Winter Garden Homes with Gated Community - Guard Community Features

Winter Garden Homes with Gated Community - Guard Community Features

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winter Garden and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Newest Winter Garden Homes with Gated Community - Guard Community Features

1414 Portmoor Way, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
Video is virtually staged. Enjoy the best of both worlds in this beautiful pool home overlooking the Stoneybrook West Golf Course, where peaceful surroundings, beautiful views, and an abundance of community amenities create the perfect lifestyle. With NO REAR NEIGHBORS and a location OVERLOOKING THE GOLF COURSE on quiet Portmoor Way, you can relax while having plenty of opportunities to stay active, socialize, and connect with neighbors. The curb appeal is welcoming as is the spacious foyer, tall ceilings, and WOOD FLOORS. The well-appointed kitchen features QUARTZ countertops, tile backsplash, stainless steel appliances, and a WALK-IN PANTRY. Enjoy the breakfast nook that opens to the family room, creating a comfortable gathering space with beautiful views of the SCREENED-IN POOL and golf course. The spacious primary suite is conveniently located downstairs and offers a large walk-in closet, an updated vanity with double sinks, a garden tub, separate shower, and linen closet. Upstairs, you'll find AIRY LOFT, laundry room with cabinet storage, three additional bedrooms, and a hall bathroom with double sinks. Additional interior highlights include a formal dining room, a PRIVATE OFFICE with stylish barn doors, and an attractive staircase with iron railing and an accent wall. The home also offers valuable updates, including a NEW ROOF (2022), AC (2019), upgraded light fixtures, tile flooring in the garage, and rain gutters. One of the greatest benefits of living in Stoneybrook West is the incredible lifestyle included with your HOA! SPECTRUM CABLE AND INTERET ARE INCLUDED IN THE HOA DUES. Spend sunny afternoons at the Olympic-sized COMMUNITY POOL and splash pad, meet neighbors at the clubhouse and FITNESS CENTER, or enjoy friendly competition on the BASKETBALL, PICKELBALL, VOLLEYBALL and TENNIS courts. For those who love the water and outdoors, the community also offers a BOAT RAMP, limited BOAT STORAGE, and a FISHING pier. Stoneybrook West is conveniently located near highly regarded schools, restaurants, shopping, major roadways including the 429, Turnpike and 408, historic downtown Winter Garden, and Central Florida's world-famous theme parks.

1414 Portmoor Way, Winter Garden

1370 Portmoor Way, Winter Garden
$755,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
Nestled within the highly desirable golf course community of Stoneybrook West in Winter Garden, this beautifully renovated 5-bedroom, 4-bathroom residence offers a perfect blend of modern finishes, spacious living areas, and exceptional Florida living. Thoughtfully updated throughout, the home features a newer roof and HVAC system, fresh interior paint, new custom kitchen and bathroom cabinetry, luxury vinyl plank flooring, new bedroom carpeting, updated lighting and ceiling fans, and a newly re-screened enclosure. At the heart of the home, the stunning remodeled kitchen showcases custom cabinetry, all new stainless steel appliances, elegant quartz countertops, designer lighting, and an oversized breakfast bar ideal for gathering and entertaining. A charming breakfast nook provides the perfect spot for casual dining while enjoying picturesque views of the golf course. The inviting living spaces are enhanced by a beautiful double-sided fireplace, creating warmth and character throughout the home. A versatile downstairs flex room and bathroom offer endless possibilities for a home office, in-law suite, or playroom. Upstairs, a loft at the top of the stairs provides additional living space for relaxing, working, or entertaining. The private primary suite serves as a peaceful retreat, featuring a generous layout, a luxurious ensuite bathroom with an oversized walk-in shower, and a private balcony overlooking the golf course—an ideal place to enjoy your morning coffee or unwind at the end of the day. Four additional bedrooms provide flexibility for family, guests, or additional workspace. The thoughtfully designed outdoor living area includes a screened pool with spa, new pool equipment and a convenient fourth bathroom with a shower accessible from the pool area, making entertaining and enjoying Florida's year-round sunshine effortless. Beyond the home, Stoneybrook West offers an exceptional lifestyle with resort-style community amenities. The HOA includes access to the Olympic-sized community pool, splash pad, clubhouse with fitness center, basketball courts, tennis courts, and pickleball courts. Residents can also enjoy the community boat ramp, and fishing pier, providing even more opportunities for outdoor recreation and relaxation. Newer Roof and HVAC. Ideally located near excellent schools, shopping, restaurants, and everyday conveniences, Stoneybrook West is guard gated and offers easy access to the 429, Florida Turnpike, and 408, as well as historic downtown Winter Garden and Central Florida's world-famous theme parks. With its extensive renovations, golf course views, private pool, and outstanding community amenities, this exceptional home offers the perfect combination of comfort, style, and location. Schedule your showing today!

