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.
Sold for $1,675,000
$1,675,000
1560 WOODLAND AVENUE, WINTER PARK, FL 32789
5beds
3,851sqft
Single Family Residence
Built in 1990
0.27 Acres Lot
$1,675,200 Zestimate®
$435/sqft
$6,964 Estimated rent
Home value
$1,675,200
$1.54M - $1.83M
$6,964/mo
Zestimate® history
Owner options
List your home for rent
$6,964/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$6,964/mo
Rent Zestimate®
Refinance and save
$11,928/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$11,928/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Refined traditional detailsLarge islandCovered lanaiGranite countertopsPeaceful courtyard style feelLarge windowsCustom built-ins
Zillow last checked:
Listing updated:
Listed by:
Chris Creegan 407-622-1111,
CREEGAN GROUP 407-622-1111,
Daniel Prior LLC 407-406-2145,
CREEGAN GROUP
Bought with:
Richard Palmano, 3120608
PALMANO GROUP RE BROKERAGE LLC
Source: Stellar MLS,MLS#: O6389070
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Rooms
- Room types: Bonus Room, Den/Library/Office, Dining Room, Storage Rooms
Other
- Features: Built-In Shelving, Ceiling Fan(s), En Suite Bathroom, Walk-In Closet(s)
- Level: First
- Area: 143 Square Feet
- Dimensions: 13x11
Primary bedroom
- Features: Ceiling Fan(s), En Suite Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 336 Square Feet
- Dimensions: 21x16
Bedroom 3
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
- Area: 180 Square Feet
- Dimensions: 15x12
Bedroom 4
- Features: Ceiling Fan(s), Jack & Jill Bathroom, Built-in Closet
- Level: Second
- Area: 238 Square Feet
- Dimensions: 17x14
Bedroom 5
- Features: Ceiling Fan(s), Jack & Jill Bathroom, Built-in Closet
- Level: Second
- Area: 210 Square Feet
- Dimensions: 15x14
Primary bathroom
- Features: Dual Sinks, En Suite Bathroom, Exhaust Fan, Granite Counters, Split Vanities, Walk-In Closet(s)
- Level: Second
- Area: 260 Square Feet
- Dimensions: 20x13
Dining room
- Features: No Closet
- Level: First
- Area: 247 Square Feet
- Dimensions: 19x13
Gym
- Features: Ceiling Fan(s), Built-in Closet
- Level: Second
- Area: 216 Square Feet
- Dimensions: 24x9
Kitchen
- Features: Breakfast Bar, Pantry, Kitchen Island, Built-in Closet
- Level: First
- Area: 221 Square Feet
- Dimensions: 17x13
Living room
- Features: Built-In Shelving, Ceiling Fan(s), No Closet
- Level: First
- Area: 475 Square Feet
- Dimensions: 25x19
Office
- Features: No Closet
- Level: First
- Area: 252 Square Feet
- Dimensions: 18x14
Heating
- Electric, Heat Pump
Cooling
- Central Air, Zoned
Appliances
- Included: Oven, Cooktop, Dishwasher, Electric Water Heater, Refrigerator
- Laundry: Inside, Laundry Room
Features
- Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), In-Law Floorplan
- Flooring: Carpet, Tile, Travertine, Hardwood
- Doors: French Doors
- Windows: Shutters, Window Treatments
- Has fireplace: Yes
- Fireplace features: Decorative, Family Room, Other Room, Master Bedroom, Wood Burning
Interior area
- Total structure area: 5,185
- Total interior livable area: 3,851 sqft
Property
Parking
- Total spaces: 2
- Parking features: Boat, Circular Driveway, Common, Driveway, Garage Door Opener, Oversized, RV Access/Parking
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Front Porch, Rear Porch, Screened
- Exterior features: Irrigation System, Lighting, Rain Gutters
- Has private pool: Yes
- Pool features: Gunite, In Ground, Screen Enclosure
- Has spa: Yes
- Spa features: In Ground
- Waterfront features: Lake, Lake Privileges
Lot
- Size: 0.27 Acres
- Features: City Lot, Landscaped, Level
- Residential vegetation: Fruit Trees, Mature Landscaping
Details
- Parcel number: 052230159203150
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Custom
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Metal
Condition
- Completed
- New construction: No
- Year built: 1990
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Public, Sewer Connected, Underground Utilities, Water Connected
Community & HOA
Community
- Features: Community Boat Ramp, Fishing, Lake, Public Boat Ramp, Water Access, Park, Playground
