2227 HOWARD DRIVE, Winter Park, FL 32789
Property image
Property image
FOR SALE
3D VIEW
0.44 ACRES

$1,100,000

  • 3 Beds
  • 2.5 Baths
  • 2,196 sqft (on 0.44 acres)

2227 HOWARD DRIVE, Winter Park, FL 32789

Est. Mortgage $7,695/mo*
Get Pre-Qualified
We estimate this home will sell faster than 100% nearby.

Home Highlights

Single-Family Home
Built in 1958
0.44 acre lot
$501/sqft
Open Parking

Local Information

  • Map ViewExplore the area around 2227 HOWARD DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 2 hours ago
Listing Provided by: Julian Correa, (407) 990-2360
THE SIMON SIMAAN GROUP, (407) 558-1396
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6437639
Also Listed on 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. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
We estimate this home will sell faster than 100% nearby.

Home Details for 2227 HOWARD DRIVE

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2196 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, PublicAppliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family RoomHas a Fireplace
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Tile, HardwoodCommon Walls: Corner Unit
Levels, Entrance, & Accessibility
Stories: 1Levels: OneAccessibility: Accessible Bedroom, Accessible Closets, Accessible Common Area, Accessible Doors, Accessible Entrance, Accessible Full Bath, Visitor Bathroom, Accessible Hallway(s)Floors: Tile, Hardwood
View
Has a ViewView: Water, Lake
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Rear PorchFencing: FencedVegetation: Trees/LandscapedOther Structures: Shed(s), Storage, WorkshopExterior: Irrigation System, Lighting, Private Mailbox, Sauna, Sidewalk, StorageFoundation: SlabNo Private Pool
Parking & Garage
Number of Carport Spaces: 2Number of Covered Spaces: 2Has a CarportNo GarageHas Open ParkingParking Spaces: 2Parking: Driveway
Frontage
WaterfrontWaterfront: Lake Front, Lake Privileges, Fishing PierRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Septic TankWater Body: LAKE FOREST

Days on Market

Cumulative Days on Market: 5Days on Market: 4

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Mid-Century Modern,Ranch
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 172230443601230

Price & Status

Price
List Price: $1,100,000Price Per Sqft: $501

Active Status

MLS Status: Active

Location

Direction & Address
City: WINTER PARKCommunity: LAKE FOREST PARK
School Information
Elementary School: Audubon Park K8Jr High / Middle School: Audubon Park K-8High School: Winter Park High

Agent Information

Listing Agent
Listing ID: O6437639

Building

Building Area
Building Area: 3032 Square Feet

Community

Community Features: Golf Carts OK, ParkNot Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.44 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6437639Water ViewWater View: Water, LakeShowing Considerations: See RemarksShowing Requirements: Appointment Only, Call Listing Agent, ShowingTimeUniversal Property Id: US-12095-N-172230443601230-R-N

Additional Information

Golf Carts OKPark

Around this home

What Locals Say about Winter Park

At least 596 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 80 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
    Flag
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
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  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
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  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
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  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
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  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
    Flag
  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
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  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
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  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
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Market trends in Winter Park

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$451K
$833MoM
Sale-to-List Price
98.0%
0.3%MoM
Price per sq ft
$287
$0MoM
Available listings
368
12MoM

Home Value

Trulia Estimate
$1.04M
Since last month
Decreased$99K (-8.7%)
Since last year
Decreased$41K (-3.8%)
Since last sale
Increased$212K (+25.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +126% in the last 10 years
MonthEstimated value
2026
September 2026$1.04M
August 2026$1.15M
July 2026$1.14M
June 2026$1.12M
May 2026$1.11M
April 2026$1.11M
March 2026$1.1M
February 2026$1.1M
January 2026$1.06M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2823 WRIGHT AVENUE, Winter Park, FL
0.06
Single-Family Home
$865,000
07/27/26
3
2
1,536
2208 HOWARD DRIVE, Winter Park, FL
0.13
Single-Family Home
$845,000
06/12/26
3
2
2,155
2129 FOSGATE DRIVE, Winter Park, FL
0.17
Single-Family Home
$920,000
12/16/25
3
3
2,515
2119 HOWARD DRIVE, Winter Park, FL
0.16
Single-Family Home
$841,500
05/22/26
4
2
2,479
3600 ETHAN LANE, Orlando, FL
0.20
Single-Family Home
$900,000
10/17/25
3
2.5
2,088
2904 PARKLAND DRIVE, Winter Park, FL
0.22
Single-Family Home
$690,000
02/20/26
3
2
1,512
210 E ROCKWOOD WAY, Winter Park, FL
0.30
Single-Family Home
$1,000,500
12/11/25
3
1.5
1,431
1960 WINTER PARK ROAD, Winter Park, FL
0.38
Single-Family Home
$892,500
06/25/26
3
3
1,864
1981 BLUE RIDGE ROAD, Winter Park, FL
0.32
Single-Family Home
$1,115,000
08/28/26
4
2
2,750

