Winter Garden Homes with Dillard Street Elem Elementary school

Winter Garden Homes with Dillard Street Elem Elementary school

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County, where picturesque landscapes meet vibrant community life. Known for its rich history, friendly atmosphere, and stunning natural beauty, Winter Garden offers a delightful blend of small-town charm and modern conveniences. With its quaint downtown area, lined with unique shops, delicious eateries, and beautiful parks, residents enjoy a lively social scene and a strong sense of community.

One of the standout features of Winter Garden is its commitment to education, particularly with the presence of Dillard Street Elementary School. Families looking to settle in this lovely area will appreciate the quality education and nurturing environment that Dillard Street offers. The school is known for its dedicated staff and engaging curriculum, making it an ideal choice for families prioritizing their children’s educational journey.

When it comes to housing, Winter Garden boasts a variety of options that cater to different lifestyles and budgets. From charming historic homes to modern developments, there’s something for everyone. Many homes in the vicinity of Dillard Street Elementary School are designed with families in mind, featuring spacious layouts, inviting backyards, and community amenities that foster a sense of togetherness.

Living in Winter Garden means embracing a lifestyle filled with outdoor activities, cultural events, and a supportive community. With beautiful parks, scenic trails, and a calendar full of local festivals, there’s always something to explore. Experience the warmth and vibrancy of Winter Garden – where your dream home awaits amidst a thriving community and excellent educational opportunities!

Newest Winter Garden Homes with Dillard Street Elem Elementary school

6 Beds ⋅ 4 Baths ⋅ Mcallister Landing SubDv. ⋅ 34787 Zip Code

A new dryer was installed in May 2024, and a new washing machine was installed in August 2025 with a two-year warranty. In June 2026, the upstairs A/C indoor unit was replaced. The installation included all labor and materials, as well as product registration for parts warranty. 1523 Juniper Hammock Street welcomes you with a striking two-story façade, graceful architectural lines, and a beautifully composed exterior that creates an impressive sense of arrival. At the rear, the home opens to a lush, peaceful setting dominated by mature trees and natural greenery, offering a refreshing backdrop and a greater sense of privacy. A partial water view from the side adds another layer of beauty without taking away from the secluded, tree-lined atmosphere. Together, the elegant exterior and serene natural surroundings create a home that feels both distinguished and wonderfully connected to the outdoors.

1523 Juniper Hammock Street, 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 ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code

Experience the perfect blend of comfort, charm, and functionality in this beautiful Winter Garden home! Featuring 4 bedrooms and 2.5 baths, this spacious residence offers an impressive second-story loft and a versatile fourth bedroom with its own half bath—perfect for guests, a media room, or flexible living space. The thoughtfully designed first floor features a private primary suite with an ensuite bath, two additional bedrooms sharing a full bath, a spacious family room, and a beautifully appointed kitchen that truly serves as the heart of the home. Kitchen features include built-ins and French doors that open to a gorgeous deck, creating an ideal setting for indoor/outdoor entertaining. A formal dining room and separate office with French doors provide additional space and privacy. Step outside to enjoy peaceful outdoor living in the landscaped backyard, complete with a private patio/deck perfect for relaxing or entertaining. A 2-car garage plus a dedicated golf cart garage adds exceptional convenience and storage. Located in highly sought-after Downtown Winter Garden, this home is close to top-rated schools, shopping, parks, West Orange Trail, and popular dining destinations. Enjoy the unique lifestyle of a golf-cart-friendly downtown district while being just minutes from everything you need. ON-SITE Generator for Hurricane season too. Recent updates include a New Roof (2023), New hot water tank, New mini-split, A/C Main (2023), and fresh interior paint (2026). Come discover all this wonderful home has to offer and make it yours!

502 Palm Drive, Winter Garden

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

8 Beds ⋅ 3 Baths ⋅ Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code

8 bedrooms. 3 full baths. Approximately 1,750 SF. Just blocks from Plant Street. Space and location set this property apart. Offering 8 bedrooms and 3 full baths across approximately 1,750 SF, the home sits on a 9,431 SF fully fenced lot—a combination of interior space and land increasingly difficult to find this close to Historic Downtown Winter Garden. Built in 1925 and sold as-is, the home presents an opportunity to update and personalize to your own vision. The flexible room count provides options for bedrooms, guest space, home offices, or additional living needs, while the generous 75' x 125' lot leaves plenty of outdoor space to create a garden, entertaining area, or backyard retreat. No HOA, city utilities, and R-2 zoning add to the property's flexibility and long-term appeal. Location is the part that cannot be renovated. Enjoy being just blocks from Plant Street, the Saturday farmers market, restaurants, cafés, shops, entertainment, and the West Orange Trail, with Lake Apopka, SR-429, and Florida's Turnpike conveniently nearby. Currently income producing, the property offers the flexibility to maintain its existing rental use or be delivered vacant upon request. 8 Bedrooms. 3 Full Baths. Approx. 1,750 SF. 0.22 Acres. 9,431 SF Lot. 75' x 125'. No HOA. Bring your vision and make the space your own in a location that's increasingly difficult to replicate. Schedule your private showing today.

