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Winter Park, FL Homes for Rent with Pool

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  • /44

    $7,000 per month

    • 4 Beds
    • 5 Baths
    • 3,302 Sq Ft
    • House for Rent

    519 Park North Ct, Winter Park, FL 32789

    Discover refined single-story living at 519 Park North Court, an exceptional luxury rental in the heart of Winter Park. This beautifully appointed four-bedroom, three-and-a-half-bath residence offers an ideal blend of elegance and comfort, with a thoughtfully designed split floor plan that ensures both privacy and functionality for modern living.The home welcomes you with a formal living room

    Kelly Price KELLY PRICE & COMPANY LLC

    519 Park North Ct, Winter Park, FL 32789
  • /14

    $1,250 - $1,800 per month

    Park Apartments

    1 - 3 Beds

    7528 Park Promenade Dr, Winter Park, FL 32792

    WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two

    7528 Park Promenade Dr, Winter Park, FL 32792
  • /15

    $1,900 per month

    • 1 Bed
    • 2 Baths
    • 1,153 Sq Ft
    • Property for Rent

    250 Carolina Ave Unit 307, Winter Park, FL 32789

    Spacious One Bedroom two full bathroom condo, open floor plan, two balconies large kitchen, laundry room, outdoor storage area. Third floor unit with elevator and under building parking. This gated community offers tennis courts, large swimming pool and community club.EXCELLENT location, one block away from Park Ave and short walk to the Winter Park sunrail station, Rollins College. Saturday

    Rod Arzouni VERANDA PARK REALTY LLC

    250 Carolina Ave Unit 307, Winter Park, FL 32789
  • /11

    $1,295 - $1,667 per month

    Solis at Winter Park

    1 - 2 Beds

    7502 Sun Key Blvd, Winter Park, FL 32792

    Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

    7502 Sun Key Blvd, Winter Park, FL 32792
  • /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 LLC

    1221 Richmond Rd, Winter Park, FL 32789
  • /29

    $1,313 - $1,912 per month

    Atlas at Winter Park

    1 - 3 Beds

    3733 N Goldenrod Rd, Winter Park, FL 32792

    Welcome home to Atlas at Winter Park!

    3733 N Goldenrod Rd, Winter Park, FL 32792
  • /30

    $1,750 per month

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Condo for Rent

    650 Trinidad Ct Unit 650, Winter Park, FL 32792

    Welcome to your dream home in the heart of Winter Park, FL. This stunning Corner Unit 2-bedroom, 2-bathroom residence offers a perfect blend of comfort and style. The house is designed with a spacious layout that ensures ample natural light in every corner. The community amenities are sure to impress, with a sparkling pool, a well-equipped gym, and tennis courts available for your leisure and

    Dawn Slaughter TRUSTHOME PROPERTIES INC

    650 Trinidad Ct Unit 650, Winter Park, FL 32792
  • /31

    $1,509 - $1,800 per month

    POSTE Winter Park

    1 - 2 Beds

    800 Semoran Park Dr, Winter Park, FL 32792

    Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

    800 Semoran Park Dr, Winter Park, FL 32792
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    $1,750 per month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 226, Winter Park, FL 32789

    Updated 2 bedrooms 1 bath conveniently located next to Winter Park Village and Trader Joes shopping center. Unit is can be furnished and is also for sale.

    Mike Wang LOKATION

    151 N Orlando Ave Unit 226, Winter Park, FL 32789
  • /17

    $1,300 - $1,855 per month

    La Aloma

    1 - 3 Beds

    3040 Aloma Ave, Winter Park, FL 32792

    La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

    3040 Aloma Ave, Winter Park, FL 32792
  • /33

    $1,250 per month

    • 1 Bed
    • 1 Bath
    • 749 Sq Ft
    • Condo for Rent

    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

    Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

    SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
  • /35

    $991 - $1,737 per month

    Carlton Arms of Winter Park

    Studio - 3 Beds

    300 Jamestown Dr, Winter Park, FL 32792

    *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

    300 Jamestown Dr, Winter Park, FL 32792
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    $8,500 per month

    • 4 Beds
    • 5 Baths
    • 3,478 Sq Ft
    • House for Rent

    1350 Lyndale Blvd, Winter Park, FL 32789

    Gorgeous, Custom & recently renovated! This home features 4 bedrooms, 3 full baths & 2 half baths. Spacious, light & bright with 10’ ceilings, Brazilian cherry floors, and a gourmet kitchen. The kitchen is a chef's dream and perfect for entertaining. It boasts natural wood cabinets, large center island, dual fuel six-burner range, wine fridge and a built-in refrigerator. It overlooks a casual

