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Winter Park, FL Homes for Rent with Pool

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    $1,150 - $2,848 per month

    Sovereignty at Winter Park Apartments

    1 - 2 Beds

    7745 Brandywood Cir, Winter Park, FL 32792

    We offer 1 and 2 bedroom apartment homes with fully equipped kitchens, garden tubs, vaulted ceilings, ornamental chair rails, and so much more. Our community has a designer clubhouse, state-of-the-art fitness center, a sparkling pool, planned social activities, a high-speed internet business center, and 24 hour emergency maintenance. Winter Park location convenient to Full Sail, UCF, Valencia,

    7745 Brandywood Cir, Winter Park, FL 32792
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    $2,375 per month

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Townhouse for Rent

    2891 Clever Ln, Winter Park, FL 32792

    Welcome home to 2891 Clever Lane, a three bedroom, two and a half bath town home with a one car garage! The kitchen overlooks the main living area and features a full suite of stainless steel appliances including the refrigerator, range, over the range microwave and dishwasher as well as plenty of cabinetry and counter top space. The half bath is located on the first floor, easily accessible for

    Justin Recca INNOVATIVE REALTY, LLC

    2891 Clever Ln, Winter Park, FL 32792
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    $1,399 - $2,751 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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    $2,400 per month

    • 2 Beds
    • 2.5 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792

    Welcome to 2340 Sun Valley Circle, Winter Park, FL 32792, a stylish 2-bedroom, 2-bath condo featuring a bonus loft that’s perfect for a office or guest space. Step into an updated layout boasting vaulted ceilings, modern luxury flooring, a remodeled kitchen, and a sleek, refreshed bathroom that feels both contemporary and timeless. In-unit laundry, two dedicated parking spaces, and smart,

    Melissa Johnson EXP REALTY LLC

    2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792
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    $1,188 - $1,545 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
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    $6,995 per month

    • 4 Beds
    • 5 Baths
    • 3,948 Sq Ft
    • House for Rent

    1205 Mayfield Ave, Winter Park, FL 32789

    Great rental opportunity in Winter Park, FL! This two-story residence is located in the TEMPLE HEIGHTS neighborhood. This large well maintained family home comes with 5 bedrooms and 4 baths in the main home with over 3,900 sqft. The home also features a separate large pool home or in-law suite. The Pool home / In-Law Suite comes with its own bathroom and kitchenette. The home has wood / vinyl

    Mo Jabr RE/MAX 200 REALTY

    1205 Mayfield Ave, Winter Park, FL 32789
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    $1,249 - $2,212 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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    $2,000 per month

    • 3 Beds
    • 3.5 Baths
    • 1,413 Sq Ft
    • Townhouse for Rent

    235 Sandlewood Trail Unit 5, Winter Park, FL 32789

    WINTER PARK: Sandlewood Creek Community - AVAILABLE NOW!! Welcome home to this great 3 bedroom, 3.5 bath, 3 story townhome in Winter Park. The kitchen is open, light and bright with all appliances, a breakfast bar and is open to the living room/dining area. The living room features a fireplace and sliding glass doors that open out onto the screened porch. Downstairs you will also find the half

    Kelly Carr CFRP REALTY LLC

    235 Sandlewood Trail Unit 5, Winter Park, FL 32789
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    $1,166 - $2,139 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
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    $2,250 per month

    • 1 Bed
    • 1.5 Baths
    • 915 Sq Ft
    • Condo for Rent

    690 Osceola Ave Unit 407, Winter Park, FL 32789

    Welcome to breathtaking waterfront living at Lake Virginia Condo community in Winter Park. Gorgeous water views from every room in this fourth floor, 915 sqft, 1-bedroom, 1.5-bathroom end unit overlooking Lake Virginia and the Lake Virginia-Osceola Canal. Step inside and immediately you’re greeted by Lake Virginia through the large floor to ceiling sliders. The roomy bedroom and bathroom provide

    Delaney Heidenescher CREEGAN GROUP

    690 Osceola Ave Unit 407, Winter Park, FL 32789
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    $1,700 - $2,691 per month

    Rosalia Winter Park 55+ Active Adult Commu...

