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$1,349,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,575 Sq. Ft.
  • Updated 5 hours ago
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Welcome to refined modern living in the heart of Winter Park. Meticulously crafted in 2020, this stunning two story residence showcases four bedrooms, three full baths, and a convenient powder bath. The main level welcomes you with an open concept design bathed in natural light, high ceilings, and seamless flow between the living and dining areas. Perfect for culinary enthusiasts, the chef inspired kitchen is appointed with smart GE Cafe appliances, a gas range, premium quartz countertops, custom cabinetry, and a spacious center island. A private main level home office provides a quiet, dedicated environment for work or study. The first floor primary retreat offers everyday luxury with direct pool access, dual walk in closets, and a spa caliber en suite bath featuring contemporary fixtures, a dedicated linen closet, and an expansive walk in super shower. Upstairs, a versatile open loft serves as an ideal second living room, game room, or media retreat, anchoring three generous guest bedrooms with ample closet space and beautifully finished full bathrooms. Step through sliding glass doors into your private outdoor sanctuary, complete with a fully screened swimming pool featuring a sun shelf, paved patio lounging, and pre plumbing ready for your custom summer kitchen. Situated in one of Central Florida's most desirable residential pockets, this address provides premier Orange County living within comfortable walking distance to top rated Winter Park High School, Glenridge Middle School, and Brookshire Elementary. Located just minutes from the vibrant shopping, dining, and cultural attractions of Park Avenue, this turnkey 2020 build seamlessly unites contemporary luxury with quintessential Winter Park convenience.

Full Property Details for 1939 Woodcrest Dr

General

  • Price: $1,349,000
  • Taxes: $15,488 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6449666
  • Updated: Today (10/17/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Gas Cooktop, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Engineered Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: Irrigation System, Private Mailbox, Sidewalk, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes

Location

  • Area: 32792 - Winter Park/Aloma
  • County: Orange
  • Development Name: 32792 - Winter Park/Aloma
  • Subdivision: ACREAGE
  • Driving Directions: From the intersection of Aloma Avenue and North Lakemont Avenue, head south on South Lakemont Avenue. Turn right onto Woodcrest Drive. Continue straight and the property will be located on your right.
  • Direction Faces: South

School Information

  • Elementary School: Brookshire Elem
  • Middle School: Glenridge Middle
  • High School: Winter Park High

Community

  • Community Name: 32792 - Winter Park/Aloma

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Connected, Natural Gas Connected

Structural Information

  • Exterior Const.: Block, Cement Siding, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,575
  • Sq. Ft. Source: Public Records
  • Year Built: 2020

Lot Features

  • Lot Size (Acres): 0.19
  • Lot Size (Sq. Ft.): 8,238
  • Lot Size: 8238
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Tax Amount: $15,488
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: COMM AT A 4X4 CONC MONUMENT MARKING THENE COR OF THE NW1/4 OF THE NW1/4 OF SEC16-22-30 TH S87-25-32W 663.45 FT TO THENW COR OF LOT 1 BLK A KENILWORTH ESTATESPB W/69 AND THE POB TH S00-29-50E 139.85 FT TH S87-25-32W 58 FT TH N00-29-50W 139.85 FT TO SA ID N SEC LINE TH N87-25-32E 58 FT TO THE POB
  • Flood Zone Info: X
  • APN: 162230000000024
  • Property ID: 162230000000024
  • Block/Lot/Section: A

Listed by La Rosa Realty Premier Llc

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Listing agent

— 1939 Woodcrest Dr —

  • La Rosa Realty Premier Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1939 Woodcrest Dr

School District:Orange County School District
NameGradesDistance
Brookshire Elementary School
2500 Cady Way, Winter Park, FL 32792
PK-50.8 mi
Glenridge Middle School
2900 Upper Park Road, Orlando, FL 32814
6-80.7 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-120.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1939 Woodcrest Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/17/2026
Listed
$1,349,000
81.07%
MLS
8/24/2020
Sold
$745,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1939 Woodcrest Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$15,488
—
$1,073,690
-1%
2025
$15,488
44%
$1,083,730
50%
2024
$10,771
4%
$720,091
3%
2023
$10,388
7%
$699,117
7%
2021
$9,699
-1%
$654,272
-3%
2022
$9,802
1%
$673,900
274%
2021
$9,699
381%
$180,000
46%
2019
$2,017
-43%
$123,624
-42%
2018
$3,524
—
$212,863
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by La Rosa Realty Premier Llc

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1939 Woodcrest Drive, Winter Park, FL 32792 (MLS# O6449666) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 1939 Woodcrest Drive is currently listed for $1,349,000 and was received on October 17, 2026. Want to learn more about 1939 Woodcrest Drive? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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