Winter Garden/Oakland Homes with Rain Gutters Exterior Features

Winter Garden/Oakland Homes with Rain Gutters Exterior Features

Welcome to the enchanting community of Winter Garden and Oakland, Florida, where charming small-town vibes meet the allure of modern living. Nestled just west of Orlando, this picturesque area is known for its lush landscapes, vibrant downtown, and rich history. With its scenic parks, delightful shops, and a thriving farmers' market, Winter Garden offers a delightful blend of outdoor recreation and community spirit.

As you explore the neighborhoods of Winter Garden and Oakland, you'll discover a variety of homes that cater to different lifestyles. One standout feature that many of these homes boast is their rain gutters. These exterior features are not just practical; they are essential for maintaining the integrity of your property. Rain gutters effectively direct water away from your home’s foundation, protecting it from potential damage and erosion. This thoughtful addition enhances the longevity of your home, allowing you to enjoy your beautiful residence worry-free.

Moreover, the homes in this region often reflect a harmonious blend of traditional charm and contemporary design. Whether you prefer a cozy bungalow or a spacious family home, you’ll find that many properties are equipped with rain gutters, ensuring that your investment remains in pristine condition throughout Florida’s diverse weather patterns.

Living in Winter Garden and Oakland means embracing a lifestyle filled with community events, outdoor adventures, and a strong sense of belonging. With its rich offerings and beautiful homes, your dream residence awaits in this charming corner of Florida. Come and discover the perfect blend of comfort and convenience in Winter Garden and Oakland today!

Newest Winter Garden/Oakland Homes with Rain Gutters Exterior Features

3 Beds ⋅ 3 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code

Welcome home! This turnkey, exquisite custom home enables you to wake up to shimmering water views of Johns Lake and step into the lakefront lifestyle you’ve been dreaming of. On an acre in a gated community, sellers spared no expense on a complete renovation— exterior to interior and down to the studs. New windows, high end finishes, and designer details in every room rival new construction. Upon entering, you’ll be captivated by an abundance of natural light, soaring ceilings and panoramic water views. The foyer leads to the spacious living/office/flex space and dining room with stunning dry bar and 180+ bottle wine fridge. The large family room with fireplace feature wall and bay window adjoins the true gourmet kitchen for open concept living, overlooking the lake and community pond with lighted fountain. A chef’s kitchen features tall kitchen cabinets for extra storage, massive center island, large sink, Fisher and Paykel double-drawer dishwasher, Scotsman pellet icemaker. The all Viking appliance pkg includes a 36” refrigerator with 30” freezer, dbl ovens, warming drawer, 6 burner induction stove top. A plumbed, built-in Miele espresso machine provides your favorite morning coffee, hot water, and more. A reverse osmosis water filtration system feeds the kitchen sink, icemakers, coffee machine. The sunroom boasts two walls of new Pella hurricane rated slider doors that flood the home with natural light and frame the stunning waterfront scenery and provides a seamless connection between indoor and outdoor living opening onto the sandstone lanai with oversized resort style sparkling saltwater pool, spa and waterfall. The lanai roof structure is unique in that the vaulted roof and screening provides all weather protection to the pool, built in bar and overflow patio area allowing for entertaining in any weather or watching the Disney fireworks or rocket launches. The lanai is outfitted with 3 large DC ceiling fans and integrated watering system. Spacious primary bedroom with lanai access overlooks the lake and boasts a spa-like bathroom with dual vanities, frameless zero entry shower, free-standing tub and large walk-in closet. The split bedroom plan allows for maximum privacy. Secondary bedrooms are spacious with oversized closets. The exterior, with its professional landscape design and lighting, is designed for play, relaxation and beauty. Enjoy direct access to Johns Lake and spend your days boating, jet skiing, kayaking, paddle boarding, fishing or simply relaxing. A paver walkway from the house leads to the expansive back yard, beachfront, and large fire pit area, perfect for play and entertaining. Private dock with remote boat lift and double jet ski lift allows for lake enjoyment with effortless access. Dock is equipped with running water, lights and no/low maintenance composite decking and handrails. The deep garage is oversized with storage racks and an additional air-conditioned bonus space to be used as a craft/exercise room/home office or air-conditioned storage. Neighborhood amenities include community dock, boat ramp, tennis/pickleball court, basketball court, cable/internet. Conveniently and centrally located with easy access to the Turnpike, 429, 408, downtown Winter Garden and Orlando, the airport, Disney, Universal and area attractions. Minutes to restaurants, shops, hospitals, West Orange Trail. Link to interactive floor plan: https://www.zillow.com/view-imx/6a573be4-fd0d-4649-9df8-88349b2426f6?initialViewType=pano

