Winter Garden/Oakland Homes with 2 Car Garage Garage Description

Winter Garden/Oakland Homes with 2 Car Garage Garage Description

Welcome to the charming communities of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. Known for its picturesque landscapes, rich history, and vibrant downtown area, this region offers a unique blend of small-town charm and modern conveniences. With its lush parks, scenic lakes, and friendly neighborhoods, Winter Garden and Oakland are perfect for families, retirees, and everyone in between.

One of the highlights of living in this beautiful area is the availability of homes featuring two-car garages. These spacious garages not only provide ample storage for your vehicles but also offer extra space for hobbies, outdoor gear, or even a workshop. Imagine having the convenience of parking your cars out of the Florida sun while still having room for your bicycles, tools, or seasonal decorations.

The homes in Winter Garden and Oakland boast a variety of architectural styles, from charming bungalows to modern designs, all with the practicality of a two-car garage. This feature is especially appealing for those who value both functionality and comfort. With easy access to major highways, shopping, and dining options, you’ll find that these homes serve as the perfect base for exploring everything Central Florida has to offer.

Whether you’re enjoying a leisurely stroll through the historic downtown Winter Garden or taking in the scenic views of the nearby lakes, you’ll quickly discover that Winter Garden and Oakland are not just places to live; they are places to thrive. Come and experience the warmth and welcoming spirit of this delightful region today!

Newest Winter Garden/Oakland Homes with 2 Car Garage Garage Description

$410,000
3 Beds ⋅ 3 Baths ⋅ Stone Crk A-1 & A-2 SubDv. ⋅ 34787 Zip Code
Location, location, location! Great opportunity to purchase a two-story 3/2.5 with a loft on the second floor and a fully fenced-in yard. The bright and functional floor plan offers plenty of room for comfortable everyday living and entertaining. The kitchen features granite countertops and stainless-steel appliances, while the spacious living areas provide a welcoming atmosphere throughout the home. Enjoy your new home!

2017 Portcastle Circle, Winter Garden
$535,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Located in the vibrant Lakeview Pointe community within Horizon West, this model-like 4-bedroom with a 2-car detached garage perfectly combines the best location with sophisticated style. Positioned across from the neighborhood pool, splash pad, playground, fitness center, park and central mailboxes, the property welcomes you with a manicured lawn, mature landscaping and a charming covered front porch. Inside, the light-filled, open-concept layout features neutral wood-look tile flooring and a chef-inspired all-white kitchen equipped with quartz countertops, crown-molded cabinetry, stainless steel appliances and a spacious island breakfast bar. A highly convenient downstairs guest bedroom offers ideal accommodations for visitors or multi-generational living, while the upper level hosts a versatile loft space alongside the primary suite complete with tray ceilings, dual vanities and two walk-in closets. You have a direct view to DISNEY FIREWORKS from the primary bedroom and bathroom. Step outside to unwind on the screened and paved lanai, your own pest-free outdoor retreat. Positioned less than 10 minutes from Walt Disney World, residents have a dedicated neighborhood fireworks viewing station. Everyday convenience is unmatched with Hamlin Town Center featuring Publix, Target, Cinepolis Luxury Cinemas and top-tier dining just minutes away. Popstroke Golf and the renowned Orange County National Golf Center are close by, plus effortless commuting via SR-429. Low HOA and No CDD, the community covers lawn care, irrigation, mulching and all of the resort-style amenities. Fun food trucks come to the neighborhood every third Wednesday of the month. You may also enjoy scenic biking and walking trails and a COMMMUNITY DOCK with access to Huckleberry Lake, delivering an elevated, lock-and-leave lifestyle.

7179 Spring Park Drive, Winter Garden
$205,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 22019039615 SubDv. ⋅ 34787 Zip Code
The lowest-priced 3-bedroom/3-bath on a higher floor at The Grove Resort & Water Park! This 5th-floor corner unit is the largest "Sable" model in the community, offering 1,544 sq ft with an open living/dining/kitchen area, a separate in-unit utility/laundry room, and a screened balcony. The kitchen features stainless steel appliances and granite counters. The primary suite includes an extra sitting area/solarium with direct balcony access, a bath with double sinks, a separate shower and soaking tub, and a large walk-in closet with a safe. Each bedroom includes a flat-screen TV. This condo-hotel offers an in-house hotel rental program that generates income to offset the cost of ownership — an ideal opportunity to own an Orlando/Disney-area vacation home just 6 miles from Walt Disney World. Resort amenities are exceptional. Surfari Water Park features the FlowRider Double Surf Simulator (one of only a few double units in the U.S.), dual water slides, a 695-foot lazy river, a zero-entry pool, and a kids' activities pool. The Springs Pools offer three full-sized pools, an oversized hot tub, a splash area, and private cabanas. Lake Austin provides catch-and-release fishing, watersports, and a lakeside pier overlooking the nature preserve. Additional amenities include a 24-hour fitness center, Flip Flop's Fun Center with a glow-in-the-dark indoor mini golf course and arcade, and a Kids' Activity Center. Dining options abound: The Springs Bar & Grill for relaxed poolside dining, Longboard Bar & Grill overlooking the FlowRider, Alfresco Market for outdoor cafe seating, and DYVE at The Terraces above the upscale pool area. The resort also offers daily transportation to Walt Disney World, Universal Orlando, and SeaWorld, plus complimentary resort-wide Wi-Fi. A rare chance to own a turnkey resort residence in one of the Orlando area's premier destinations.

