1560 Woodland Avenue, Winter Park, FL 32789
Local realty services provided by:Bingham Realty ERA Powered
1560 Woodland Avenue,Winter Park, FL 32789
$1,675,000
- 5 Beds
- 5 Baths
- - sq. ft.
- Single family
- Sold
Listed by: chris creegan, daniel prior llc.
Office: creegan group
MLS#:O6389070
Source:MFRMLS
Sorry, we are unable to map this address
Price summary
- Price:$1,675,000
About this home
Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite offers 3,851 square feet of living space, remarkable flexibility, and the kind of charm that simply cannot be replicated. Buyers will also appreciate the peace of mind that comes with major recent updates, including a metal roof installed in 2017, two HVAC units replaced in 2026, a third HVAC unit replaced in 2022, and two water heaters installed in 2025. The pool was resurfaced in 2025, the exterior and interior of the home was painted in 2025, & the house has also been completely re-plumbed! From the moment you arrive, the home makes a lasting impression with its large brick front porch, circular driveway, mature landscaping, detached oversized 2 car garage, and classic architectural presence. Large windows and thoughtfully designed living spaces fill the home with natural light, while hardwood floors, custom built-ins, plantation shutters, fireplaces, and refined traditional details create a warm and inviting feel throughout. This is the perfect blend of classic Winter Park charm and functional modern updates.
The floor plan offers both elegance and versatility. In addition to five bedrooms, the home features an office space that can also serve as a formal living room, library, or flex space depending on your needs. The spacious family room is anchored by one of the home’s two wood burning fireplaces and opens beautifully to the outdoor living area, creating an easy flow for both everyday living and entertaining.
The kitchen offers granite countertops, custom cabinetry, abundant counter space, a large island, and lots of natural light. It is open, functional, and well positioned at the heart of the home, allowing the next owner to enjoy it as is or make it their own. The primary suite is generously sized, featuring its own fireplace, an oversized bathroom with large walk-in shower, extensive vanity space, and a huge custom closet. One of the most special features of this home is the attached in-law suite, with its own separate entrance while still remaining accessible from the main home. Complete with a living room, bedroom, full bathroom, and kitchenette, this apartment style space offers exceptional flexibility for multigenerational living, live in family, guests, or even potential income producing use.
Outside, the screened pool and spa area is a true highlight. Beautifully integrated into the architecture of the home, this private outdoor setting offers a covered lanai, lush tropical landscaping, and a peaceful courtyard style feel that makes it easy to relax, entertain, and enjoy Florida living year-round. The large paver driveway and detached garage create an impressive amount of parking and enhance the home’s unique layout and curb appeal. All of this is located less than 1.5 miles from Rollins College, Park Avenue, downtown Winter Park, public access to the Winter Park Chain of Lakes, and all the dining, shopping, boating, and everyday convenience that make this area so desirable. This is more than just a home. It is a rare chance to enjoy the Winter Park lifestyle in a custom home full of character, flexibility, and lasting value....
Contact an agent
Home facts
- Year built:1990
- Listing ID #:O6389070
- Added:59 day(s) ago
- Updated:May 10, 2026 at 07:29 AM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Flooring:Carpet, Tile, Travertine, Wood
- Dining Description:Eat In Kitchen, Formal Dining Room
- Kitchen Description:Built-In Oven, Cooktop, Dishwasher, Eat-in Kitchen, Kitchen/Family Room Combo, Refrigerator, Stone Counters
- Bedroom Description:High Ceilings, Primary Bedroom Upstairs, Split Bedroom, Walk-In Closet(s)
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Electric, Heat Pump
- Central air:Yes
Structure and exterior
- Roof:Metal
- Year built:1990
- Lot Features:Landscaped, Level
- Architectural Style:Custom
- Construction Materials:Block, Stucco
- Exterior Features:Front Porch, Lighting, Rain Gutters, Rear Porch, Screened
- Foundation Description:Slab
- Levels:2 Story
Schools
- High school:Winter Park High
- Middle school:Maitland Middle
- Elementary school:Lakemont Elem
Utilities
- Water:Public, Water Connected
- Sewer:Public, Public Sewer, Sewer Connected
Finances and disclosures
- Price:$1,675,000
- Tax amount:$11,737 (2024)
Features and amenities
- Appliances:Built-in Oven, Cooktop, Dishwasher, Electric Water Heater, Irrigation Equipment, Refrigerator
- Laundry features:Inside, Laundry Room
- Amenities:BB/HS Internet Available, Built-In Features, Cable Available, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Irrigation Equipment, Kitchen/Family Room Combo, Open Floorplan, Phone Available, Primary Bedroom Upstairs, Split Bedroom, Stone Counters, Thermostat, Underground Utilities, Walk-In Closet(s), Window Treatments
- Pool features:Gunite, In Ground, Private Pool, Screen Enclosure
Parking
- Parking description:Boat, Circular Driveway, Common, Driveway, Garage Door Opener, Oversized, RV Access/Parking
- Garage:Yes
- Garage spaces:2
New listings near 1560 Woodland Avenue
$530,000Pending3 beds 2 baths1,275 sq. ft.1921 Kimbrace Place, WINTER PARK, FL 32792
MLS# O6390018Listed by: COMPASS FLORIDA LLC- New
$175,000Active2 beds 2 baths990 sq. ft.Address Withheld By Seller, WINTER PARK, FL 32792
MLS# O6406448Listed by: SOGO REAL ESTATE SERVICES LLC - New
$1,375,000Active3 beds 3 baths2,000 sq. ft.266 W Lyman Avenue, WINTER PARK, FL 32789
MLS# O6406526Listed by: MAROON REALTY GROUP LLC - New
$595,000Active3 beds 2 baths1,396 sq. ft.616 Fitzwalter Drive, WINTER PARK, FL 32792
MLS# O6403982Listed by: EXP REALTY LLC - New
$400,000Active2 beds 1 baths913 sq. ft.2482 Roxbury Road, WINTER PARK, FL 32789
MLS# O6406443Listed by: COLDWELL BANKER REALTY - New
$824,000Active4 beds 5 baths3,040 sq. ft.4348 Steed Terrace, WINTER PARK, FL 32792
MLS# O6406018Listed by: LPT REALTY, LLC - New
$4,200,000Active5 beds 7 baths5,500 sq. ft.141 W Lake Sue Avenue, WINTER PARK, FL 32789
MLS# O6406437Listed by: THE AGENCY FL - New
$2,075,000Active2 beds 2 baths2,304 sq. ft.311 E Morse Boulevard #1-3, WINTER PARK, FL 32789
MLS# O6406368Listed by: FANNIE HILLMAN & ASSOCIATES - New
$410,000Active3 beds 2 baths1,402 sq. ft.7532 Azurebrook Court, WINTER PARK, FL 32792
MLS# O6406380Listed by: RE/MAX TOWN & COUNTRY REALTY - New
$1,195,000Active4 beds 3 baths2,723 sq. ft.220 W Reading Way, WINTER PARK, FL 32789
MLS# O6405775Listed by: PREMIER SOTHEBY'S INTL. REALTY