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$1,850,000
New Listing

1560 WOODLAND AVENUE
WINTER PARK, FL 32789

For Sale|Single Family Residence|Active
5
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
3,851
SqFt
$480
/SqFt
1990
Built
Subdivision:
COMSTOCK PARK
County:
Orange
Call Now: (561) 935-3331
Is this the listing for you? We can help make it yours.
(561) 935-3331
1560 WOODLAND AVENUE1560 WOODLAND AVENUE1560 WOODLAND AVENUE1560 WOODLAND AVENUE
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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. 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. 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 re-plumbed! 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, kayaking, 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.

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Listing Snapshot
Price 
$1,850,000
Days On Site 
0 Days
Bedrooms 
5
Inside Area (SqFt) 
3,851 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
0.27 Acres
Year Built 
1990
MLS® Number 
O6389070
Status 
Active
Property Tax 
$11,736.79
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
2 hours agoListing updated with changes from the MLS®
5 hours agoListing first seen on site
General Features
Acres 
0.27
Direction Faces 
North
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Number Of Stories 
2
Parking 
BoatCircular DrivewayCommonDrivewayGarage Door OpenerOversized
Pets 
Yes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
5185
Utilities 
Cable AvailableElectricity Connected
Water Source 
Public
Zoning 
R-1A
Interior Features
Appliances 
CooktopDishwasherElectric Water HeaterRefrigerator
Cooling 
Central AirZoned
Fireplace 
Yes
Fireplace Features 
DecorativeFamily RoomWood Burning
Flooring 
CarpetTileWood
Furnished 
Negotiable
Heating 
Heat Pump
Interior 
Built-in FeaturesCrown MoldingEat-in KitchenHigh CeilingsOpen FloorplanStone CountersWalk-In Closet(s)
Laundry Features 
Laundry Room
Spa 
Yes
Window Features 
Window CoveringsShuttersWindow Treatments
Bedroom 3 
Dimensions - 15x12Level - FirstFeatures - Ceiling Fan(s)
Bedroom 4 
Dimensions - 17x14Level - SecondFeatures - Ceiling Fan(s)
Bedroom 5 
Dimensions - 15x14Level - SecondFeatures - Ceiling Fan(s)
Dining Room 
Dimensions - 19x13Level - First
Gym 
Dimensions - 24x9Level - SecondFeatures - Ceiling Fan(s)
Kitchen 
Dimensions - 17x13Level - FirstFeatures - Breakfast Bar
Living Room 
Dimensions - 25x19Level - FirstFeatures - Ceiling Fan(s)
Master Bathroom 
Dimensions - 20x13Level - SecondFeatures - Double Vanity, Granite Counters
Master Bedroom 
Dimensions - 21x16Level - SecondFeatures - Ceiling Fan(s)
Office 
Dimensions - 18x14Level - First
Primary Bedroom 2 
Dimensions - 13x11Level - FirstFeatures - Ceiling Fan(s)
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Exterior Features
Construction Details 
BlockStucco
Exterior 
LightingRain Gutters
Lot Features 
LandscapedLevel
Patio And Porch 
Front PorchRear PorchScreened
Pool Features 
GuniteIn GroundScreen EnclosurePrivate
Private Pool 
Yes
Roof 
Metal
Spa 
Yes
Spa Features 
In Ground
Waterfront Features 
Lake Privileges
Windows/Doors 
Window CoveringsShuttersWindow Treatments
Community Features
Community Features 
ParkPlayground
Financing Terms Available 
CashConventionalVA Loan
MLS Area 
32789 - Winter Park
Township 
22
Schools
School District
Unknown
Elementary School
Lakemont Elem
Middle School
Maitland Middle
High School
Winter Park High
Listing courtesy of CREEGAN GROUP (407) 622-1111



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-03-11 10:56 PM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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