14501 Grove Resort Avenue Unit 2542, Winter Garden
$475,000
3 Beds ⋅ 2 Baths ⋅ Crown Point Spgs SubDv. ⋅ 34787 Zip Code
Welcome to a home where the Florida lifestyle takes center stage. Tucked within the established Crown Point Springs community on a spacious corner lot, this is the kind of place where mornings start slowly, weekends are spent outside, and some of Winter Garden’s favorite destinations are just minutes from home. The backyard is truly where this home comes to life. Start your morning with coffee on the lanai overlooking the backyard, pick fresh fruit from your own fruit trees, and spend the afternoon floating in the screened-in pool. The fenced yard adds another layer of privacy and functionality, while the pool enclosure creates a space made for everything from quiet afternoons with a book to weekend barbecues with family and friends. It’s easy to imagine the rhythm of life here—music playing by the pool, dinner on the patio, kids or pets enjoying the fenced yard, and evenings winding down with a drink overlooking the water. Inside, comfortable gathering spaces make everyday living just as enjoyable. The kitchen offers plenty of countertop space, stainless steel appliances, and a tiled backsplash, whether you're making a quick breakfast before heading downtown or preparing dinner for a house full of friends. When cooler Florida evenings arrive, the wood-burning fireplace creates the perfect setting for a cozy night at home. The home has also benefited from a number of improvements over the past several years, including a 2024 roof and HVAC system, 2023 water heater and microwave, 2024 dishwasher, and 2021 pool pump. The pool was also resurfaced in 2022, and the interior was painted in 2021. But what the owners have loved most extends beyond the property itself. Crown Point Springs is a great community with friendly neighbors, a low HOA, and golf-cart accessibility, all while being close to the heart of Downtown Winter Garden. That means weekends don't have to involve much planning. Take the golf cart out for a ride, spend Saturday morning exploring the Downtown Winter Garden Farmers Market, grab brunch or browse the shops along Plant Street, or hop on your bike for a ride along the West Orange Trail. After your nearby activities, head home for an afternoon by your own pool. It's a lifestyle that gives you the best of both worlds—the energy and charm of Winter Garden when you want it and your own private retreat when you're ready to come home. Pool days, golf-cart rides, and Plant Street nights—this is the Winter Garden lifestyle you've been waiting for.

1009 Spring Loop Way, Winter Garden
$379,000
3 Beds ⋅ 3 Baths ⋅ Villas/Tucker Oaks SubDv. ⋅ 34787 Zip Code
Welcome to your beautifully updated home in the gated community of Winter Garden. This charming residence offers 3 bedrooms, 2.5 baths, 2-car garage, and approximately 1,737 sq. ft. of comfortable living space. In 2025, this home underwent a $53K renovation, featuring a modern kitchen with 42” shaker white cabinets with undermount lighting and quartz counters, stainless steel appliances, and a double oven for added convenience. The renovation also includes kitchen and bathroom upgrades, frameless shower doors, LVP flooring on the upstairs level and stairs, interior and exterior paint, new drapes, and elevated finishes throughout. Additional details include crown molding and 5” baseboards. Enjoy peace of mind with an A/C unit (3 years old) and a new roof (2025). Relax or entertain on the screen-covered patio with pond views. The garage floors feature non-slip coating, and the home includes all-new light fixtures, ceiling fans, and updated lighting. Additional benefits include a security system for added safety and convenience. Community amenities include a pool, playground, dog park, basketball courts, BBQ grills, and walking trails, perfect for everyday enjoyment. Located near Downtown Plant St, Fowler’s Grove, and with convenient access to 429 and the Florida Turnpike, you’re close to dining, shopping, entertainment, and major travel routes. Schedule your showing today!

