For sale
1611 Chestnut AveWinter Park, FL 32789
- 4 beds
- 4 baths
- 2,916 sq ft
- 0.17 acres
- Built 1973
Listing courtesy of OLYMPUS EXECUTIVE REALTY INC · MLS# O6449003
About this home
Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.
| Property type | Single Family Residence |
|---|---|
| Community | Lake Knowles Terrace |
| County | Orange |
| Year built | 1973 |
| HOA | None |
| Taxes | $3,697 (2026) |
| Days on market | 12 |
| MLS # | O6449003 |
Interior
Carbon Monoxide Detector(s), Ceiling Fans(s), Crown Molding, High Ceilings, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
Appliances
Dishwasher, Disposal, Dryer, Electric Cooktop, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
Flooring
Ceramic Tile, Hardwood, Luxury Vinyl
Exterior
Courtyard, Private Yard, Rain Gutters, Sidewalk, Sprinkler Metered, Storage
Community
Street Lights
Heating & cooling
Central, Electric / Central Air
Construction
Block, Stucco, Frame
Roof
Shingle
Estimate your monthly payment
Principal & interest
- Loan amount
- Down payment
Rate shown is Freddie Mac's average 30-year rate (October 15, 2026). Principal and interest only; taxes, insurance and any HOA are extra. Not a loan offer.
Location
Keep looking
Similar homes in Winter Park
For Sale1735 Demetree Dr
Winter Park, FL 32789
4 BD | 3 BA | 2,787 Sq.Ft.
$1,050,000
Courtesy of EXP REALTY LLC
For Sale2330 Westminster Ct.
Winter Park, FL 32789
5 BD | 3 BA | 3,296 Sq.Ft.
$985,000
Courtesy of FANNIE HILLMAN & ASSOCIATES
For Sale2052 Wood Thrush Ln
Winter Park, FL 32792
4 BD | 3 BA | 2,807 Sq.Ft.
$900,000
Courtesy of KELLER WILLIAMS ADVANTAGE REALTY
For Sale1517 Harmon Ave
Winter Park, FL 32789
4 BD | 4 BA | 2,135 Sq.Ft.
$1,049,000
Courtesy of BEYCOME OF FLORIDA LLC
For Sale2572 Fifeshire Dr
Winter Park, FL 32792
4 BD | 3 BA | 2,578 Sq.Ft.
$899,900
Courtesy of PREMIER SOTHEBY'S INTL. REALTY
For Sale618 Blairshire Cir
Winter Park, FL 32792
4 BD | 3 BA | 1,876 Sq.Ft.
$875,000
Courtesy of REAL BROKER, LLC
Listing information is provided by Stellar MLS as distributed by MLS Grid, for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Based on information submitted to the MLS GRID as of October 29, 2026 at 11:30 PM Eastern. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listings shown with the listing brokerage.