55 photos in the listing
1611 Chestnut Avenue
Winter Park, FL 32789 · Orange County
$985,000
4
Beds
4
Baths
2,916
Sq ft
1973
Year built
Location
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.
Facts & features
Interior
- Bedrooms
- 4
- Bathrooms
- 4
- Living area
- 2,916 sq ft
- Stories
- 2
- Flooring
- Ceramic Tile, Hardwood, Luxury Vinyl
- Appliances
- Dishwasher, Disposal, Dryer, Electric Cooktop, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
- Features
- 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)
- Fireplace
- Yes
- Cooling
- Central Air
- Heating
- Central, Electric
Exterior & lot
- Lot size
- 0.17 acres
- Construction
- Block, Stucco, Frame
- Roof
- Shingle
- Features
- Courtyard, Private Yard, Rain Gutters, Sidewalk, Sprinkler Metered, Storage
Financial
- Price / sqft
- $338/sqft
- Annual tax
- $3,697.24
- Tax year
- 2026
Utilities
- Utilities
- Cable Connected, Electricity Connected, Fiber Optics, Public, Sewer Connected, Sprinkler Meter, Underground Utilities, Water Connected
- Water
- Public
- Sewer
- Public Sewer
Property
- Property type
- Single Family
- Year built
- 1973
- Subdivision
- Lake Knowles Terrace
- Days on market
- 7 days
Estimate your monthly cost
Twenty percent down over thirty years at 6.5%. Insurance is not included.
- Principal & interest
- $4,981
- Property tax
- $308
- Estimated monthly
- $5,289
Ask about this property
Answered from this listing’s own figures and the sales around it.
Similar homes nearby
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Oct 13, 2026 | Listed | $985,000 | — |
Neighbourhood
The schools below come from the MLS record for this home. Walking, transit and cycling figures for Winter Park, FL are not connected yet, so this page does not show them.
About this area
WINTER PARK, FL sits in Orange County. Asking prices on the 8 nearest homes we hold run from $875,000 to $2,549,000, with $1,759,500 in the middle. Those are asking prices, not closed sales. The MLS record names Lakemont Elem (elementary), Maitland Middle (middle), Winter Park High (high) as the assigned schools.
Written from this listing’s own record and the homes we hold nearby.
- Elementary school
- Lakemont Elem
- Assigned school from the MLS record
- Middle school
- Maitland Middle
- Assigned school from the MLS record
- High school
- Winter Park High
- Assigned school from the MLS record
Frequently asked questions
What would 1611 CHESTNUT AVENUE, WINTER PARK cost per month?
About $5,289 a month: $4,981 principal and interest, $308 property tax. That assumes 20% down at 6.5% over 30 years, and leaves out insurance.
Is 1611 CHESTNUT AVENUE, WINTER PARK priced fairly?
Comparable homes nearby put it between $1,604,077 and $1,845,551, with $1,724,814 in the middle. Those are asking prices, not closed sales: 8 properties of the same type within three miles, each within 20% of this one's size and a bedroom either way, at a median of $592 a square foot.
How does 1611 CHESTNUT AVENUE, WINTER PARK compare to nearby homes?
8 comparable properties within three miles. The nearest: 1550 PALM AVENUE, WINTER PARK, FL at $1,829,000, 2,706 sq ft, 0.05 miles away; 1600 ONECO AVENUE, WINTER PARK, FL at $875,000, 2,538 sq ft, 0.09 miles away; 1581 MAGNOLIA AVE, WINTER PARK, FL at $1,425,000, 2,642 sq ft, 0.19 miles away.
How long has 1611 CHESTNUT AVENUE, WINTER PARK been on the market?
5 days on the market.
Has the price of 1611 CHESTNUT AVENUE, WINTER PARK changed?
The price has not moved since it was listed.
How big is 1611 CHESTNUT AVENUE, WINTER PARK?
4 bed, 4 bath, 2,916 square feet. That is $338 a square foot.
What year was 1611 CHESTNUT AVENUE, WINTER PARK built?
Built in 1973.
What is the HOA fee at 1611 CHESTNUT AVENUE, WINTER PARK?
The feed lists no association fee for this property.
What are the property taxes at 1611 CHESTNUT AVENUE, WINTER PARK?
Property tax works out to about $308 a month, $3,697 a year, on the 2026 assessment.
Is 1611 CHESTNUT AVENUE, WINTER PARK still available?
It is still on the market.
Listing
- Listed by
- Gunel Aydamirli
- Brokerage
- OLYMPUS EXECUTIVE REALTY INC
- MLS number
- MFR813775758
Listing information is deemed reliable but is not guaranteed.