
1711 Chestnut Ave, Winter Park, FL 32789
What This House Offers
Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from... Interlachen Country Club and Winter Park Racquet Club,and is zoned for Lakemont Elementary,Maitland Middle,and Winter Park High School. Inside,natural light pours through windows in every room,giving the home a bright,airy feel throughout. The main living areas feature classic plantation shutters,while all bedrooms are fitted with blinds,a thoughtful touch that makes every space feel finished and move-in ready. Warm engineered hardwood floors,recessed lighting,and a flowing open layout connect the living room,dining area,and family room with ease. The chef's kitchen is the heart of the home,featuring granite countertops,a large center island,rich wood cabinetry,stainless steel appliances,and a professional-grade range hood,all opening into the spacious family room with its slate tile floors,wood-burning fireplace,built-in shelving,and French doors to the backyard. The primary suite overlooks the pool and rear yard,offering a serene and private feel. Its spa-inspired en suite bath features a dual-sink vanity,a walk-in tiled shower,and a private access directly to the backyard and pool,making it ideal for those who love to start or end the day outdoors. The second bedroom enjoys its own en suite bath. A third full bath serves the remaining bedrooms,beautifully updated with designer gold fixtures,modern vanity,and stylish lighting. The split bedroom layout offers privacy and flexibility for families,guests,or a dedicated home office. Out back,your private oasis awaits with a sparkling pool,concrete deck,lush lawn,and towering mature oaks creating that quintessential Winter Park canopy. Pool and lawn maintenance are included in rent,so you can simply enjoy. The attached 2-car garage includes laundry. No pets. No exceptions. MLS# O6396000
Unit
- $4,150 / month
- 4 Beds
- 3 Baths
- 2288 sq. ft.
- Available Now
Home Features
- Fireplace
Community Features
- Garages
- Pool
1711 Chestnut Ave is a single-family home for rent in Winter Park, FL
Fees and Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
One-Time Basics
Due at Application
- Application Fee Per Applicant$50
Due at Move-In
- Security Deposit - Refundable$5,000
- Garage
Property Fee Disclaimer Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.
Home Details
Home Design
- Built in 1963
- Single Family Detached Home
Interior Spaces
- Family Room with Fireplace
- Family Room Off Kitchen
- Shades
- Plantation Shutters
- Crown Molding
- Recessed Lighting
- French Doors
- Combination Dining and Living Room
- Ceiling Fan
- Shelving
- 2288 Sq Ft Home
- 1-Story Property
Kitchen
- Granite Countertops
- Eat-In Kitchen
- Solid Wood Cabinet
- Range with Range Hood
- Dishwasher
- Disposal
Flooring
- Engineered Wood
- Tile
- Slate Flooring
Bedrooms and Bathrooms
- Shower Only
- Window or Skylight in Bathroom
- Walk-In Closet
- Bathtub with Shower
- Multiple Shower Heads
- En-Suite Bathroom
- Single Vanity
- 3 Full Bathrooms
- 4 Bedrooms | 3 Bathrooms
- 4 Bedrooms
- Private Water Closet
Laundry
- Dryer
- Laundry in Garage
- Washer
Home Security
- Home Security System
- Fire and Smoke Detector
Parking
- 2 Car Attached Garage
- Garage Door Opener
Pool
- In Ground Pool
- Gunite Pool
- Pool Deck
- Outside Bathroom Access
- Diving Board
Outdoor Features
- Deck
- Front Porch
- Patio
- Rain Gutters
- Private Mailbox
- Exterior Lighting
Lot Details
- 15847 Sq Ft Lot
- Oversized Lot
- South Facing Home
- Back Yard Fenced
- Well Sprinkler System
Schools
- Lakemont Elementary School
- Maitland Middle School
- Winter Park High School
Utilities
- Central Heating and Cooling System
- High Speed Internet
- Cable TV Available
- Phone Available
- Underground Utilities
- Public Water Source
- Electricity Connected
- Sewer Connected
- Water Connected
- Electric Water Heater
- Public Sewer
- Vented Exhaust Fan
Listing and Financial Details
- Security Deposit $5,000
- Property Available on 2026-04-02
- 12-Month Minimum Lease Term
- $50 Application Fee
- Assessor Parcel Number 32-21-30-1708-01-070
- Tenant pays for cleaning fee
- The owner pays for grounds care, pest control, pool maintenance
- 8 to 12-Month Minimum Lease Term
- Residential Lease
Community Details
Overview
- No Home Owners Association
- Conwill Estates Subdivision
- Total HOA Annual Fees
- Total HOA Monthly Fees
Pet Policy
- No Pets Allowed
Explore Commute Options
- Drive Time--
- Walk Time--
- Bike Ride Time--
- Public Transit--
Get In Touch
Winter Park, FL 32789

Information is provided by My Florida Regional MLS DBA Stellar MLS. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright © 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved.
Area Scores
Walkability
Fairly walkable50 / 100
Transit
Minimal public transit10 / 100
Driveability
Moderately drivable70 / 100
Bikeability
Fairly bikeable50 / 100
Travel and Transit



Local Education
Primary and Secondary Schools
Maitland Middle
Grades 6-8
Public
Data provided by GreatSchools.org © 2026. All rights reserved.
Colleges and Universities
School
Commute Time (Distance)
Rollins College
Drive: 7 min (2.4 mi)
Valencia College, Winter Park
Drive: 8 min (3.1 mi)
Full Sail University
Drive: 9 min (3.7 mi)
Florida Hospital College
Drive: 13 min (4.7 mi)
Discover Lake Maitland, Winter Park, FL
Shopping Centers
Shoppers will appreciate 1711 Chestnut Ave proximity to Winter Park Corners, Lake Howell Plaza, and Interlachen Village. Winter Park Corners is 1 mile away, and Lake Howell Plaza is within a 24 minute walk.
Parks and Recreation
Recreational activities near 1711 Chestnut Ave are plentiful. Discover 4 parks within 4.6 miles, including Blue Jacket Park, Audubon Center for Birds of Prey, and Trotters Park.
Airports
Living in Lake Maitland provides easy access to Orlando International, located just 26 minutes from 1711 Chestnut Ave. Another nearby airport is Orlando Sanford International, located 19.5 miles away.
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