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2131 Tall Oak Drive, Winter Garden
$858,000
5 Beds ⋅ 3 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Welcome to Wintermere Pointe, one of Winter Garden’s most established gated communities, and to a residence defined by scale, light, and thoughtful renovation. The home’s symmetrical facade and covered entry create a strong architectural presence, leading into a dramatic double-height foyer framed by expansive arched windows. Natural light reflects across Italian porcelain flooring, while a striking split-face stone accent wall extends vertically alongside the staircase, adding texture and depth to the open space. The fully renovated kitchen is both refined and functional, featuring waterfall quartz countertops, custom solid-wood cabinetry, marble designer backsplash, integrated wine storage, stainless steel appliances, under-cabinet lighting, and a contrasting island that anchors the room. The open layout connects seamlessly to the family room, where oversized windows overlook the fenced backyard and fill the space with natural light. Upstairs, luxury vinyl plank flooring replaces carpet entirely, creating continuity and durability throughout. According to public records, the home offers 5 bedrooms and 3 bathrooms, plus an additional bathroom added by the current owner. The primary suite combines comfort and modern elegance, offering tray ceilings, direct access to the backyard, and a spa-inspired bathroom finished with large-format marble-look tile, a walk-in shower, and a dedicated vanity area. A dedicated cinema room delivers a true theater experience, the perfect setting for movie nights and gatherings. It’s an exceptional feature for entertaining or quiet evenings at home. Situated on a .28-acre fenced lot with mature landscaping, the property includes a 3-car garage and an extended driveway accommodating up to six vehicles. Major improvements include the roof (2018), A/C unit (2025), and septic system (2020). Located minutes from SR-429 and Winter Garden Village, the home offers convenient access to shopping, dining, and everyday amenities while preserving the privacy of gated living.

2131 Tall Oak Drive, Winter Garden

2006 Wintermere Pointe Drive, Winter Garden
$740,000
5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Virtually Staged. Tucked away on a cul-de-sac within the gated community of Wintermere Pointe, this spacious 5-bedroom, 4-bath pool home is situated on an oversized homesite of more than 1/4 acre with a beautiful wooded backdrop. The private backyard provides an inviting setting for outdoor living, featuring a screened pool and patio that create the perfect space for entertaining or simply enjoying the natural surroundings. Designed with one of the community’s most sought-after floor plans, this home offers exceptional flexibility with generous living spaces throughout. The formal living and dining rooms are sized to accommodate large furniture, while the centrally located family room flows seamlessly into the kitchen and outdoor living areas. The home office is thoughtfully positioned adjacent to the primary suite, making it equally suitable as a fifth bedroom, nursery, den, or private workspace. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, abundant cabinet storage, and a full appliance package, including a 5-burner glass cooktop range with a convection oven. The adjacent dinette overlooks the pool and backyard, while replacement sliding glass doors installed in 2017 provide direct access from the living room, dinette, family room, and primary suite to the screened patio and pool. The spacious primary suite features wood flooring, coffered ceilings, double closets, and oversized sliding glass doors that open directly to the pool area. The ensuite bath features dual vanities with stone countertops, a relaxing garden tub, a separate shower, and a private water closet. The secondary bedrooms are generously sized and conveniently located for easy access to the home’s full bathrooms, each enhanced with updated vanities and mirrors. A full bath located just off the family room also serves as an ideal pool bath. Just beyond the kitchen and laundry room, a hallway provides access to the 3-car garage and a wood staircase leading to the expansive bonus room. Complete with a full bath, walk-in closet, and newer windows overlooking the oversized backyard and wooded backdrop, this versatile space is ideal as a guest suite, sixth bedroom, recreation room, media room, home gym, or private retreat. Numerous updates provide added value and peace of mind, including multiple replacement windows (2015), a new roof (2016), replacement sliding glass doors and front entry door (2017), a new paver driveway (2020), a new water heater (2020), and a new HVAC system (2025). Wintermere Pointe is a gated community offering residents a playground and tennis courts. Conveniently located with access to Lake Whitney Elementary, SunRidge Middle School, and West Orange High School, the home also provides easy access to shopping, dining, major roadways, and many of Central Florida’s most popular destinations.