    1 - 2 Beds

    3045 Aloma Ave, Winter Park, FL 32792

    Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar—all with an attentive team at your

    3045 Aloma Ave, Winter Park, FL 32792
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    $2,000 per month

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

    640 N Park Ave Unit 4, Winter Park, FL 32789

    MORE PICTURES TO COME! Welcome to the heart of Winter Park! This beautiful first floor condo is located in one of the town’s most iconic buildings, Park Aire. Nestled between the famous Winter Park Golf Course and downtown area where shopping and dining are a must! Other close by attractions include, the Morse Museum, Central Park, Hannibal Square and Scenic Boat Tours. This updated condo

    Flory Clark UNITED REAL ESTATE PREFERRED

    640 N Park Ave Unit 4, Winter Park, FL 32789
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    $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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    $3,500 per month

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Townhouse for Rent

    2774 Bright Bird Ln, Winter Park, FL 32792

    Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same time! Schedule a

    Ana Sampaio Pereira Willeman FLORIDA CONNEXION PROPERTIES

    2774 Bright Bird Ln, Winter Park, FL 32792
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    $1,499 - $1,899 per month

    The Vista at Winter Park

    2 Beds

    4704 Lucier Ct, Winter Park, FL 32792

    Move in special- 2nd Full Month Free!*Restricted units only*Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will

    4704 Lucier Ct, Winter Park, FL 32792
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    $2,295 per month

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft
    • House for Rent

    731 Bongart Rd, Winter Park, FL 32792

    This 3 bedroom, 2 bath pool home with 2 car garage includes: Living Room, Dining Room, Family Room, Carpet & Vinyl on a nice corner lot! Great Location! Pool service is included with monthly rent!. *Bonus Amenity Included* - All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit

    Mo Jabr RE/MAX 200 REALTY

    731 Bongart Rd, Winter Park, FL 32792
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    $1,250 - $1,800 per month

    Park Apartments

    1 - 3 Beds

    7528 Park Promenade Dr, Winter Park, FL 32792

    WELCOME TO THE PARK APARTMENTS! 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 swimming pools, work

    7528 Park Promenade Dr, Winter Park, FL 32792
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    $1,705 per month

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

    851 Miles Ave Unit 8, Winter Park, FL 32789

    UNBELIEVABLE PRICE DROP! This gorgeous 2 bedroom 1 bathroom condo is ready to go, and priced for you! This unit is a second floor corner condo, located in the serene and peaceful Aragon Condo community. Centrally located in Winter Park, only 5 minutes to downtown, Rollins College, Orlando Health and so much more. Featuring an open floor plan, stainless steel appliances, wood flooring throughout,

    Michael Mones LPT REALTY, LLC

    851 Miles Ave Unit 8, Winter Park, FL 32789
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    $1,489 - $1,779 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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    $1,840 per month

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Condo for Rent

    7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792

    Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all within reach of central Florida's vibrant offerings. Strategically positioned minutes from the

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792
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    $1,245 - $2,650 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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    $1,550 per month

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

    1695 Lee Rd Unit D212, Winter Park, FL 32789

    This great second floor two-bedrooms 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

    giuseppina moriconi GM SUNSHINE REALTY LLC

    1695 Lee Rd Unit D212, Winter Park, FL 32789
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    $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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    $1,050 per month

    • 1 Bath
    • 549 Sq Ft
    • Condo for Rent

    3071 George Mason Ave Unit 5, Winter Park, FL 32792

    Community offers a swimming pool and playground. Assigned and guest parking available. HOA maintains exterior and common areas Location, Location, Location! Live just minutes from everything, Universities, Winter Park, top schools, downtown Orlando, shopping plazas, hospitals, and more. Easy access to SR 436, 408, and I-4 puts all of Central Florida at your fingertips. This move-in-ready condo

    Katherine Bordelon CASTLE & COTTAGE REALTY LLC

    3071 George Mason Ave Unit 5, Winter Park, FL 32792
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    $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
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    $1,599 per month

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

    225 Lewfield Cir, Winter Park, FL 32792

    Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling

    Steve Simpson 407 PROPERTIES

    225 Lewfield Cir, Winter Park, FL 32792
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    $1,236 - $2,599 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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    $2,490 per month

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft
    • House for Rent

    7431 Portside Ct, Winter Park, FL 32792

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    7431 Portside Ct, Winter Park, FL 32792
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    $1,250 - $1,680 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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    $1,697 per month

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

    Unlisted Address

    REDUCED! Winter Park 2 Bedroom Upgraded Townhouse. This unit is tiled throughout with Granite counter tops No carpet to worry about here !! Open Living Dining area with an eat in area in kitchen also~~ Laundry closet in kitchen ~~ Private Patio ~~ 2 Designated parking spaces ~~ Must See!

