421 COBBLESTONE POINTE DRIVE, Winter Garden, FL 34787
OFF MARKET

421 COBBLESTONE POINTE DRIVE
Winter Garden, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,159 sqft (on 0.38 acres)

$537,900

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $3,801/mo*
Refinance Your Home

$537,900

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $3,801/mo*
Refinance Your Home
3 Beds
2 Baths
2,159 sqft
(on 0.38 acres)

Home Value

Trulia Estimate
$538K
Since last month
Decreased$3K (-0.6%)
Since last year
Increased$4K (+0.8%)
Since last sale
Decreased$1K (-0.2%)
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 +96% in the last 10 years
MonthEstimated value
2026
August 2026$538K
July 2026$541K
June 2026$544K
May 2026$539K
April 2026$535K
March 2026$530K
February 2026$533K
January 2026$534K
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
224 BLACK SPRINGS LANE, Winter Garden, FL
0.06
Single-Family Home
$485,000
04/27/26
3
2
1,916
242 BLACK SPRINGS LANE, Winter Garden, FL
0.07
Single-Family Home
$495,000
05/12/26
3
2
1,909
769 HOME GROVE DRIVE, Winter Garden, FL
0.36
Single-Family Home
$524,500
08/21/26
3
2
2,305
714 HOME GROVE DRIVE, Winter Garden, FL
0.26
Single-Family Home
$525,000
09/18/25
4
2
1,992
615 GROVES END LANE, Winter Garden, FL
0.14
Single-Family Home
$539,000
11/05/25
4
2.5
2,523
279 DOE RUN DRIVE, Winter Garden, FL
0.24
Single-Family Home
$599,000
07/23/26
3
2.5
2,435
414 WRANGLER ROAD, Winter Garden, FL
0.43
Single-Family Home
$675,000
11/03/25
3
2
1,995
503 FIRST CAPE CORAL DRIVE, Winter Garden, FL
0.45
Single-Family Home
$540,000
07/22/26
4
2
2,365
530 SETTING SUN DRIVE, Winter Garden, FL
0.57
Single-Family Home
$535,000
04/09/26
3
2
2,365

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
235 COUNTRY COTTAGE LANE, Winter Garden, FL 34787
0.04
$640,600
3
2
2,238
Off Market
224 BLACK SPRINGS LANE, Winter Garden, FL 34787
0.06
$485,000
3
2
1,916
Recently Sold
218 BLACK SPRINGS LANE, Winter Garden, FL 34787
0.06
$535,600
4
2
2,238
Off Market
242 BLACK SPRINGS LANE, Winter Garden, FL 34787
0.07
$495,000
3
2
1,909
Recently Sold
461 HOME GROVE DRIVE, Winter Garden, FL 34787
0.08
$631,200
4
2.5
2,860
Off Market
615 GROVES END LANE, Winter Garden, FL 34787
0.14
$539,000
4
2.5
2,523
Recently Sold
309 BLACK SPRINGS LANE, Winter Garden, FL 34787
0.15
$536,900
3
2.5
2,529
Off Market
14420 SUNBRIDGE CIRCLE, Winter Garden, FL 34787
0.18
$1,141,100
5
4
4,436
Off Market
648 HOME GROVE DRIVE, Winter Garden, FL 34787
0.19
$459,300
4
2
1,865
Off Market
14516 SUNBRIDGE CIRCLE, Winter Garden, FL 34787
0.20
$875,000
6
4
4,501
Recently Sold
14403 SUNBRIDGE CIRCLE, Winter Garden, FL 34787
0.20
$685,100
3
3
2,812
Off Market

Local Information

  • Map ViewExplore the area around 421 COBBLESTONE POINTE DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2007
Lot Size
0.38 acres
Living Area
2,159 sqft
Price/Sqft
$249
Parking
2 Car Garage
HOA
$115/Monthly

