Welcome home to this beautifully maintained property on more than a third of an acre in one of Winter Park's favorite neighborhoods -- affectionately known as the Tree Streets! 1711 Chestnut Ave blends classic Florida design with intentional, modern systems. In both the front and back of the home, you'll appreciate the attention to detail in the landscape design, which will be in full bloom each Spring. The irrigation system for the lawn is on it's own well system. Enter the home to enjoy two separate living spaces, a split plan that offers a spacious primary suite and three secondary bedrooms, and three full bathrooms. The kitchen has been renovated to include custom cabinetry, granite countertops, and stainless steel appliances. It is open to the Family Room with an incredible view of the oversized backyard and pool. The mature landscaping out back offers privacy to enjoy this retreat, complete with ample space for outdoor living and entertaining! Some notable upgrades to this property include brand new HVAC systems (2) in 2021 and 2022, water heater in 2019, hurricane-rated windows between 2015-2017, home security in 2015, engineered hardwood flooring in 2015, custom wood shutters in 2017, new pool pump in 2016, and a re-plumb in 2005. Zoned for highly rated Orange County Public Schools (Lakemont, Maitland, and Winter Park), you're also central to some of the best shopping and dining in Winter Park: 2 miles from Park Avenue, 0.4 miles from the Winter Park YMCA, 0.3 miles from Phelps Park (playground, pickleball, tennis), 1.5 miles from the nearest Publix, 1.1 miles from Interlachen Country Club, and 14 miles from Orlando International Airport.
For sale
$1,040,000
1711 Chestnut Ave, Winter Park, FL 32789
4beds
2,720sqft
Est.:
Single Family Residence
Built in 1963
0.36 Acres Lot
$987,200 Zestimate®
$382/sqft
$-- HOA
What's special
Granite countertopsOversized backyardCustom cabinetryLandscape designEngineered hardwood flooringCustom wood shuttersStainless steel appliances
- 7 hours
- on Zillow |
- 194 |
- 16 |
Zillow last checked: 7 hours ago
Listing updated: 14 hours ago
Listing Provided by:
Courtney Pelfrey 407-454-0538,
MILLER GRANT AND COMPANY 407-399-6031
Source: Stellar MLS,MLS#: O6335913
Originating MLS: Orlando Regional

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Open house
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 232 Square Feet
- Dimensions: 14.5x16
Great room
- Level: First
- Area: 391.5 Square Feet
- Dimensions: 14.5x27
Kitchen
- Features: Stone Counters
- Level: First
- Area: 247.25 Square Feet
- Dimensions: 21.5x11.5
Heating
- Central, Electric, Exhaust Fan, Heat Pump
Cooling
- Central Air, Zoned
Appliances
- Included: Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Range, Range Hood, Refrigerator, Washer
- Laundry: In Garage
Features
- Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
- Flooring: Engineered Hardwood, Slate
- Doors: French Doors
- Windows: Shutters, Skylight(s), Window Treatments
- Has fireplace: Yes
- Fireplace features: Family Room
Interior area
- Total structure area: 2,803
- Total interior livable area: 2,720 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage Door Opener
- Attached garage spaces: 2
Features
- Levels: One
- Stories: 1
- Patio & porch: Deck, Front Porch, Patio
- Exterior features: Irrigation System, Lighting, Private Mailbox, Rain Gutters
- Has private pool: Yes
- Pool features: Deck, Diving Board, Gunite, In Ground, Outside Bath Access
- Fencing: Fenced
Lot
- Size: 0.36 Acres
- Features: Cleared, City Lot, Irregular Lot, Oversized Lot
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 322130170801070
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Mid-Century Modern,Traditional
- Property subtype: Single Family Residence
Materials
- Block
- Foundation: Slab
- Roof: Built-Up,Shingle
Condition
- New construction: No
- Year built: 1963
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Phone Available, Public, Sewer Available, Sewer Connected, Sprinkler Well, Underground Utilities, Water Available, Water Connected
Community & HOA
Community
- Security: Security System
- Subdivision: CONWILL ESTATES
HOA
- Has HOA: No
- Pet fee: $0 monthly
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $382/sqft
- Tax assessed value: $696,790
- Annual tax amount: $4,152
- Date on market: 8/20/2025
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Unimproved, Asphalt, Paved
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