2006 Wintermere Pointe Drive, Winter Garden

2025 Wintermere Pointe Drive, Winter Garden
$715,000
5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Virtually Staged. Fabulous 5 bedroom, 4 bath pool home lovingly cared for by the original owners. Situated near the end of a cul-de-sac on an almost ½-acre lot with a fully fenced backyard in the gated community of Wintermere Pointe! A long driveway provides ample parking and leads to the OVERSIZED 3-CAR GARAGE, which was extended an additional 4 feet during construction to provide exceptional storage space. Inside, this spacious and thoughtfully designed home features tile flooring throughout the main living areas downstairs, wood laminate flooring in the family room, and brand new carpet on the staircase and in the upstairs 5th bedroom. The desirable 3-way split bedroom floor plan provides wonderful privacy for family and guests. Featuring loads of storage throughout, including an oversized under-stair storage closet in the back hall, a generously sized linen closet in the alcove between Bedrooms 2 and 3, and an additional storage closet in the laundry room. The primary suite is privately located on one side of the home and features French doors opening to the lanai and pool, two walk in closets and a beautifully UPDATED primary bath with new flooring, separate vanities that offer plenty of storage, quartz countertops, a renovated shower with glass surround and updated showerhead plus a private water closet with a new commode. All commodes throughout home have been replaced with "comfort height" commodes. At the heart of the home is the spacious kitchen offering abundant cabinetry, granite countertops and LG stainless appliances (Bosch dishwasher) replaced in 2022. The kitchen opens to the family room w/surround sound, creating a comfortable and inviting space for everyday living and entertaining. Upstairs, the huge 5th bedroom offers incredible flexibility with two walk in closets and a private bathroom - perfect for guests, multigenerational living, a bonus room or private retreat. Outdoor living is exceptional! A huge Florida room was added across the back of the home, providing additional all-season living and entertaining space beyond the screened pool and lanai. The expansive, fully fenced backyard and almost ½-acre homesite provide plenty of room to enjoy the Florida lifestyle. MAJOR UPDATES INCLUDE: ALL NEW energy-efficient windows (June 2023) and doors (2024), Water softener (February 2024), Water heater (September 2023), garage door opener (2021), Roof (May 2017) and HVAC (September 2015) with annual maintenance service. AC ducts were inspected with boots resealed to drywall and collars in June 2019, then professionally cleaned and inspected in March 2024. Annual septic service, including draining and filter cleaning, was completed in January 2026, and the dryer vent was cleaned in April 2026. The transferable termite bond renews in November 2026. Additional improvements include replacement of the sprinkler meter including the majority of electrical sprinkler valves, gutter cleaning and sealing and installation of Gutter Guards in March 2025, along with replacement of two electrical valves at the pool pump. THE LOCATION IS FANTASTIC! Just 5 minutes to Winter Garden Village for abundant shopping and dining, including the new Seasons 52 coming soon. Approximately 10 minutes to charming Downtown Winter Garden with its popular restaurants, shops and Saturday Farmers Market and approximately 16 minutes to Disney! Zoned for highly rated Lake Whitney Elementary, SunRidge Middle, and West Orange High School. This home is truly a special opportunity!

2025 Wintermere Pointe Drive, Winter Garden

2049 Wintermere Pointe Drive, Winter Garden
$580,000
5 Beds ⋅ 3 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Brand new roof is in the process of being installed and new soft carpet flooring! This well-maintained pool home is designed to maximize comfort and functionality. Its practical features, comfortable living spaces, and spacious bedrooms, including a downstairs guest suite, create a versatile floor plan that can accommodate the ever-changing needs of life. The kitchen comes equipped with plenty of cabinetry and countertop space, a pantry closet, an island, and a breakfast bar, providing ample room for preparing and sharing meals and storing items in between. In total, there are five bedrooms, all of which are roomy; however, the primary suite is huge, measuring 28x14 feet, with a seating area, and a large closet, offering the perfect private retreat. The two secondary bathrooms are split between the two floors, ensuring convenience for daily routines. Outside, the expansive covered lanai and sparkling pool create the perfect space for relaxation and entertaining guests. Location advantages include proximity to Winter Garden Village, placing many shopping, dining, and entertainment options within seconds. The property also sits conveniently close to local schools, parks, and highway access, providing countless more daily conveniences and entertainment options well within reach. This combination of indoor comfort, outdoor amenities, and strategic location creates an appealing opportunity, just waiting for you. Schedule your private showing today!

