289 Windley Dr, St Augustine, FL 32092
OFF MARKET

289 Windley Dr
St Augustine, FL 32092

  • 4 Beds
  • 3.5 Baths
  • 3,016 sqft

$621,900

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $3,769/mo*
Refinance Your Home

$621,900

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $3,769/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,016 sqft

Homes for sale near 289 Windley Dr

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Apartments for Rent

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Local Information

Map showing home location
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-- mins to
Commute Destination

Description

This elegant 2-story home that is both, welcoming and glamorous. Enjoy lounging on your spacious lanai overlooking the woods with a hot cup of coffee. You will love the private study with stunning 8-foot double glass doors. The gourmet kitchen has an abundance of cabinets and a 36-inch 5 Burner Gas Cooktop and a stunning 36-inch range hood. Luxurious first floor master suite overlooking the woods. 2nd floor bedrooms provide large closets and the guest suite includes a private bath, an ideal arrangement for visiting loved ones. Soaring 2-story family room with double stacked windows to enjoy sunny Florida perfect weather. The 3-car garage offers storage for seasonal décor with a beautiful paver driveway and paver walk up to your front porch. Live your perfect lifestyle in Shearwater
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 289 Windley Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile
Interior Details
Types of Rooms: Walk In Closet, Dining Room, Library
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Windows, Doors, Floors & Walls
Double Paned Windows

Property Information

Year Built
Year Built: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Bungalow

Exterior Features

Exterior Home Features
Exterior: Wood, Cement ConcreteGardenPatioPorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Lot Information

Lot Area: 7200 sqft

Price History for 289 Windley Dr

DatePriceEventSource
09/14/2020$473,885Sold
realMLS #1040464
07/25/2020$493,885PendingAgent Provided
07/15/2020$493,885PriceChange
Agent Provided
05/02/2020$489,885PriceChange
Agent Provided
04/14/2020$487,885PriceChange
Agent Provided
03/22/2020$492,205PriceChange
Agent Provided
03/19/2020$490,645PriceChange
Agent Provided
03/04/2020$490,725PriceChange
Agent Provided
03/03/2020$486,325PendingAgent Provided
02/27/2020$486,325Listed For SaleAgent Provided
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Comparable Sales for 289 Windley Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
300 Windley Dr, Saint Augustine, FL
0.04
Single-Family Home
$598,000
12/29/25
4
3
2,896
138 ANCLOTE Way, Saint Augustine, FL
0.15
Single-Family Home
$585,000
06/24/25
4
3
2,678
162 Bluffton Ct, Saint Augustine, FL
0.10
Single-Family Home
$510,000
08/12/25
4
2
2,648
489 WINDLEY Drive, Saint Augustine, FL
0.18
Single-Family Home
$725,000
07/17/25
4
4
3,202
175 ANCLOTE Way, Saint Augustine, FL
0.13
Single-Family Home
$575,000
12/09/25
3
2.5
2,676
162 BLUFFTON Court, Augustine, FL
0.10
Single-Family Home
$510,000
08/06/25
4
2
2,289
107 MOORINGS Court, Saint Augustine, FL
0.07
Single-Family Home
$450,000
03/27/26
4
2
2,126
77 PALISADE Drive, Saint Augustine, FL
0.27
Single-Family Home
$623,000
07/25/25
4
3.5
2,860
45 TOTTEN Way, Saint Augustine, FL
0.22
Single-Family Home
$605,000
02/20/26
4
3
2,756
71 WOODSONG Lane, Saint Augustine, FL
0.28
Single-Family Home
$650,000
01/23/26
4
3.5
3,179

Assigned Schools

These are the assigned schools for 289 Windley Dr.
View nearby schools on GreatSchools
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 Saint Augustine

At least 668 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 90 % Say car is needed

