Winter Garden/Oakland Homes with Private Entrance Exterior Features

Winter Garden/Oakland Homes with Private Entrance Exterior Features

Welcome to Winter Garden and Oakland, two charming towns nestled in the heart of Orange County, Florida. Known for their rich history and vibrant community, these picturesque locations offer a unique blend of small-town charm and modern conveniences, making them a perfect place to call home.

Winter Garden is renowned for its historic downtown area, where you can stroll along the tree-lined streets, browse local boutiques, and savor delicious cuisine at family-owned restaurants. The community hosts a variety of events throughout the year, including farmers' markets and seasonal festivals, fostering a strong sense of camaraderie among residents. Just a short drive away, Oakland offers a serene atmosphere with beautiful parks and scenic lakes, ideal for outdoor enthusiasts and families alike.

When it comes to real estate in this delightful region, homes with private entrance exterior features are particularly sought after. These properties provide an added layer of privacy and convenience, making them perfect for families, guests, or even home-based businesses. Imagine coming home to a beautifully designed residence that offers a secluded entrance, allowing you to unwind in peace after a long day.

With a range of architectural styles and sizes, you’ll find homes that cater to diverse tastes and budgets. Whether you prefer a cozy cottage or a spacious modern abode, Winter Garden and Oakland have something for everyone. Embrace the opportunity to live in a community that celebrates its heritage while offering the comforts of contemporary living. Discover your dream home in Winter Garden or Oakland today!

Newest Winter Garden/Oakland Homes with Private Entrance Exterior Features

$1,800,000
6 Beds ⋅ 4 Baths ⋅ Na SubDv. ⋅ 34787 Zip Code
TWO HOMES FOR THE PRICE OF ONE.... Explore this stunning 10-acre lakefront estate in southwest Winter Garden with everything you’ve been dreaming of within 20 minutes of all the major theme parks in Central Florida. This beautiful tree-lined property offers privacy, shade, and plenty of space for both you and your animals. The owners have enjoyed using the land as a family ranch and oasis for many years, making it an ideal home for horse owners or those who just want to get away to relax and create lasting memories. You’ll also love the peaceful waterfront setting, where you can enjoy breathtaking sunsets. Beyond the incredible land, the property includes a spacious 3,196-square-foot main home with four bedrooms, three bathrooms, fireplace, screened patio and swimming pool with outdoor spa. In 2017 owners built a 1,200-square-foot guest house with a two-car garage, perfect for visitors or extra living space. Both homes are equipped with metal roof and screened porches. Despite its peaceful country feel, you’re still conveniently close to hospitals, restaurants, and shopping. If you’re looking for a property that combines the beauty of ranch living with laid back comfort and convenience, this is the perfect place to call home.

16945 W Phil C Peters Road, Winter Garden
$784,000
4 Beds ⋅ 4 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Incredible opportunity in sought-after Twinwaters. Built in 2018, this beautifully maintained and HIGHLY UPGRADED, energy-efficient POOL residence is move-in ready and offers the perfect combination of comfort, style, and functionality. The thoughtfully designed 4-bedroom, 3.5 bath ONE-LEVEL Avallon floor plan features an expansive gourmet kitchen that seamlessly overlooks the spacious family room, creating an ideal setting for everyday living and effortless entertaining. The adjoining breakfast nook with extended built-in cabinetry and an additional dedicated beverage refrigerator is perfect for morning coffee, casual meals, or gathering with family and friends. The "pocket office" just off the kitchen ensures no space is wasted and makes for unbelievable utility with everything you need right at your fingertips. From the custom wall treatments, crown molding, and upgraded light fixtures to the tranquil brick paver front porch to enjoy the neighborhood, you won't sacrifice a thing at this home. The generously sized primary suite serves as a private retreat with two walk-in closets, dual vanities, and a well-appointed en-suite bath. All bedrooms boast walk-in closets, making storage a breeze. The sparkling pool is the center of outdoor entertainment and is screened-in, surrounded by manicured grounds. Residents of Twinwaters enjoy exceptional community amenities, including a resort-style swimming pool, park, and playground, all within a convenient location close to great schools, shopping, dining, and major roadways. Designed with advanced energy-efficient construction, this home promotes a healthier, quieter lifestyle while helping reduce monthly utility costs. This property may be under audio/visual surveillance.

