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1711 CHESTNUT AVENUE Winter Park, FL ^$ 4,150

1711 CHESTNUT AVENUE

^$ 4,150

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1711 CHESTNUT AVENUE

Winter Park, FL, 32789

^$ 4,150

Bedrooms4 Baths3.0 Sq 2,288

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Property for Rent in Winter Park, FL

for $4,150 with 4 bedrooms and 3 full baths. This 2,288 square foot property was built in 1963 on a lot size of 0.36.

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.

Rental Active

Price

^$ 4,150

Bedrooms

Full Bath

Taxes

^$ 0

Style

Single Family Residence

Lot Size

0.36

Year Built

1963

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6396000

Features

General

Sewer Public Sewer

Heating Central Electric

Cooling Central Air

Utilities BB/HS Internet Available Cable Connected Electricity Connected Phone Available Sewer Connected Sprinkler Well Underground Utilities Water Connected

Possession Rental Agreement

Appliances Dishwasher Disposal Dryer Electric Water Heater Range Range Hood Refrigerator Washer

Garage Spaces 2

Patio/Porch Features Deck Front Porch Patio

Pool Features Deck Diving Board Gunite In Ground Outside Bath Access

Security Features Security System Smoke Detector(s)

Pets Allowed No

Year Built 1963

Tenant Pays Cleaning Fee

Levels One

Property Subtype Single Family Residence

County Orange

New Construction false

Property Type Residential Lease

Attached Garage true

Subdivision Name CONWILL ESTATES

Facing Direction South

Garage Y/N true

Total Rooms 11

Full Baths 3

Status Active

Directions Head east on Palmer Avenue. Turn left onto Phelps Avenue. Continue on Phelps Avenue then turn right onto Chestnut Avenue. Proceed along Chestnut Avenue and the home will be on your left.

High School Winter Park High

City WINTER PARK

Senior Community Y/N false

MLS Area 32789 - Winter Park

Lot Size Units Square Feet

Lot Size Square Feet 15847

Carport Y/N false

Elementary School Lakemont Elem

Middle/Junior High School Maitland Middle

Ok to Lease 12 Months

Availability Date 2026-04-02

Building Area Units Square Feet

Living Area Units Square Feet

Standard Status Active

Occupancy Type Vacant

Lease Amount Frequency Monthly

Minimum Lease 8-12 Months

Water Access Y/N false

Water View Y/N false

Interior

Interior Amenities Ceiling Fan(s) Crown Molding Eating Space In Kitchen Kitchen/Family Room Combo Living Room/Dining Room Combo Primary Bedroom Main Floor Solid Wood Cabinets Stone Counters Walk-In Closet(s) Window Treatments

Flooring Engineered Hardwood Slate Tile

Furnished Y/N Unfurnished

Fireplace Features Family Room

Total Stories 1

Air Conditioning Y/N true

Heating Y/N true

Window Features Shades Shutters

Fireplace Y/N true

Half Baths 0

Laundry Features In Garage Inside Laundry Closet

Total Bedrooms 4

Total Baths 3

Exterior

Exterior Amenities French Doors Irrigation System Lighting Private Mailbox Rain Gutters

Fencing Fenced Full Backyard

Parking Features Garage Door Opener

Lot Features City Lot Oversized Lot

Water Source Public

Lot Size Area 15847

Spa false

Building Area Total 2803

Lot Size Acres 0.36

Road Surface Type Unimproved Asphalt Paved

Private Pool true

Waterfront Y/N false

Covered Spaces 2

Road Frontage Type Street Unpaved

* Excluded Features

List By

Premier Sotheby's Intl. Realty

Broker

drew@hennerco.com

Nearby

Trends
Schools

About Winter Park, FL

31,074 Population

11% Since 2002

^$68,913 Median Income

43.49 Median Age

21% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

0 Elementary School

0 Middle School

Winter Park High High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
4/3/2026	$4,150		Listed Price

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1711 CHESTNUT AVENUE, Winter Park, FL, 32789 is a Property for Rent at $4,150 with 2,288 sqft and a lot size of 0.36. 1711 CHESTNUT AVENUE has 4 bedrooms, 3.0 baths, and was built in 1963. The property's zip code is 32789 which is in Winter Park, FL

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Data is updated as of 4/20/2026.

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1711 CHESTNUT AVENUE

Property for Rent in Winter Park, FL

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