263 Deer Isle Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Winding Bay SubDv. ⋅ 34787 Zip Code

Located in the desirable Winding Bay community in Horizon West, this impeccably maintained home offers 3 spacious bedrooms, 2.5 bathrooms and a versatile flex room that can easily serve as a home office, playroom or potential 4th bedroom. Luxury tile flooring, upgraded in 2025, flows throughout the entire home for a clean and consistent look that is stylish, durable and easy to maintain. The kitchen serves as the centerpiece of the main living space, featuring an oversized island, custom range hood, upgraded cabinetry with crown molding, hard-wired under-cabinet lighting and abundant counter and storage space. Crown molding, oversized baseboards, decorative columns, and custom finishes bring an elevated feel and distinctive detail to the interior. The spacious owner’s suite features plantation shutters and a beautiful en-suite bathroom, fully upgraded in 2026 with floor-to-ceiling tile, modern finishes and a large walk-in closet. The two secondary bedrooms share a convenient Jack-and-Jill bathroom. Double sliding doors lead to the screened lanai with sun shades, overlooking the fully fenced backyard with iron fencing. In the evening, relax outdoors and enjoy views of the Disney fireworks in the distance, adding a special touch to the Florida lifestyle. Additional features include an extended driveway with pavers, gutters, whole-home security camera system, whole-home water softener, reverse osmosis filtration in the kitchen and a dedicated garage outlet for an additional refrigerator or freezer. Solar panels provide an added energy-efficiency benefit, with electric bills averaging approximately $34 during the hot summer months. With no carpet, extensive upgraded tile flooring, flexible living space, a renovated owner’s bathroom, solar panels, and numerous thoughtful upgrades, this Horizon West home is truly move-in ready. This home offers convenient access to shopping, dining, schools, major roadways, and the many amenities throughout Winter Garden and West Orange County. Schedule your showing today!

10750 Petrillo Way, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!

1016 Catori Road, Oakland

5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

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. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 5 bedrooms, 4 full bathrooms, a loft, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and a refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. Three additional first-floor bedrooms and two bathrooms provide comfort and privacy for everyone. Upstairs, enjoy an additional 709 square feet of flexible living space, complete with a generous loft, private fifth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

285 Crystal Wood Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Johns Landing SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful and impeccably maintained 4-bedroom, 2.5-bath home in the desirable Johns Landing community of Oakland! This exceptional family home offers space, comfort, flexibility, and all the features buyers are looking for. The spacious floor plan includes a large bonus room and an additional room currently being used as an office, which can easily be converted back to a bedroom to suit your family's needs. The heart of the home is the generously sized kitchen, complete with a convenient kitchen nook—perfect for everyday meals, morning coffee, and family gatherings. Wood and carpet flooring add warmth and character throughout the home. Step outside and prepare to be impressed by the enclosed patio, featuring a spectacular built-in bar and entertaining area that truly sets this home apart. It is the perfect place to relax, entertain family and friends, watch the big game, or create unforgettable memories year-round. This home has been lovingly cared for and is immaculate inside and out. The roof is approximately three years old, the water heater is approximately three years old, and the air-conditioning system was recently serviced approximately three months ago. Located in the gated Johns Landing community, residents enjoy an array of amenities and recreational opportunities. This is more than a house—it is a beautiful place to call home, with the space, features, and flexibility today's buyers desire. Come see it for yourself—you'll immediately appreciate the pride of ownership and everything this special home exemplifies. Schedule your private showing today; this one is truly worth seeing!