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1350 Lyndale Blvd, Winter Park, FL 32789
  • /27

    $1,355 - $2,131 per month

    Westmount at Winter Park

    Studio - 3 Beds

    1701 Lee Rd, Winter Park, FL 32789

    Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

    1701 Lee Rd, Winter Park, FL 32789
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    $4,650 per month

    • 2 Beds
    • 2 Baths
    • 1,143 Sq Ft
    • Condo for Rent

    104 S Interlachen Ave Unit 114, Winter Park, FL 32789

    Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct pool + garden access. From the main hallway, you enter into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    104 S Interlachen Ave Unit 114, Winter Park, FL 32789
  • /30

    $1,230 - $2,780 per month

    Signal Pointe

    1 - 3 Beds

    2500 Howell Branch Rd, Winter Park, FL 32792

    Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

    2500 Howell Branch Rd, Winter Park, FL 32792
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    $3,400 per month

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Condo for Rent

    690 Osceola Ave Unit 203, Winter Park, FL 32789

    Experience upscale living in this stunning 2-bedroom, 2-bath luxury condo featuring gorgeous raw wood floors in this breathtaking lakefront complex situated on the shores of the Winter Park Chain of Lakes and walking distance to Park Avenue, shopping, museums, restaurants and parks. The open-concept layout offers a seamless flow between the living, dining, and kitchen areas—perfect for both

    Nancy Bhavsar ANNE ROGERS REALTY GROUP INC

    690 Osceola Ave Unit 203, Winter Park, FL 32789
  • /35

    $1,251 - $2,048 per month

    Venue At Winter Park

    1 - 3 Beds

    5 Autumn Breeze Way, Winter Park, FL 32792

    Come home to Venue—a community nestled in the heart of Winter Park. Venue is designed to make your living experience better than it has ever been before.When it comes to finding the perfect floor plan for your lifestyle, we have you covered. Choose from our newly renovated 1, 2, and 3-bedroom residences offering refined interior finishes and premier features that are sure to fit all of your

    5 Autumn Breeze Way, Winter Park, FL 32792
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    $1,850 per month

    • 2 Beds
    • 1.5 Baths
    • 1,219 Sq Ft
    • Condo for Rent

    200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792

    Experience the best of Winter Park living in this highly sought-after 2-bedroom, 1.5-bathroom 2-story condo located in the Four Seasons community! This beautiful unit features modern light fixtures, stainless steel appliances, and upgraded flooring throughout. Enjoy the convenience of an included washer and dryer. Unwind on your private, fenced porch, perfect for entertaining. Four Seasons offers

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792
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    $1,236 - $2,425 per month

    Village Park Senior

    1 - 3 Beds

    550 W Denning Dr, Winter Park, FL 32789

    WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

    550 W Denning Dr, Winter Park, FL 32789
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    $1,350 per month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Condo for Rent

    3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792

    Great location in Winter Park! This 2-bedroom, 2-bath apartment offers comfortable living with easy access to everything you need. Open Parking in front and located close to Full Sail University, UCF, Valencia College, and major roads like University Blvd and SR-436 (Semoran Blvd). Enjoy being just minutes from shopping centers, grocery stores, coffee shops, and restaurants, including Publix,

    Julio Lopez JCL REALTY INC

    3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792
  • /35

    $976 - $1,373 per month

    Golden Oaks

    2 - 3 Beds

    7701 Acorn Woods Cir, Winter Park, FL 32792

    Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

    7701 Acorn Woods Cir, Winter Park, FL 32792
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    $1,750 per month

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Townhouse for Rent

    7412 Woodburn Ct Unit 23, Winter Park, FL 32792

    Great townhouse in Winter Park. Winter Park Schoolls. Close to everything, shopping, Costco, restaurants, Valencia Community College East Campus and The University of Central Florida. Close to Siemens and Lockheed Martin. Easy access to main Arteries 408 to all others. The townhouse has been professionally painted in 2019 and new cabinets doors were placed in the kitchen in 2020. New disposal and