16736 Gullfloss Terrace, Winter Garden
$429,900
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Virtually Staged. OBTAINABLE LUXURY IN SUMMERLAKE! This MOVE-IN-READY, Energy Star Certified townhome offers the perfect blend of style, comfort, luxury and convenience with 3 bedrooms, 2.5 baths, a 2-car garage, and 1,738 square feet of thoughtfully designed living space. Recently refreshed with NEW interior PAINT and NEW CARPETING, this home welcomes you from the moment you step onto the covered front porch. Inside, the open-concept floor plan is enhanced by contemporary wood-look tile flooring throughout the first level, creating a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly into the beautifully appointed kitchen featuring granite countertops, rich 42-inch wood cabinetry, stainless steel appliances, a large center island with sink and breakfast bar, walk-in pantry, and a convenient built-in desk workspace. Whether preparing meals or entertaining guests, the open design keeps everyone connected. Step outside to your private, partially fenced courtyard with brick pavers—an ideal setting for morning coffee, outdoor dining, or relaxing after a busy day. The courtyard leads directly to the detached 2-car garage for added convenience. Upstairs, you'll find all three bedrooms, the laundry area, and new carpeting throughout. The spacious primary suite easily accommodates a king-size bed and features a large walk-in closet and an en-suite bath with dual granite vanities, a garden tub, and separate shower. Two additional bedrooms share a full bath with granite countertops. Located in the highly desirable Summerlake community, residents enjoy outstanding resort-style amenities including a community pool, clubhouse with fitness center and recreation room, pickleball/tennis and basketball courts, playgrounds, zip line, parks, dog park, and scenic walking trails. The home is conveniently located near Summerlake Elementary School and a neighborhood park. Summerlake, Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! As an added entertainment bonus, enjoy spectacular nightly Disney fireworks from designated viewing areas throughout the community. Just minutes from Hamlin Town Center, Cinépolis Luxury Cinemas, Orange County National Golf Center & Lodge, shopping, dining, and major roadways. This luxurious, beautifully updated home offers an exceptional opportunity to enjoy one of Horizon West's most sought-after communities. Experience the perfect combination of modern comfort, recent updates, and an outstanding Florida lifestyle. Lawn maintenance is included. Exterior scheduled to be painted!

8150 Red Stopper Lane, Winter Garden
$275,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
NEWLY UPDATED LAMINATE FLOORING THROUGHOUT THE MAIN AREAS, BEDROOMS, AND STAIRS!!!! kITCHEN AND BATHROOMS HAVE CERAMIC TILE!!!! This amazing ready to move in 2 bed / 2 bath condo in the pristine gated community of Southern Pines with a lot of amenities. Located in the heart of charming Winter Garden and only 15 miles to Orlando. Condo Includes: 1 car GARAGE - Bonus room which is attached to living room, Walk-in closets in both bedrooms and In-unit laundry closet. Community Features Include: Water, internet, exterior & community maintenance included, amenities: Oversized Swimming pool and gazebo lounge areas - Spa / Hot Tub, Fully equipped fitness center with attached playroom, Indoor Basketball Court & Racquetball Court, Outdoor Pickleball / Tennis Court & Beach Volleyball Court, Covered Playground, Outdoor Kitchen including charcoal grills, mini fridge, sink & vending machines, Carwash station, Easy to access mailboxes at front of the community. Schedule your showing today.