About this House

One or more photo(s) has been virtually staged. LOCATION!!! LOCATION!! LOCATION!! Welcome home to your NEW upgraded 3-bedroom, 2-bathroom home on an OVERSIZED lot just under ½ acre-the largest in the neighborhood. You will LOVE keeping a super clean house with TILE in every room. Conveniently next to the Winter Garden Village with access to Target, Best Buy, Lowe's, Ulta, LA Fitness, and much more.Home features a freshly painted exterior (Aug 2025), all-new high-efficiency, solar-tinted, double-pane vinyl windows (May 2025). Inside, you'll find premium faux wood plank tile flooring and custom baseboards throughout (2021), a fully renovated common bathroom (2025), and a remodeled primary bathroom (2021), both with high-end toilets and fixtures. The kitchen is equipped with appliances less than 2 years old, and the laundry room was upgraded with a sink and custom millwork in 2021. The high-efficiency SEER-rated HVAC system with Variable Frequency Drive was installed in 2021. Enjoy outdoor living with a hurricane-hardened PVC fence featuring steel-embedded concrete posts, a large aluminum swing gate, and a separate man gate. Additional features include Grobe and Moen faucets, a full ADT security system with 2 cameras (service ready to reactivate), a new Ring doorbell (May 2025), and added attic access. Ideally situated near the Turnpike, 429, 408, and West Colonial-this home offers space, style, and unmatched location. Don't miss this opportunity!
421 COBBLESTONE POINTE DRIVE, Winter Garden, FL 34787 is a 3 bedroom, 2 bathroom, 2,159 sqft single-family home built in 2007. It last sold for $538,700 on Oct 10, 2025 (4% below the $559,000 asking price). It is currently off market. The Trulia Estimate is $537,900, with a rent estimate of $2,888/month.
Last check for updates: about 18 hours ago
Listed by Erica Diaz, (407) 897-5400
HOMEVEST REALTY, (407) 897-5400
Paul Duhon, (407) 446-4127
HOMEVEST REALTY, (407) 897-5400
Bought with: Jared Jones, PA, (407) 906-5000, EXP REALTY LLC, (407) 375-9142
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6342570
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

Home Details for 421 COBBLESTONE POINTE DRIVE

Interior Features

Interior Details
Number of Rooms: 5Types of Rooms: Primary Bedroom, Dining Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2159 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Phone Available, Public, Street Lights, Underground Utilities, Water ConnectedAppliances: Convection Oven, Disposal, Electric Water Heater, Microwave, RefrigeratorDisposalLaundry: Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Double Pane Windows, ENERGY STAR Qualified Windows, RodsFlooring: TileCommon Walls: Corner Unit
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Patio, Rear PorchFencing: Stone, VinylVegetation: Fruit TreesExterior: Garden, Lighting, Other, Private Mailbox, SidewalkFoundation: SlabGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener
Frontage
Road Frontage: Street Dead-EndRoad Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 11

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: StuccoNot a New ConstructionNo Additional Parcels
Property Information
Condition: CompletedParcel Number: 262227166000010

Price & Status

Price
List Price: $559,000
Status Change & Dates
Off Market Date: Fri Sep 26 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER GARDENCommunity: COBBLESTONE OF WINTER GARDEN
School Information
Elementary School: Maxey ElemJr High / Middle School: SunRidge MiddleHigh School: West Orange High

Building

Building Area
Building Area: 2832 Square Feet

Community

Community Features: Deed Restrictions, Gated Community - No Guard, SidewalksNot Senior Community

HOA

HOA Fee Includes: OtherHOA Name: Aspire Community Management/ MauriceHOA Phone: 407-614-6144Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $115/Monthly

Lot Information

Lot Area: 0.38 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6342570Back On Market Date: Mon Sep 22 2025Showing Considerations: Pet(s) on PremisesShowing Requirements: Appointment Only, Call Agent 2, Gate Code Required, ShowingTimeUniversal Property Id: US-12095-N-262227166000010-R-N

Additional Information

HOA Amenities: Gated

Price and Tax history

DateEventPrice
Oct 10, 2025
Source: Stellar MLS #O6342570
Sold
$538,700
Sep 29, 2025
Source: Stellar MLS #O6342570
Pending
$559,000
Sep 22, 2025
Source: Stellar MLS #O6342570
PendingToActive
$559,000
Sep 18, 2025
Source: Stellar MLS #O6342570
Pending
$559,000
Sep 10, 2025
Source: Stellar MLS #O6342570
Listed For Sale
$559,000

