Sarasota's Premier Homes

1560 WOODLAND AVENUE

WINTER PARK , FL 32789

MLS#: O6389070

$1,850,000

Status: Active
Listing number: O6389070
Listing provided by: CREEGAN GROUP
Listing agent phone: None
Last update: 2 days ago
New on site 3 days ago
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COMSTOCK PARK - Residential

Property

Beds

5

Full Baths

4

1/2 Baths

1

Year Built

1990

Sq.Footage

3,851

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.

Features & Amenities

Interior

  • Other Interior Features

    Built-in Features, Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Stone Counters, Walk-In Closet(s)

  • Total Bedrooms

    5

  • Bathrooms

    4

  • 1/2 Bathrooms

    1

  • Cooling YN

    YES

  • Cooling

    Central Air, Zoned

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Heat Pump

  • Pet friendly

    Yes

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Block, Stucco

  • Other Exterior Features

    Lighting, Rain Gutters

  • Parking

    Boat, Circular Driveway, Common, Driveway, Garage Door Opener, Oversized

  • Patio and Porch Features

    Front Porch, Rear Porch, Screened

  • Pool

    Yes

  • Pool Features

    Gunite, In Ground, Screen Enclosure, Private

  • Waterfront YN

    NO

Area & Lot

  • Lot Features

    Landscaped, Level

  • Lot Size(acres)

    0.27

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

Price

  • Sales Price

    $1,850,000

  • Tax Amount

    $11,736.79

  • Sq. Footage

    3, 851

  • Price/SqFt

    $480

HOA

  • Association

    No

School District

  • Elementary School

    Lakemont Elem

  • Middle School

    Maitland Middle

  • High School

    Winter Park High

Property Features

  • Stories

    2

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    15

  • Water Source

    Public

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Location

County

Orange

Elementary School

Lakemont Elem

Middle School

Maitland Middle

High School

Winter Park High

Listing Courtesy of Chris Creegan , CREEGAN GROUP

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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.

1560 WOODLAND AVENUE

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