- Security: Smoke Detector(s)
- Pet fee: $0 monthly
- Subdivision: COMSTOCK PARK
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $435/sqft
- Tax assessed value: $1,277,887
- Annual tax amount: $11,736
- Date on market: 3/11/2026
- Cumulative days on market: 16 days
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Brick
Price history
| Date | Event | Price |
|---|---|---|
| 5/8/2026 | Sold | $1,675,000-9.5%$435/sqft |
Source:  Stellar MLS #O6389070 Report a problem | ||
| 3/27/2026 | Pending sale | $1,850,000$480/sqft |
Source: Stellar MLS #O6389070 Report a problem | ||
| 3/11/2026 | Listed for sale | $1,850,000-7.5%$480/sqft |
Source: Stellar MLS #O6389070 Report a problem | ||
| 12/1/2025 | Listing removed | $1,999,000$519/sqft |
Source: Stellar MLS #O6293517 Report a problem | ||
| 9/15/2025 | Price change | $1,999,000-7%$519/sqft |
Source: Stellar MLS #O6293517 Report a problem | ||
| 3/28/2025 | Listed for sale | $2,150,000+238.6%$558/sqft |
Source: Stellar MLS #O6293517 Report a problem | ||
| 3/18/2011 | Sold | $635,000-9.2%$165/sqft |
Source: Stellar MLS #O4958720 Report a problem | ||
| 6/18/2010 | Price change | $699,000-6.2%$182/sqft |
Source: NRT Florida #O4958720 Report a problem | ||
| 4/14/2010 | Price change | $745,000-6.3%$193/sqft |
Source: NRT Florida #O4958720 Report a problem | ||
| 1/29/2010 | Price change | $794,900-3.6%$206/sqft |
Source: NRT Florida #O4958720 Report a problem | ||
| 10/4/2009 | Price change | $824,500-5.7%$214/sqft |
Source: Fannie Hillman & Associates #O4920099 Report a problem | ||
| 8/29/2009 | Listed for sale | $874,500+27.7%$227/sqft |
Source: Fannie Hillman & Associates #O4920099 Report a problem | ||
| 11/25/2003 | Sold | $685,000$178/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $11,737 +3.8% | $771,962 +3% |
| 2023 | $11,305 +6.3% | $749,478 +3% |
| 2022 | $10,632 +1% | $727,649 +3% |
| 2021 | $10,522 -0.2% | $706,455 +1.4% |
| 2020 | $10,545 +0.7% | $696,701 +2.3% |
| 2019 | $10,473 +0.5% | $681,037 +1.9% |
| 2018 | $10,420 | $668,339 -10.6% |
| 2017 | $10,420 +0.8% | $747,766 +1.6% |
| 2016 | $10,333 +2.1% | $736,148 +1.4% |
| 2015 | $10,125 -3.2% | $725,912 +11.4% |
| 2014 | $10,458 +2.1% | $651,874 +4.1% |
| 2013 | $10,239 +1% | $625,924 +2.3% |
| 2012 | $10,136 +10.6% | $611,883 +10.3% |
| 2011 | $9,161 +2% | $554,703 -1.2% |
| 2010 | $8,980 | $561,270 -17.6% |
| 2009 | -- | $680,934 -13.4% |
| 2008 | $9,261 +1.3% | $786,515 -6.2% |
| 2007 | $9,143 -6.6% | $838,470 +28.1% |
| 2006 | $9,789 -0.2% | $654,340 +12.6% |
| 2005 | $9,805 +4.4% | $580,956 +7.7% |
| 2004 | $9,392 +20.3% | $539,481 +21.9% |
| 2003 | $7,809 +14.2% | $442,489 +14.1% |
| 2002 | $6,840 +5.3% | $387,829 +6.7% |
| 2001 | $6,497 +9.1% | $363,468 +10% |
| 2000 | $5,957 | $330,401 |
Find assessor info on the county website
Neighborhood: 32789
Nearby homes
- $1,121,5003 bd3 ba2.5k sqft1550 Woodland Ave, Winter Park, FL 32789Off Market
- $1,414,2004 bd3 ba2.7k sqft1570 Woodland Ave, Winter Park, FL 32789Off Market
- $826,5003 bd2 ba1.4k sqft1530 Woodland Ave, Winter Park, FL 32789Off Market
- $2,229,7004 bd5 ba3.9k sqft1590 Woodland Ave, Winter Park, FL 32789Off Market
- $1,559,1004 bd2 ba2.4k sqft1551 Dale Ave, Winter Park, FL 32789Off Market
- $2,568,4005 bd6 ba4.6k sqft1561 Dale Ave, Winter Park, FL 32789Off Market
- $1,012,9003 bd2 ba2k sqft1531 Dale Ave, Winter Park, FL 32789Off Market
- $1,546,3004 bd4 ba3.2k sqft1555 Woodland Ave, Winter Park, FL 32789Off Market
Nearby schools
GreatSchools rating
- 7/10Lakemont Elementary SchoolGrades: K-5Distance: 0.3 mi
- 6/10Maitland Middle SchoolGrades: 6-8Distance: 2 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 1.6 mi
Schools provided by the listing agent
- Elementary: Lakemont Elem
- Middle: Maitland Middle
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,675,200
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,675,200
- Florida
- Orange County
- Winter Park
- 32789
- 1560 WOODLAND AVENUE
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Winter Park Topics