    Dyna Stephens POWERHOUSE BROKERS INT'L

    7412 Woodburn Ct Unit 23, Winter Park, FL 32792
  • /35

    $1,455 - $2,620 per month

    Stonecastle Apartment Homes

    1 - 3 Beds

    2015 New Stonecastle Terrace, Winter Park, FL 32792

    Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

    2015 New Stonecastle Terrace, Winter Park, FL 32792
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    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft
    • Townhouse for Rent

    2349 Inagua Way, Winter Park, FL 32792

    Well maintained townhome in Winter Park. This home features updated bathrooms, ceramic tile, dining area and kitchen. The atrium has been enclosed making an excellent computer area. All major systems are routinely serviced. This home also has private backyard that is fully fenced. The community neighborhood features 2 large pools and tennis court. Convenient to major shopping center, fitness

    Laura Forty-Garcia RE/MAX CENTRAL REALTY

    2349 Inagua Way, Winter Park, FL 32792
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    $1,400 per month

    • 2 Beds
    • 1 Bath
    • 851 Sq Ft
    • Condo for Rent

    2500 Lee Rd Unit 212, Winter Park, FL 32789

    Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

    2500 Lee Rd Unit 212, Winter Park, FL 32789
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    $1,995 per month

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft
    • Townhouse for Rent

    7473 Belle River Ct Unit 16, Winter Park, FL 32792

    OWNER OFFERING ONE MONTH RENT CREDIT!!Spacious 3 Bed / 2.5 Bath Townhome-Style Condo in Hidden Oaks, Winter Park Welcome to this beautiful 3-bedroom, 2.5-bath townhome-style condo featuring modern finishes and a serene setting. Enjoy cooking in the kitchen with elegant granite countertops, durable tile flooring downstairs, and stylish luxury vinyl plank flooring upstairs. Step outside to your

    Michael Barr PREMIUM PROPERTIES R.E SERVICE

    7473 Belle River Ct Unit 16, Winter Park, FL 32792
  • /25

    $1,233 - $3,006 per month

    ARIUM Winter Park

    1 - 2 Beds

    3250 Bishop Park Dr, Winter Park, FL 32792

    Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

    3250 Bishop Park Dr, Winter Park, FL 32792
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    $1,795 per month

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Townhouse for Rent

    7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792

    This rental townhouse-style condo in the Hidden Oaks community of Winter Park offers both comfort and convenience. It features 2 bedrooms and 2.5 bathrooms, with an inviting open-concept living and dining area on the main floor. Enjoy the convenience of a guest half bath and a fully equipped kitchen with updated appliances, a breakfast nook or flexible space, and an indoor laundry room with a

    Kerry Jeffcoat-Squeteri COMPASS FLORIDA LLC

    7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792
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    $3,275 per month

    • 3 Beds
    • 1.5 Baths
    • 1,058 Sq Ft
    • House for Rent

    304 Granada Dr, Winter Park, FL 32789

    Property Id: 2306077Welcome to our renovated Winter Park home! This modern one-story property features 3 bedrooms plus a Loft. Enjoy the large backyard with an extra-large pool , furnished Gazebo and outdoor shower. Great Neighborhood with amazing schools. This home has an EV charger energy efficient appliances, security alarm and security cameras.To many feature's and amenities to

    304 Granada Dr, Winter Park, FL 32789
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    $15,500 per month

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

    1860 Via Contessa, Winter Park, FL 32789

    Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Viasneighborhood,offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcomingatmosphere.Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

    Sylvester Harding SIERRA REALTY GROUP LLC

    1860 Via Contessa, Winter Park, FL 32789
  • /20

    $4,150 per month

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft
    • House for Rent

    1470 Lone Feather Trail, Winter Park, FL 32792

    Welcome to this inviting rental opportunity in the charming district of Winter Park, FL. Nestled in a vibrant area, this property offers a delightful experience for those looking to enjoy a serene lifestyle while still being close to modern conveniences.Key property features include spacious bedrooms and well-appointed bathrooms, all designed with comfort in mind. With ample square

    1470 Lone Feather Trail, Winter Park, FL 32792
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    $8,900 per month

    • 4 Beds
    • 3.5 Baths
    • 3,341 Sq Ft
    • House for Rent

    1530 Via Tuscany, Winter Park, FL 32789

    Newly Remodeled Pool home located on premier street in Winter Park. This 4 bedroom home has just been totally updated with very tasteful upgrades. Notable items include: new paint in and out, new flooring in foyer, kitchen, baths. All baths remodeled, new light fixtures, new pavers on rear patio and pool, new landscaping package. The kitchen features new stone counters and backsplash. Also there

