closets, a spa-inspired bathroom with a deep soaking tub, frameless glass shower, and dual vanities. A versatile loft provides additional space for a home theater, gym, or play area, while the first-floor guest suite ensures comfort and privacy for visitors. The private backyard invites you to create your own oasis—whether adding a pool, summer kitchen, or lush garden escape. Enjoy resort-style amenities including a community pool, playground, and picturesque walking trails, all surrounded by pristine lakes and lush landscaping. Twinwaters is ideally situated near Horizon West, top-rated schools, fine dining, boutique shopping, and major highways for an easy commute to downtown Orlando and world-famous attractions. This home truly embodies the ultimate blend of luxury, location, and lifestyle—a rare opportunity to live beautifully in one of Central Florida’s premier communities.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Jay Winston (407-497-1112)

Remarks: Rare Gated Lakefront Retreat with Grandfathered Boat Access on Lake Luntz Discover resort-style living in this one-of-a-kind gated lakefront home in the heart of Winter Garden. Nestled on a quiet, tree-lined cul-de-sac, this 5-bedroom, 5-bathroom, 4,365 Sq Ft home offers a smart layout designed for both everyday living and entertaining. The first-floor bedroom and full bath are ideal for guests or multi-generational living, while upstairs includes a loft, media room, and three additional bedrooms, including one en-suite and a Jack-and-Jill setup. Enjoy endless lake views from the screened pool with grotto seating and waterfall, or entertain indoors in the Florida Grill/Bar room featuring a refrigerator, freezer, deep fryer, griddle, bar sink, dishwasher, and full pool/guest bath. The primary suite is a true retreat with double walk-in closets, spa-style bath, garden tub, walk-in shower, and dual water closets. Lake enthusiasts will love the boathouse, covered dock, and boat lift, complete with power and water, along with multiple watercraft options including a pontoon slip (~20’), jet ski slip for 2, power lifts, and additional space for non-powered boats. Additional bonus spaces include a garage under air with a separate gym/rec room. Outdoor living abounds with a beachfront-style area, wood-burning fireplace, granite bar-top seating, and spectacular sunset views. This is a rare opportunity to own the only home on Lake Luntz with grandfathered boat access, offering a private lakefront lifestyle you won’t find anywhere else.

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

Listing Agent: Keegan Siegfried (813-670-7226)

Remarks: One or more photo(s) has been virtually staged. Welcome to 1226 Portmoor Road in the highly sought-after, manned-gated Golf community of Stoneybrook West! This stunning 5-bedroom, 3-bath golf-view home offers over 2,800 square feet of beautifully updated living space. Designed for both comfort and entertaining, the home features formal living and dining rooms, a spacious family room, and a desirable first-floor guest bedroom with a full bath. The chef’s kitchen shines with granite countertops, stainless steel appliances, and an extra refrigerator in the garage. Upstairs, enjoy new laminate flooring, generously sized bedrooms, and a luxurious primary suite with tray ceilings and a private balcony overlooking the course. Step outside to your upgraded screened lanai and low-maintenance turf backyard—perfect for relaxing or hosting gatherings. A NEW ROOF (2021), A NEW A/C (2022), and A NEW Water Heater (2023) add peace of mind. Residents enjoy a Jr. Olympic pool, fitness center, clubhouse, dock, tennis, basketball, playground, high-speed internet, cable, and discounted golf—all minutes from Winter Garden Village, major highways, hospitals, theme parks, and Orlando International Airport.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Shirley Botansky (407-704-0874)