1016 Windward Way, Saint Augustine, FL 32080
OFF MARKET

1016 Windward Way
Saint Augustine, FL 32080

  • 3 Beds
  • 2 Baths
  • 1,580 sqft

$449,200

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $2,822/mo*
Refinance Your Home

$449,200

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $2,822/mo*
Refinance Your Home
3 Beds
2 Baths
1,580 sqft

Local Information

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

Description

Enjoy the warm ocean breezes and star-lite nights from this 3 bedroom, 2 bath, Island home. Just minutes to St. Augustine's beautiful beaches and historic downtown, this property offers convenience and comfort and the best of Florida living. Located in one of Anastasia's desirable communities, peace and privacy can be enjoyed from the front door to the back. An open and spacious concept boast of natural light throughout. A split floor plan is perfect for a young family, retirees, or perspective buyers waiting before they decide to purchase a home. A cozy kitchen provides for a quaint breakfast nook overlooking a privacy-fenced backyard. The master bed and bath is quite and secluded, overlooking the peace and serenity of the backyard. Charming is a paved courtyard in the front and a screened lanai in the back. This property provides an enjoyable year-around lifestyle among the delightful palms and citrus. Over 1580 sq. ft of spacious living. Extras include a pantry, washer and dryer, and 2 car garage. Perfect for perspective renters ready to settle into comfortable and relaxing island living. One year lease term. First Month's Rent, Last Month's Rent and Security deposit equal to one month's rent. Applicants must has credit over 600, verifiable rental history & employment and pass a background check.

One year lease term. First Month's Rent, Last Month's Rent and Security deposit equal to one month's rent. Applicants must has credit over 600, verifiable rental history & employment and pass a background check.
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
Patio
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 1016 Windward Way

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Other, Carpet
Appliances & Utilities
DishwasherDryerWasher

Exterior Features

Exterior Home Features
Roof: CompositionExterior: StuccoFoundation Type: ConcretePatio
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 2003Year Updated: 2003
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 5227 sqft

Price History for 1016 Windward Way

DatePriceEventSource
12/27/2022ListingRemovedZillow Rentals
12/15/2022$2,600Listed For RentZillow Rentals
03/07/2003$43,500Sold
N/A
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Property Tax and Assessment

Year2024
Tax$2,520
Assessment$433,829
Home facts updated by county records

Comparable Sales for 1016 Windward Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1021 Windward Way, Saint Augustine, FL
0.03
Single-Family Home
$496,000
01/29/26
3
2
1,512
1109 Compass Row, Saint Augustine, FL
0.07
Single-Family Home
$450,000
12/30/25
3
2
1,580
816 Captains Dr, Saint Augustine, FL
0.06
Single-Family Home
$452,000
09/11/25
3
2
1,424
972 Windward Way, Saint Augustine, FL
0.10
Single-Family Home
$430,000
07/31/25
3
2
1,512
980 Windward Way, Saint Augustine, FL
0.09
Single-Family Home
$390,000
11/21/25
3
2
1,512
984 Windward Way, Saint Augustine, FL
0.09
Single-Family Home
$470,000
08/14/25
3
2
1,660
1121 Compass Row, Saint Augustine, FL
0.09
Single-Family Home
$435,000
05/08/26
3
2
1,443
1116 Compass Row, Saint Augustine, FL
0.06
Single-Family Home
$539,900
02/13/26
3
2
1,580
2372 Commodores Club Blvd, Saint Augustine, FL
0.20
Single-Family Home
$405,000
12/19/25
3
2
1,656
116 Tidal Ln, Saint Augustine, FL
0.22
Single-Family Home
$515,000
12/12/25
3
2
1,540

Nearby homes

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Assigned Schools

These are the assigned schools for 1016 Windward Way.
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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 yards are well-kept

  • 79 % Say there's holiday spirit

  • 74 % Say it's quiet

  • 74 % Say people would walk alone at night

  • 69 % Say parking is easy

  • 68 % Say kids play outside

  • 63 % Say there's wildlife

  • 63 % Say there are sidewalks

  • 60 % 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

Sourced by Trulia users. 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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1016 Windward Way, Saint Augustine, FL 32080 is a 3 bedroom, 2 bathroom, 1,580 sqft single-family home built in 2003. This property is not currently available for sale. 1016 Windward Way was last sold on Mar 7, 2003 for $43,500. The current Trulia Estimate for 1016 Windward Way is $449,200.