20744 Windemere Ct, Sterling, VA 20165
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Property image
OFF MARKET

20744 Windemere Ct
Sterling, VA 20165

  • 4 Beds
  • 3.5 Baths
  • 3,838 sqft (on 0.33 acres)

$1,057,700

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,156/mo*
Refinance Your Home

$1,057,700

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $6,156/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,838 sqft
(on 0.33 acres)

Local Information

  • Map ViewExplore the area around 20744 Windemere Ct.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1993
Lot Size
0.33 acres
Living Area
3,838 sqft
Price/Sqft
$276
Parking
Garage

About this House

This single-family home is located at 20744 Windemere Ct, Sterling, VA. 20744 Windemere Ct is in Sterling, VA and in ZIP code 20165. This property has 4 bedrooms, 4 bathrooms and approximately 3,838 sqft of floor space. This property has a lot size of 0.33 acres and was built in 1993.
20744 Windemere Ct, Sterling, VA 20165 is a 4 bedroom, 4 bathroom, 3,838 sqft single-family home built in 1993. It last sold for $665,000 on Jul 1, 2015. It is currently off market. The Trulia Estimate is $1,057,700, with a rent estimate of $4,732/month.

Home Details for 20744 Windemere Ct

Interior Features

Interior Details
BasementAtticTypes of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, WorkshopCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: BrickFoundation Type: ConcreteGardenLawnPorchSprinkler System
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1993Year Updated: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Building

Fitness & Sports
Basketball CourtTennis Court
Community rooms
Fitness Center

Additional Information

Sport Court

Price History for 20744 Windemere Ct

DatePriceEventSource
07/01/2015$665,000Sold
N/A
06/01/2015$664,900PendingAgent Provided
05/30/2015$664,900Listed For SaleAgent Provided

Market trends in Sterling

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$636K
$3.17KMoM
Sale-to-List Price
100.9%
0.3%MoM
Price per sq ft
$311
$2MoM
Available listings
201
16MoM
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Property Tax and Assessment

Year2025
Tax$7,121
Assessment$884,540
Home facts updated by county records

Comparable Sales for 20744 Windemere Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7 Abbey Cir, Sterling, VA
0.30
Single-Family Home
$700,000
06/26/26
4
2.5
2,280
46554 Pebblebrook Pl, Sterling, VA
0.22
Single-Family Home
$855,000
05/15/26
4
4
2,190
20888 Nerine Ct, Sterling, VA
0.33
Single-Family Home
$1,180,000
06/30/26
5
3.5
3,815
20617 Avalon Ct, Sterling, VA
0.28
Single-Family Home
$950,000
07/21/26
4
3
2,955
20622 Langford Ct, Sterling, VA
0.29
Single-Family Home
$820,000
08/20/25
4
2.5
2,348
20893 Nerine Ct, Sterling, VA
0.36
Single-Family Home
$975,000
06/23/26
4
3.5
3,670
20608 Middlecreek Ct, Sterling, VA
0.36
Single-Family Home
$850,000
11/05/25
4
3
2,948
46447 Saffron Ct, Sterling, VA
0.30
Single-Family Home
$975,000
07/15/26
4
3.5
3,423
20687 Smithfield Ct, Sterling, VA
0.33
Single-Family Home
$702,000
12/15/25
3
3.5
2,884
46409 Woodlake Pl, Sterling, VA
0.35
Single-Family Home
$794,000
08/25/25
4
2.5
2,316

Nearby homes

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Assigned Schools

These are the assigned schools for 20744 Windemere Ct.
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 Sterling

At least 387 Trulia users voted on each feature.