417 Southern Pecan Circle Unit 201, Winter Garden
$380,000
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 3 SubDv. ⋅ 34787 Zip Code
Discover refined, low-maintenance living in this impeccably cared-for townhome located in the sought-after Watermark community of Horizon West. Built by Meritage Homes in 2018 with a focus on energy efficiency, this residence combines comfort, style, and everyday functionality. The main level showcases an open-concept layout with elegant tile flooring throughout, leading into a well-appointed kitchen designed for both daily living and entertaining. Highlights include 42-inch cabinetry with crown molding, polished granite countertops, and a spacious walk-in pantry. Step outside to a private brick-paver lanai, along with access to a detached two-car garage. Upstairs, you’ll find all three bedrooms, including a peaceful primary suite featuring dual granite vanities and a generous walk-in closet. The secondary bedrooms are equally well-sized, sharing a full bathroom with granite finishes. An upstairs laundry room—with washer and dryer included—adds extra convenience. This home is complete with all essential appliances. Living in the Watermark community means enjoying an array of resort-style amenities such as a pool, spa, fitness center, tennis courts, splash pad, playground, picnic areas, and a beautifully appointed clubhouse ideal for gatherings. Conveniently located near top-rated schools, Hamlin Town Center, Walt Disney World, and major roadways including 429, 408, 192, and the Turnpike, this home offers a lifestyle. Don’t miss the opportunity to enjoy everything Florida living has to offer in this vibrant and amenity-rich community. Property is tenant occupied. Showings by appointment only. Listing Agent can provide a video tour of the property upon request.

14031 Picard Alley, Winter Garden
$699,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Phase 2 SubDv. ⋅ 34787 Zip Code
Welcome to this ELEGANTLY UPGRADED and nearly new 2-bedroom, 2-bath residence in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where resort-style living meets everyday sophistication. Perfectly situated on one of ONLY TWO PREMIUM HOMESITES of its kind within the community, this exceptional property enjoys a truly rare distinction: an EXCLUSIVE SIDE EASEMENT that creates exceptional privacy, expanded green space, and a level of openness rarely found in community living, with no immediate neighbor on one side and convenient proximity to the clubhouse area. From the moment you arrive, the home impresses with its REFINED CURB APPEAL, lush landscaping, and a spacious 2-car garage enhanced with CUSTOM STORAGE SOLUTIONS. Inside, a bright OPEN-CONCEPT LAYOUT welcomes you with abundant natural light and meticulous attention to detail throughout every space. The Kitchen is a TRUE SHOWPIECE, equipped with premium stainless steel appliances, a GAS COOKTOP, BUILT-IN OVEN, a CUSTOM BUILT-IN PANTRY WITH PULL-OUT DRAWERS, generous cabinetry, and stone countertops, all seamlessly flowing into the living and dining areas. The Living Room has been elevated with an INTEGRATED SURROUND SOUND SYSTEM, creating the perfect setting for daily enjoyment and entertaining. The Primary Suite is a private retreat featuring a CUSTOM-DESIGNED WALK-IN CLOSET SYSTEM and a well-appointed en-suite bath with dual vanities, generous storage, and a walk-in shower. An additional SECONDARY BEDROOM provides comfortable accommodations for family or guests, while the DEDICATED DEN, enhanced with UPGRADED HIGH BASEBOARDS and RECESSED LIGHTING, offers the flexibility of a home office, hobby room, or formal sitting area. CUSTOM CLOSET SYSTEMS throughout ensure every space is as functional as it is beautiful. Step outside to where this property truly STANDS APART. The expansive SCREENED-IN LANAI opens to an EXTENDED OUTDOOR DECK and a fully appointed BUILT-IN OUTDOOR KITCHEN (BBQ Area), all framed by CUSTOM OUTDOOR LIGHTING, creating an exceptional outdoor retreat designed for year-round Florida living. Additional highlights include a WHOLE-HOME WATER FILTRATION AND SOFTENER SYSTEM, FRESH INTERIOR PAINT throughout, and additional RECESSED LIGHTING both inside and outside that elevates the home's ambiance day and night. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a 12,000 SF clubhouse with coffee bar, lounge, and wine lockers, a sparkling pool, state-of-the-art fitness center, tennis courts, and a vibrant social calendar, along with included cable and internet, fostering the active and connected lifestyle that Del Webb is famous for. IDEALLY LOCATED in Winter Garden, you are just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for boutique shops, dining, and a weekly farmers market. Enjoy outdoor recreation along the WEST ORANGE TRAIL, or take a short drive to WORLD-CLASS ATTRACTIONS including Walt Disney World Resort and Universal Studios. Convenient access to FL-429 and major roadways makes it easy to enjoy the very best of Central Florida. This exceptional residence offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living on one of the community's most coveted homesites, where every upgrade has been thoughtfully chosen and every detail meticulously executed. Homes of this caliber and setting are a TRUE RARITY in Del Webb Oasis. Now is the time, don't miss your chance to call this home.

