1085 WINDLEY Drive, Saint Augustine, FL 32092
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OFF MARKET

1085 WINDLEY Drive
Saint Augustine, FL 32092

  • 5 Beds
  • 4.5 Baths
  • 4,167 sqft

$856,200

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $5,330/mo*
Refinance Your Home

$856,200

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $5,330/mo*
Refinance Your Home
5 Beds
4.5 Baths
4,167 sqft

Local Information

  • Map ViewExplore the area around 1085 WINDLEY Drive.
  • Schools1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2024
Living Area
4,167 sqft
Price/Sqft
$205
Parking
Garage
HOA
$20/Monthly

About this House

Stunning & Immaculate! This 5 bedroom, 4.5 bath home is ''like new!'' Offering over 4,000 sf it was just completed by Dreamfinders last February and is their brilliantly designed Montauk II floor plan which is perfectly situated on a premium preserve lot just around the corner from the Kayak Club! This home is in turn-key condition and features many upgrades! Layout offers spaious and open rooms with 10' ceilings including formal foyer, formal dining room, wine room, butler's pantry, study/office, beautifully appointed kitchen with stainless appliances, spectacular island with dining for 8, fabulous great room with built-ins, grand owner's suite w/ 2 walk-in closets & luxurious bathroom, bedrooms 2, 3 & 4 are downstairs w/br 4 offering flex space as home office or den with electric fireplace and custom built-ins! Upstairs offers large bonus room + 5th bedroom & 4th bath. Extras include attached 3 car garage, superb closet storage & easterly facing covered patio w/ retractable screens! Shearwater is one of St Johns County's premier master-planned communities that offers fabulous resort-style amenities such as miles of sidewalks and trails, parks, swimming and lap pools, 3 story water slide, winding lazy river, tennis, Kayak Club and Fitness Lodge + dog park and community garden! Please be sure to view the photos towards the end of the slide show for pics of these spectacular amenities!
1085 WINDLEY Drive, Saint Augustine, FL 32092 is a 5 bedroom, 5 bathroom, 4,167 sqft single-family home built in 2024. It last sold for $868,500 on May 29, 2025 (3% below the $899,000 asking price). It is currently off market. The Trulia Estimate is $856,200, with a rent estimate of $4,382/month.

Home Details for 1085 WINDLEY Drive

Active Status

MLS Status: Closed

Interior Features

Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4167 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Sewer Connected, Water ConnectedAppliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Gas Cooktop, Microwave, Refrigerator, WasherDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 2
View
No View

Exterior Features

Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Electric Vehicle Charging Station(s),Garage,Garage Door Opener,Off Street
Frontage
Not on Waterfront

Property Information

Year Built
Year Built: 2024
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Not a New Construction
Property Information
Parcel Number: 0100163500

Price & Status

Price
List Price: $899,000
Status Change & Dates
Off Market Date: Tue May 27 2025Possession Timing: Close Of Escrow

Location

Direction & Address
City: St. AugustineCommunity: Shearwater
School Information
Elementary School: Timberlin CreekJr High / Middle School: Switzerland PointHigh School: Beachside

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $236/Annually

Lot Information

Lot Area: 8276.4 sqft

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 2057272
Last check for updates: about 5 hours ago
Listed by TED MILLER, (904) 463-1731
MILLER & COMPANY REAL ESTATE, (904) 388-0000
Bought with: SATHIYAN NATESAN, (210) 649-8282, CENTURY 21 LIGHTHOUSE REALTY, (904) 562-5652
Source: realMLS, MLS#2057272

Price History for 1085 WINDLEY Drive

DatePriceEventSource
05/29/2025$868,500Sold
realMLS #2057272
04/16/2025$899,000PriceChange
realMLS #2057272
01/02/2025$935,000PriceChange
realMLS #2057272
11/18/2024$950,000Listed For SalerealMLS #2057272
03/05/2024$952,304Sold
N/A

Market trends in Saint Augustine

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$418K
$1.67KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$226
$2MoM
Available listings
1897
43MoM
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Property Tax and Assessment

Year2025
Tax$13,138
Assessment$730,567
Home facts updated by county records

Comparable Sales for 1085 WINDLEY Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
66 MAGDALENO Court, Saint Augustine, FL
0.10
Single-Family Home
$779,000
10/30/25
5
4
3,661
638 WINDLEY Drive, Saint Augustine, FL
0.43
Single-Family Home
$855,000
01/16/26
5
4.5
4,031
843 WINDLEY Drive, Saint Augustine, FL
0.25
Single-Family Home
$755,000
10/06/25
4
3.5
3,051
224 TILDEN Court, Saint Augustine, FL
0.18
Single-Family Home
$569,900
01/16/26
5
3.5
2,662
165 SUMTER Place, Saint Augustine, FL
0.19
Single-Family Home
$705,000
05/18/26
4
3
3,167
46 SUMTER Place, Saint Augustine, FL
0.23
Single-Family Home
$780,000
03/06/26
4
3
2,912
49 PERMIT Court, Saint Augustine, FL
0.49
Single-Family Home
$835,000
03/23/26
5
3.5
3,760
102 FELASCO Way, Saint Augustine, FL
0.28
Single-Family Home
$622,500
04/01/26
3
3.5
3,148
52 DADE Court, Saint Augustine, FL
0.39
Single-Family Home
$584,000
01/30/26
5
3.5
2,664

Nearby homes

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Assigned Schools

These are the assigned schools for 1085 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 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 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
    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
  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

362 pet-friendly rentals in Saint Augustine, FL

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Homes for sale near 1085 WINDLEY Drive

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Off Market Homes Near 1085 WINDLEY Drive

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Frequently asked questions about 1085 WINDLEY Drive

  • What is 1085 WINDLEY Drive estimated to be worth?
    Trulia's estimated value for 1085 WINDLEY Drive in Saint Augustine, FL is $856,200.
  • What is the price history for 1085 WINDLEY Drive?
    1085 WINDLEY Drive in Saint Augustine, FL last sold for $868,500 in May 2025.
  • 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 $418K. That is down $1.67K from the prior month.
  • Does 1085 WINDLEY Drive have air conditioning?
    Yes, 1085 WINDLEY Drive in Saint Augustine, FL has air conditioning.
  • Does 1085 WINDLEY Drive have laundry facilities?
    Yes, 1085 WINDLEY Drive in Saint Augustine, FL has in-unit laundry.
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.