2 Days Ago
Location
1521 Chestnut Ave, Winter Park, FL 32789, USA
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Amenities for 1521 Chestnut Ave
Features
| Balcony | Central Air |
| Fireplace | High Ceilings |
| Zoned Heating |
Grounds
| Garage Parking | Outdoor Space |
| Swimming Pool |
Other
| Seven Rooms |
Units, floor plans, amenities, dimensions, details, availability, and prices may be approximate and subject to change. Please contact a community representative for more information.
Policies and fees
Applicants
Applicants
One-time.
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REQUIRED FEES
Security Deposit
One-time. Refundable.
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About 1521 Chestnut Ave
Property Status: Active Gorgeous single-family home in the "tree streets" of Winter Park now available for rent or purchase. Private pool, two car garage, fabulous location and newer construction! Don't wait! Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light-filled living room complete with a designer fireplace and custom built-in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an in-ground pool, a fully fenced yard, tongue-in-groove wood ceiling, and pre-plumbing in place for your dream summer kitchen—ideal for entertaining year-round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first-floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multi-generational living. This home boasts well-thought-out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like-new home! Located just steps from Phelps Park and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to rent or own this exceptional home in the heart of Winter Park! Office Phone: (941) 279-3630 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Property highlights
We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.How 1521 Chestnut Ave compares to other nearby properties.
Positives
- More space
- The 4-bedroom is 401 sqft larger than other listings nearby
- Elementary school nearby
- There is an elementary school 1 mile away
- Fireplace
- Upgraded in-unit features
- Images Available
- There are at least 10 photos of this address
Considerations
- No in-unit dishwasher
- Dishwashers aren't available
Address details
| Zip code | 32789 |
|---|---|
| Type | House for rent |
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Rent trends in Winter Park
4-bedroom apartments at 1521 Chestnut Ave cost about 57% more than the average rent price for 4-bedroom apartments in Winter Park.
Median rents as of Apr 11 2026.
Winter Park
| Month | Median Rent |
|---|---|
| April 2024 | $4,750 |
| May 2024 | $4,591 |
| June 2024 | $3,958 |
| July 2024 | $3,525 |
| August 2024 | $3,400 |
| September 2024 | $3,062 |
| October 2024 | $2,999 |
| November 2024 | $3,619 |
| December 2024 | $3,350 |
| January 2025 | $3,260 |
| February 2025 | $3,033 |
| March 2025 | $3,160 |
| April 2025 | $3,187 |
| May 2025 | $3,275 |
| June 2025 | $3,612 |
| July 2025 | $4,649 |
| August 2025 | $6,642 |
| September 2025 | $5,359 |
| October 2025 | $4,464 |
| November 2025 | $4,355 |
| December 2025 | $4,087 |
| January 2026 | $4,541 |
| February 2026 | $4,494 |
| March 2026 | $4,465 |
| April 2026 | $4,316 |
Affordability calculator
Can I afford to live at 1521 Chestnut Ave?
Bedrooms
4+ bedroomsRent-to-income ratio
30%
Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income
$260,000/yr
With your selected rent-to-income ratio, you'd ideally want to make $260,000 annually to afford this 4-bedrooms monthly rent price of $6,500.
For more information on rent affordability, visit our rent calculator.
Schools near 1521 Chestnut Ave
Lakemont Elementary School
901 n lakemont ave
winter park, FL, 32792
PK, K-5Public
B+
Audubon Park School
1500 falcon dr
orlando, FL, 32803
PK, K-8Public
A-
OCVS Virtual Instruction Program
1600 silver star rd
orlando, FL, 32804
K-12Public
OCVS Virtual Franchise
1600 silver star rd
orlando, FL, 32804
K-12Public
A-
Orange County Virtual School
1600 silver star rd
orlando, FL, 32804
K-12Public
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Internet available near 1521 Chestnut Ave
Neighborhood
Getting around Winter Park near 1521 Chestnut Ave
Walking
5/10
Some shops and stores are within a few minutes.
Driving
7/10
This area is close to freeways and has adequate parking options.
Cycling
5/10
More spots are within biking distance and some roads are cyclist-friendly.
Transit
1/10
FYI, there are little to no public transit options within walking distance.
Points of interest for 1521 Chestnut Ave, Winter Park
Groceries
3/10
At least one supermarket within a 30-minute walk
Shopping
6/10
Several shops within walking distance
Cafes
3/10
Some cafés within walking distance
Restaurants
5/10
Some restaurants within a few minutes’ walk
Primary schools
6/10
At least one elementary school within a 20-minute walk
High schools
0/10
Closest high school further than a 30-minute walk
Parks
5/10
Moderate amount of park space nearby
Nightlife
2/10
Few or no bars within walking distance
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