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Winter Park, FL Homes for Rent

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  • /22

    $2,800 per month

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • House for Rent

    3326 Young St, Winter Park, FL 32792

    Available to view and rent Sept. 6th. Adorable, Newly Renovated 4 Bedroom, 2 Bathroom home with a large fenced yard. Fresh paint and brand-new vinyl flooring throughout. All new energy-efficient windows and doors. Lots of natural light with brand and new cabinets and quartz countertops in the kitchen along with Stainless Steel Appliances. Split bedroom floor plan. The primary bedroom features a

    Agent Photo

    Shelley Davis

    REMI EMERSON RESIDENTIAL

    (321) 250-5179

    3326 Young St, Winter Park, FL 32792
  • /68

    $8,650 per month

    • 5 Beds
    • 5 Baths
    • 4,953 Sq Ft
    • House for Rent

    2851 Dorell Ave Unit 10, Orlando, FL 32814

    NEWLY LISTED HOME IN BALDWIN PARK-NEWELY PAINTED INTERIOR WITH NEUTRAL PAINT. NEW PHOTOS COMMING SOON. Welcome home to this Gorgeous Courtyard Style floor Plan that boasts a beautiful pond view and just steps from the pool and pavilion at High Park. This 5-bedroom, 5-bath estate home offers a spacious open floorplan and a range of desirable features. As you enter home you will be greeted by a

    Agent Photo

    Bruce Kalin

    JC FLORIDA REALTY LLC

    (321) 384-9558

    2851 Dorell Ave Unit 10, Orlando, FL 32814
  • /85

    $1,627 - $3,599 per month

    Berkshire Winter Park

    Studio - 3 Beds

    1874 Harmon Ave, Winter Park, FL 32789

    Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

    1874 Harmon Ave, Winter Park, FL 32789
  • /8

    $1,750 per month

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

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

    Great rent . First flour . Two bedrooms' and two bathroom in great quite safe community. 3 miles from SAM Wearhouse. Its clean and ready to move in.

    Amin Abraham FLORIDA REALTY INVESTMENTS

    3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792
  • /52

    $1,249 - $2,029 per month

    Serena Winter Park

    1 - 2 Beds

    2890 Red Lion Square, Winter Park, FL 32792

    Serena Winter Park is a newly remodeled apartment community. Our one and two bedroom apartment floor plans feature contemporary upgrades, large windows, spacious walk in closets, open kitchen styles and fantastic storage spaces. Our bungalow flats also offer private entry and patio. Our pet-friendly apartment community includes an all new impeccable 24-hour fitness center and billiards lounge! A

    2890 Red Lion Square, Winter Park, FL 32792
  • /17

    $1,725 per month

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

    851 Miles Ave Unit 21, Winter Park, FL 32789

    Enjoy a quiet but beautiful space at Aragon Condominiums. This first-floor corner unit allows for privacy with only one adjoining neighbor. It is a perfect place to call home with upgrades all around, including granite countertops, washer and dryer in unit, and a community pool just right outside your door. It is conveniently located in Winter Park, where you can enjoy many shops, restaurants,

    Richard Traynor FLORIDA ONE REAL ESTATE LLC

    851 Miles Ave Unit 21, Winter Park, FL 32789
  • /37

    $1,293 - $3,121 per month

    Cranes Landing Apartments

    1 - 3 Beds

    3440 N Goldenrod Rd, Winter Park, FL 32792

    Incredible Move In Specials!Pay No Rent till November 1st!!! Receive a small kitchen appliance if you Look & Lease the same day!!!LIMITED TIME ONLY!!!Open House Saturday 10am - 4pm

    3440 N Goldenrod Rd, Winter Park, FL 32792
  • /16

    $1,345 per month

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Townhouse for Rent

    2183 Crandon Ave Unit 1/2, Winter Park, FL 32789

    This 2 bedroom, 1 bathroom, 2nd floor unit is located in the heart of Winter Park. Enjoy all Downtown Winter Park has, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious living area, a lovely kitchen, a screened patio area, and a shared laundry

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    2183 Crandon Ave Unit 1/2, Winter Park, FL 32789
  • /20

    $1,349 - $2,599 per month

    Sapphire Winter Park

    1 - 3 Beds

    1743 Semoran Cir N, Winter Park, FL 32792

    Sapphire Winter Park offers the ultimate luxury oasis as a sanctuary of good living tucked away on 26-acres of lush landscaping. Located in the city of Winter Park, Florida, select apartments offer brand new washer & dryer, modern white shaker cabinets, quartz countertops, contemporary light & utility fixtures, stainless-steel appliances and vinyl wood floors in main areas with carpet in each