15139 Canopy Cover Drive, Winter Garden
$419,900
3 Beds ⋅ 3 Baths ⋅ Storey Grove Ph 1b-1 SubDv. ⋅ 34787 Zip Code
Beautifully maintained and thoughtfully upgraded townhome in the Storey Grove community of Winter Garden. This 3-bedroom, 2.5-bath residence features an open-concept floor plan, quartz countertops, stainless steel appliances, a spacious primary suite, and a private two-car garage. Recent improvements include a whole-home water softener system, whole-home electrical surge protection, and two dedicated electric vehicle charging stations. Residents have access to community amenities including a pool, fitness center, walking trails, playgrounds, and parks. Conveniently located near shopping, dining, entertainment, major roadways, and area attractions.

11025 Suspense Drive, Winter Garden
$271,000
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa SubDv. ⋅ 34787 Zip Code
Highly motivated seller, The Grove Resort and Waterpark is a short-term rental complex. This Unit is the Jasmine Model (1,396 sq.ft) located on the second floor of condominium III. It is a 3-bedroom, 2-Bathroom Unit. King size bed in the Master Bedroom and the guest rooms will have one Queen size bed. Sleeper sofa in the living room. Excellent opportunity for investment and fun since the owner is authorized to make personal owner reservations for a maximum of 179 consecutive nights. Amenities include 3 pools, a waterpark, a fitness center, a boat dock and water activities with access to Lake Austin. full service concierge, 24 hours security, complementary shuttle service to Disney World, Universal Studios and SeaWorld.

14501 Grove Resort Avenue Unit 3211, Winter Garden
$495,000
4 Beds ⋅ 3 Baths ⋅ Watermark Phase 2c SubDv. ⋅ 34787 Zip Code
Beautiful corner-lot home located in the highly desirable Watermark community in Horizon West, Winter Garden. This impressive property offers the perfect combination of modern design, comfort, and an unbeatable location. This well-appointed two-story residence features 4 bedrooms, 2 full bathrooms, and a convenient half bath. All bedrooms are located on the second floor, including a spacious primary suite designed for privacy and relaxation. A versatile loft area upstairs provides additional flexibility, ideal for a home office, media room, or extra living space. The open-concept layout creates a seamless flow between the living, dining, and kitchen areas, making it perfect for both everyday living and entertaining. The kitchen is equipped with contemporary cabinetry, quality countertops, and modern appliances, offering both style and functionality. The home features ceramic tiles flooring in the main living areas for a sleek and modern look, while the carpeted bedrooms provide added comfort. Energy Star certification and enhanced insulation contribute to greater energy efficiency, helping reduce utility costs. Step outside to enjoy a charming front porch, perfect for relaxing and taking in the neighborhood ambiance. Residents of Watermark enjoy access to exceptional resort-style amenities, including a community pool with splash pad, clubhouse, fitness center, tennis courts, playgrounds, and scenic walking trails. Conveniently located near top-rated schools, shopping, and dining, this home is just a short 15-minute drive from Walt Disney World, making it an ideal location for both homeowners and investors. Don’t miss the opportunity to own a beautiful home in one of Horizon West’s most sought-after communities. Currently tenant occupied; tenants agree to vacate the property with a 30-day notice if requested by the buyer. See the professional video attached.

