5821 Winterhaven Dr, Windcrest, TX 78239
Property image
Property image
OFF MARKET

$277,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,386 sqft

5821 Winterhaven Dr, Windcrest, TX 78239

Est. Refi. Payment $2,011/mo*
Refinance Your Home

Home Value

Trulia Estimate
$278K
Since last month
Decreased$7K (-2.3%)
Since last year
Decreased$18K (-5.9%)
Since last sale
Increased$69K (+33.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +30% in the last 10 years
MonthEstimated value
2026
October 2026$278K
September 2026$281K
August 2026$285K
July 2026$287K
June 2026$289K
May 2026$290K
April 2026$286K
March 2026$285K
February 2026$284K
January 2026$281K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5814 Winterhaven Dr, Windcrest, TX
0.03
Single-Family Home
-
11/04/25
3
2
2,251
9301 Windboro Dr, Windcrest, TX
0.11
Single-Family Home
-
05/15/26
3
2
2,067
9202 Jole Cove, Windcrest, TX
0.03
Single-Family Home
-
01/15/26
3
3
2,401
9113 BONNY BRK, Windcrest, TX
0.08
Single-Family Home
-
08/19/26
3
2.5
2,331
5806 northgap, Windcrest, TX
0.08
Single-Family Home
-
01/23/26
2
2
2,472
641 Richfield Dr., Windcrest, TX
0.21
Single-Family Home
-
04/23/26
3
2
1,960
5830 Bronco, San Antonio, TX
0.20
Single-Family Home
-
06/25/26
4
2.5
2,246
526 Crestway Dr, Windcrest, TX
0.26
Single-Family Home
-
06/03/26
3
2
2,155
9718 Battle Pass, San Antonio, TX
0.27
Single-Family Home
-
04/24/26
5
3
2,527
9834 Dull Knife, San Antonio, TX
0.46
Single-Family Home
-
03/26/26
3
2
1,496

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5825 Winterhaven Dr, Windcrest, TX 78239
0.01
$303,200
3
3
2,456
Off Market
5817 Winterhaven Dr, Windcrest, TX 78239
0.01
$279,600
3
2
2,412
Off Market
9201 Jole Cv, Windcrest, TX 78239
0.02
$254,900
3
2
2,209
Off Market
5813 Winterhaven Dr, Windcrest, TX 78239
0.02
$263,200
3
2
2,093
Off Market
9205 Jole Cv, Windcrest, TX 78239
0.03
$257,500
2
2.5
2,082
Off Market
5818 Winterhaven Dr, Windcrest, TX 78239
0.03
$306,400
3
2
2,421
Off Market
5818 Winterhaven Dr, San Antonio, TX 78239
0.03
-
-
-
-
Off Market
5822 Winterhaven Dr, Windcrest, TX 78239
0.03
$265,100
3
3
2,432
Off Market
5809 WINTERHAVEN DR, Windcrest, TX 78239
0.03
$299,000
3
2.5
2,737
For Sale
5826 Winterhaven Dr, Windcrest, TX 78239
0.03
$265,100
3
2
2,064
Off Market
5814 Winterhaven Dr, Windcrest, TX 78239
0.03
$165,200
3
2
2,251
Off Market
9202 Jole Cove, Windcrest, TX 78239
0.03
-
3
3
2,401
Recently Sold
9206 Jole Cv, Windcrest, TX 78239
0.04
$278,600
3
3
2,151
Off Market
9209 Jole Cv, Windcrest, TX 78239
0.04
$238,800
3
2
1,923
Off Market
5830 Winterhaven Dr, Windcrest, TX 78239
0.04
$255,100
2
2
2,141
Off Market
5803 Winterhaven Dr, San Antonio, TX 78239
0.04
-
-
-
-
Off Market
5810 Winterhaven Dr, Windcrest, TX 78239
0.04
$284,600
3
2
2,478
Off Market
9210 Jole Cv, Windcrest, TX 78239
0.04
$308,700
3
2.5
2,378
Off Market
5805 Winterhaven Dr, Windcrest, TX 78239
0.04
$283,500
3
2
2,615
Off Market
5834 Winterhaven Dr, Windcrest, TX 78239
0.04
$268,600
3
3
2,448
Off Market

Local Information

  • Map ViewExplore the area around 5821 Winterhaven Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1978
2,386 sqft
$116/sqft
Garage

About this House

What's unique:Garden home communitySplit masterHigh cathedral ceilingSpacious homeBamboo floorsWhite wood shutters
Just reduced! Huge open spaced home in a quite neighborhood. Bamboo Floors throughout. New roof, flat top stove/ double oven, side by side refrigerator, built in microwave, all kitchen appliances are stainless steel. Additional double wide refrigerator will remain. White wood shutters remain. High cathedral ceiling with a top rock to bottom fireplace in living area and a split master. Circular breakfast bar, Screened Florida room overlooking a covered patio. Near Randolph and Fort Sam Houston.
5821 Winterhaven Dr, Windcrest, TX 78239 is a 3 bedroom, 2 bathroom, 2,386 sqft single-family home built in 1978. It was last sold on Jun 13, 2023. More recently, it was listed as a rental in June 2013 with an asking price of $1,395 per month. That rental listing was removed on August 23, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $277,500, with a rent estimate of $2,107/month.

