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$1,000 - $1,700Studio to 3 Bedroom Apartments Available Now
District On Baldwin Park
5590 Baldwin Park StOrlando, FL 32807
Cheap Apartments for Rent in the Winter Park Neighborhood of Orlando, FL from $400 (36 Rentals)
Search the lowest-cost Apartments available for rent right now in the Winter Park area of Orlando.
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$1,100 - $1,500Studio to 1 Bedroom Apartments Available Now
Hillcrest Hampton House
2000 Hillcrest StOrlando, FL 32803
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$1,205 - $2,580Studio to 2 Bedroom Apartments Available Now
Shoreview at Baldwin Park
1001-1009 Shoreview DrOrlando, FL 32807
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$1,300 - $1,9851 to 3 Bedroom Apartments Available Now
Avenues of Baldwin Park
5800 Auvers BlvdOrlando, FL 32807
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$1,363 - $1,7991 to 2 Bedroom Apartments Available Now
Adele Place
7595 Sun Tree CirOrlando, FL 32807
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$1,375
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Studio Apartment Available Mar 7Total Monthly Price
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$1,375
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$1,375
715 Palm Dr, Unit 715 Palm Dr. #2
715 Palm DrOrlando, FL 32803
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$1,399 - $1,979
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1 to 3 Bedroom Apartments Available NowTotal Monthly Price
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$1,359 - $1,939
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$40
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$1,399 - $1,979
Bellancia Apartments
7325 Goldenpointe BlvdOrlando, FL 32807
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$1,400 - $2,5002 to 3 Bedroom Apartments Available Now
Virginia Drive Apartments
1216 Virginia DrOrlando, FL 32803
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1 Bedroom Apartments
Baldwin Meadows Apartments
5599 Old Cheney HwyOrlando, FL 32807
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
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2 Bedroom Apartments
On Baldwin Pond
829 Lowell BlvdOrlando, FL 32803
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Studio Apartments
1219 Oregon St
1219 Oregon StOrlando, FL 32803
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$976 - $1,3732 to 3 Bedroom Apartments Contact Us For Availability
Golden Oaks
7701 Acorn Woods CirWinter Park, FL 32792
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$991 - $1,737Studio to 3 Bedroom Apartments Contact Us For Availability
Carlton Arms of Winter Park
300 Jamestown DrWinter Park, FL 32792
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$1,094 - $1,4911 to 3 Bedroom Apartments Available Now
Winter Park Woods Apartments
349 Scottsdale SqWinter Park, FL 32792
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$1,150 - $2,8481 to 2 Bedroom Apartments Available Now
Sovereignty at Winter Park Apartments
7745 Brandywood CirWinter Park, FL 32792
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$1,193 - $1,763
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1 to 2 Bedroom Apartments Available Mar 7Total Monthly Price
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$1,033 - $1,603
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$160
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$1,193 - $1,763
Seabrook
3114 Terry Brook DrWinter Park, FL 32792
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$1,236 - $2,4251 to 3 Bedroom Apartments Available Now
Village Park Senior
550 W Denning DrWinter Park, FL 32789
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$1,249 - $2,0851 to 3 Bedroom Apartments Available Now
Cranes Landing Apartments
3440 N Goldenrod RdWinter Park, FL 32792
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
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$1,255 - $1,9751 to 3 Bedroom Apartments Available Now
Central Place At Winter Park
7000 University BlvdWinter Park, FL 32792
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$1,269 - $2,8761 to 3 Bedroom Apartments Available Now
Summerlin at Winter Park Apartments
3207 Rosebud LnWinter Park, FL 32792
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$1,269 - $2,032
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Studio to 3 Bedroom Apartments Available NowTotal Monthly Price
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$1,239 - $2,002
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$30
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$1,269 - $2,032
The Taylor at Winter Park
2000 Village LnWinter Park, FL 32792
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$1,284 - $2,744
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1 to 2 Bedroom Apartments Available NowTotal Monthly Price
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$1,022 - $2,482
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$262
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$1,284 - $2,744
ARIUM Winter Park
3250 Bishop Park DrWinter Park, FL 32792
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$1,295 - $2,0751 to 3 Bedroom Apartments Available Now
Oak Reserve at Winter Park
541 Oak Reserve LnWinter Park, FL 32792
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$1,298 - $2,0311 to 3 Bedroom Apartments Available Now
Venue At Winter Park
5 Autumn Breeze WayWinter Park, FL 32792
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$1,300 - $1,8551 to 3 Bedroom Apartments Contact Us For Availability
La Aloma
3040 Aloma AveWinter Park, FL 32792
3212 Netherwood Dr
Winter ParkFL32792
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$1,330 - $1,750Studio to 2 Bedroom Apartments Available Now
Park East - Park Knowles Apartments
311 N Knowles AveWinter Park, FL 32789
The Soul of the City Beautiful: What Life in Orlando Is Really Like
Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.
