Active Under Contract
Single family home for sale at 2227 Howard Dr, Winter Park, FL 32789 | MLS# O6437639 | Listing updated on 2026-09-28
Photo 1 of Single family home for sale at 2227 Howard Dr, Winter Park, FL 32789 | MLS# O6437639 | Listing updated on 2026-09-28
Photo 2 of Single family home for sale at 2227 Howard Dr, Winter Park, FL 32789 | MLS# O6437639 | Listing updated on 2026-09-28
Photo 3 of Single family home for sale at 2227 Howard Dr, Winter Park, FL 32789 | MLS# O6437639 | Listing updated on 2026-09-28
Photo 4 of Single family home for sale at 2227 Howard Dr, Winter Park, FL 32789 | MLS# O6437639 | Listing updated on 2026-09-28
47+
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Street View

$1,100,000

Monthly Est:$5,475

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,196sqft

2227 Howard Dr, Winter Park, FL 32789

$5,475/moEst:

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  • Single Family Residence

  • Built in 1958

  • $-- HOA

  • 18,991 sqft lot

  • $501/sq.ft

Description

Under contract-accepting backup offers. A rare corner lot in one of Winter Park's most established, increasingly in-demand Lake Forest Park neighborhood. This mid-century home has been meticulously maintained. With beautiful hardwood floors and updated systems throughout, there's nothing left to do but move in.
The lot is the story here. A stunning mature oak anchors the front yard, and the corner position with no north-facing neighbor gives you privacy that's hard to find this close to town. Out back, a covered porch overlooks Lake Forest, plus a private sauna and a large shed built for a workshop, storage, or a future ADU. Quiet, shaded, genuinely peaceful. The kind of
backyard people forget exists in-town.
The street is whisper-quiet and made for evening walks, with Lake Forest views most homes in the area can't touch.
Move in as-is and enjoy a home that's already been cared for the right way. Or use the lot and elevation to add a second story and expand the lake views, or build new entirely. Lake Forest is in the middle of a real transformation, with new luxury construction going up throughout the neighborhood. This lot puts you ahead of that curve - schedule your private viewing today.

  • Houzeo last checked: 7 minutes ago
  • Listing updated: September 28, 2026 at 7:04 pm
  • Listing Provided by: Julian Correa (407) 990-2360 | THE SIMON SIMAAN GROUP (407) 558-1396
  • Source: Stellar MLS-FL | MLS#: O6437639 Stellar MLS-FL

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Orange County

  • City

    Winter Park

  • Neighborhood

    --

  • Year Built

    1958

  • HOA Fees

    -

  • Finished Area

    2,196 sqft

  • Lot Size

    18,991 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6437639

  • MLS Status

    Pending

  • Days on Market

    40

  • Cumulative Days on Market

    24

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

  • Living Room

    Level: First

    Area: 288.00 Square Feet

    Dimensions: 16x18

  • Dining Room

    Level: First

    Area: 180.00 Square Feet

    Dimensions: 12x15

  • Family Room

    Level: First

    Area: 418.00 Square Feet

    Dimensions: 19x22

  • Kitchen

    Level: First

    Area: 196.00 Square Feet

    Dimensions: 14x14

  • Primary Bedroom

    Level: First

    Area: 154.00 Square Feet

    Dimensions: 14x11

  • Bedroom 2

    Level: First

    Area: 132.00 Square Feet

    Dimensions: 12x11

  • Bedroom 3

    Level: First

    Area: 180.00 Square Feet

    Dimensions: 15x12

Interior

  • Heating

    Central

  • Flooring

    Tile, Wood

  • Sewer

    Septic Tank

  • Interior Features

    Ceiling Fans(s), Crown Molding, Split Bedroom, Stone Counters, Thermostat

  • Exterior Features

    Lighting, Private Mailbox, Sauna, Sidewalk, Storage

  • Cooling

    Central Air

  • Appliances

    Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer

Construction

  • Year Built

    Year Built: 1958

  • Home type

    Single Family Residence

  • Construction Materials

    Block, Stucco

  • Foundation Details

    Slab

  • Architectural Style

    Mid Century Modern, Ranch

  • Roof

    Shingle

Utilities & Energy

  • Fireplace Features

    Family Room

  • Laundry Features

    Inside, Laundry Room

  • Security Features

    Security System

  • Utilities

    Bb/hs Internet Available, Public

  • Water Source

    Public

  • Parking Features

    Driveway

Other Features

  • Lot Features

    Corner Lot, City Limits, Oversized Lot, Private

  • Community Features

    Golf Carts Ok, Park

  • Patio And Porch Features

    Covered, Rear Porch

  • Vegetation

    Trees/landscaped

  • Subdivision Name

    Lake Forest Park

Price History

DateEventPrice

09/28/2026

Source: mls_logoStellar MLS-FL #MFRO6437639

Contingent (Active Under Contract)

$1,100,000

$501/sqft

09/01/2026

Source: mls_logoStellar MLS-FL #MFRO6437639

Listed for Sale

$1,100,000 +24344.44%

$501/sqft

10/20/2025

Source: mls_logoStellar MLS-FL #MFRO6315452

Sold

$4,500 -4.26%

$2/sqft

09/29/2025

Source: mls_logoStellar MLS-FL #MFRO6315452

Listed for Sale

$4,700 +4.44%

$2/sqft

09/29/2025

Source: mls_logoStellar MLS-FL #MFRO6315452

Price Decreased

$4,500 -5.26%

$2/sqft

Show more

Nearby Homes

Based on information from Stellar MLS® through Oct 12, 2026, 04:30AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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