57 Windswept Way, Saint Augustine, FL 32092
Living Room
Upstairs Loft/Bonus Room
OFF MARKET

$502,300

Trulia Estimate
as of Oct 15, 2026
  • 4 Beds
  • 2.5 Baths
  • 2,400 sqft

57 Windswept Way, Saint Augustine, FL 32092

Home Highlights

Single-Family Home
2,400 sqft
$209/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 57 Windswept Way.
  • Schools1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Beautiful ensuite bathroomPlenty of natural lightPeaceful preserve lotEpoxy garage floor
You'll love this gorgeous 4-bed, 2.5-bath home tucked away on a peaceful preserve lot in Shearwater. The bright and spacious primary suite is on the main floor, complete with a beautiful ensuite bathroom and plenty of natural light.

Upstairs offers two bonus flex spaces perfect for a home office, playroom, or cozy media area. The home also includes an epoxy garage floor, water softener, and washer and dryer for added convenience.

Enjoy all the resort-style amenities Shearwater has to offer: a lazy river, zero-entry pool, lap pool, two clubhouses, parks, walking trails, tennis courts, and a full fitness center with aerobic room.

Built just three years ago, this home feels like new and is completely move-in ready. Don't miss your chance to live in one of the area's most sought-after communities!

12 month minimum lease. Open to longer with no rent increase!

Small dogs allowed.
Owner pays trash pick up, pest control and lawn fertilizer.
Tenant pays all other utilities and lawn maintenance.
All Shearwater amenities are available to renter.
Smoke Free Home
Renters Insurance Required
57 Windswept Way, Saint Augustine, FL 32092 is a 4 bedroom, 3 bathroom, 2,400 sqft single-family home. It last sold for $536,950 on Jan 28, 2022 (17,798% above the $3,000 asking price). More recently, it was listed as a rental in October 2025 with an asking price of $3,400 per month. That rental listing was removed on January 9, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $502,300, with a rent estimate of $3,013/month.

Home Details for 57 Windswept Way

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central Air
Levels, Entrance, & Accessibility
Floors: Carpet, Tile

Exterior Features

Parking & Garage
Parking: Attached, On Site

Building

Community rooms
Fitness Center

Additional Information

Tennis Court(s)

Comparable Sales for 57 Windswept Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
111 WINDSWEPT Way, Saint Augustine, FL
0.05
Single-Family Home
$455,000
02/20/26
4
2.5
2,319 sqft
149 WINDSWEPT Way, Saint Augustine, FL
0.09
Single-Family Home
$508,000
04/28/26
4
2.5
2,342 sqft
126 TILDEN Court, Saint Augustine, FL
0.15
Single-Family Home
$480,000
02/26/26
4
2.5
2,357 sqft
31 TILDEN Court, Saint Augustine, FL
0.14
Single-Family Home
$445,900
02/23/26
4
3
2,027 sqft
137 Tilden Ct, Saint Augustine, FL
0.16
Single-Family Home
$446,000
11/10/25
4
3
2,028 sqft
113 SADLER Court, Saint Augustine, FL
0.19
Single-Family Home
$480,000
06/10/26
4
3
2,027 sqft
201 TILDEN Court, Saint Augustine, FL
0.23
Single-Family Home
$540,000
10/07/26
4
3
2,027 sqft
184 COBALT Lane, Saint Augustine, FL
0.21
Single-Family Home
$494,900
06/26/26
4
3
2,027 sqft
137 TILDEN Court, Augustine, FL
0.18
Single-Family Home
$446,000
11/07/25
4
3
2,027 sqft
21 YARDLEY Court, Saint Augustine, FL
0.26
Single-Family Home
$580,000
09/22/26
4
3
2,461 sqft

Nearby homes

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Around this home

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

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 79% say there's holiday spirit
  • 63% say there are sidewalks
  • 60% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
At least 670 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

  • 70 % Say parking is easy

  • 68 % Say kids play outside

  • 63 % Say there's wildlife

  • 63 % Say there are sidewalks

  • 60 % Say neighbors are friendly

  • 56 % 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

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Great place to raise your family. The kids are kind and friendly and the schools are awesome! Plenty of community parks."
    0
    Flag
  • Trulia User
    "Great place to raise kids "
    0
    Flag
  • 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
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  • 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
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  • 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
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  • Lesley Plott
    "The neighborhood is car dependent but public transportation is easily accessible. The area is growing rapidly."
    0
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  • 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
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  • 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
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  • 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
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  • 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
  • Sabena H.
    "No public transportation. Still a little remote, but is building quickly. Bartram Trail School district."
    2
    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
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  • 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
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  • 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
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  • 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
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LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jan 9, 2026
Source: Zillow Rentals
ListingRemoved
$3,000
Dec 23, 2025
Source: Zillow Rentals
PriceChange
$3,000
Price decreased by 5%
Dec 1, 2025
Source: Zillow Rentals
PriceChange
$3,149
Price decreased by 2%
Nov 19, 2025
Source: Zillow Rentals
PriceChange
$3,200
Price decreased by 3%
Nov 5, 2025
Source: Zillow Rentals
PriceChange
$3,300
Price decreased by 3%

Frequently asked questions about 57 Windswept Way

  • What is 57 Windswept Way estimated to be worth?
    Trulia's estimated value for 57 Windswept Way in Saint Augustine, FL is $502,300.
  • What is the price history for 57 Windswept Way?
    57 Windswept Way in Saint Augustine, FL last sold for $536,950 in January 2022.
  • Is Saint Augustine a buyer's or seller's market?
    Saint Augustine is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Saint Augustine?
    The median sale price in Saint Augustine is $434K. That is up $5K from the prior month.
  • Does 57 Windswept Way have air conditioning?
    Yes, 57 Windswept Way in Saint Augustine, FL has air conditioning.
  • Does 57 Windswept Way have laundry facilities?
    Yes, 57 Windswept Way in Saint Augustine, FL has in-unit laundry.

Homes for rent near 57 Windswept Way

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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