12

Winter Park, FL Houses for Rent with Community Pool

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  • /78

    $11,000 per month

    • 5 Beds
    • 4 Baths
    • 4,200 Sq Ft
    • House for Rent

    1814 Barker Dr, Winter Park, FL 32789

    Stunning newer-construction luxury home in Winter Park offering 5 bedrooms, 4 baths, and 4,100 sq ft of modern living. Sleek architectural lines, abundant natural light, and seamless indoor–outdoor flow define this exceptional residence. The chef’s kitchen features premium stainless steel appliances, breakfast bar, custom cabinetry, and a large walk-in pantry. The spacious living area includes a

    Tab Bish LLC REAL BROKER, LLC

    1814 Barker Dr, Winter Park, FL 32789
  • /34

    $4,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,196 Sq Ft
    • House for Rent

    1091 Wildmeadow Run, Winter Park, FL 32792

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    Maggie Walas FORTUNE INTERNATIONAL REALTY

    1091 Wildmeadow Run, Winter Park, FL 32792
  • /35

    $4,500 per month

    • 4 Beds
    • 3 Baths
    • 1,808 Sq Ft
    • House for Rent

    1802 Arbor Park Dr, Winter Park, FL 32789

    Welcome home to this beautifully maintained 4-bedroom, 3-bath pool home located in Winter Park’s highly desirable Tree Streets neighborhood—an area known for its charming, tree-lined roads and peaceful atmosphere. Situated on an oversized .27-acre lot, one of the largest in the community, this property offers rare space and privacy while still being close to everything Winter Park has to offer.

    Jorge Perez Gonzalez TBRO REALTY LLC

    1802 Arbor Park Dr, Winter Park, FL 32789
  • /37

    $5,900 per month

    • 4 Beds
    • 3 Baths
    • 2,741 Sq Ft
    • House for Rent

    220 W Reading Way, Winter Park, FL 32789

    Welcome to your dream home! This recently renovated gem in the highly coveted Forrest Hills area of Winter Park is now available for rent. Surrounded by enchanting brick streets and majestic trees, this charming residence has been thoughtfully upgraded by the new owner, offering a perfect blend of modern amenities and classic charm. As you step onto the inviting front covered porch, you'll be

    Thomas Hewitt HEWITT RESIDENTIAL, LLC

    220 W Reading Way, Winter Park, FL 32789
  • /90

    $13,500 per month

    • 8 Beds
    • 6 Baths
    • 7,000 Sq Ft
    • House for Rent

    1860 Via Contessa, Winter Park, FL 32789

    Exceptional Lease Opportunity | The Vias, Winter Park$13,500/mo | $15,000 Security Deposit | One-Year Lease | Pets Considered (Owner Approval) | Available NowRarely does a home of this caliber come to market for lease. Set on a quiet cul-de-sac in one of Winter Park's most prestigious enclaves — the coveted Vias neighborhood — this magnificent 7,000 SF residence delivers an unmatched

    Kelly Price KELLY PRICE & COMPANY LLC

    1860 Via Contessa, Winter Park, FL 32789
  • /14

    $5,895 per month

    • 4 Beds
    • 3 Baths
    • 2,207 Sq Ft
    • House for Rent

    1235 Via Estrella, Winter Park, FL 32789

    Rare opportunity to lease a spacious 4-bedroom, 3-bath home in one of Winter Park's most coveted enclaves — The Vias. Spanning 2,207 SF, this sun-drenched residence sits just a short stroll from the prestigious Winter Park Racquet Club. Flooded with natural light, the open-concept living spaces feature beautiful bamboo wood floors, a well-appointed kitchen with white cabinetry and a large island,

    Kelly Price KELLY PRICE & COMPANY LLC

    1235 Via Estrella, Winter Park, FL 32789
  • /32

    $3,475 per month

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • House for Rent

    1850 Whitehall Dr, Winter Park, FL 32789

    This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1850 Whitehall Dr, Winter Park, FL 32789
  • /27

    $17,000 per month

    • 4 Beds
    • 5 Baths
    • 3,658 Sq Ft
    • House for Rent

    1742 Temple Dr, Winter Park, FL 32789

    An Enduring Work of Art: Winter Park’s Modern MasterpieceThis is more than just a property; it is an iconic masterpiece. Tucked within one of Winter Park’s most exclusive enclaves, this stunning four-bedroom, five-bathroom ground-up renovation offers a refined lifestyle where modern luxury and intelligent functionality converge.From the moment you enter it’s clear this home was designed

    Mark Anthony Buot ROI AVE LLC

    1742 Temple Dr, Winter Park, FL 32789
  • /43

    $19,000 per month

    • 5 Beds
    • 5.5 Baths
    • 5,164 Sq Ft
    • House for Rent

    1221 Richmond Rd, Winter Park, FL 32789

    Owner/Builder/Agent - An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park—offering deeded lake access to the Winter Park Chain of Lakes. This architectural showpiece was honored as the 2024

    Christopher Salhab LA ROSA REALTY HORIZONS LLC

    1221 Richmond Rd, Winter Park, FL 32789
  • /42

    $2,950 per month

    • 3 Beds
    • 2 Baths
    • 1,747 Sq Ft
    • House for Rent

    1807 N Park Ave, Winter Park, FL 32789

    Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

    Jason Hamilton THE REALTY MEDICS

    1807 N Park Ave, Winter Park, FL 32789
  • /14

    $6,950 per month

    • 4 Beds
    • 2.5 Baths
    • 2,470 Sq Ft
    • House for Rent

    1420 Lyndale Blvd, Maitland, FL 32751

    LOOK NO FURTHER! This completely remodeled POOL home boast a spacious 4 bedroom's and 2.5 bathroom's that are situated on an oversized corner lot. From the moment you enter the front door, you can notice the large new tile floors, complimented by all custom cabinetry, high end light fixtures and a spacious floor plan. A gourmet kitchen with beautiful, light quartz counters to compliment the navy

    Jason Zinno RE/MAX ASSURED

    1420 Lyndale Blvd, Maitland, FL 32751
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