5939 BLAKEFORD DRIVE, Windermere, FL 34786
OFF MARKET

$1,521,700

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 3,922 sqft (on 0.39 acres)

5939 BLAKEFORD DRIVE, Windermere, FL 34786

Est. Refi. Payment $10,810/mo*
Refinance Your Home
Currently Off Market - Sold Mar 19, 2025 for $1,555,000

Home Value

Trulia Estimate
$1.52M
Since last month
Decreased$11K (-0.7%)
Since last year
Decreased$19K (-1.2%)
Since last sale
Decreased$32K (-2.1%)
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 +68% in the last 10 years
MonthEstimated value
2026
August 2026$1.52M
August 2026$1.52M
July 2026$1.53M
June 2026$1.54M
May 2026$1.53M
April 2026$1.52M
March 2026$1.5M
February 2026$1.51M
January 2026$1.52M
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
0.14
Single-Family Home
$1,550,000
06/11/26
5
5
3,520
0.06
Single-Family Home
$2,000,000
06/24/26
4
4
3,906
0.09
Single-Family Home
$1,400,000
04/08/26
5
3
3,013
0.39
Single-Family Home
$1,335,000
05/11/26
5
4.5
4,257
0.24
Single-Family Home
$1,375,000
12/17/25
4
4
3,813
0.31
Single-Family Home
$1,675,000
11/12/25
4
4
4,240
0.31
Single-Family Home
$1,650,000
02/17/26
6
4
3,894
0.39
Single-Family Home
$1,600,000
01/13/26
5
4.5
5,704
0.38
Single-Family Home
$1,875,000
07/24/26
4
4.5
4,013
0.28
Single-Family Home
$2,100,000
08/14/26
4
4.5
4,257

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
0.06
$2,000,000
4
4
3,906
Recently Sold
0.05
$1,431,100
4
3
2,996
Off Market
0.09
$2,087,200
4
4
3,985
Off Market
0.10
$1,385,300
5
4
3,530
Off Market
0.09
$1,400,000
5
3
3,013
Recently Sold
0.14
$1,478,300
5
3.5
3,494
Off Market
0.13
$1,065,300
5
3.5
2,976
Off Market
0.14
$1,550,000
5
5
3,520
Recently Sold
0.15
$1,104,900
3
3
-
Off Market
0.14
$988,800
3
2.5
2,614
Off Market
0.16
$1,265,000
4
3
2,937
Recently Sold

Local Information

  • Map ViewExplore the area around 5939 BLAKEFORD DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
0.39 acre lot
3,922 sqft
$388/sqft
Garage
HOA $277/mo

About this House

Beautiful Victorian style home with gorgeous pond and golf views has been nicely updated...and it’s ready for a new family to enjoy!!!! This home is located overlooking the 13th hole in the desirable golf community of Keene's Pointe, home of the Jack Nicklaus designed Golden Bear Club! 24 Hour guard gated community !This home features 5 bedrooms and 5 full baths. Walking into the front door, you will be welcomed by high ceilings, curved stairs with an impressive chandelier and a warm formal and dining area.The chefs size kitchen has been beautifully renovated with top of the line stain steel appliances, a wall oven and a massive island perfect for entertaining. The Primary bedroom is downstairs with a custom designed closet to help organize and a bathroom with a soaking tub and separate shower. Upstairs you will find a very spacious room perfect for a playroom or movie theater and 4 bedrooms with 2 bathrooms. Decorative crown moulding throughout the home. Enjoy swimming in this beautiful pool overlooking the water, and imagine peaceful evenings just sitting on this patio with a glass of wine watching Florida’s beautiful sunsets. "Roof was replaced two years ago, One HVAC Unit was replaced on 2024, Two Gas Water Heaters were replace on 2025"
5939 BLAKEFORD DRIVE, Windermere, FL 34786 is a 5 bedroom, 5 bathroom, 3,922 sqft single-family home built in 1999. It last sold for $1,555,000 on Mar 19, 2025 (6% below the $1,650,000 asking price). More recently, it was listed as a rental in November 2017 with an asking price of $5,500 per month. That rental listing was removed on March 20, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,521,700.
Last check for updates: about 17 hours ago
Listed by Daniela Ledo, (407) 844-5069
B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE, (321) 297-7264
Oscar Rodriguez, (321) 297-7264
B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE, (321) 297-7264
Bought with: Oscar Rodriguez, (321) 297-7264, B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE, (321) 297-7264
Co-Buyer's Agent: Daniela Ledo, (407) 844-5069, B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE, (321) 297-7264
Originating MLS: Osceola
Source: Stellar MLS, MLS#S5115840
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 5939 BLAKEFORD DRIVE