    1743 Semoran Cir N, Winter Park, FL 32792
  • /24

    $1,650 per month

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

    1250 S Denning Dr Unit 233, Winter Park, FL 32789

    Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open

    Samuel Kingsford STOCKWORTH REALTY GROUP

    1250 S Denning Dr Unit 233, Winter Park, FL 32789
  • /103

    $2,156 - $6,454 per month

    Paseo at Winter Park Village

    1 - 3 Beds

    940 W Canton Ave, Winter Park, FL 32789

    Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

    940 W Canton Ave, Winter Park, FL 32789
  • /57

    $3,300 per month

    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft
    • House for Rent

    2128 Sycamore Dr, Winter Park, FL 32789

    MOVE-IN READY! Don’t miss this fantastic opportunity to rent a beautiful 3-bedroom, 2-bathroom home situated on a spacious .23-acre corner lot. This property has undergone a complete upgrade inside and out, making it perfect for those looking for a fresh start. Key Features: • Newer Septic Tank: Ensures peace of mind and efficiency. • 2016 Roof: A reliable roof that adds to the home’s longevity.

    Luis Perez Garcia EXP REALTY LLC

    2128 Sycamore Dr, Winter Park, FL 32789
  • /25

    $1,449 - $1,659 per month

    Indigo Winter Park

    1 Bed

    220 S Semoran Blvd, Winter Park, FL 32792

    Indigo Winter Park is a lavishly landscaped apartment home community. Each of our one bedroom, one bathroom apartments feature laminate flooring, carpeted bedrooms, washers & dryers, walk in closets, screened in patios, maple wood cabinetry, gas stoves and efficient appliances. Our pet-friendly apartment community includes three resort style pools, bbq grilling stations, two double tennis courts,

    220 S Semoran Blvd, Winter Park, FL 32792
  • /26

    $1,325 per month

    • 1 Bed
    • 1 Bath
    • 502 Sq Ft
    • Apartment for Rent

    1950 Killarney Dr Unit 2, Winter Park, FL 32789

    Neat and clean, 2nd floor apartment in the highly desirable Winter Park zip code of 32789. Recent updates include vinyl flooring throughout, refinished bathroom tub, new vanity, newer AC units, newer ceiling fans and redone screened porch. 1-car garage with automatic door opener. Rent includes water and lawn car. Beautiful setting across the street and views of Lake Killarney. Great Winter Park

    Terry Diederich KELLER WILLIAMS REALTY AT THE PARKS

    1950 Killarney Dr Unit 2, Winter Park, FL 32789
  • /43

    $1,255 - $1,898 per month

    Seabrook

    1 - 2 Beds

    3114 Terry Brook Dr, Winter Park, FL 32792

    The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

    3114 Terry Brook Dr, Winter Park, FL 32792
  • /32

    $2,067 per month

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft
    • House for Rent

    1038 Lundy Ct, Winter Park, FL 32792

    CHARMING 3 BEDRM HOME FOR RENT IN WINTER PARK!Property Has Been Professionally Refurbished, Very Clean Property, Move In Ready, 2 Car Garage, Plenty Of Parking, Corner Lot, Screened-In Patio, Fenced-In Yard, Backyard Storage Shed, Huge Master Suite, Ceiling Fans In Many Rooms, Eat-In Kitchen, Upgraded Kitchen, Hardwood Flooring, Tile Flooring, Freshly Painted, Just 20 Minutes To Downtown

    Jay Myers ORLANDO REALTY & PROPERTY MGNT

    1038 Lundy Ct, Winter Park, FL 32792
  • /28

    $1,559 - $1,589 per month

    Elon Winter Park

    1 Bed

    712 Nicolet Ave, Winter Park, FL 32789

    Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

    712 Nicolet Ave, Winter Park, FL 32789
  • /38

    $2,550 per month

    • 3 Beds
    • 3.5 Baths
    • 1,787 Sq Ft
    • Townhouse for Rent

    7613 Aloma Pines Ct, Winter Park, FL 32792

    Beautiful town home in the gated community of Aloma Trails! This 3 bedroom, 2.5 bath, 1,787sqft, two-story town home will be ready for you to move in! The town home features an open floor plan with 18" tiled floors throughout the first floor living area, kitchen and dining room, all bathrooms and the inside utility room. The kitchen features dark walnut 42" cabinetry, granite counter tops, plenty

