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Winter Park, FL Homes for Rent

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  • /18

    $1,750 Per Month

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

    Unlisted Address

    Gorgeous FULLY FURNISHED 1 Bedroom/1 Bath apartment with private entrance, in Winter Park. This attached apartment has been thoughtfully renovated with beautiful Luxury European Design. This apartment features a private courtyard and private entrance. Upon entering you will be greeted by a spacious living room fitted with a sofa chase, 55” Flat Screen Television, a small dining table/desk, modern

    Agent Photo

    Nicholas Wild

    GATE PROPERTIES & MANAGEMENT INC

    Unlisted Address
  • /2

    Call for Price

    • 3 Beds

    770 Annesley Place, Winter Park, FL 32789

    The Oxford at Winter Park

    770 Annesley Place, Winter Park, FL 32789
  • /26

    $1,350 Per Month

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

    2500 Lee Rd Unit 244, Winter Park, FL 32789

    Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

    Agent Photo

    Rustina Gibson

    RE/MAX VANTAGE

    2500 Lee Rd Unit 244, Winter Park, FL 32789
  • /81

    Starting at $1,851

    Total Monthly Price

    • 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.

    Vintage Winter Park Apartments

    7490 Dwell Well Way, Winter Park, FL 32792
  • /36

    $2,750 Per Month

    • 3 Beds
    • 2 Baths
    • 1,302 Sq Ft
    • House for Rent

    1627 Orange Ave, Winter Park, FL 32789

    Charming 3-bedroom, 2-bath bungalow located in the highly desirable, well-established Orwin Manor neighborhood in the City of Winter Park. Ideally situated between Downtown Orlando and Park Avenue, this home is just minutes from AdventHealth Hospital, Rollins College, and offers convenient access to I-4. The spacious retreat is located just across the hall from a beautifully renovated bathroom.

    Agent Photo

    Peter Dang

    ALLIANCE RENTAL HOMES

    1627 Orange Ave, Winter Park, FL 32789
  • /53

    Starting at $1,412 Per Month

    • 1 - 3 Beds

    3440 N Goldenrod Rd, Winter Park, FL 32792

    Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

    Cranes Landing Apartments

    3440 N Goldenrod Rd, Winter Park, FL 32792
  • /26

    Starting at $1,215 Per Month

    • 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

    Central Place At Winter Park

    7000 University Blvd, Winter Park, FL 32792
  • /131

    Starting at $1,425 Per Month

    • 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,

    Oak Reserve at Winter Park

    541 Oak Reserve Ln, Winter Park, FL 32792
  • /75

    Starting at $1,692 Per Month

    • 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.

    Bainbridge Winter Park

    1400 Morgan Stanley Ave, Winter Park, FL 32789
  • /28

    Starting at $1,597 Per Month

    • 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

    Elon Winter Park

    712 Nicolet Ave, Winter Park, FL 32789
  • /43

    Starting at $1,291 Per Month

    • 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

    Seabrook

    3114 Terry Brook Dr, Winter Park, FL 32792
  • /50

    Starting at $1,115 Per Month

    • 1 - 3 Beds

    349 Scottsdale Square, Winter Park, FL 32792

    This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

    Winter Park Woods Apartments

    349 Scottsdale Square, Winter Park, FL 32792
  • /17

    Starting at $1,299 Per Month

    • 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

    Sapphire Winter Park

    1743 Semoran Cir N, Winter Park, FL 32792
  • /35

    Starting at $1,329 Per Month

    • 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

    Summerlin at Winter Park Apartments

    3207 Rosebud Ln, Winter Park, FL 32792
  • /39

    Starting at $910 Per Month

    • 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.

    San Jose Apartments

    2353 Winter Woods Blvd, Winter Park, FL 32792
  • /50

    Starting at $1,695 Per Month

    • 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.