9231 Grand Island Way, Winter Garden
$495,000
4 Beds ⋅ 3 Baths ⋅ Highland Rdg Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to this exceptional home located in the highly sought-after Highland Ridge community. This beautifully maintained 4-bedroom, 2 full bathroom and 1 half bathroom residence offers generous living space and a unique blend of classic curb appeal with modern interior upgrades. The home features an open-concept layout designed for both everyday living and entertaining. The kitchen is designed for both function and style, showcasing a large island, stainless steel appliances, ample counter space, and a convenient corner pantry. It seamlessly connects to the dining and family areas, creating a welcoming and cohesive living space. Wood-look luxury vinyl plank flooring throughout main living areas on the first floor. Upstairs, you’ll find a spacious loft that can be used as a media room or flexible living area, along with a conveniently located laundry room and four bedrooms. The primary suite offers a well-designed en-suite bathroom and a walk-in closet, while the remaining bedrooms share a full bath. Ideally situated in the vibrant Winter Garden area, Highland Ridge residents enjoy access to a pool, playground, and half basketball court. The community is just minutes from the Hamlin shopping and dining district, with convenient access to major highways. Located less than 15 minutes from Walt Disney World, under 30 minutes from Universal Orlando and Downtown Orlando, and approximately 35 minutes from Orlando International Airport. Several renowned golf courses are also nearby. The property is located at the end of a quiet street with minimal traffic, this home offers exceptional privacy and tranquility, backing onto a natural preserve with no rear neighbors. Watch the attached professional video. Easy to show and move-in ready.

12362 Bracco Street, Winter Garden
$325,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium Ii SubDv. ⋅ 34787 Zip Code
Experience resort-style ownership in this beautifully appointed 2-bedroom, 2-bathroom condo located at 14501 Grove Resort Ave, Unit 1614 in the highly sought-after Grove Resort & Water Park in Winter Garden. This spacious, fully furnished unit features an open-concept layout with a modern kitchen complete with granite countertops, stainless steel appliances, and rich wood cabinetry, seamlessly flowing into a bright living and dining area with sliding glass doors that lead to a private screened balcony overlooking lush grounds and water views. The primary suite offers generous space, large windows for natural light, and an en-suite bathroom with dual vanities, soaking tub, and separate walk-in shower, while the second bedroom provides comfortable accommodations for guests or additional occupants. Thoughtful finishes, high ceilings, and durable flooring throughout create a clean and inviting interior designed for both relaxation and durability in a hospitality setting. This property is part of a mandatory, professionally managed hotel rental program, offering a truly hands-off ownership experience. The exclusive rental manager maintains full control over leasing and daily operations, including marketing, bookings, cleaning, and maintenance, allowing owners to enjoy passive income potential without the responsibilities of self-management. The Grove Resort is a premier destination known for its exceptional amenities, including multiple resort-style pools, a lazy river, water slides, a full-service water park, on-site restaurants and bars, a fitness center, spa services, and lakefront activities on Lake Austin. Ideally located just minutes from Walt Disney World, this property offers convenient access to Orlando’s world-famous attractions, including Universal Studios and SeaWorld, as well as nearby shopping and dining at Winter Garden Village, Hamlin Town Center, and a wide variety of local restaurants. Major roadways such as FL-429 and US-192 provide easy connectivity throughout Central Florida, and Orlando International Airport is within a reasonable drive for both domestic and international travel. Whether you are seeking a turnkey investment opportunity or a vacation property within a world-class resort environment, this unit offers a unique blend of comfort, convenience, and income potential in one of Central Florida’s most desirable destinations.

14501 Grove Resort Avenue Unit 1614, Winter Garden
$599,999
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully designed, architect-crafted townhome, freshly repainted throughout and lovingly maintained by its original owners. From the moment you step inside, you’re greeted by a bright, open-concept layout filled with thoughtful upgrades and elegant details. The main level flows effortlessly, featuring a stylish living and dining area bathed in natural light and accented with refined crown molding. At the heart of the home, the gourmet kitchen impresses with granite countertops, a modern backsplash, ample cabinetry, and an oversized island perfect for entertaining. Transom light doors lead to a screened-in, covered patio—your private retreat to relax and enjoy Florida’s year-round sunshine. Upstairs, the spacious primary suite offers a true escape, complete with a luxurious en-suite bathroom featuring dual vanities, a garden tub, a separate glass-enclosed shower, and tasteful finishes throughout. One of the standout features is the bonus apartment—ideal for guests, extended family, or even as an income-producing opportunity. Completing the home is a 2-car garage with a sleek epoxy finish, combining durability with a clean, polished look. This property is just 17 minutes away from Disney. Schedule your showing today.

8807 Fountain Palm Aly, Winter Garden
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