    Justin Recca INNOVATIVE REALTY, LLC

    7613 Aloma Pines Ct, Winter Park, FL 32792
  • /23

    $1,733 - $5,956 per month

    Juno Winter Park

    Studio - 3 Beds

    1305 Morgan Stanley Ave, Winter Park, FL 32789

    Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

    1305 Morgan Stanley Ave, Winter Park, FL 32789
  • /23

    $1,900 per month

    • 3 Beds
    • 2 Baths
    • 1,165 Sq Ft
    • Condo for Rent

    200 Saint Andrews Blvd Unit 1205, Winter Park, FL 32792

    Discover this highly desirable 3-bedroom, 2-bath condo in the sought-after Four Seasons community of Winter Park! This spacious unit welcomes you with a warm, inviting atmosphere and a layout designed for comfort and functionality. The large dining area flows seamlessly into a generous family room, which opens to your private porch, perfect for relaxing or entertaining.The kitchen is

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    200 Saint Andrews Blvd Unit 1205, Winter Park, FL 32792
  • /110

    $1,300 - $2,075 per month

    Oak Reserve at Winter Park

    1 - 3 Beds

    541 Oak Reserve Ln, Winter Park, FL 32792

    Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

    541 Oak Reserve Ln, Winter Park, FL 32792
  • /14

    $1,600 per month

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

    3060 George Mason Ave Unit 10, Winter Park, FL 32792

    Welcome to 3060 George Mason Avenue, Unit 10C—a cozy and inviting 1-bedroom, 1-bathroom retreat in the heart of beautiful Winter Park,Florida! This charming apartment provides bright and comfortable living space, perfect for those seeking convenience and tranquility. The property is just minutes from Winter Park's vibrant restaurants, boutiques, cultural venues, and picturesque parks. Whether

    Tiago Ferreira MANAGER PROP

    3060 George Mason Ave Unit 10, Winter Park, FL 32792
  • /43

    $1,875 - $3,243 per month

    Bainbridge Winter Park

    1 - 3 Beds

    1400 Morgan Stanley Ave, Winter Park, FL 32789

    Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

    1400 Morgan Stanley Ave, Winter Park, FL 32789
  • /38

    $2,100 per month

    • 2 Beds
    • 1 Bath
    • 1,027 Sq Ft
    • House for Rent

    1450 Cavendish Rd, Winter Park, FL 32789

    WINTER PARK - Located in the highly desirable ORWIN MANOR neighborhood, this charming one-story 2BR/1BA single-family home offers 1,027 sq.ft. of living space, thoughtfully blending its original character with modern updates. The living room provides a comfortable and cozy gathering space, while the adjoining dinette is filled with natural light, creating an inviting setting for casual meals or

    Margaret Steiner KELLER WILLIAMS REALTY AT THE PARKS

    1450 Cavendish Rd, Winter Park, FL 32789
  • /74

    $1,500 - $5,091 per month

    Vintage Winter Park Apartments

    1 - 3 Beds

    7490 Dwell Well Way, Winter Park, FL 32792

    Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

    7490 Dwell Well Way, Winter Park, FL 32792
  • /37

    $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
  • /40

    $1,395 - $2,647 per month

    The Taylor at Winter Park

    Studio - 3 Beds

    2000 Village Ln, Winter Park, FL 32792

    5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

    2000 Village Ln, Winter Park, FL 32792
  • /48

    $2,850 per month

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • House for Rent

    2682 Tierra Cir, Winter Park, FL 32792

    Charming & Recently Updated 4-Bed / 2-Bath Rental in Winter Park: Welcome to 2682 Tierra Circle, a tasteful and modernized rental situated in the well-known area of Winter Park. This single-story home offers approximately 1,874 square feet of living space, showcasing fresh interior, brand-new flooring, and an intelligently laid-out split floor plan that enhances both privacy and versatility. The

    Bobby Keen KEEN REALTY GROUP, INC.

    2682 Tierra Cir, Winter Park, FL 32792
  • /50

    $1,497 - $2,018 per month

    Calibre Bend Apartments

    1 - 2 Beds

    3924 Calibre Bend Ln, Winter Park, FL 32792

    Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

    3924 Calibre Bend Ln, Winter Park, FL 32792
  • /18

    $1,680 per month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Apartment for Rent

    2923 Antique Oaks Cir Unit GE, Winter Park, FL 32792

    Discover your new home! This beautiful 2-bedroom, 2-bathroom apartment offers the perfect balance between comfort and style. Ideal for families, couples, or professionals looking for a modern and functional space.?? Key Features:2 spacious bedrooms with closets2 modern, well-ventilated full bathroomsOpen-concept living and dining roomKitchen equipped with cabinets and a