  • 89 % Say there are sidewalks

  • 88 % Say it's dog friendly

  • 86 % Say car is needed

  • 77 % Say kids play outside

  • 73 % Say there's holiday spirit

  • 73 % Say yards are well-kept

  • 72 % Say parking is easy

  • 68 % Say it's quiet

  • 66 % Say people would walk alone at night

  • 58 % Say there's wildlife

  • 55 % Say neighbors are friendly

  • 55 % Say they plan to stay for at least 5 years

  • 54 % Say streets are well-lit

  • 54 % Say it's walkable to grocery stores

  • 50 % Say it's walkable to restaurants

  • 34 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Stefanie
    "Super friendly and lots of space for dogs to play and meet other pals. Awesome area, truly awesome. "
    0
    Flag
  • Linamufti
    "We have holiday parties and coffee hours there many community centers and facilities available for use"
    0
    Flag
  • Fdevlin08
    "Great professional class neighborhood and very quiet. Neighbors are respectful and offer help if needed. Everyone maintains their yard and house."
    0
    Flag
  • Julie Carter
    "There’s good paths and baggies for dog waste. Owners are good about using leashes. It is a safe area. "
    0
    Flag
  • Julie Carter
    "It is a safe neighborhood and a good place to raise children. The schools are great and there’s a lot of activities for families. "
    0
    Flag
  • Lilovayass
    "Lowe’s island is very unique location with walking distance to the plaza and very family oriented ! "
    0
    Flag
  • Hbk_gaurav007
    "I work from home, no commute but drives are very good otherwise. A lot of people around here overspeed and jump stop signs/traffic lights. High accident prone area."
    0
    Flag
  • Kamica
    "Traffic can be heavy during peak hours . However, I left for work at 5:30am so I don’t encounter much traffic at that time of the morning. "
    0
    Flag
  • J Porter
    "They have plenty of doggie bag stations. Many people are pet friendly and they are trails/sidewalks all over the neighborhood. "
    1
    Flag
  • J Porter
    "nice neighborhood. Great neighbors. Nice schools. You feel very safe and the neighborhood is clean and well kept. "
    0
    Flag
  • Triston Smith
    "The folks that are here are pretty dog friendly. I’ve not seen people be antagonistic toward them or their owners and they have free reign. "
    0
    Flag
  • Torrance Thomas
    "I always catch my neighbor, walking the dog pooping in my front yard and walking away. Thanks to the ring cam"
    0
    Flag
  • Muzamilmukhtar6
    "Keep them safe and sound and dont move and be nice and nice to animals kind animals love animals no hate"
    2
    Flag
  • Trulia User
    "Friendly neighborhood very nice clothes to Dulles airport 45 to 40 minutes to Washington DC 20 minutes from Alexandria and more"
    0
    Flag
  • Trulia User
    "Countryside community is Safe, convenient with a good school. People in the neighborhood is very friendly. "
    0
    Flag
  • Besa N.
    "I love Sterling you can find anything you need schools are great and family oriented people! Highly recommended "
    8
    Flag
  • Nicholas R.
    "Very pet friendly. Lots of awesome dogs and their owners are always friendly. Plenty of waste baskets with bags too. "
    0
    Flag
  • Handoko S.
    "w&od trail is a fun place to exercise, casual walk and biking where you can access to the local brewey and cafe"
    1
    Flag
  • Bobbonnette
    "There are lots of families, parks and recreation centers, close to shopping, churches and schools. There are some lower income units in area where I live. "
    0
    Flag
  • Nino1031
    "pools, trails, parks, tennis courts, basketball, and playgrounds. this has it all. love my neighborhood."
    0
    Flag
  • Dmspiv7
    "It is quite and peaceful and everyone is friendly and helpful. Lots of Community things to do. The schools are great. "
    1
    Flag
  • Milleram88
    "Amazing neighborhood for raising children, great schools, and awesome for those who want a little getaway from the hustle and bustle of northern VA"
    0
    Flag
  • KIESHIA B.
    "it's nice and it is extremely close to shops, shopping mall and restaurants. it is quiet and seems pretty safe. "
    1
    Flag
  • Kevin B.
    "This is a very kid friendly neighborhood. Plenty of kids play here safely. Schools are nearby. Playgrounds as well."
    0
    Flag
  • Jinasfun
    "many families and very nice neighbors. community feel. close bars, restaurants and grocery. many parks and nature trails."
    0
    Flag
  • Kevin B.
    "Sterling doesn't have a robust public transportation system. Mainly a system for office commuters in lieu of a commuter rail system. "
    0
    Flag
  • Aaron_lawson2003
    "I've lived in the neighborhood for over a year now and found the amenities plentiful and the people in the area being very dog friendly. "
    0
    Flag
  • Jorge C.
    "Depending on the day, it can be a little longer but not horrible. With the new road construction right now it is putting more of a stress on traffic and time. "
    0
    Flag
  • Gi N.
    "Horrible if you don’t get on the highway by 5:30 am. Difference is an hour additional time if you leave at 7:00 vs 5:30 am"
    4
    Flag
  • Denise W.
    "Ok, considering I’m within a mile of a bus route. The traffic is horrible in the area. ..............."
    2
    Flag
  • Imthenachoman
    "Great suburban community for young families or grandparents. Average schools. No traffic. Diverse community. "
    0
    Flag
  • Ibrahim A. B.
    "There are many nice people here and it is mostly quiet, peaceful, tranquil and people often just mind their own lives...(:"
    0
    Flag
  • Ktiglg04
    "This neighborhood is where I grew up and it has continued to be a family friendly place throughout the years."
    0
    Flag
  • Sidselita76
    "This is a safe area, close to everything. It has safe and good schools. There is a couple of parks around but also stores! Like Walmart or costo!"
    0
    Flag
  • Gwyncan
    "We’ve live here almost 5 years, we love it here. Very well managed community with awesome maintenance team. Snow removal is especially nice. They pick up trash out our door daily. We love having a large balcony and our own garage too."
    7
    Flag
  • Kyle P.
    "Sterling used to be a real nice place live but then MS-13 moved in now they have a lot of games and your kids get in trouble I have a 15 year old son we got to a fight at school and is now on probation for it he was getting bored I stood up to the bully and the bully won "
    0
    Flag
  • Jona F.
    "I have lived for three years and I think a great place .. with much tranquility .. and areas to enjoy with family hosts"
    1
    Flag
  • Stoorai
    "Education, human values, mixed race, gender, age. Everyone is very friendly and welcome each new nighbor when they move in "
    0
    Flag
  • Mon7860
    "This community is good. People are very friendly. We have sidewalk, car parking. But less groceries.little more traffic as well, anyways I feel really good."
    0
    Flag
  • Couragesoccer
    "Nothing special right now it’s a transnational neighborhood. Nothing close expect basic chains zzzzzz"
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

