404 S Winterbrooke Drive, Olathe, KS 66062
404 S Winterbrooke Drive is a 4-bed, 3.5-bath, 1,660 sq ft home in Havencroft, Olathe, KS, listed at $335,000 on April 15, 2026. HouseLoop Vision saw fireplace, deck and open floor plan in its 31 listing photos (as of November 5, 2026).
$335,000
404 S Winterbrooke Drive, Olathe, KS 66062
About this home
Welcome home to this beautifully updated traditional two-story nestled on a charming, tree-lined street. Offering both comfort and functionality, the main level features two expansive living spaces—perfect for entertaining, relaxing, or creating a flexible layout to suit your lifestyle. The fully updated kitchen shines with modern finishes and flows seamlessly into the living areas, while the beautifully renovated bathrooms add a touch of luxury throughout the home. A true laundry room adds everyday convenience, and the spacious two-car garage provides ample storage. Upstairs, you'll find generously sized bedrooms, including a primary suite with a private en suite bath. Hardwood floors run throughout the home, enhancing its warmth and timeless appeal. Step outside to enjoy the fully fenced, flat backyard—ideal for gatherings, pets, or play. The large unfinished basement offers incredible potential for additional living space, a home gym, or media room. Located just minutes from highway access, shopping, dining, and entertainment hubs in Olathe, and situated within award-winning school boundaries, this home combines classic charm with modern updates in a highly desirable location.
HouseLoop Vision — AI-detected features from listing photos
HouseLoop's photo analysis of 404 S Winterbrooke Drive, Olathe, KS 66062 identified fireplace, deck, open floor plan, big backyard, fenced yard and mature trees, plus 28 more features. The home is a sold 4-bedroom, 3.5-bath, 1,660-square-foot single family residence, MLS #2614612.
Key HouseLoop Vision features
- Open floor plan
- Kitchen island
- White kitchen
- Granite counters
- Shaker cabinets
- Stainless steel appliances
- Breakfast nook
- Updated kitchen
- Kitchen backsplash
- Subway tile backsplash
- Gray countertops
- Fireplace
- Statement lighting
- Brick fireplace
- Staircase
- Gray vanity
- Deck
- Big backyard
- Fenced yard
- Mature trees
- Fire pit
- Paver patio
- Asphalt shingle roof
- Brown exterior
- Concrete driveway
- Siding exterior
- Wood fence
- Wood deck
- Flat lot
- Hardwood floors
- Exposed brick wall
- White trim
- Accent wall
- Attached garage
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary Bedroom
- Level: Second
- Dimensions: 11 × 13
Bedroom 2
- Level: Second
- Dimensions: 9 × 11
Bedroom 3
- Level: Second
- Dimensions: 8 × 9
Bedroom 4
- Level: Second
- Dimensions: 8 × 10
Family Room
- Features: Ceiling Fan(s)
- Level: First
- Dimensions: 11 × 20
Living Room
- Level: First
- Dimensions: 11 × 21
Dining Room
- Level: First
Heating
- Heating: Forced Air
Cooling
- Cooling: Attic Fan, Electric
Appliances
- Laundry: In Basement
Features
- Flooring: Wood
- Basement: Concrete, Sump Pump
- Fireplace features: Family Room
Interior area
- Finished area above ground: 1,660 sqft
- Total interior livable area: 1,660 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Faces Front
Lot
- Size: 0.21 Acres
- Patio & porch: Deck
Construction
Type & style
- Home type: Residential
- Architectural style: Single Family Residence
Materials
- Materials: Shingle Siding
Condition
- Year built: 1968
- Age: 51-75 Years
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Highlights
Outdoor & Lot
- Deck
- Fenced Yard
Interior
- Hardwood Floors
Layout
- Basement
Garage & Parking
- Attached Garage
Financial & listing details
- Annual tax amount: $4,611 / yr
No HOA on this home.
Property tax history
| Year | Property tax | Assessed value |
|---|---|---|
| 2025 | $4,611 | $41,607 |
| 2024 | $4,272 | $38,168 |
| 2023 | $4,180 | $36,547 |
| 2022 | $3,732 | $31,786 |
| 2021 | — | $28,497 |
| 2020 | $3,469 | $27,864 |
| 2019 | — | $26,335 |
| 2018 | — | $22,333 |
| 2017 | $2,635 | $20,734 |
| 2016 | $2,388 | $19,297 |
| 2015 | $2,312 | $18,699 |
| 2013 | $2,125 | $17,296 |
Where it’s at
Nearby schools
Olathe · HouseLoop school ratings
- Tomahawk Elementary School7
- Indian Trail Middle School4
- Olathe North Sr High School8
Price & tax history
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Similar listings and the Olathe market
Look throughout Olathe, Kansas
There are currently 521 homes for sale in Olathe, with 279 under contract. Homes here sell for a median of $470,894 and go under contract in a median of 18 days. This home is priced $135,894 below the Olathe median.
Olathe sits in Johnson County, which covers 31 zip codes and 1,981 homes for sale. Nearby Overland Park runs a higher median at $505,000; Shawnee is lower at $425,000.
Listed by Sold On KC, Inc
Listed April 15, 2026 10:12 PM · Source: Heartland MLS as distributed by MLS GRID · MLS #2614612
HouseLoop last checked:
Listing updated:
Listed for
$335,000
Sale price not disclosed
404 S Winterbrooke Drive, Olathe, KS 66062
HouseLoop user activity
HouseLoop last checked:
About this home
Welcome home to this beautifully updated traditional two-story nestled on a charming, tree-lined street. Offering both comfort and functionality, the main level features two expansive living spaces—perfect for entertaining, relaxing, or creating a flexible layout to suit your lifestyle. The fully updated kitchen…
HouseLoop Vision — AI-detected features from listing photos
HouseLoop's photo analysis of 404 S Winterbrooke Drive, Olathe, KS 66062 identified fireplace, deck, open floor plan, big backyard, fenced yard and mature trees, plus 28 more features. The home is a sold 4-bedroom, 3.5-bath, 1,660-square-foot single family residence, MLS #2614612.