Market trends in Winter Garden

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$583K
$3.33KMoM
Sale-to-List Price
98.3%
0.2%MoM
Price per sq ft
$254
$3MoM
Available listings
760
4MoM

Around this home

What Locals Say about Winter Garden

At least 513 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say there are sidewalks

  • 86 % Say car is needed

  • 83 % Say parking is easy

  • 81 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 76 % Say it's quiet

  • 75 % Say streets are well-lit

  • 74 % Say people would walk alone at night

  • 72 % Say yards are well-kept

  • 61 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 54 % Say there's wildlife

  • 50 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • jhp331
    "A rated schools and lots to do for families "
    0
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  • Trulia User
    "Its great to live this area we have market and restauran near us . We can walk when we want in our neighboorhood. We have parks schools near us …"
    0
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  • Amanda
    "Great safe area for all ages and diversity. Good schools, lots of shopping, dining, nearby and more coming."
    0
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  • Ypgs9v7hpd
    "It is a nice area and the schools are nice. It is good area to raise children away from the tourists area and the city ."
    0
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  • Ypgs9v7hpd
    "The only thing that is unique about this neighborhood is the people that are friendly and the kids get along great. The only downside of living here in Wintergarden is it’s not enough places to go out to eat and it is not enough places for kids to hang out or teenagers to hang out and the closest place for teenagers to hang out is at the Wintergarden Grove area where you have to take off the exit 9, which I think that’s a bit too far for them to hang out when they can remain closer, it would be better if they had a place to hang out within the neighborhood. Also, Price is over here for a living is very high so if you’re not making a decent amount of money, it is expensive even the apartments that are surrounding it. It’s expensive.."
    0
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  • Emilye Chasen
    "Downtown events occur all the time. Christmas, Halloween, 4th of July etc. Santa comes down my street"
    1
    Flag
  • Ypgs9v7hpd
    "I’ve living here for the last 3 yrs. It’s nice area, people are nice. It’s nice area to raise your family there."
    0
    Flag
  • Heather Kotyk
    "I work near the airport and the commute using the turnpike and I4 is about 25-30 minutes. Traffic is usually manageable and continuously is moving "
    0
    Flag
  • Erin
    "There are many families in the neighborhood, a great playground and an A rated school nearby. There’s also a grocery store and pharmacy conveniently within a mile. "
    0
    Flag
  • Maria Rojas
    "Great place to have a family, lots of parks and activities for kids. Amazing schools and the community is very united. Most communities have hoa "
    0
    Flag
  • Rosa Aguilar
    "There’s lots of places, activities, parks, trails to take kids. There’s also lots of churches with daycare and city programs for children to take part in."
    0
    Flag
  • Andres.toro
    "Mostly all good schools. A lot of parks (and a few others upcoming) and services are increasing in availability. "
    0
    Flag
  • Logan Mahalek
    "The historic area of downtown winter garden boasts local shops and restaurants and also hosts a farmers market every weekend. There is also plenty of name brands within 15 minutes "
    0
    Flag
  • Cfbranf3rd
    "I’m don’t have a commute, as I’m retired. I’m in Cypress Reserve, and Avalon Road can be a nightmare at school drop off/pick up times."
    0
    Flag
  • Kelly
    "Beautiful, safe & friendly area. Winter Garden is a great place to raise a family! This is a very active area with tons of activities. Lots of wildlife & opportunities to get in touch with nature. Big, beautiful Florida birds and animals all around. Great restaurants too! "
    0
    Flag
  • Geisha
    "In Winter Garden for the area's of Horizon West, Hamlin, Summerlake, Waterleight, The Grove is amazing is like living in a perfect community bubble completely recomend"
    0
    Flag
  • Catherine Law
    "There is a private lake side park and a bbq area. Dogs poop trash and bags available. Dogs need to be on leash all the time. No many houses are fenced. "
    0
    Flag
  • Vanessaasantini
    "Wonderful , Safe, beatiful, peaceful, very good, clean, good school, nice and bog city Close to supermarket, gas station "
    2
    Flag
  • Aj2636
    "Halloween costume parties for kids. Community Easter egg hunts. Santa Claus visits on a fire truck. Community watch parties for football games. A soccer field, tennis courts, pickleball courts and basketball courts that allow the neighborhood to enjoy each other’s company. During COVID, we had live music performances in the park."