  • 79 % Say there's holiday spirit

  • 79 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 73 % Say it's quiet

  • 69 % Say parking is easy

  • 68 % Say kids play outside

  • 64 % Say there are sidewalks

  • 63 % Say there's wildlife

  • 59 % Say neighbors are friendly

  • 55 % Say they plan to stay for at least 5 years

  • 53 % Say streets are well-lit

  • 40 % Say there are community events

  • 35 % Say it's walkable to restaurants

  • 31 % Say it's walkable to grocery stores

Learn more about our methodology.
  • Trulia User
    "My neighborhood is attractive and peaceful. It’s green and full of unique houses and friendly people. The only problem is that the traffic is loud and too fast. "
    1
    Flag
  • Trulia User
    "There are nice decorations for each holiday. Other than that it’s just a friendly neighborhood and everyone is friendly and nice. "
    0
    Flag
  • Xavier.rivera11
    "Its very safe. I like it a lot. A lot of families and friendly people. I feel that the area is growing and still needs more activities in the amenity to have a better community "
    1
    Flag
  • Tiffany Villano
    "It’s a great community. Lots of kids and amenities Both close to Jacksonville downtown and Saint Augustine Lots of shopping food commercial lots of restaurants"
    0
    Flag
  • Ilester1862
    "I’ve lived in this neighborhood for over 5 years and love it. Neighbors are great and care for their homes. Very active community. Feel safe."
    1
    Flag
  • Tiffany Villano
    "Schools are decent. Lots to do every where even though people complain that there isnt. There’s more infrastructure to come in the next couple years. Overall quiet calm communities working families Love it here "
    0
    Flag
  • Gregory McCain
    "Lots of space for walking dogs in natural surroundings including small lakes and ponds. Almost everyone uses a leash when walking their dog."
    0
    Flag
  • Trulia User
    "Fish market, veggie stand and a historical park all in walking very short distance and no HOA, intercoastal is right here too"
    0
    Flag
  • Connie Worley
    "It is quiet and off the main road. Neighbors are friendly and polite. There is a good mixture of families, middle aged and retirees. The neighborhood borders a state preserve, so no development will be allowed to the east. It’s only a ten minute drive to the beach."
    0
    Flag
  • Evan Martinez
    "It is a kid friendly neighborhood, the can play unsupervised in culdasac and neighbors watch out for them "
    0
    Flag
  • Qgsdn2x7dk
    " Nice it’s really nice to live here and grow up here very kid friendly and great for walks I love it here"
    0
    Flag
  • Lesley Plott
    "The neighborhood is car dependent but public transportation is easily accessible. The area is growing rapidly."
    0
    Flag
  • kathyafleming
    "From here it’s walkable to work eats and downtown. All the sites are within walking distance. It’s a great community for walking. There is a drawbridge off the island so traffic can back up but it clears fast. It’s a slower pace. "
    0
    Flag
  • 66alice69
    "Busy on week days commute times morning and But easy travel mid day and also weekends best on Sunday"
    0
    Flag
  • Syn2267
    "Having a Friendly dog and pick up after your dog. Master should be able to tame their dog. Not curbing your dog. "
    0
    Flag
  • Nichols
    "We have lived in our neighborhood for four years. Everything that we could want is only a 10 minute drive from us"
    0
    Flag
  • Randi Simmons
    "Trailmark is a family friendly Neighborhood and beautiful community. It is a gem of a place to live! "
    0
    Flag
  • stewart_mendenhall
    "We have many miles of walkways as well as a dog park. There are a lot of people that walk their dogs through our neighborhood and all seem very friendly for the most part. "
    0
    Flag
  • kathyafleming
    "St augustine is growing rapidly. Sometime you wait 15 or 20 minutes in traffic to get downtown. It’s friendly but be prepared to have ups and downs in traffic if you are carting children to snd from activities. "
    0
    Flag
  • Trulia User
    "Principals in downtown is shady af. Staff is smug. No counselors so be mindful of how the school handles students mental health."
    0
    Flag
  • kathyafleming
    "You can walk downtown or to restaurants and brewery’s on the boulevard. It’s got wide quiet residential streets and beautiful trees. People are friendly and everyone knows everyone else. There are amazing landmarks near by, a marina, the lighthouse and the Castillo. "