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
2228 HOWARD DRIVE, Winter Park, FL 32789
0.05
$2,460,000
4
3.5
3,294
For Sale
2228 HOWARD DRIVE LOT 1, Winter Park, FL 32789
0.05
-
-
-
-
Off Market
2217 HOWARD DRIVE, Winter Park, FL 32789
0.09
$1,094,800
3
2
2,387
Off Market
2823 WRIGHT AVENUE, Winter Park, FL 32789
0.06
$865,000
3
2
1,536
Recently Sold
2823 WRIGHT AVENUE LOT 10, Winter Park, FL 32789
0.06
$865,000
-
-
-
Recently Sold
2361 MULBRY DRIVE, Winter Park, FL 32789
0.11
$2,150,000
4
4
3,130
Recently Sold
674 RANDY LANE, Winter Park, FL 32789
0.12
$953,900
3
2
2,449
Off Market
2837 WRIGHT AVENUE, Winter Park, FL 32789
0.08
$989,200
3
2
2,220
Off Market
2208 HOWARD DRIVE, Winter Park, FL 32789
0.13
$845,000
3
2
2,155
Recently Sold
2341 MULBRY DRIVE, Winter Park, FL 32789
0.13
$499,300
3
1
1,165
Off Market
2335 MULBRY DRIVE, Winter Park, FL 32789
0.13
$477,600
2
1
1,013
Off Market

Price and Tax history

DateEventPrice
Sep 1, 2026
Source: Stellar MLS #O6437639
Listed For Sale
$1,100,000
Oct 20, 2025
Source: Zillow Rentals
ListingRemoved
$4,500
Oct 13, 2025
Source: Zillow Rentals
PriceChange
$4,500
Price decreased by 4%
Sep 30, 2025
Source: Zillow Rentals
PriceChange
$4,700
Price decreased by 1%
Sep 14, 2025
Source: Zillow Rentals
PriceChange
$4,750
Price decreased by 1%

LGBTQ Local Legal Protections

Julian Correa, THE SIMON SIMAAN GROUP, (407) 558-1396
Agent Phone: (407) 990-2360

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Frequently asked questions about 2227 HOWARD DRIVE

  • What is the estimated monthly payment for 2227 HOWARD DRIVE?
    Based on a $1,100,000 list price with 20% down at today's rates, the estimated monthly payment for 2227 HOWARD DRIVE in Winter Park, FL is approximately $7,823 (about $5,795 principal & interest, $1,953 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 2227 HOWARD DRIVE compare to homes in Winter Park?
    2227 HOWARD DRIVE in Winter Park, FL is listed at $1,100,000, about 144% above the $451K median sale price in Winter Park.
  • What do residents say about Winter Park?
    Residents describe Winter Park, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Winter Park, FL.
  • What are the closest schools to 2227 HOWARD DRIVE?
    The closest schools to 2227 HOWARD DRIVE in Winter Park, FL are AUDUBON PARK SCHOOL (Pre-K/Elementary/Middle, rated 10/10), Winter Park High School (rated 7/10).
  • Does 2227 HOWARD DRIVE have air conditioning?
    Yes, 2227 HOWARD DRIVE in Winter Park, FL has air conditioning.
  • Does 2227 HOWARD DRIVE have laundry facilities?
    Yes, 2227 HOWARD DRIVE in Winter Park, FL has in-unit laundry.
2227 HOWARD DRIVE, Winter Park, FL 32789 is a 3 bedroom, 3 bathroom, 2,196 sqft single-family home built in 1958. This property is currently available for sale and was listed by Stellar MLS on Sep 1, 2026. The MLS # for this home is MLS# O6437639.