    0
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  • Cara Conley
    "The area is established and offers. Great amenities within 15 minutes. Clean and safe and welcoming."
    1
    Flag
  • Isaac Peterson
    "Very friendly and helpful neighbors, and the schools are awesome. Very safe "
    2
    Flag
  • Aj2636
    "I’ve lived here for 11 years. It’s close to shopping. The neighborhood feels comfortable with homes far apart from each other. Nice lakes nearby that most neighborhoods have access to. Hospital close-by for emergencies."
    1
    Flag
  • Felton.amanda
    "I lived here for 10 years and just now moving this month. The neighborhood is safe not a lot of crime just a few thieves here and there that steal packages from ppls door steps occasionally."
    1
    Flag
  • Dismiki24
    "Lots of dogs in our neighborhood but many don’t pick up after their dogs. There is a dog park nearby "
    0
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  • Jason M.
    "We see people walk their dogs all the time. The neighborhood has dog stations for easy to dispose of waste. "
    0
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  • Megan E.
    "You will love it! Lots of dog owners and very kind. Lots of doggy poop bag stations as we all know! Great dog parks and trails to go on lovely long walks. "
    13
    Flag
  • Zimmiac
    "Everything is very nice ,and the persons are very nice ,very quite area and the schools are good also,parks and events as well very nice"
    0
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  • Lil D.
    "The people and shops are great. Love all the bike tails as well. Every Saturday they have the farmers market and quite enjoyable to go to and walk around. "
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  • John D. H.
    "average, plenty of bus access, no major traffic issues. normal boring vanilla winter garden. lahdeedah"
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  • Hollister M.
    "Lots of dogs. Most people are very polite about their dogs. People with cats do not keep them indoors and they roam the streets a lot. Most people pick up after their dogs and keep them on leashes."
    0
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  • Jim
    "It’s an amazing place to love. Doesn’t feel like living in Florida. I love living the country and still being close to Disney"
    6
    Flag
  • Cathy
    "Great it is safe and very homey the people are friendly and irs all clean. Very close to shopping places to eat and nice bars "
    5
    Flag
  • Jonathancrespo21
    "We have a neighborhood Facebook page open to everyone and we use this to communicate with each other regularly. We participate in food drives, raise money for special causes, and even sponsor dinners for our local police, firefighters, and nurses."
    0
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  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
    0
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  • Valerie
    "Weekend Farmers Market. Beautiful downtown area. Older historic feeling. Very convenient with shops food and stores. Best city I've lived in since being here in Florida."
    0
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  • jay j
    "People love dogs. They are loving animals that make everyone happy when they see them. Most people now a days have dogs"
    0
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  • Nicola O.
    "Some neighbors don’t clean up after their pets or leave their pets on the balcony barking all night long, but there is a lot of open grass fields and dog stations all throughout. "
    0
    Flag
  • Candy H.
    "Winter Garden Farmer’s Market and shows going on at the Garden Theatre, along with more dog friendly mom and pop places."
    0
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  • Ryanm1995
    "They will love this neighborhood. Bright open space to walk around. We also have a lot of friendly dog in our neighborhood. "
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 421 COBBLESTONE POINTE DRIVE

  • What is 421 COBBLESTONE POINTE DRIVE estimated to be worth?
    Trulia's estimated value for 421 COBBLESTONE POINTE DRIVE in Winter Garden, FL is $537,900.
  • What is the price history for 421 COBBLESTONE POINTE DRIVE?
    421 COBBLESTONE POINTE DRIVE in Winter Garden, FL last sold for $538,700 in October 2025.
  • Is Winter Garden a buyer's or seller's market?
    Winter Garden is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Garden?
    The median sale price in Winter Garden is $583K. That is down $3.33K from the prior month.
  • Does 421 COBBLESTONE POINTE DRIVE have air conditioning?
    Yes, 421 COBBLESTONE POINTE DRIVE in Winter Garden, FL has air conditioning.
  • Does 421 COBBLESTONE POINTE DRIVE have laundry facilities?
    Yes, 421 COBBLESTONE POINTE DRIVE in Winter Garden, FL has laundry facilities.

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