Winter Garden Homes with Attached Property Description

Winter Garden Homes with Attached Property Description

Welcome to Winter Garden, Florida—a delightful gem nestled in the heart of Orange County. Known for its vibrant community and picturesque landscapes, Winter Garden offers a unique blend of small-town charm and modern amenities. With a rich history dating back to the 19th century, this city is renowned for its beautifully preserved downtown area, where cobblestone streets are lined with quaint shops, delightful eateries, and a lively farmers market that brings the community together every weekend.

Winter Garden is not just about stunning scenery and community spirit; it also boasts excellent schools, beautiful parks, and a variety of recreational activities. The West Orange Trail, a scenic pathway perfect for walking, biking, and jogging, winds through the city, offering residents an opportunity to enjoy the great outdoors year-round. Additionally, its proximity to major attractions like Walt Disney World and Universal Studios makes it an ideal location for families and adventure-seekers alike.

When it comes to real estate, Winter Garden showcases a diverse array of homes with attached property options. Whether you’re looking for a charming bungalow, a modern townhouse, or a spacious family home, the housing market here has something for everyone. Many properties feature attached garages, private backyards, and open-concept living spaces, perfect for entertaining or enjoying quiet evenings at home.

Discover the warmth and welcoming atmosphere of Winter Garden, where every home tells a story and every street invites you to explore. Your perfect home awaits in this enchanting Florida city!

Newest Winter Garden Homes with Attached Property Description

3 Beds ⋅ 4 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code

Downtown Winter Garden becomes part of everyday life at this one-of-nine residence at 30 North Park, where a covered balcony overlooks the West Orange Trail and Plant Street’s dining, shops, and gathering spots are only a short stroll away. Arranged across three thoughtfully designed levels, the home balances connected gathering spaces with room to work and unwind. The main level brings the kitchen, dining area, and living room together beneath tall ceilings. An oversized island anchors the kitchen, complemented by quartz countertops, tall two-tone cabinetry, stainless steel appliances, and natural-gas cooking. Decorative wood beams, built-ins, and a gas fireplace feature wall give the living room character, while sliding glass doors extend the space to the balcony. Each of the three bedroom suites includes a walk-in closet and private full bathroom. Two suites occupy the upper level, including the primary with fitted closet storage, dual sinks, a glass-enclosed shower, and a separate water closet, while the second-level suite is currently arranged as a window-lined office. A ground-level bonus room with an adjoining fourth full bath creates another adaptable space for media, fitness, hobbies, or guests. Engineered hardwood and designer tile keep the interior carpet-free, while upper-level laundry, a tankless water heater, zoned HVAC, spray-foam ceiling insulation, and an attached rear-entry two-car garage add practical convenience. From quiet time on the balcony to mornings on the trail and evenings along Plant Street, this home pairs polished, flexible interiors with a distinctly downtown Winter Garden lifestyle.

72 N Park Avenue Unit 8, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code

Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Orange Cove SubDv. ⋅ 34787 Zip Code

Single family residence

735 Hurley Drive, Winter Garden

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

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

2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Close to Amenities | Covered Lanai | Dedicated Study. New Construction - November Completion! Welcome to the Caicos at 11234 Silver Trumpet Loop in Esplanade at McKinnon Groves! This charming new home offers a bright, open-concept layout that brings the kitchen, dining area, and great room together at the heart of the home. Sliding glass doors open to the covered lanai, extending the living space outdoors for relaxing mornings or evening gatherings. Tucked at the back, the primary suite serves as a private retreat with a spacious bathroom and generous walk-in closet. A secondary bedroom, full bathroom, and versatile study provide comfortable accommodations for guests and the flexibility to create a home office, hobby room, or additional living space. Additional Highlights Include: tray ceiling pkg, double pocket doors at study, and single pocket door at bed 2 into bath. Photos are for representative purposes only. MLS#O6436550 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11234 Silver Trumpet Loop, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Corner Lot | Covered Lanai | No Rear Neighbors. New Construction - December Completion! Welcome to the Caicos at 11199 Silver Trumpet Loop in Esplanade at McKinnon Groves! This thoughtfully designed new home features an open-concept floor plan that seamlessly connects the kitchen, dining area, and great room, creating a bright and welcoming space for everyday living. Sliding glass doors extend the living area to the covered lanai, making indoor-outdoor living effortless. The primary suite offers a peaceful retreat with a spacious bathroom and generous walk-in closet. A secondary bedroom, full bathroom, and dedicated study provide comfortable accommodations for guests and the flexibility to work from home. Additional Highlights Include: tray ceiling pkg, double pocket doors at study, 8' interior doors, single pocket door at primary bath, single pocket door at bedroom 2 to bath, and extended flooring to primary suite. Photos are for representative purposes only. MLS#O6436537 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11199 Silver Trumpet Loop, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code

