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Homes for Rent near Dillard Street Elementary

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  • /35

    $1,650 - $1,750 per month

    Garden City Apartments

    2 Beds

    521 S Park Ave, Winter Garden, FL 34787

    Garden City Apartments is nestled in the heart of Downtown Winter Garden, Florida. Within walking distance or a quick golf cart ride to Historic Plant Street, life is full of excitement with local arts and entertainment, trails and restaurants galore you will surely feel at home and safe living in our newly renovated industrial designed family-friendly apartments. We have a mix between

    521 S Park Ave, Winter Garden, FL 34787
  • /27

    $3,200 per month

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • House for Rent

    116 Timbercreek Pines Cir, Winter Garden, FL 34787

    Available Nov. 20th, 2025***Beautiful home with fenced in yard in Downtown Winter Garden. Available Nov 15th, 2025. 1 year lease preferred. Showings will need to be scheduled with listing agent. Enjoy the Downtown Golf cart district with boutique shopping, casual, and fine dining, Saturday Farmer's Market, and all the downtown parades and events that the city of Winter Garden celebrates. Just a

    Joshua Earley OPTIMA ONE REALTY, INC.

    116 Timbercreek Pines Cir, Winter Garden, FL 34787
  • /16

    $2,435 per month

    • 3 Beds
    • 2 Baths
    • 1,976 Sq Ft
    • House for Rent

    510 E Fullers Cross Rd, Winter Garden, FL 34787

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2579.90. That covers your base rent, $2435.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    510 E Fullers Cross Rd, Winter Garden, FL 34787
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    $2,700 per month

    • 3 Beds
    • 2 Baths
    • 2,102 Sq Ft
    • House for Rent

    607 Grassy Stone Dr, Winter Garden, FL 34787

    Great Golf cart community with pool and playground a short walk from home. Also the West Orange Trail entrance for 22 miles of biking, walking etc. Spacious plan with formal living, dining, Separate family room open to kitchen. Split bedroom. Covered back patio. All appliances, blinds. Laminate wood flooring throughout including bedrooms. Charming Downtown Winter Garden with many shops,

    Peggy Johnson FLAMINGO REALTY OF ORLANDO

    607 Grassy Stone Dr, Winter Garden, FL 34787
  • /16

    $2,595 per month

    • 3 Beds
    • 2 Baths
    • 1,790 Sq Ft
    • House for Rent

    1048 Spring Loop Way, Winter Garden, FL 34787

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    1048 Spring Loop Way, Winter Garden, FL 34787
  • /24

    $4,200 per month

    • 3 Beds
    • 3.5 Baths
    • 2,242 Sq Ft
    • Townhouse for Rent

    145 S Park Ave, Winter Garden, FL 34787

    Rare opportunity to lease this LUXURY tri-level townhome in Downtown Winter Garden! No need to worry about stairs as this property has a private in-unit ELEVATOR. Downstairs you will find one bedroom with ensuite bathroom, as well as a two-car garage with TESLA electric car charger. The BRIGHT and OPEN kitchen and main living area is on the second level, along with a half bath. The kitchen has

    Laura Orge KELLER WILLIAMS REALTY AT THE PARKS

    145 S Park Ave, Winter Garden, FL 34787
  • /20

    $2,975 per month

    • 5 Beds
    • 4 Baths
    • 3,406 Sq Ft
    • House for Rent

    1137 Burland Cir, Winter Garden, FL 34787

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3119.90. That covers your base rent, $2975.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1137 Burland Cir, Winter Garden, FL 34787
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    $4,000 per month

    • 4 Beds
    • 3 Baths
    • 2,368 Sq Ft
    • House for Rent

    427 Tierra Verde Ln, Winter Garden, FL 34787

    Fully FURNISHED pristine custom home nestled in the sought-after gated community of Lake Cove Pointe! this stunning 4-bed, 3-bath house is a masterpiece of comfort and style. Located in the heart of the Winter Garden Golf Cart District, this residence offers a unique blend of luxury, convenience, and tranquility.Property Features: • Spacious 4 bedrooms with ample natural light; The

    Sherry Wang KELLER WILLIAMS CLASSIC

    427 Tierra Verde Ln, Winter Garden, FL 34787
  • /18

    $2,945 per month

    • 4 Beds
    • 2 Baths
    • 2,543 Sq Ft
    • House for Rent

    744 Westcliffe Dr, Winter Garden, FL 34787

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    744 Westcliffe Dr, Winter Garden, FL 34787
  • /49

    $4,500 per month

    • 3 Beds
    • 3.5 Baths
    • 1,730 Sq Ft
    • Townhouse for Rent

    125 S Park Ave, Winter Garden, FL 34787

    Highly Sought After 3 story townhome community located on the downtown strip of Main Street Old Winter Garden. Beautifully appointed with ceramic tile throughout main living and all wet areas. Gourmet kitchen with all upgraded appliances, including gas stove and built in microwave. 8-foot center island with sink and 4 counter seat spaces. Just off the kitchen and pantry is a small but cozy

    Billy Cannon, Jr BHHS FLORIDA REALTY

    125 S Park Ave, Winter Garden, FL 34787
  • /18

    $1,624 per month

    • 3 Beds
    • 1 Bath
    • 898 Sq Ft
    • House for Rent

    1020 Lincoln Terrace, Winter Garden, FL 34787

    Are you on the hunt for a cozy new home in a great location? I've got just the place for you - 1020 Lincoln Terrace. This 3-bedroom, 1-bath house is ready and waiting for a new tenant, and we're offering 1 months free of rent to sweeten the deal.Nestled in a quiet, residential neighborhood, this home offers the perfect blend of comfort and convenience. Step inside and you'll be

    1020 Lincoln Terrace, Winter Garden, FL 34787
  • /16

    $2,945 per month

    • 4 Beds
    • 2 Baths
    • 2,545 Sq Ft
    • House for Rent

    1814 Americus Minor Dr, Winter Garden, FL 34787

    Monthly Recurring Fees:$20.00 - Smart Home$10.95 - Utility ManagementMaymont Homes is committed to clear and upfront pricing. In addition to the advertised rent, residents may have monthly fees, including a $10.95 utility management fee, a $25.00 wastewater fee for homes on septic systems, and an amenity fee for homes with smart home technology, valet trash, or other community

    1814 Americus Minor Dr, Winter Garden, FL 34787
  • /20

    $3,015 per month

    • 4 Beds
    • 3 Baths
    • 3,029 Sq Ft
    • House for Rent

    543 Hearthglen Blvd, Winter Garden, FL 34787

    This property is professionally managed by AMH, a leading single-family rental company. We work to simplify your rental experience by offering self-guided tours and a streamlined leasing process you can complete all online, all on your own schedule. Once moved in, we provide maintenance support that you can rely on, so you can enjoy your weekends stress-free. We look forward to welcoming you

    543 Hearthglen Blvd, Winter Garden, FL 34787
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