    Michell Carrasquero GLOBALWIDE REALTY LLC

    2923 Antique Oaks Cir Unit GE, Winter Park, FL 32792
  • /26

    $1,295 - $1,965 per month

    Central Place At Winter Park

    1 - 3 Beds

    7000 University Blvd, Winter Park, FL 32792

    Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

    7000 University Blvd, Winter Park, FL 32792
  • /20

    $3,400 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Townhouse for Rent

    775 Maryland Ave, Winter Park, FL 32789

    Newly Remodeled!! This 2 bed 1 bath duplex in the heart of Winter Park is just a few short blocks from Rollins College and Park Avenue. Offering a brand new kitchen with stainless steel appliances and quartz counter top, a full size washer and dryer and new flooring throughout. There is one bed and bath downstairs and a spacious 2nd bedroom upstairs making the space very versatile for roommates

    Alexis Magargee ROAM FLORIDA REALTY LLC

    775 Maryland Ave, Winter Park, FL 32789
  • /36

    $1,366 - $2,854 per month

    Summerlin at Winter Park Apartments

    1 - 3 Beds

    3207 Rosebud Ln, Winter Park, FL 32792

    These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

    3207 Rosebud Ln, Winter Park, FL 32792
  • /23

    $1,695 per month

    • 2 Beds
    • 2 Baths
    • 987 Sq Ft
    • House for Rent

    200 Saint Andrews Blvd Unit 3502, Winter Park, FL 32792

    This lovely 2 bedroom, 2 bathroom ground floor unit in the Four Seasons community is located in the heart of Winter Park. Enjoy all Downtown Winter Park has, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include vinyl plank flooring throughout, spacious

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    200 Saint Andrews Blvd Unit 3502, Winter Park, FL 32792
  • /44

    $1,257 - $3,626 per month

    Liv at Winter Park Apartment Homes

    Studio - 3 Beds

    4755 N Goldenrod Rd, Winter Park, FL 32792

    Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

    4755 N Goldenrod Rd, Winter Park, FL 32792
  • /97

    $11,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,104 Sq Ft
    • House for Rent

    1661 Hillcrest Ave, Winter Park, FL 32789

    Owner open to 9+ month lease period. Luxurious Winter Park Retreat with Stunning Features! Welcome to 1661 Hillcrest Avenue, a masterpiece of coastal design nestled in the heart of the highly sought after Winter Park. This exceptional property presents an exclusive opportunity to rent a home crafted by the Parade of Home Winner, Lazarus Development Group. This elegant home boasts 4 bedrooms, 3.5

    Domenique Lombardo ROYALTY R E BOUTIQUE INC

    1661 Hillcrest Ave, Winter Park, FL 32789
  • /50

    $1,670 - $3,383 per month

    Seven41 Winter Park

    Studio - 2 Beds

    741 Clay St, Winter Park, FL 32789

    Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

    741 Clay St, Winter Park, FL 32789
  • /25

    $1,750 per month

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

    1250 S Denning Dr Unit 232, Winter Park, FL 32789

    1 Gig Internet included in rent. Less than 1 mile from Rollins College and Park Ave in the highly desirable 32789 Winter Park zip code. This 2-Bedroom, 2-Bath hidden gem backs up to Mead Botanical Gardens. Also, less than 5 miles from from Downtown Orlando. This light-filled home features a brand-new kitchen with granite countertops & appliances, fresh paint, updated bathrooms, new carpet,

    Robert Isaac Rodriguez RE/MAX DOWNTOWN

    1250 S Denning Dr Unit 232, Winter Park, FL 32789
  • /39

    $903 - $1,535 per month

    San Jose Apartments

    1 - 3 Beds

    2353 Winter Woods Blvd, Winter Park, FL 32792

    Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

    2353 Winter Woods Blvd, Winter Park, FL 32792
  • /16

    $3,995 per month

    • 3 Beds
    • 3 Baths
    • 1,750 Sq Ft
    • House for Rent

    1641 Chestnut Ave, Winter Park, FL 32789

    Welcome to your new home nestled along Winter Park’s coveted tree-lined Chestnut Avenue. This beautiful 3 bedroom, 3 bathroom home blends classic charm with modern updates and is perfectly situated near Park Avenue, Phelps Park, the YMCA, Winter Park golf course, and Lakemont Elementary School. Upon entering, you’ll be greeted by gleaming hardwood floors flowing through an inviting, light-filled

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    1641 Chestnut Ave, Winter Park, FL 32789

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Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Frequently Asked Questions

What are the most popular neighborhoods in Winter Park, FL for renters?
The most popular neighborhoods in Winter Park, FL for renters are Baldwin Park, Lake Howell, College Park, Audubon Park and Colonialtown North.
What are the most popular zip codes in Winter Park, FL for renters?
The most popular zip codes in Winter Park, FL for renters include 32789, 32751, 32792, 32803 and 32814.
How to Rent a Home