208 3rd Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Lake Cove Pointe 46/58 SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this beautifully maintained custom home located in the gated community of Lake Cove Pointe, within the Winter Garden Golf Cart District. Conveniently located just minutes from Historic Downtown Winter Garden, this home offers easy access to dining, shopping, theater, entertainment, and local avente. A paver driveway and path lead to the charming front porch and welcoming entry. Inside, this nearly 2, 400-square-foot home features 4 bedrooms, 3 full baths, and a spacious three-way split floor plan designed for comfort and privacy. The main living areas feature attractive wood-look ceramic tile, with carpet in the family room and bedrooms. The well-appointed kitchen offers white cabinetry, beautiful countertops, and glass-pane display cabinets for added character and storage. The spacious Owner's Suite includes custom closets, a comfortable sitting area, and French doors leading to the screened-in patio. The Owner's Bath features a large shower and freestanding soaking tub. Enjoy Florida outdoor living from the screened-in patio, complete with a convenient wet bar and sink, making it an ideal space for entertaining or relaxing. The property also offers an immaculate two-car garage with new epoxy flooring, plus a separate third golf cart garage/workshop combination, providing excellent flexibility for golf cart storage, hobbies, or additional workspace. Recent updates include a 2019 roof, 2019 A/C, a Rheem 60-gallon hybrid water heater installed approximately nine months ago, and lifetime garage door springs! installed last summer. Located in a desirable gated community and close to Historic Downtown Winter Garden, this well-maintained home combines a thoughtful floor plan, attractive updates, excellent garage space, and convenient access to all that Winter Garden has to offer.

427 Tierra Verde Lane, Winter Garden

Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code

Most Winter Garden listings sell on charm. This one sells on the rent roll. Eight rooms currently rented — seven at $175 weekly and one at $200 — generating $1,425 per week / $74,100 annualized gross income at current rents. In place, occupied, and income producing. The land adds another layer to the opportunity. Situated on approximately 0.22 acres / 9,500+ SF with a 75' x 125' lot, the fully fenced property offers R-2 zoning, no HOA, city water and city sewer, along with ample yard space and future flexibility. Hold the existing income while exploring the property's longer-term expansion or redevelopment potential, subject to applicable zoning requirements and City approvals. The location carries its own value. Just a few blocks from Historic Downtown Winter Garden, Plant Street, the West Orange Trail, shops, restaurants and the farmers market, with SR-429, Florida's Turnpike and Lake Apopka nearby. The surrounding area continues to evolve with renovated properties and new construction. 0.22 Acres. 9,500+ SF Lot. R-2. Eight Rented Rooms. $1,425/Week Gross. Income in place. Land underneath. Future upside ahead. A rare opportunity to own all three near Downtown Winter Garden—schedule your private showing today.

208 3rd Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Vinings Add Winter Garden SubDv. ⋅ 34787 Zip Code

Discover this beautifully maintained 4-bedroom, 2-bath home nestled in the heart of historic Winter Garden. Featuring a spacious open floor plan with approximately 1,774 square feet of living space, this home offers generous living and dining areas ideal for everyday living and entertaining. The kitchen provides ample cabinet and counter space and opens seamlessly to the main living area. The split-bedroom layout offers privacy for the primary suite, while the additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the convenience of an attached two-car garage, central air conditioning, and a large fenced backyard with plenty of room for outdoor entertaining, gardening, or pets. Located just minutes from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning restaurants, boutique shopping, the West Orange Trail, the Winter Garden Farmers Market, and numerous community events throughout the year. Conveniently located near SR-429, the Florida Turnpike, Downtown Orlando, major employers, and world-renowned theme parks. No HOA makes this an outstanding opportunity for homeowners and investors alike.

300 S Woodland Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Oakglen Estates SubDv. ⋅ 34787 Zip Code

Located in the Oakglen Estates community of Winter Garden, this spacious 4-bedroom, 3-bathroom home offers a functional open layout, tall ceilings and plenty of room to live and entertain. The updated kitchen features an oversized island, abundant cabinetry and a large pantry conveniently connected to the laundry room, which also provides exterior access. Luxury vinyl flooring runs throughout the main living areas, with brand-new carpet in two guest bedrooms. The spacious primary suite features additional closet/shelving, two walk-in closets and a large en-suite bathroom with a soaking tub and separate shower stall. Both guest bathrooms have been beautifully remodeled. Step outside to enjoy a private fenced backyard with a built-in sunshade, exterior electric perimeter dog fence and a variety of fruit trees, including guava and berry bushes. The home offers the space, updates and functionality today's buyers are looking for, all within a well-established Winter Garden neighborhood. Enjoy easy access to Winter Garden's Historic Downtown, Lake Apopka, the West Orange Trail for biking and walking, shopping, dining and the many amenities that make Winter Garden such a sought-after place to call home. Homes in this established community don't come to market often—don't miss your opportunity to make 531 Hearthglen Blvd your own.

531 Hearthglen Boulevard, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Add 02 SubDv. ⋅ 34787 Zip Code

This Downtown Winter Garden stunner has continued to evolve with thoughtful, high-value upgrades that make it even more exceptional today. Located in the much sought after golf cart district and just steps from Plant Street’s restaurants, markets, and year-round events, this home blends timeless character with modern convenience in a way few properties can match. Originally reimagined with a full professional remodel in 2023 — including brand-new roof, windows, electrical, plumbing, insulation, luxury vinyl plank flooring, Bosch appliances, Carrara quartz surfaces, and a magnificent, redesigned kitchen. Additional upgrades include a newly constructed one-car garage with parking pad - 2026 and a whole-home generator providing both functionality and peace of mind rarely found in homes of this era. These additions compliment the already impressive split-floorplan featuring 4 bedrooms (and bonus room), 2.5 baths, an oversized island kitchen with fireplace feature wall, gallery-style windows, and a private primary suite with walk-in closet. Every inch of this home reflects quality, style, and intention — from the high-grade materials used throughout to the continued improvements that elevate daily living. Homes like this, with extensive permitted renovations and meaningful new upgrades, simply do not come to market often in Winter Garden. Homes this special in the heart of Winter Garden are rarely available for long — claim it before it’s gone.

368 N Boyd Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Cypress floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

650 Medora Way, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award- winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Maple floor plan, offering 4 bedrooms, 3.5 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

611 Sigler Drive, Winter Garden

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