239 Largovista Drive, Oakland

4 Beds ⋅ 3 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code

Welcome to 14975 Winter Stay Drive, where the work has already been done and the upgrades go far beyond builder basics. Thoughtfully improved inside and out, this Horizon West home pairs a warm, finished feel with the kind of practical upgrades you will appreciate for years to come. At the heart of the home, the kitchen features KitchenAid appliances installed in 2024. LVP flooring was added in 2025 and flows throughout the bedrooms. Plantation shutters, installed in 2026, add a polished finishing touch. Even the laundry room has been elevated with built-in cabinetry, granite countertops and additional storage. Outside is where this home really sets itself apart. The custom gunite pool, completed in 2024, features a swim shelf, heater AND chiller, upgraded screen enclosure and child safety fence, making it just as enjoyable in the heat of summer as it is on a cool Florida evening. The covered lanai was transformed into an outdoor living space with a fireplace, TV accent wall and recessed lighting, creating a true extension of the home for entertaining or relaxing year-round. The upgrades continue behind the scenes with a fully paid 15kW solar system, generator back-feed hookup, French drains along the east-facing gutters and downspouts, and overhead garage storage racks. Located in Winter Garden's sought-after Horizon West area, this is a home that has been intentionally upgraded, carefully maintained and designed to be lived in. Skip the projects and start enjoying the pool, the outdoor living space and everything this home has to offer from day one.

14975 Winter Stay Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code

Almost New & Move-In Ready! Built in 2024, this beautifully maintained corner-unit townhome offers the perfect combination of modern style, comfort, and functionality. Featuring 4 full bedrooms and 3 full bathrooms, the thoughtfully designed floor plan includes a convenient first-floor bedroom, ideal for a home office, guest suite, or private bedroom. The home showcases upgraded tile flooring throughout the main living areas and stylish granite countertops, creating a clean and contemporary feel. The spacious kitchen comes fully equipped with stainless steel appliances, including refrigerator, microwave, and dishwasher, plus a washer and dryer for added convenience. Enjoy Florida living from the screened-in back porch, perfect for relaxing or entertaining while enjoying the outdoors. A private 2-car garage located at the rear of the home provides secure parking and additional storage. Residents enjoy an impressive selection of community amenities, including a resort-style pool, fitness center, gathering area, playground, and community mailbox. With its desirable corner-unit location, modern finishes, flexible first-floor bedroom, and excellent amenities, this almost-new townhome is an exceptional opportunity for both homeowners and investors. Come see why this beautiful 2024 townhome is the perfect place to call home!

14075 Lochend Way, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Ests/Lakeview Preserve SubDv. ⋅ 34787 Zip Code

This is a rare opportunity to find a popular Roseland floorplan loaded with upgrades, perfectly located on a quiet cul-de-sac on a private lot with no rear neighbors and extra space on this oversized lot! Best of all, you can enjoy picturesque views of Johns Lake right from the front yard! Inside, you are greeted with a beautiful double glass door entry, soaring dramatic ceilings, and elevated light fixtures that create an immediate sense of openness and grandeur. Luxury vinyl plank floors throughout bring warmth to the home. To the right, you have an oversized flex room with French doors, making a perfect home office, play area, or home gym. The formal dining room provides a great space to gather around meals for family nights or holiday hosting. The butler's pantry features a wine fridge and added cabinets, while the walk-in pantry is truly impressive with built-in shelving. The kitchen is truly the heart of the home, featuring stunning quartz countertops, cream cabinets, upgraded lighting, and a beautiful tile backsplash. Transom windows in the backsplash pour natural light into the kitchen. The open breakfast area is perfect for enjoying quick meals with the family and overlooks the great room, which has custom accent walls and an elevated light fixture to enhance the space. Triple windows above brighten the room, & the 12ft slider door overlooks the extended lanai and huge flat yard—with plenty of space to add a pool and outdoor kitchen! Downstairs features a massive guest suite that can serve as a second master bedroom, complete with its own ensuite bath, upgraded shower, and large walk-in closet—perfect for in-laws or guests to have their own retreat! There is also another full-sized bath downstairs with a shower and a door leading out to the lanai for quick access from the future pool area. Heading upstairs, there are 4 additional bedrooms, 3 full baths, and the laundry room. Elegant open railings bring added character across the catwalk over the living room. Directly at the top of the stairs, French doors lead to your primary retreat. You are greeted by a sitting area with a large window and a massive primary suite with a tray ceiling and picturesque windows looking over the yard and trees beyond. To the left is your stunning ensuite bathroom with split vanities, lots of natural light, a soaking tub, a large walk-in shower with a bench, and dual closets (one with built-ins). The other three oversized bedrooms add similar quality, each with direct ensuite access to a bathroom (including two sharing a Jack-and-Jill bath). The laundry room features built-in cabinets and two washer/dryer sets side by side, allowing you to handle two loads at a time—perfect for large or busy families! Over in the garage, vehicle enthusiasts and storage seekers will marvel at the pristine three-car garage, complete with sleek epoxy flooring, heavy-duty overhead storage racks, and a private car wash station for ultimate convenience. The exclusive gated community offers resort-style amenities including a clubhouse, swimming pool, splash pad, and playground—all with a low HOA fee and no CDD. The community is perfectly located on the border of Clermont and Winter Garden, offering access to all both cities have to offer! You are just 15 minutes from Winter Garden Village for shopping, dining, and SR-429 access into Orlando, and within 20 minutes from both downtown Clermont and downtown Winter Garden. Come tour this stunning property today!