2049 Wintermere Pointe Drive, Winter Garden

2031 Wintermere Pointe Drive, Winter Garden
$550,000
4 Beds ⋅ 2 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Virtually Staged. $10,000 TOWARD BUYER’S CLOSING COSTS! SELLER MOTIVATED TO SELL!!! NEWLY TRANSFORMED AS OF AUGUST 19, 2026—COME TAKE A FRESH LOOK AND FALL IN LOVE! Discover the complete Florida lifestyle in this move-in-ready, 4-bedroom, 2-bathroom saltwater pool home located in Winter Garden’s gated Wintermere community. Offering oversized 0.31-acre lot, this home combines a spacious interior, an incredible backyard, added privacy, and convenient access to everything Central Florida has to enjoy! The home’s refreshed presentation was completed as of August 19, 2026, creating an exciting opportunity for buyers to experience its transformation in person. Inside, you will find an inviting open floor plan, an updated kitchen, comfortable living and entertaining spaces, and a spacious primary suite. Step outside and discover your private Florida retreat, complete with a sparkling saltwater pool, relaxing pool jets, screened lanai, and an oversized fenced backyard. With no rear residential neighbors, this property provides additional privacy and plenty of room for swimming, entertaining, pets, outdoor activities, or simply relaxing in the Florida sunshine. PROPERTY HIGHLIGHTS: • 4 bedrooms • 2 bathrooms • Approximately 1,960 heated square feet • Oversized 0.31-acre lot • Sparkling saltwater pool • Relaxing pool jets • Screened lanai • Updated kitchen • Open floor plan • Spacious primary suite • Oversized fenced backyard • No rear residential neighbors • Gated Wintermere community • Quiet cul-de-sac location • Indoor laundry room • Two-car garage • Extended driveway • Move-in ready BUYER INCENTIVE: The seller is offering $10,000 toward the buyer’s allowable closing costs, subject to the terms of an accepted contract and lender approval. Conveniently located near SR-429, SR-408, Winter Garden Village, Hamlin, shopping, restaurants, Orlando-area employment centers, and Walt Disney World, this home offers suburban space with outstanding Central Florida accessibility. The transformation is complete, the pool is ready, and your Winter Garden lifestyle is waiting. Come take a fresh look, schedule your tour, and fall in love! Call your Favorite Realtor | Broker Right NOW! Check to see if you Qualify for Hometown Heros! Up to $35,000!

2031 Wintermere Pointe Drive, Winter Garden

2237 Wintermere Pointe Drive, Winter Garden
$490,000
4 Beds ⋅ 2 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Welcome to this one-story 4 bed/2 Bath home, located on over 1/4 acre (0.36 acres) CORNER LOT within the CITY LIMITS of the Historical town of Winter Garden, Florida. This Ryland and Rutenburg built home, completed in 2000, has been well maintained over the years. Upon entering you are welcomed with beautiful laminate wood flooring and FRESHLY PAINTED WALLS throughout. Natural light is infused throughout the home as you walk through your Formal Dining and Living Rooms. Your kitchen is nestled in the heart of the home with an island for additional counter space, and a peninsula overlooking your Family Room. A great open floor plan for both entertaining and relaxing. Centrally located just outside of your main living areas is where you will find your screened patio and OVERSIZED FENCED YARD. This backyard can accommodate both a large pool and still have enough space to create your own OASIS in the remaining yard space! Back indoors your will find your Primary Suite offering Dual Sinks, Dual Walk-In Closets, WALK -IN SHOWER, and three additional bedrooms. ADDITIONAL UPGRADES INCLUDE: Gutters, Recently Painted Interior AND Exterior, NEW HVAC (2024), Roof (2016). NEIGHBORHOOD AMENITIES include: GATED COMMUNITY, Tennis Courts and Playground for only $92 MONTHLY. Don't miss your opportunity to live in this amazing community just moments away from shopping, hospitals, and major highways. Schedule your showing today!

2237 Wintermere Pointe Drive, Winter Garden

2031 Wintermere Pointe Drive, Winter Garden
$469,000
4 Beds ⋅ 2 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Opportunity Awaits – 4 Bedroom Pool Home in a Prime Location! Welcome to this spacious 4-bedroom, 2-bath home tucked away on a quiet dead-end street in a highly desirable neighborhood. As you enter the home, you will find a generous open floor plan and a beautiful kitchen. The primary bedroom features an en suite bathroom with a double vanity, separate shower and garden tub. Step out to a large enclosed patio and a fully fenced backyard featuring a private pool- perfect for relaxing or entertaining. There’s also an additional fenced-in area, ideal for pets, gardening, or creating your own outdoor retreat. Conveniently located just minutes from shopping, dining, and everyday essentials, you'll love the balance of peaceful living and easy access to everything you need. With your personal touch, this property can truly shine and become your dream home or a fantastic investment opportunity. Schedule your showing today!

2031 Wintermere Pointe Drive, Winter Garden

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