1370 Portmoor Way, Winter Garden

13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden

14501 Grove Resort Avenue Unit 1218, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park, where vacation ownership meets the full Orlando resort lifestyle! This beautifully furnished 2-bedroom, 2-bath condo-hotel residence offers a spacious, comfortable retreat just minutes from Walt Disney World and Central Florida’s world-famous attractions. Designed for both relaxation and convenience, the residence features an open living and dining area, a fully equipped kitchen with stainless steel appliances, generous cabinetry and counter space, in-suite washer and dryer, and a private screened balcony—the perfect place to enjoy your morning coffee or unwind after a day at the parks. The spacious primary suite offers a private bath with dual vanities, soaking tub and separate shower, while the second bedroom and full bath provide plenty of room for family and guests. At The Grove, the resort itself is part of the experience. Spend the day at Surfari Water Park featuring a 695-foot lazy river, dual water slides, zero-entry pool, kids’ activity pool and exciting FlowRider® Double surf simulator. Looking for a slower pace? Relax at The Springs Pools with three full-size pools and an oversized hot tub, enjoy the natural beauty of Lake Austin, work out in the 24-hour fitness center, or take advantage of the resort’s restaurants, bars, family activities and recreation. The resort also offers transportation to Walt Disney World, Universal Orlando and SeaWorld, making it easy for guests to experience everything Orlando has to offer. Disney Springs is approximately 11 miles away, with SeaWorld, Universal Orlando, Epic Universe and countless dining, shopping and entertainment destinations all within easy reach. Ownership is made even more convenient by an association fee that includes many of the expenses normally handled separately, including electricity, water, sewer, trash, cable, internet, pest control, security, common-area and building maintenance, and recreational facilities.* Whether you're searching for your own Florida vacation getaway, a second home near the theme parks, or a furnished resort property with vacation-rental potential, Unit 1218 offers the opportunity to own where millions of visitors come to vacation every year. Come for the parks. Stay for the resort. Own a piece of the Orlando vacation lifestyle at The Grove Resort & Water Park.

14501 Grove Resort Avenue Unit 1218, Winter Garden

14501 Grove Resort Unit 2304, Winter Garden
$165,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Short Sale. Experience the Ultimate Orlando Resort Lifestyle & Investment Opportunity! Welcome to The Grove Resort & Water Park, one of Central Florida’s premier vacation destinations, ideally located just minutes from Walt Disney World and close to Universal Studios, SeaWorld, Margaritaville Resort, shopping, dining, and Orlando International Airport. Enjoy a fully furnished, turnkey 2-bedroom, 2-bath condominium that offers the perfect blend of comfort, style, and investment flexibility. The spacious open-concept floor plan features a beautifully appointed kitchen, bright great room, oversized windows, and a private balcony overlooking the peaceful courtyard. The split-bedroom layout provides privacy, while two spa-inspired bathrooms feature garden tubs, tiled showers, and dual vanities. With a sleeper sofa in the living room, the residence comfortably accommodates up to six guests. Step outside your front door and discover an extraordinary resort experience. The spectacular Surfari Water Park features a FlowRider® surf simulator, dueling water slides, lazy river, splash park, activity pool, zero-entry pool, and private cabanas with food and beverage service. Additional amenities include multiple pools and hot tubs, a 20-acre activity lake with private dock, fishing, fitness center, full-service spa, arcade, game room, and an array of on-site dining options including Longboard Bar & Grill, Valencia Restaurant, Element Bar & Lounge, Alfresco Market, and Byte. Convenient shuttle transportation to Disney World, Universal Studios, and SeaWorld adds even more appeal for vacation guests. As a short-term rental property, owners may enjoy personal use, while professional on-site management can handle bookings, housekeeping, maintenance, and guest services. Whether you're looking for a personal Orlando getaway, a vacation home, or a hands-off investment opportunity, this property offers an exceptional combination of resort amenities, flexibility, convenience, and income potential. Experience the magic of Orlando while owning your own piece of the vacation lifestyle at The Grove Resort & Water Park!

14501 Grove Resort Unit 2304, Winter Garden

14501 Grove Resort Avenue Unit 2219, Winter Garden
$269,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code
Welcome to Unit 2219 at The Grove Resort & Water Park Orlando, where resort-style living meets an exceptional ownership opportunity just minutes from Central Florida’s world-famous attractions. This beautifully appointed 3-bedroom, 2-bath residence comes fully furnished and ready to enjoy. The spacious open-concept layout provides plenty of room for owners and guests, while the private balcony overlooking a peaceful water view creates the perfect setting to relax after a day enjoying everything Orlando has to experience. The primary suite features a spacious bathroom with a separate walk-in shower and soaking tub, offering the comfort and convenience expected from a full-service resort residence. Owners have access to The Grove’s extensive resort-style amenities, including water attractions, multiple swimming pools, dining options, fitness facilities, spa services, recreational areas, and much more. For owners seeking a hands-off approach, The Grove offers an optional professional resort management and rental program, providing the convenience of having the property managed and rented when not being personally enjoyed. Whether you are looking for a Florida vacation home, a furnished resort property, or an investment opportunity with professional management available, Unit 2219 offers a unique combination of comfort, convenience, and resort amenities in the Orlando area.

14501 Grove Resort Avenue Unit 2219, Winter Garden

Start Your Search

How much is your home worth?

Get instant property value now!