    Seven41 Winter Park

    741 Clay St, Winter Park, FL 32789
  • /50

    Starting at $1,614 Per Month

    • 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

    Calibre Bend Apartments

    3924 Calibre Bend Ln, Winter Park, FL 32792
  • /44

    Starting at $1,098 Per Month

    • 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

    Liv at Winter Park Apartment Homes

    4755 N Goldenrod Rd, Winter Park, FL 32792
  • /50

    Starting at $1,804 Per Month

    • 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,

    Juno Winter Park

    1305 Morgan Stanley Ave, Winter Park, FL 32789
  • /50

    Starting at $2,193 Per Month

    • 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

    Paseo at Winter Park Village

    940 W Canton Ave, Winter Park, FL 32789
  • /50

    Starting at $1,000 Per Month

    • 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

    District On Baldwin Park

    5590 Baldwin Park St, Orlando, FL 32807
  • /18

    Starting at $1,330 Per Month

    • Studio - 2 Beds

    311 N Knowles Ave, Winter Park, FL 32789

    Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

    Park East - Park Knowles Apartments

    311 N Knowles Ave, Winter Park, FL 32789
  • /36

    Starting at $1,148 Per Month

    • 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

    The Taylor at Winter Park

    2000 Village Ln, Winter Park, FL 32792
  • /30

    Starting at $2,097

    Total Monthly Price

    • 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

    Rosalia Winter Park 55+ Active Adult Community

    3045 Aloma Ave, Winter Park, FL 32792
  • /27

    Starting at $1,355

    Total Monthly Price

    • Studio - 3 Beds

    1701 Lee Rd, Winter Park, FL 32789

    There's 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

    Westmount at Winter Park

    1701 Lee Rd, Winter Park, FL 32789
  • /30

    Starting at $1,235 Per Month

    • 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

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
  • /35

    Starting at $925 Per Month

    • 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,

    Golden Oaks

    7701 Acorn Woods Cir, Winter Park, FL 32792
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    Starting at $1,441 Per Month

    • 1 - 2 Beds

    3935 Sutton Place Blvd, Winter Park, FL 32792

    Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

    Alvista Winter Park

    3935 Sutton Place Blvd, Winter Park, FL 32792
  • /35

    Starting at $1,592

    Total Monthly Price

    • 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

    Stonecastle Apartment Homes

    2015 New Stonecastle Terrace, Winter Park, FL 32792
  • /16

    Starting at $1,599 Per Month

    • 2 Beds

    4704 Lucier Ct, Winter Park, FL 32792

    *Restricted units only*App and Admin special for only $175!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

    The Vista at Winter Park

    4704 Lucier Ct, Winter Park, FL 32792
  • /35

    Starting at $1,613 Per Month

    • 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

    Berkshire Winter Park

    1874 Harmon Ave, Winter Park, FL 32789
  • /11

    Starting at $1,317

    Total Monthly Price

    • 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

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
  • /20

    $2,149 Per Month

    • 3 Beds
    • 2 Baths
    • 1,921 Sq Ft
    • House for Rent

    1546 Peruvian Ln, Winter Park, FL 32792

    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 $2293.90. That covers your base rent, $2149.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1546 Peruvian Ln, Winter Park, FL 32792
  • /29

    Starting at $1,482

    Total Monthly Price

    • 1 - 3 Beds

    3733 N Goldenrod Rd, Winter Park, FL 32792

    Welcome home to Atlas at Winter Park!

    Atlas at Winter Park

    3733 N Goldenrod Rd, Winter Park, FL 32792
  • /35

    Starting at $1,995 Per Month

    • 1 Bed

    520 N Orlando Ave, Winter Park, FL 32789

    Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

    The Lofts of Winter Park Village

    520 N Orlando Ave, Winter Park, FL 32789
  • /31

    Starting at $1,424 Per Month

    • 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

    POSTE Winter Park

    800 Semoran Park Dr, Winter Park, FL 32792
  • /35

    Starting at $1,475 Per Month

    • Studio - 3 Beds

    433 W New England Ave, Winter Park, FL 32789

    We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

    Hannibal Square

    433 W New England Ave, Winter Park, FL 32789
  • /35

    Starting at $1,064 Per Month

    • Studio - 3 Beds

    300 Jamestown Dr, Winter Park, FL 32792

    Carlton Arms of Winter Park is a well established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff. We offer an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

    Carlton Arms of Winter Park

    300 Jamestown Dr, Winter Park, FL 32792
  • /20

    Starting at $1,343 Per Month

    • 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

    ARIUM Winter Park

    3250 Bishop Park Dr, Winter Park, FL 32792
  • /20

    $2,625 Per Month

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • House for Rent

    4040 Waterview Loop, Winter Park, FL 32792

    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 $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    4040 Waterview Loop, Winter Park, FL 32792

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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

How much does it cost to rent a home in Winter Park, FL?
The median rent for a home in Winter Park, FL is $2,149 per month, though prices vary by neighborhood, size, and property type. As of August 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Winter Park, FL?
To comfortably afford the median rent in Winter Park, FL, a household needs to earn roughly $85,960 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,149 per month in Winter Park, FL, renters typically need to show $6,447 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Winter Park, FL?
In Winter Park, FL, the price-to-rent ratio is 19.0, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Winter Park, FL are best for renting a home?
The best neighborhood for renting in Winter Park, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include Baldwin Park, Lake Howell, Audubon Park, Colonialtown North and Ivanhoe Village, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
197
Median Rent
$2,149
Median Single Family Home Rent
$2,650
Median Townhouse Rent
$2,505
Median Condo Rent
$1,650
How to Rent a Home