1424 Scarlet Oak Loop, Winter Garden
$515,000
3 Beds ⋅ 2 Baths ⋅ Harbor SubDv. ⋅ 34787 Zip Code
A rare opportunity in downtown Winter Garden awaits! This beautifully maintained 3 bedroom, 2 bathroom home presents a chance to enjoy the vibrant lifestyle of downtown Winter Garden's golf cart district, complete with a new roof and a water heater less than two years old. A spacious driveway and manicured front lawn create a welcoming first impression. Inside, the home features a functional layout designed with both comfort and entertaining in mind. The dining area sits just off the entry and connects directly to the kitchen, making everything from casual dinners to larger gatherings feel seamless. The kitchen combines practicality with charm, featuring stainless steel appliances, built-in shelving, high ceilings, and a bright atmosphere. Overlooking the living room, it keeps the main living spaces connected while adding convenience to everyday life.The living room serves as a cozy gathering space centered around a functioning wood-burning fireplace, creating the perfect setting for relaxing evenings at home. A thoughtful split-bedroom layout provides added privacy, with the primary suite positioned separately from the secondary bedrooms. The primary bedroom includes direct access to the oversized screened-in patio and a private en suite bathroom featuring a tub and separate shower. The additional bedrooms are generously sized with natural light and ample storage, providing comfortable accommodations for family members, guests, or a home office. Step outside and enjoy an oversized screened-in patio complete with a ceiling fan, giving you the ideal place to relax outdoors while staying protected from Florida's elements and pests. Beyond the patio, the large fenced backyard provides plenty of room for four-legged friends, and little ones to roam freely without worry, or to accommodate fun activities like gardening or hosting loved ones. The options are limitless! A dedicated shed adds additional outdoor storage for tools, bikes, and recreational gear. Another standout benefit is the extremely low HOA, with the current HOA paid through June 2027, giving the next owner even more value and peace of mind. Living within Winter Garden's golf cart district means you can easily enjoy the area's beloved farmers market, boutique shopping, local restaurants, community festivals, and events without having to go far. Major highways are also conveniently nearby, along with excellent schools. With a new roof, newer water heater, spacious outdoor living areas, and an unbeatable downtown Winter Garden location, this home presents an exciting opportunity to create a space that truly reflects your style and vision. Come see the possibilities, make this home your own, and start enjoying the Winter Garden lifestyle today. Schedule your private tour!

217 Harbor Drive, Winter Garden
$899,000
3 Beds ⋅ 3 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome Home! The neighbors call this one of the best kept secrets in Oasis! One of the few homes in the community that have an amazing view of the Disney fireworks from your screened in porch! The seller has spared no expense in making this home truly move in ready. As soon as you walk in, you'll be greeted by high ceilings, beautiful tile floors and plenty of light! This home features the maximum amount of recessed lighting offered by the builder in every single room. This home truly has a gourmet kitchen, featuring an oversized kitchen island and plenty of cabinet/countertop space and a KitchenAid refrigerator. The corner pantry features a custom closet by design buildout. This beautiful kitchen will truly bring out your inner chef! In addition, the kitchen overlooks the dining room and living room perfect for entertaining! The home features custom smart blinds throughout the first floor. The seller spared no expense in upgrading this property, featuring custom closets by design in the master bedroom, mudroom and laundry room as well as the garage! This home comes with full home water purification system. FULLY paid off solar panels at closing! The upstairs loft and third bedroom have exotic wood throughout. Located minutes from Walt Disney World Resort, Hamlin Town Center & Downtown Winter Garden. Contact the listing agent today to schedule!

13355 Sunny Retreat Lane, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Oakland Trails SubDv. ⋅ 34787 Zip Code
Welcome to this energy efficient two story home built in 2020, ideally located in the highly desirable Town of Oakland with direct access to the West Orange Trail and excellent proximity to Historic Downtown Winter Garden. Situated on a spacious .21 acre lot, this residence offers 2,614 square feet of living space, 4 bedrooms, 2.5 bathrooms, a 2 car garage, and an open concept floor plan. The first floor features a formal living area, open kitchen with granite countertops a double oven, stainless steel appliances, eat-in dining space and a family room with upgraded luxury laminate flooring. Upstairs you’ll find all four bedrooms, two full bathrooms, and a versatile bonus/flex loft area. The bedrooms feature ceiling fans and spacious walk-in closets. Additional highlights include excellent storage throughout the home, generously sized under stair storage, and a separate drop zone. Step outside to enjoy bespoke landscaping with wired outdoor lighting, garden beds for your next harvest, an extended patio creating the perfect outdoor oasis. Conveniently located adjacent to the community pool, this home offers both comfort and convenience. Enjoy easy access to Orlando's theme parks, shopping, dining, and recreation, including the nearby 22-mile paved West Orange Trail as well as the Nature Preserve, perfect for walking, biking, and outdoor activities. A newly built Costco and an array of restaurants are also nearby. Easy access to Turnpike, 429, 408 making any commute a breeze. Enjoy the charm of the Town of Oakland while being just minutes from Winter Garden and Orlando. Schedule your tour today!