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 5, Bathroom 4, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 3922 Square Feet
Appliances & Utilities
Utilities: Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sprinkler MeterAppliances: Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Range, Range Hood, Refrigerator, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: GasSpa: Heated, In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Ceramic Tile, Hardwood
View
Has a ViewView: Golf Course, Water, Pond

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Patio, ScreenedVegetation: Trees/LandscapedExterior: Balcony, Garden, Irrigation System, LightingFoundation: Block, SlabGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Garage
Pool
Pool: In GroundPool
Frontage
Waterfront: Pond AccessRoad Surface Type: Asphalt, ConcreteNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 65

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Victorian
Building
Construction Materials: HardiPlank TypeNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 292328407400190

Price & Status

Price
List Price: $1,650,000
Status Change & Dates
Off Market Date: Tue Mar 04 2025Possession Timing: Negotiable

Active Status

MLS Status: Sold

Location

Direction & Address
City: WINDERMERECommunity: KEENES POINTE
School Information
Elementary School: Windermere ElemJr High / Middle School: Bridgewater MiddleHigh School: Windermere High School

Building

Building Area
Building Area: 5266 Square Feet

Community

Community Features: Clubhouse, Community Mailbox, Deed Restrictions, Gated Community - Guard, Golf Carts OK, Golf, Park, Playground, SidewalksNot Senior Community
Other
Playground

HOA

HOA Fee Includes: 24-Hour Guard, TrashHOA Name: Leland ManagementHOA Phone: 407-909-9099Association for this Listing: OsceolaHas an HOAHOA Fee: $277/Monthly

Lot Information

Lot Area: 0.39 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: S5115840Water ViewWater View: Water, PondShowing Requirements: Appointment Only, ShowingTimeUniversal Property Id: US-12095-N-292328407400190-R-N

Additional Information

HOA Amenities: Gated,Park,Playground,Recreation Facilities,Security

Price and Tax history

DateEventPrice
Mar 19, 2025
Source: Stellar MLS #S5115840
Sold
$1,555,000
Mar 5, 2025
Source: Stellar MLS #S5115840
Pending
$1,650,000
Feb 20, 2025
Source: Stellar MLS #S5115840
PendingToActive
$1,650,000
Jan 16, 2025
Source: Stellar MLS #S5115840
Pending
$1,650,000
Dec 20, 2024
Source: Stellar MLS #S5115840
PriceChange
$1,650,000
Price decreased by 4%

Market trends in Windermere

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$856K
$41.5K
MoM
Sale-to-List Price
96.8%
0.4%
MoM
Price per sq ft
$297
$5
MoM
Available listings
274
22
MoM

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 271 Trulia users voted on each feature.
  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 80 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "

LGBTQ Local Legal Protections

Frequently asked questions about 5939 BLAKEFORD DRIVE

  • What is 5939 BLAKEFORD DRIVE estimated to be worth?
    Trulia's estimated value for 5939 BLAKEFORD DRIVE in Windermere, FL is $1,521,700.
  • What is the price history for 5939 BLAKEFORD DRIVE?
    5939 BLAKEFORD DRIVE in Windermere, FL last sold for $1,555,000 in March 2025.
  • Is Windermere a buyer's or seller's market?
    Windermere is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windermere?
    The median sale price in Windermere is $856K. That is up $41.5K from the prior month.
  • Does 5939 BLAKEFORD DRIVE have air conditioning?
    Yes, 5939 BLAKEFORD DRIVE in Windermere, FL has air conditioning.
  • Does 5939 BLAKEFORD DRIVE have a pool?
    Yes, 5939 BLAKEFORD DRIVE in Windermere, FL has a pool.

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