4817 Fair Winds Court, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Crown Point Springs SubDv. ⋅ 34787 Zip Code

Live in Winter Garden’s Golf Cart District! This charming 3 bed, 2 bath home with an office/den in one of Winter Garden’s most desirable communities, Crown Point Springs. This home has an open floor plan with split bedrooms, an enclosed patio, fenced yard, inside laundry room and a two-car attached garage. The foyer will welcome you into the home with the formal dining on your left and the French door enclosed office/den on your right (currently being used as a game/theatre room. You will love the ceramic tile floors in the formal dining and family rooms. Walk further into the heart of the home - the kitchen, that features painted cabinets and counters, a new stainless steel stove, dishwasher and fridge. The breakfast nook overlooks the yard. The kitchen is open to the family room that has a brick front wood burning fireplace. A French door leads to the enclosed patio – what a great space to enjoy your morning coffee or relax after a long day! The spacious yard is fenced in and there’s plenty of room for a pool. The owner’s suite is off the kitchen and features and en-suite bath with an updated “adult height” vanity with two sinks, a glass enclosed shower and a walk-in closet. The guest bedrooms are on the other side of the home and share the guest bath that features an updated “adult height” one sink vanity and a tub/shower combo. This home has been lovingly maintained! Additional updates include a new roof (2026), new garage door, new fan in the family room, interior paint, cabinets for additional storage in the laundry room and the washer & dryer are included! This home has leased solar panels that the Buyer will have to take over, making the electricity bill low. Community is located minutes away from downtown Winter Garden, half a mile from the West Orange Trail, close to Chapin Station where you can enjoy picnic areas, playground, a tennis and basketball court. Crown Point Springs is also close to Newton Park where you’ll find a boardwalk, boat ramp, grills, picnic tables and playground, etc. Take your golf cart to Plant Street’s restaurants, boutiques, theater, festivals, and the popular Saturday farmer’s market. Close to top-rated schools, Winter Garden Village, AdventHealth, Publix, 429, and the Florida Turnpike. Don't miss this chance to own a home in one of Central Florida’s most desirable communities. Schedule your showing today!