Key HouseLoop Vision features
- Open floor plan
- Kitchen island
- White kitchen
- Granite counters
- Shaker cabinets
- Stainless steel appliances
- Breakfast nook
- Updated kitchen
- Kitchen backsplash
- Subway tile backsplash
- Gray countertops
- Fireplace
- Statement lighting
- Brick fireplace
- Staircase
- Gray vanity
- Deck
- Big backyard
- Fenced yard
- Mature trees
- Fire pit
- Paver patio
- Asphalt shingle roof
- Brown exterior
- Concrete driveway
- Siding exterior
- Wood fence
- Wood deck
- Flat lot
- Hardwood floors
- Exposed brick wall
- White trim
- Accent wall
- Attached garage
Is this your home?
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Estimated Sales Range
HouseLoop Home Value History
Property Details
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary Bedroom
- Level: Second
- Dimensions: 11 × 13
Bedroom 2
- Level: Second
- Dimensions: 9 × 11
Bedroom 3
- Level: Second
- Dimensions: 8 × 9
Bedroom 4
- Level: Second
- Dimensions: 8 × 10
Family Room
- Features: Ceiling Fan(s)
- Level: First
- Dimensions: 11 × 20
Living Room
- Level: First
- Dimensions: 11 × 21
Dining Room
- Level: First
Heating
- Heating: Forced Air
Cooling
- Cooling: Attic Fan, Electric
Appliances
- Laundry: In Basement
Features
- Flooring: Wood
- Basement: Concrete, Sump Pump
- Fireplace features: Family Room
Interior area
- Finished area above ground: 1,660 sqft
- Total interior livable area: 1,660 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Faces Front
Lot
- Size: 0.21 Acres
- Patio & porch: Deck
Construction
Type & style
- Home type: Residential
- Architectural style: Single Family Residence
Materials
- Materials: Shingle Siding
Condition
- Year built: 1968
- Age: 51-75 Years
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Highlights
Outdoor & Lot
- Deck
- Fenced Yard
Interior
- Hardwood Floors
Layout
- Basement
Garage & Parking
- Attached Garage
HOA and Amenities
No HOA on this home.
Nearby schools
GreatSchools rating
- 7Tomahawk Elementary School
- 4Indian Trail Middle School
- 8Olathe North Sr High School
Schools provided by the listing agent
- District: Olathe
- Elementary: Tomahawk
- Middle: Indian Trail
- High: Olathe West
Price history
Tax
- Annual tax amount: $4,611 / yr
Property tax history
| Year | Property tax | Assessed value |
|---|---|---|
| 2025 | $4,611 | $41,607 |
| 2024 | $4,272 | $38,168 |
| 2023 | $4,180 | $36,547 |
| 2022 | $3,732 | $31,786 |
| 2021 | — | $28,497 |
| 2020 | $3,469 | $27,864 |
| 2019 | — | $26,335 |
| 2018 | — | $22,333 |
| 2017 | $2,635 | $20,734 |
| 2016 | $2,388 | $19,297 |
| 2015 | $2,312 | $18,699 |
| 2013 | $2,125 | $17,296 |
Similar listings and the Olathe market
Look throughout Olathe, Kansas
There are currently 521 homes for sale in Olathe, with 279 under contract. Homes here sell for a median of $470,894 and go under contract in a median of 18 days. This home is priced $135,894 below the Olathe median.
Olathe sits in Johnson County, which covers 31 zip codes and 1,981 homes for sale. Nearby Overland Park runs a higher median at $505,000; Shawnee is lower at $425,000.
This home's area
Popular searches in Olathe, KS
Search nearby cities
Olathe, KS homes for sale by zip code for sale · median sale · days to contract
HouseLoop analysis of Heartland MLS data distributed by MLS GRID · trailing 12 months. Median sale price: the median closed price among sold homes in that zip over the same window.
Counties homes for sale · median list price
Listed by Sold On KC, Inc
Listed April 15, 2026 10:12 PM · Source: Heartland MLS as distributed by MLS GRID · MLS #2614612
HouseLoop last checked:
Listing updated:
Insights on 404 S Winterbrooke Drive
This 1968 Havencroft home took 60 days to receive an accepted offer, suggesting moderate market demand relative to subdivision activity. Strong engagement—3,304 page views and 200 saves—indicates genuine buyer interest, likely driven by the home's well-documented outdoor features.
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|---|---|
| 14659 S Garnett Street | Highlands of Kensington |
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| 16639 S Legler Street | Stonebridge Trails |
| 11200 W 169th Street | Mills Ranch |
| 9201 W 145th Street | Wellington Park Parkside |
Frequently asked questions
How much did 404 S Winterbrooke Drive sell for?
404 S Winterbrooke Drive was listed at $335,000 and sold in Jul 2026. Individual sold prices aren't published here, but the surrounding data tells the story: it featured Fireplace, Deck, Open floor plan per HouseLoop Vision.
How fast did 404 S Winterbrooke Drive sell?
It went under contract in 60 days.
What features did this home have?
HouseLoop Vision detected: Fireplace, Deck, Open floor plan, Big backyard, Fenced yard, Mature trees, Kitchen island, Hardwood floors.
What schools serve 404 S Winterbrooke Drive?
This home is in the Olathe school district (Olathe South High School). Verify the exact attendance boundary for this address before relying on it.