Home Details for 5821 Winterhaven Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Other, Hardwood
Interior Details
Number of Rooms: 6Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: BrickFoundation Type: SlabPatioPorch
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1978Year Updated: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 4791 sqft

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Jun 13, 2023
Source: LERA MLS #1685007
Sold
--
May 23, 2023
Source: LERA MLS #1685007
Pending
$295,000
May 11, 2023
Source: LERA MLS #1685007
Contingent
$295,000
May 4, 2023
Source: LERA MLS #1685007
Listed For Sale
$295,000
May 31, 2017
Source: N/A
Sold
--

Market trends in Windcrest

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
44
3MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Windcrest

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 82% say there's holiday spirit
  • 57% say there are sidewalks
  • 54% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
At least 40 Trulia users voted on each feature.

  • 94 % Say yards are well-kept

  • 90 % Say it's dog friendly

  • 88 % Say parking is easy

  • 83 % Say car is needed

  • 82 % Say there's holiday spirit

  • 76 % Say it's quiet

  • 66 % Say people would walk alone at night

  • 63 % Say they plan to stay for at least 5 years

  • 57 % Say there are sidewalks

  • 54 % Say neighbors are friendly

  • 52 % Say streets are well-lit

  • 52 % Say kids play outside

  • 45 % Say there's wildlife

  • 33 % Say there are community events

  • 27 % Say it's walkable to restaurants

  • 26 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Roger M.
    "short commute to airport, Ft Sam Houston, and Randolph AFB. Austin TX is less than an hour away. Can be at the coast in about two hours."
    0
    Flag
  • Lizzyturner
    "The neighborhood I live in is very safe. I exercise at night and feel 100% at ease. Lots of people walking dogs and being friendly."
    0
    Flag
  • JoAnne C.
    "it has gotten better over the past 20 years that we have lived here. Roads, Exits and Access roads hove been improved significantly. Easy access to grocery stores, shopping centers, Walmart, Restaurants and Entertainment Venues. Amusement Parks are very close and easy to get to. "
    1
    Flag
  • Joe M.
    "Nice area. Houses tend to have foundation issues for that area. But very nice older homes. Surrounding area is not great but inside Windcrest seems very safe"
    1
    Flag
  • Jamesestes26
    "citywide Christmas decorating contest, Fourth of July , Memorial Day ,and Fiesta parades , Trunk or Treating, Runs and Bike races."
    1
    Flag
  • Roger
    "lived here 4 years...quite, safe, convenient to downtown, the airport, and a short drive north to Austin..."
    1
    Flag
  • Kristine D. S.
    "Speed limit is a FIRM AND ENFORCES 20 MPH. Quiet streets. Municipal golf course is pretty to walk around in side streets "
    1
    Flag
  • Theodore Mylenbusch
    "Windcrest has been a quiet, welcoming neighborhood since 1975 when I moved to nearby San Antonio. I moved to Windcrest in 2004 and I found the people of Windcrest to be the multi-generational “secret sauce” behind all the continuous armth."
    1
    Flag
  • Destinyvelez
    "On the highway it depends but in windcrest the speed limit is always 20 and everyone always follows it"
    1
    Flag
  • Theodore V. M.
    "I’ve lived here for twelve years. I love this area and the access it affords to major thoroughfares and arteries to move about the city easily."
    1
    Flag
  • Jakob S.
    "Quiet and mostly friendly neighborhood. Some neighbors know each other more than others. Yards are kept up. "
    2
    Flag
  • Rjkendricks
    "It's very safe place to stay. they have there own police department and is not far from stores for shopping."
    1
    Flag
  • Roger M.
    "lived here 3 years....quiet neighborhood...Great support from Windcrest city services...easy access to San Antonio and Austin shopping and eating"
    0
    Flag
  • carrie
    "Windcrest is a great community with a lot to offer. There are parks, walking trails with exercise equipment, an elementary, middle and high school all very close. Shopping, restaurants, banking, transportation is all right here. The lots are larger and the roads maintained. The people and city are friendly. It has local fire, police and ambulance service, that are friendly and quick to respond. "
    1
    Flag
  • Karen U.
    "We love this quiet neighborhood, with plenty of places to walk and run, a pond very close by and caring neighbors. It is like a tiny jewel of a place, with busy streets and people just a few blocks away, yet people, old and young, enjoy the quiet and small town feel of recognizing almost everyone that you pass. There is a vision for a future here too with constant improvements made by the City of Windcrest. It feels very safe and is a lovely place to live no matter what your age. The underground utilities also give it a very clean, open look. We live in a corner lot very close to the Autumn Sunset pond. The elementary school is very nice here in Windcrest, just being completely rebuilt, and we use private school after that so I can't comment on the secondary schools. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5821 Winterhaven Dr

  • What is 5821 Winterhaven Dr estimated to be worth?
    Trulia's estimated value for 5821 Winterhaven Dr in Windcrest, TX is $277,500.
  • What is the price history for 5821 Winterhaven Dr?
    5821 Winterhaven Dr in Windcrest, TX last sold in June 2023.
  • Is Windcrest a buyer's or seller's market?
    Windcrest is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Windcrest?
    Residents describe Windcrest, TX as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Windcrest, TX.
  • Does 5821 Winterhaven Dr have air conditioning?
    Yes, 5821 Winterhaven Dr in Windcrest, TX has air conditioning.
  • How big is the lot at 5821 Winterhaven Dr?
    The lot at 5821 Winterhaven Dr in Windcrest, TX is about 0.11 acres (5,009 sq ft).

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