1750 Standing Rock Circle, Oakland
$750,000
4 Beds ⋅ 3 Baths ⋅ Valencia Shores SubDv. ⋅ 34787 Zip Code
Welcome to 301 Valencia Ct., a well maintained 4bedroom 2.5 bath home situated on a large, beautifully landscaped lot with mature trees and established landscaping in desirable Winter Garden. This inviting home offers a comfortable and functional floor plan with plenty of space for everyday living, entertaining and hosting family and friends. Inside a beautiful stone fireplace creates a warm and inviting focal point, while the interior laundry room adds everyday convenience. Step outside to enjoy the spacious backyard, with plenty of room to add a pool, creating the opportunity to design your own private Florida retreat. One of the property’s standout features is its location within the Winter Garden golf cart district, allowing you to enjoy the sought after golf cart lifestyle. Take a golf cart ride toward historic downtown Winter Garden and enjoy its popular restaurants, shops, Farmers market, entertainment, community events and small town charm.Numerous updates have been made to the home to include a new roof in 2021, A/C 2020, master bathroom,guest bathroom remodel in 2023 and Kitchen 2017.

301 Valencia Court, Winter Garden
$559,900
5 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to this spacious and inviting two-story home in the desirable Summerlake community! Offering five bedrooms and three full bathrooms, this thoughtfully designed home provides plenty of room for comfortable everyday living and entertaining. Relax on the welcoming front porch before stepping inside, where the living room offers flexible space for a home office, den, or study. Continue into the open-concept family room, dinette, and kitchen, the perfect gathering place for family and friends. The kitchen features stainless steel appliances, a gas range, ample cabinetry, and a center island with additional seating. A guest bedroom and full bathroom complete the first floor, providing a private and convenient space for visitors. Upstairs, the spacious primary suite is privately located at the rear of the home and includes a walk-in closet and an en-suite bathroom with dual vanities, a garden tub, and a separate shower. Three additional bedrooms, a full bathroom with dual sinks, and a conveniently located laundry room complete the second floor. Sliding glass doors from the family room open to a covered rear lanai, offering a comfortable space to relax and enjoy the outdoors. The home also features a rear-entry garage. Residents of Summerlake enjoy an impressive selection of community amenities, including a clubhouse, resort-style pool, fitness center, dog park, playground, parks, sidewalks, and tennis courts. This wonderful home combines space, comfort, and an amenity-rich lifestyle—schedule your private showing today!

7618 Bluejack Oak Drive, Winter Garden
$599,000
4 Beds ⋅ 2 Baths ⋅ Lakeview Pointe/Horizon West Ph SubDv. ⋅ 34787 Zip Code
This inviting split floor plan gives everyone space to unwind in comfort. The gourmet kitchen—complete with a central island—makes cooking effortless and flows seamlessly into the café and gathering room, creating the perfect setting for everyday living and unforgettable moments. Enjoy peaceful Florida evenings on the front patio with scenic skyline views, or host a cookout on the spacious covered lanai accented with elegant brick pavers. This home is priced to sell and delivers the warm, welcoming feeling of truly finding “home.” Lakeview Pointe is a fully maintained community located just about a mile from Disney, offering quick access to the 429, Winter Garden Village, Hamlin Town Center, and top-rated schools. The reasonable monthly HOA includes Lawn Care along with access to the amenity center that includes a fitness facility, resort-style pool with splash pad, playground, cabana, and park. Residents can watch the sunset from the pier on Lake Huckleberry or enjoy nightly Disney fireworks from the pavilion. Come experience everything Lakeview Pointe has to offer!

7278 Twilight Bay Drive, Winter Garden
$560,000
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenity | Flat Lot | Dedicated Home Office | Low HOA Dues. New Construction - November Completion! Welcome to the Ashwood at 14751 Field Daisy Drive in Harvest at Ovation! This thoughtfully designed three-story home offers flexible living with a private study near the entry, an open-concept great room, and a spacious kitchen with a large island that keeps everyone connected. Upstairs, the inviting primary suite provides a peaceful retreat, while two secondary bedrooms and a convenient laundry room add everyday comfort. The third-floor game room with a full bath creates the perfect space for entertaining, hobbies, or overnight guests. A covered lanai and charming front porch extend your living space outdoors, and the two-car garage provides plenty of room for storage and convenience. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: French doors at study and quartz countertops at kitchen. Photos are for representative purposes only. MLS#O6436927

14751 Field Daisy Drive, Winter Garden
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