1553 Spring Ridge Circle, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Wintermere Harbor Ph 02 48 21 SubDv. ⋅ 34787 Zip Code

Welcome home to this one-story pool home situated on an oversized lot that overlooks a pond! ***NEW WINDOWS, NEW COMMODES, 2022 ROOF, 2020 SMART POOL*** Tucked into the back of this gated community, this spacious oasis is ready for its next owners. One of Florida's most popular floor plans features a formal living space at the entrance of the home, casual living space in the middle of the home, the primary suite privately on one side of the home, and the 3 secondary bedrooms on the other side of the home. Choose to repurpose the "formal living space" into whatever your wants and needs may be, or use them as the formal living room and formal dining room as the builder intended. The primary suite has an extension included and is ready to be used as yet another flex space. French doors open from this extension right onto the covered outdoor living space. The primary bathroom boasts a soaking tub, dual vanities, and 2 custom closets. The casual living space is open and inviting with the kitchen, large dining nook, and family room, and lots of natural light brightens this space up even more by way of a wall of sliding glass doors that lead to the outdoor living space, another door with a window that also leads to the outdoor living space, and a set of bay windows in the dining nook. Bedrooms 2 and 3 are located down a hallway off of the casual living space and have a full bathroom they share. The 4th bedroom is in the back of the home with its own bathroom. Step out back to the screened in patio which holds a gorgeous pool with a sun shelf and waterfall, covered portion, and extension under the screen for total and full enjoyment opportunities! Continue outside of the screen enclosure to the fully fenced in backyard that overlooks a pond. Whether looking for peace and serenity or fun and activity, this home has a solution to it all! Inquire today to for a private viewing to see if this gem will become your next home!

2039 Harbor Cove Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Mezzano Townhomes SubDv. ⋅ 34787 Zip Code

Welcome to this modern two-story townhome in Winter Garden. 2,024 square feet of interior living space, this home features 3 bedrooms and 3 full bathrooms, including a primary suite on the upper level and a full bedroom with a full bathroom conveniently located on the main level. The open-concept layout seamlessly connects the kitchen, dining, and gathering areas, creating an inviting space for daily living and entertaining. The kitchen is outfitted with quartz countertops, 42-inch cabinetry with crown molding, and a multi-functional center island. Additional highlights include an upper-level loft, a dedicated laundry room, smart home technology, and a private paver courtyard connecting the residence to a detached two-car garage equipped with an electric vehicle charging outlet. Residents enjoy access to community amenities, including a swimming pool and playground, with convenient proximity to local shopping, dining, and major thoroughfares.

7025 Twilight Bay Drive, Winter Garden

6 Beds ⋅ 6 Baths ⋅ East Garden Manor Add 03 Rep SubDv. ⋅ 34787 Zip Code

Coming back to market soon after SIGNIFIGANT PRICE REDUCTION- SELLER IS MOTIVATED! RARE DUAL-RESIDENCE PROPERTY | NO HOA | MINUTES TO DOWNTOWN WINTER GARDEN Built in 2021 on a prime corner lot, this custom property features two complete attached residences under one roof. Designed for maximum privacy, each home faces a separate street, featuring its own street address, private covered front porch, and dedicated 2-car garage (4 garage spaces total). Ideal for house-hacking, multi-generational living, or long-term dual-rental income. --- KEY PROPERTY SPECS: Total Living Space: 2,876 heated sq ft Total Bed / Bath: 6 Bedrooms | 4 Full Baths | 2 Half Baths Layout: Identical two-story layouts (3 Beds / 2.5 Baths per side) Parking: 4 total garage bays (2 attached 2-car garages) + separate driveways Year Built: 2021 (Block construction, double-pane windows, zoned HVAC) HOA: None — no monthly fees, no restrictive rental caps --- THE RESIDENCES: Wilson Street Unit: Upgraded with luxury vinyl plank flooring, open-concept living, and an upgraded kitchen featuring stone countertops, gas cooking, and French doors leading out to patio space. Upstairs holds a primary suite with walk-in closet and private bath, plus two guest bedrooms and a second full bath. Maple Street Unit: Turnkey and low-maintenance with clean tile and durable laminate flooring. Features an open living/dining layout, powder bath on the main floor, and 3 bedrooms with 2 full baths upstairs. --- THE LOCATION: Minutes to Historic Downtown Winter Garden, Plant Street dining, breweries, and the award-winning Farmers Market Direct proximity to the West Orange Trail Quick access to SR-50, the 429, and Florida’s Turnpike for easy Central Florida commutes Live in one side and offset your mortgage with the other, keep extended family next door, or rent both for strong cash flow. Contact us today to schedule your private tour!

402 E Maple Street, Winter Garden

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