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$1,358 - $2,9671 to 2 Bedroom Apartments Available Now
Alvista Winter Park
3935 Sutton Place BlvdWinter Park, FL 32792
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1 to 3 Bedroom Apartments
Tuscany at Aloma
6999 Aloma AveWinter Park, FL 32792
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1 to 2 Bedroom Apartments
El Cortez Apartments
210 E Morse BlvdWinter Park, FL 32789
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1 to 3 Bedroom Apartments
Winter Park Oaks
325 Balfour DrWinter Park, FL 32792
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1 to 4 Bedroom Apartments
Goldenrod Pointe
5560 Solidago DrWinter Park, FL 32792
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Studio to 3 Bedroom Apartments
Mizell at Winter Park
600 N Semoran BlvdWinter Park, FL 32792
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1 to 2 Bedroom Apartments
Sun Bay Apartments
7001 Aloma AveWinter Park, FL 32792
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Studio to 3 Bedroom Apartments
Azure Winter Park
3650 Summer Wind DrWinter Park, FL 32792
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1 to 2 Bedroom Apartments
Whisper Lake Apartments
3250 Whisper Lake LnWinter Park, FL 32792
Top Neighborhoods Near Orlando Major Employers
Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara
Showing Results 1-36, Page 1 of 1
Winter Park, Orlando, FL Local Guide
How much does it cost to rent an apartment in Winter Park?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winter Park Studio Apartments | $1,705 | $991 | $2,635 |
| Winter Park 1 Bedroom Apartments | $1,947 | $1,044 | $6,415 |
| Winter Park 2 Bedroom Apartments | $2,142 | $976 | $6,395 |
| Winter Park 3 Bedroom Apartments | $2,523 | $1,099 | $5,794 |
| Winter Park 4 Bedroom Apartments | $3,826 | $3,826 | $3,826 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 36 rentals with your search options within a 2 mile radius of the Winter Park Neighborhood of Orlando, FL.
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Winter Park, Orlando, FL Local Guide
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Cheapest Available Winter Park Apartments for Rent
The cheapest available apartment rental in the Winter Park area of Orlando, FL is a Studio unit found at District On Baldwin Park priced from $1,000. Hillcrest Hampton House has the second lowest priced unit, which is a Studio apartment currently listed from $1,100. Here are the most affordable Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| District On Baldwin Park | E235xecutive Studio | Studio,1BA | $1,000 |
| Hillcrest Hampton House | Studio | Studio,1BA | $1,100 |
| Shoreview at Baldwin Park | 1x1A | 1BR,1BA | $1,205 |
| Sovereignty at Winter Park Apartments | A2 | 1BR,1BA | $1,215 |
| Village Park Senior | One Bedroom One Bath | 1BR,1BA | $1,236 |
| Cranes Landing Apartments | Egret (Renovated) A2Rwi | 1BR,1BA | $1,280 |
| Oak Reserve at Winter Park | The Charleston | 1BR,1BA | $1,295 |
| Venue At Winter Park | Sable L | 1BR,1BA | $1,298 |
| The Taylor at Winter Park | A6R | 1BR,1BA | $1,299 |
| Avenues of Baldwin Park | Anson (Standard) B1wm | 2BR,2BA | $1,300 |
Best Value Apartments for Rent in Winter Park, FL
As of February 26, 2026 the best value apartment in the Winter Park area is the $1.11 price per square foot 2 Bed 1 Bath Model at Virginia Drive Apartments in the in the North Orange neighborhood starting from $1,500. The second greatest value Winter Park apartment is the Three Bedroom Model at Bellancia Apartments starting at $1,979 with a $1.52 price per square foot in the Baldwin Park neighborhood. Here is today’s list of the best values for Winter Park apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Virginia Drive Apartments | 2 Bed 1 Bath | 2BR,1BA | $1.11 |
| Bellancia Apartments | Three Bedroom | 3BR,2BA | $1.52 |
| Oasis Club | The Palms | 3BR,2BA | $1.50 |
| POSTE Winter Park | The Cypress | 2BR,2BA | $1.71 |
| Azure Winter Park | Park+ | 2BR,2BA | $1.71 |
| Goldenrod Pointe | Three Bedroom Two Bath | 3BR,2BA | $1.45 |
| Avenues of Baldwin Park | Anson (Partial Renovation) B1pwm | 2BR,2BA | $1.70 |
| Cranes Landing Apartments | Ibis (Standard) b1wi | 2BR,2BA | $1.71 |
| Sovereignty at Winter Park Apartments | A2 | 1BR,1BA | $1.62 |
| Summerlin at Winter Park Apartments | Aqua | 1BR,1BA | $1.73 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleYour Guide to the Perfect Orlando Neighborhood for Student Renters
Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com
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The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Best Local Schools in Winter Park, Orlando, FL
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Lifestyle Ratings
ApartmentHomeLiving.com compiles millions of data points to bring you our detailed rental analysis called 'Lifestyle Ratings' - a comparison of neighborhoods, cities and towns, and rental properties across Florida and customized analysis for Orlando, Florida. Our Lifestyle Ratings help you zero-in on the perfect place to call home. This takes in many factors including our Star Ratings to compare for the best proximity to parks and outdoor amenities, luxury amenities, pet-friendly features, places that make kids happy, proximity to transit, in addition to floorplans, availablity, and pricing. Use Lifestyle Search in the site filter options on this page - and find your Perfect place!
Frequently Asked Questions about Cheap Winter Park Apartments
What is a cheap apartment in Winter Park?
A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Winter Park is under $1,300.
What is the price of a cheap apartment in Winter Park?
The cheapest apartment in Winter Park is District On Baldwin Park which is listed at $1,044, while the average apartment in Winter Park costs $3,826.
What types of apartments are the cheapest in Winter Park?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 118 regular apartments in Winter Park that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
How do the prices of cheap apartments compare to the average apartment in Winter Park?
Cheap apartments in Winter Park have an average cost of $447 which is $3,379 cheaper than the average rent for all rentals in Winter Park.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Helpful Local Expert Guides
An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
Written by: Darla Ferrara
For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.
Your Guide to the Perfect Orlando Neighborhood for Student Renters
Written by: Darla Ferrara
There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.
Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers
Written by: Darla Ferrara
When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.
The Soul of the City Beautiful: What Life in Orlando Is Really Like
Written by: Darla Ferrara
When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.
Articles, How-To's, and Tips
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.