    Dan Haber CORCORAN PREMIER REALTY

    1530 Via Tuscany, Winter Park, FL 32789
  • /9

    $1,900 per month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • Townhouse for Rent

    652 Grenadine Ct, Winter Park, FL 32792

    Newly remodeled, large, well-kept 2 bed, 2 full bath located in Winter Park, within walking distance to Full Sail and minutes from UCF, Valencia, Winter Park Hospital and many other employers. This beautiful, single story townhome is in a quiet, family-friendly neighborhood. A large kitchen and dining area are great for entertaining. This unit fronts a greenspace affording you privacy and a

    652 Grenadine Ct, Winter Park, FL 32792
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    $1,100 per month

    • 1 Bath
    • 546 Sq Ft
    • Condo for Rent

    7417 Daniel Webster Dr Unit 3, Winter Park, FL 32792

    Cozy condo in The Colonies Community. This unit is Ground floor 1 bed 1bath with a community Pool. Ceramic Tile throughout the unit, stainless steal appliances, washer and dryer hookup with a porch area. Conveniently located close to supermarkets, shopping, Orlando airport and much more. You don't want to miss this opportunity. Contact us now!

    Georgina Pinango ROMAN'S PRO REALTY LLC

    7417 Daniel Webster Dr Unit 3, Winter Park, FL 32792
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    $1,000 - $1,825 per month

    District On Baldwin Park

    Studio - 3 Beds

    5590 Baldwin Park St, Orlando, FL 32807

    Join us at District on Baldwin Park in Orlando, where you'll revel in luxurious apartment living and resort-style amenities minutes from shopping, entertainment, restaurants and recreation. Lounge by one of our three sparkling pools, sip a cup of coffee and surf the net in our Internet cafe?? or chat with neighbors over cards in our clubhouse. At District on Baldwin Park, you get the resort

    5590 Baldwin Park St, Orlando, FL 32807
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    $1,700 per month

    • 2 Beds
    • 2 Baths
    • 1,066 Sq Ft
    • Condo for Rent

    3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792

    Great Furnished unit . First flour . Two bedrooms' and two bathroom in great quite safe community. 1 miles from SAM Wearhouse at Golden Road.It is new pint and include washer and dryer. Its clean and ready to move in.It is option to Buy also , Contact the owner for details

    Amin Abraham FLORIDA REALTY INVESTMENTS

    3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792
  • /9

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Townhouse for Rent

    2963 Upper Park Rd, Orlando, FL 32814

    Available for rent on 12-15-2025. Experience upscale living in this renovated Baldwin Park townhome. This 1,800 sq/ft townhome is minutes away from Blue Jacket Park and centrally located in the heart of Baldwin Park. This impressive townhome delivers both style and functionality in one of Orlando's most desirable neighborhoods. The well-appointed kitchen boasts warm wood cabinets, granite

    2963 Upper Park Rd, Orlando, FL 32814
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    $2,599 per month

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Condo for Rent

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792

    FURNISHED CORPORATE/EXECUTIVE RENTAL "THE FLORENCE" ,TOWNHOUSE COMMUNITY BOAST 2 BED/2.5 BATH EXECUTIVE CONDO IN THE HIDDEN OAKS COMMUNITY, WINTER PARK FLORIDA. THIS ELEGANT HOME FEATURES 1031 SQ. FT. OF LIVING SPACE, AND COMMUNITY POOL. 32'' AND 90" CABINETS IN THE SCANDINAVIAN DESIGNED KITCHEN. PORCELAIN TILE FLOORS IN THE KITCHEN AND BATHROOMS. FULLY EQUIPPED LAUNDRY ROOM FOR YOUR CONVENIENTLY

    Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792
  • /30

    $1,550 per month

    • 2 Beds
    • 1.5 Baths
    • 1,085 Sq Ft
    • Condo for Rent

    316 Scottsdale Square Unit 316, Winter Park, FL 32792

    Welcome to 316 Scottsdale Square, a delightful 2-bedroom, 1 and half bathroom condo located in desirable Winter Park. This home features a spacious open floor plan with natural light, ideal for comfortable living. The kitchen includes modern appliances and overlooks the cozy living area, perfect for entertaining. The utility room is equipped with a washer and dryer, plus extra storage space for

    Tyann Huynh JADE KEY REALTY LLC

    316 Scottsdale Square Unit 316, Winter Park, FL 32792

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