    0
    Flag
  • kathyafleming
    "Driving is easy but crowded during tourist season. Mornings are generally not bad at all. At 5 pm commute may be crowded x "
    0
    Flag
  • Elizabeth Skidmore
    "There aren’t any open areas to walk with your dog and the community areas do not have doggie bags or disposal areas. Also many of the neighbors post signs that are not dog friendly, even for something as harmless as walking on their grass "
    30
    Flag
  • Renee Hulse
    "Old town USA. You can fish, kayak, hike and swim. The amenities are wonderful and the neighbors are even better"
    6
    Flag
  • Xtxp5qb76x
    "No side walks to scoot around, not many activities organised by the county, libraries don’t offer as much for kids as other states. Even thought great place to raise a family "
    9
    Flag
  • Sabena H.
    "No public transportation. Still a little remote, but is building quickly. Bartram Trail School district."
    2
    Flag
  • Vicki.perry
    "Great for families. Palencia has an elementary school in the community. Lots of places to ride your bike and take walks too."
    4
    Flag
  • Adrianna H.
    "There is No dog park. Which would be nice. But plenty of walk ways and trails to walk. Most of the dogs are very friendly. "
    9
    Flag
  • Peter T.
    "Nice place to live many people very friendly it’s hot though bring sun screen and water but also bug spray because mosquitos are a plenty "
    4
    Flag
  • Adrianna H.
    "Every Friday is Food Truck Friday up at the amenity center. Also kids sporting events and certain holiday activities as well. "
    0
    Flag
  • Srrossi
    "Quiet. Plenty of Law Enforcement in the neighborhood. I trust my neighbors. I enjoy my 2 mile walk through our neighborhood."
    0
    Flag
  • Sarah K.
    "This town is growing as a dog friendly area. There is a lot of neighborhoods and local businesses that allow dogs. Most people are super excited to great your and your pup. "
    1
    Flag
  • Candice S.
    "Christmas stroll and lights display make this town special. Small town feel, fabulous food. History makes this place special."
    1
    Flag
  • Kristen K.
    "You need transportation for this community. There is no public transportation. You average about 30 minutes from most places ."
    0
    Flag
  • Richard D.
    "There are a lot of them in the neighborhood. Many people own dogs, but it is important to pick up after pets and not let them run wild."
    1
    Flag
  • Egbacro
    "Epic theatre is close by, and downtown is about a 10min drive. The beach is located in Anastasia Island which has a lot of activities. the Lighthouse is nearby, and Saint Augustine’s beach is through the 312 bridge. There is an Amphitheatre close by which has many local and international events. Loads of restaurants, wine tasting and bars, shops/boutiques, museums including the Fountain of youth ca be visited."
    1
    Flag
  • Tkendall344
    "Always an event. St Augustine people care regardless if they know you or not the community always come together during crisis or when someone need assistance. We are St. Augustine Strong"
    0
    Flag
  • Terri.degrande
    "No specific events. It’s just a nice, established, well-maintained neighborhood with a cheap home owners association that really is functional, and neighbors are friendly and range widely in age. There’s tons of sidewalks, parks, ponds, wildlife, and very easy access to all types of stores and restaurants. "
    1
    Flag
  • Melvinemccall
    "Neighbors watch out for each other and are always ready to help. Cookouts about twice a year in the neighborhood open to all "
    0
    Flag
  • Jacqueline
    "We do not have many events in our neighborhood we only have quarterly yard sales. The neighbors are friendly and the neighborhood is beautiful."
    0
    Flag

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Homes for rent near 289 Windley Dr

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Off Market Homes Near 289 Windley Dr

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289 Windley Dr, St Augustine, FL 32092 is a 4 bedroom, 4 bathroom, 3,016 sqft single-family home built in 2020. This property is not currently available for sale. 289 Windley Dr was last sold on Sep 14, 2020 for $473,885. The current Trulia Estimate for 289 Windley Dr is $621,900.