102 pet-friendly rentals in Sterling, VA

Explore by feature - Garage

94 rentals with a garage in Sterling, VA

Explore by feature - Air Conditioning

149 rentals with air conditioning in Sterling, VA

Explore by feature - Pool

104 rentals with a pool in Sterling, VA

Explore by feature - Washer/dryer

117 rentals with a washer/dryer in Sterling, VA

Explore by feature - Outdoor Space

51 rentals with an outdoor space in Sterling, VA

Homes for sale near 20744 Windemere Ct

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Off Market Homes Near 20744 Windemere Ct

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Frequently asked questions about 20744 Windemere Ct

  • What is 20744 Windemere Ct estimated to be worth?
    Trulia's estimated value for 20744 Windemere Ct in Sterling, VA is $1,057,700.
  • What is the price history for 20744 Windemere Ct?
    20744 Windemere Ct in Sterling, VA last sold for $665,000 in July 2015.
  • Is Sterling a buyer's or seller's market?
    Sterling is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Sterling?
    The median sale price in Sterling is $636K. That is up $3.17K from the prior month.
  • Does 20744 Windemere Ct have air conditioning?
    Yes, 20744 Windemere Ct in Sterling, VA has air conditioning.
  • Does 20744 Windemere Ct have laundry facilities?
    Yes, 20744 Windemere Ct in Sterling, VA has in-unit laundry.