    Joseph Adkins THE REALTY FACTOR INC

    Unlisted Address
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    $1,201 - $2,977 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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    $5,600 per month

    • 4 Beds
    • 4 Baths
    • 3,654 Sq Ft
    • House for Rent

    960 Georgia Ave, Winter Park, FL 32789

    Quintessential Winter Park Stunner. This well appointed home is situated on a half acre corner lot just two blocks away from Winter Park's shopping and dining district, Park Avenue. Surrounded by majestic oak trees you find this classic 4 bedroom, 4 bath home with 3600sq ft of living space. An abundance of natural light welcomes you in the homes central hub, the Family Room. Anchored by one of

    Alison Ashby CORCORAN PREMIER REALTY

    960 Georgia Ave, Winter Park, FL 32789
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    $1,645 per month

    • 2 Beds
    • 2.5 Baths
    • 1,230 Sq Ft
    • Condo for Rent

    7296 Daniel Webster Dr Unit 1, Winter Park, FL 32792

    Welcome to 7296 Daniel Webster Dr Unit 1, a spacious and well-kept 2-bedroom, 2.5-bath townhome offering 1,230 sq ft of comfortable living in the heart of Winter Park. The main floor features a bright living and dining area with wood-style flooring, a half bath, a dedicated laundry room with washer/dryer hookups, and a beautifully updated kitchen with rich wood cabinetry, granite countertops, and

    7296 Daniel Webster Dr Unit 1, Winter Park, FL 32792
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    $1,399 per month

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

    1000 S Semoran Blvd Unit 703, Winter Park, FL 32792

    Spacious one-bedroom condominium in Golfside Villas! This move in ready first-floor unit includes a large living room, Dining room with patio, open kitchen with New stainless steel appliances, Great location. Minutes from Baldwin Park and Full Sail, Golfside Villas has excellent access via Semoran Boulevard to downtown Winter Park, UCF, downtown Orlando and the Orlando International Airport.

    Gregorio Henriques CENTURY 21 CARIOTI

    1000 S Semoran Blvd Unit 703, Winter Park, FL 32792
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    $1,500 per month

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

    3045 Aaron Burr Ave Unit C, Winter Park, FL 32792

    Property Id: 2093281Condominium for rent unit A ,on the Bottom floor of a 2 story building. Private parking spot requires decal but there's plenty of parking for guests. Gated pool and camera monitored entrances at “The Colonies “ on Goldenrod Rd in south Winter Park . 1 bedroom 1 bath kitchen and living area over 900 square feet. Back door sliding glass door opens to courtyard. This

    3045 Aaron Burr Ave Unit C, Winter Park, FL 32792
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    $1,695 per month

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

    851 Miles Ave Unit 9, Winter Park, FL 32789

    Imagine living in this completely renovated two-bedroom, one-bathroom second-floor condominium unit near downtown Winter Park at Aragon Condos. This intimate, two-building, two-story condominium community comprises just twenty-eight units focused around a central courtyard.Features include: • Recently remodeled kitchen including all cabinetry, countertops, marble tile backsplash,

    Richard Traynor FLORIDA ONE REAL ESTATE LLC

    851 Miles Ave Unit 9, Winter Park, FL 32789
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    $1,110 - $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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    $5,050 per month

    • 4 Beds
    • 3 Baths
    • 2,422 Sq Ft
    • House for Rent

    2627 Verona Trail, Winter Park, FL 32789

    Beautiful 4 bedroom/ 3 bath Pool home for rent in Winter Park Range, D/W, Disposal, Central Heat and A/C.

    Rick Sein REALSOURCE PROPERTY MANGNT LLC

    2627 Verona Trail, Winter Park, FL 32789
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    $2,895 per month

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Townhouse for Rent

    3486 Bougainvillea Dr Unit B, Winter Park, FL 32792

    Location! Location! Location! This exactly what you are looking for, a nice home in a great location. This a great unit featuring a nice kitchen with stainless steel appliances, and an updated flooring with luxury vinyl plank. This unit has an indoor heated swimming pool with an exercise room. This property is located near all of the main central Florida colleges. Come and enjoy with your family

    Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

    3486 Bougainvillea Dr Unit B, Winter Park, FL 32792
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    $1,500 per month

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

    2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792

    Welcome to this beautifully renovated 1-bedroom, 1-bathroom first-floor condo in the highly desirable Parkview Village community. This spacious and well-maintained unit features a modern, updated kitchen and bathroom, a large walk-in closet, and an in-unit washer and dryer for your convenience. The open-concept living and dining area creates a comfortable and functional layout, perfect for

    Julian Quezada INTERINVESTMENTS REALTY, INC.

    2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792

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