66 WINDLEY Drive, Saint Augustine, FL 32092
FOR SALE

66 WINDLEY Drive
Saint Augustine, FL 32092

  • 4 Beds
  • 3 Baths
  • 2,684 sqft

$585,000

Original price: $590,000
Est. Mortgage $3,596/mo*
Get Pre-Qualified

$585,000

Original price: $590,000
Est. Mortgage $3,596/mo*
Get Pre-Qualified
4 Beds
3 Baths
2,684 sqft
We estimate this home will sell faster than 97% nearby.

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Welcome to this beautiful David Weekley former model home located in the highly sought after Shearwater community. This 4 bedroom, 3 bath home boasts all of the bells and whistles, designed with an inviting open floor plan, ideal for both everyday living and entertaining. The spacious kitchen features granite countertops, stainless steel appliances, and plenty of cabinetry, seamlessly flowing into the main living and dining areas. Tile flooring runs throughout the main living spaces for easy maintenance, while the bedrooms offer cozy carpet for added comfort. Retreat to the oversized primary suite, complete with a luxurious en-suite bathroom featuring a soaking tub, separate shower, and ample space to unwind. Added bonus- There is a whole house water filtration system and reverse osmosis system in the kitchen. Three additional bedrooms and two full baths provide plenty of room for family, guests, or a home office. Curb appeal shines with a pavered driveway, lush landscaping, spacious 3-car garage not to mention you are a short walking distance away from the amenity center and walking trails! Residents enjoy resort-style amenities including a clubhouse, pool with slide, playground, walking trails, sports courts, and more--perfect for an active lifestyle and social living. This home truly has it all--space, upgrades, and an unbeatable community setting. Schedule your private showing today!
We estimate this home will sell faster than 97% nearby.

Home Highlights

Parking
3 Car Garage
Outdoor
Porch, Patio
View
No Info
HOA
$19/Monthly
Price/Sqft
$218
Listed
45 days ago

Home Details for 66 WINDLEY Drive

Active Status

MLS Status: Active

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2684 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Natural Gas Connected, Sewer Connected, Water ConnectedAppliances: Dishwasher, Gas Range, Microwave, Refrigerator, Tankless Water HeaterDishwasherMicrowaveRefrigerator
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Patio
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached,Garage
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Days on Market: 45

Property Information

Year Built
Year Built: 2019
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Not a New ConstructionNot Attached Property
Property Information
Condition: Updated/RemodeledParcel Number: 0100133010

Price & Status

Price
List Price: $585,000Price Per Sqft: $218
Status Change & Dates
Possession Timing: Close Of Escrow

Location

Direction & Address
City: St. AugustineCommunity: Shearwater

Agent Information

Listing Agent
Listing ID: 2136507

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $225/Annually

Lot Information

Lot Area: 10018.8 sqft

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 2136507

Additional Information

HOA Amenities: Pool,Children's Pool,Clubhouse,Fitness Center,Jogging Path,Pickleball,Playground,Tennis Court(s)
Last check for updates: about 5 hours ago
Listing courtesy of TIFFANY BRADDOCK, (904) 608-8503
JASON MITCHELL REAL ESTATE FLORIDA, LLC., (754) 307-0607
Source: realMLS, MLS#2136507
Also Listed on realMLS.

Price History for 66 WINDLEY Drive

DatePriceEventSource
04/13/2026$585,000PriceChange
realMLS #2136507
03/24/2026$590,000Listed For SalerealMLS #2136507
05/06/2021$560,000Sold
realMLS #1075772
03/05/2021$565,400PendingrealMLS #1075772
03/01/2021$565,400PriceChange
realMLS #1075772
02/09/2021$557,400PriceChange
realMLS #1075772
01/28/2021$549,900PriceChange
realMLS #1075772
01/26/2021$559,597PriceChange
realMLS #1075772
12/29/2020$564,247Listed For SalerealMLS #1075772

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Property Tax and Assessment

Year2024
Tax$9,125
Assessment$543,876
Home facts updated by county records

Comparable Sales for 66 WINDLEY Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
45 TOTTEN Way, Saint Augustine, FL
0.07
Single-Family Home
$605,000
02/20/26
4
3
2,756
138 ANCLOTE Way, Saint Augustine, FL
0.15
Single-Family Home
$585,000
06/24/25
4
3
2,678
300 Windley Dr, Saint Augustine, FL
0.21
Single-Family Home
$598,000
12/29/25
4
3
2,896
175 ANCLOTE Way, Saint Augustine, FL
0.20
Single-Family Home
$575,000
12/09/25
3
2.5
2,676
685 WINDLEY Drive, Saint Augustine, FL
0.28
Single-Family Home
$580,000
11/18/25
4
3
2,684
247 BEALE Avenue, Saint Augustine, FL
0.15
Single-Family Home
$450,000
07/31/25
4
3
2,191
162 BLUFFTON Court, Augustine, FL
0.19
Single-Family Home
$510,000
08/06/25
4
2
2,289
99 COBALT Lane, Saint Augustine, FL
0.34
Single-Family Home
$505,000
10/10/25
4
2.5
2,294
49 PERMIT Court, Saint Augustine, FL
0.14
Single-Family Home
$835,000
03/23/26
5
3.5
3,760

Assigned Schools

These are the assigned schools for 66 WINDLEY Drive.
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. "
    0
    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

LGBTQ Local Legal Protections

TIFFANY BRADDOCK, JASON MITCHELL REAL ESTATE FLORIDA, LLC., (754) 307-0607
Agent Phone: (904) 608-8503
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. Data is deemed reliable but is not guaranteed accurate by realMLS.
66 WINDLEY Drive, Saint Augustine, FL 32092 is a 4 bedroom, 3 bathroom, 2,684 sqft single-family home built in 2019. This property is currently available for sale and was listed by realMLS on Mar 24, 2026. The MLS # for this home is MLS# 2136507.