Under Construction. What's Special: Covered Extended Lanai | Dedicated Study | Close to Park. New Construction - December Completion! Welcome to the Caicos at 11202 Silver Trumpet Loop in Esplanade at McKinnon Groves! This thoughtfully designed new home has an open-concept layout where the spacious kitchen overlooks the dining area and great room, creating a bright and inviting gathering space. From here sliding doors lead to the covered lanai for effortless indoor-outdoor enjoyment. Tucked at the rear of the home, the primary suite provides a relaxing retreat with a spacious bathroom and generous closet. A secondary bedroom, bathroom, and dedicated study provide comfort and privacy for guests, along with a space to work from home. Additional Highlights Include: double pocket doors at study, 8' interior doors, single pocket door at primary bath, single pocket door at bedroom 2 to bath, and extended flooring to primary suite. Photos are for representative purposes only. MLS#O6436496 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11202 Silver Trumpet Loop, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code

Welcome to low-maintenance living in the heart of Winter Garden! This charming 2-bedroom, 2-bathroom condominium offers approximately 840 sq ft of comfortable living space in the established Townhomes of Winter Garden community. Enjoy an open floor plan with a bright living and dining area, functional kitchen, and two well-appointed bedrooms, including a primary suite with its own bathroom. In-unit laundry (washer and dryer) adds everyday convenience. The community features a sparkling pool, exterior maintenance, and landscaping included in the HOA, making this an easy, lock-and-leave lifestyle. Prime location just minutes from Historic Downtown Winter Garden’s shops, restaurants, farmers market, and the West Orange Trail. Quick access to Highway 50, Winter Garden Village (shopping, dining, and more), and major roadways for easy commuting throughout Central Florida. Ideal for first-time buyers, downsizers, or investors seeking a solid rental property in a desirable Winter Garden location. Pets are typically allowed (buyer to verify HOA rules). Schedule your private showing today!

300 Eron Way Unit 1, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Encore/Ovation Ph 4b SubDv. ⋅ 34787 Zip Code

Welcome to this beautiful end-unit townhome in the desirable Encore at Ovation community. Conveniently located less than 10 minutes from Disney Property, with quick access to US-192, US-27, and SR-429, you’ll be able to enjoy all Central Florida has to offer. The lot features a backloading two-car garage and a private patio area, perfect for a quiet morning coffee or a cookout with friends. The home is also set between a quaint tree-lined sidewalk to the front and open green space to the back, adding to the feeling of privacy. Inside, enjoy a thoughtfully designed layout that includes an open concept kitchen/living/dining area, ample counter and cabinet space, a dedicated pantry, a large laundry room with plenty of storage, and a separate den for multiple gathering spots. Upstairs, relax in your large primary suite with a walk-in closet and updated ensuite bathroom. You can even catch the Magic Kingdom fireworks from your window! This home is not only immaculately maintained but also upgraded for your convenience. A whole-house water filtration/softener system, kitchen sink reverse osmosis (RO) system, HVAC air ionizer and UV light system have all been recently installed. Additionally, the roof, exterior painting, driveway upkeep, yard maintenance, landscaping, and pest control are all taken care of by the HOA, making this property perfect for those using it as a secondary home, or simply looking for a low-maintenance lifestyle. Reach out to book your private showing today!

15877 Tollington Alley, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code

Welcome to The Grove Resort & Water Park Orlando, a premier vacation resort just minutes from Walt Disney World. This spacious 3-bedroom, 3-bath condominium is located on the 3rd floor of Building 2, offering exceptional convenience to the main lobby and resort amenities. Designed for vacation enjoyment and investment potential, the residence features a spacious open floor plan, well-appointed kitchen, comfortable living and dining areas, and three bedrooms and baths providing plenty of room for family and guests. Enjoy your own Orlando vacation retreat and take advantage of rental income . The Grove offers an impressive resort experience with Surfari Water Park, multiple pools, a lazy river, FlowRider surf simulator, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, and complimentary transportation to Walt Disney World. Whether your goal is creating memorable Florida vacations, generating rental income, or enjoying the best of both, this Building 2 location offers convenience, flexibility, and investment potential in one of Orlando’s most popular vacation destinations. Vacation when you want. Earn rental income when you don’t.

14501 Grove Resort Avenue Unit 2342, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code

Under Construction. Ready in December 2026! 3 Level Townhome with 3 Bedrooms! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms with a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by a Study room. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.

15213 Groveside Road, Winter Garden

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