1508 Winchester Drive is a 4-bed, 4.5-bath, 4,294 sq ft home in Hunters Ridge, Pleasant Hill, MO, listed at $495,000 on May 5, 2026. HouseLoop Vision saw covered front porch, finished basement and traditional style in its 40 listing photos (as of November 15, 2026).
$495,000
1508 Winchester Drive, Pleasant Hill, MO 64080
About this home
Calling all nature lovers, sports enthusiasts, bird watchers, and chefs—this home truly has something for everyone! Nestled on a large, treed lot backing to wooded greenspace, you’ll enjoy peaceful views, abundant wildlife, and a private, scenic setting. The expansive kitchen is designed to impress, offering generous space for both the chef and sous chef—perfect for entertaining or everyday living. For recreation and fun, the property features a 14x85 batting cage with 3 golf chipping areas and 2 putting holes. There is also a 16x25 rec room addition complete with a golf simulator. The main-level owner’s suite provides large bedroom with pampering bath complete with a enlarged tub with jacuzzi jets, while the upper-level private suite with full bath is ideal for guests or a quiet in-home office. The walkout lower level includes two additional bedrooms, a spacious living area, and a third full bath—perfect for extended stays (your guests may never want to leave!).
HouseLoop Vision — AI-detected features from listing photos
HouseLoop's photo analysis of 1508 Winchester Drive, Pleasant Hill, MO 64080 identified covered front porch, finished basement, traditional style, tall ceilings, fireplace and deck, plus 36 more features. The home is a sold 4-bedroom, 4.5-bath, 4,294-square-foot single family residence, MLS #2618421.
Key HouseLoop Vision features
- Open floor plan
- Kitchen island
- Double oven
- Stainless steel appliances
- Breakfast nook
- Wood kitchen cabinets
- Kitchen backsplash
- Raised-panel cabinets
- Finished basement
- Tall ceilings
- Fireplace
- Home office
- Statement lighting
- Tray ceiling
- Stone fireplace
- Wall of windows
- Recessed lighting
- Staircase
- Wood stair railing
- Main-floor primary bedroom
- Double vanity
- White vanity
- Covered front porch
- Deck
- Big backyard
- Mature trees
- Sport court
- Brown roof
- Asphalt shingle roof
- Two-tone exterior
- Concrete driveway
- Mixed exterior materials
- Wood deck
- Concrete patio
- Flat lot
- Traditional style
- Hardwood floors
- Accent wall
- Mixed-finish hardware
- Beige walls
- Carpet
- Attached garage
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Full bathrooms: 4
- 1/2 bathrooms: 1
Heating
- Heating: Natural Gas
Cooling
- Cooling: Electric
Appliances
- Included: Dishwasher, Disposal, Microwave, Refrigerator, Electric Range
- Laundry: Main Level
Features
- Features: Ceiling Fan(s), Custom Cabinets, Pantry, Stained Cabinets, Vaulted Ceiling(s), Walk-In Closet(s)
- Flooring: Carpet, Wood
- Basement: Basement BR, Finished, Full, Walk-Out Access
- Fireplace features: Living Room
- Other rooms: Breakfast Room, Entry, Family Room, Great Room, Main Floor Primary Bedroom, Recreation Room
Interior area
- Finished area above ground: 4,294 sqft
- Total interior livable area: 4,294 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Door Opener, Garage Faces Front
Lot
- Size: 0.41 Acres
- Features: Adjoin Greenspace, Estate Lot, Level, Many Trees
- Patio & porch: Deck, Porch
Construction
Type & style
- Home type: Residential
- Architectural style: Single Family Residence
Materials
- Materials: Brick/Mortar
Condition
- Year built: 1999
- Age: 21-30 Years
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Highlights
Outdoor & Lot
- Deck
- Covered Patio
- Mature Trees
- Acreage
- Adjoins Greenspace
Kitchen
- Walk-in Pantry
Interior
- Hardwood Floors
- Tall Ceilings
- Two-Story Living Room
Layout
- Main Floor Primary
- Basement
- Finished Basement
- Walk-out Basement
- In-law Suite
- Bonus Room
Garage & Parking
- Attached Garage
Financial & listing details
- Annual tax amount: $4,042 / yr
No HOA on this home.
Property tax history
| Year | Property tax | Assessed value |
|---|---|---|
| 2025 | $4,042 | $63,300 |
| 2024 | $4,040 | $56,020 |
| 2023 | $4,011 | $56,020 |
| 2022 | $3,496 | $47,920 |
| 2021 | $3,400 | $47,920 |
| 2020 | — | $40,340 |
| 2019 | — | $40,340 |
| 2018 | $2,508 | $36,200 |
| 2017 | $2,508 | $36,200 |
| 2016 | $2,399 | $34,480 |
| 2015 | $2,399 | $34,480 |
| 2014 | $2,439 | $34,480 |
Where it’s at
Nearby schools
Pleasant Hill · HouseLoop school ratings
- Pleasant Hill Intermediate School6
- Pleasant Hill Middle School6
- Pleasant Hill High School7
Price & tax history
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Similar listings and the Pleasant Hill market
Look throughout Pleasant Hill, Missouri
There are currently 81 homes for sale in Pleasant Hill, with 17 under contract. Homes here sell for a median of $365,000 and go under contract in a median of 26 days. This home is priced $130,000 above the Pleasant Hill median.
Pleasant Hill sits in Jackson County, which covers 51 zip codes and 2,939 homes for sale. Nearby Lee's Summit runs a higher median at $410,000; Kansas City is lower at $299,950 with more inventory.
Listed by ReeceNichols Shewmaker
Listed May 05, 2026 02:00 PM · Source: Heartland MLS as distributed by MLS GRID · MLS #2618421
HouseLoop last checked:
Listing updated:
Listed for
$495,000
Sale price not disclosed
1508 Winchester Drive, Pleasant Hill, MO 64080
HouseLoop user activity
HouseLoop last checked:
About this home
Calling all nature lovers, sports enthusiasts, bird watchers, and chefs—this home truly has something for everyone! Nestled on a large, treed lot backing to wooded greenspace, you’ll enjoy peaceful views, abundant wildlife, and a private, scenic setting. The expansive kitchen is designed to impress, offering generous…
HouseLoop Vision — AI-detected features from listing photos
HouseLoop's photo analysis of 1508 Winchester Drive, Pleasant Hill, MO 64080 identified covered front porch, finished basement, traditional style, tall ceilings, fireplace and deck, plus 36 more features. The home is a sold 4-bedroom, 4.5-bath, 4,294-square-foot single family residence, MLS #2618421.
Key HouseLoop Vision features
- Open floor plan
- Kitchen island
- Double oven
- Stainless steel appliances
- Breakfast nook
- Wood kitchen cabinets
- Kitchen backsplash
- Raised-panel cabinets
- Finished basement
- Tall ceilings
- Fireplace
- Home office
- Statement lighting
- Tray ceiling
- Stone fireplace
- Wall of windows
- Recessed lighting
- Staircase
- Wood stair railing
- Main-floor primary bedroom
- Double vanity
- White vanity
- Covered front porch
- Deck
- Big backyard
- Mature trees
- Sport court
- Brown roof
- Asphalt shingle roof
- Two-tone exterior
- Concrete driveway
- Mixed exterior materials
- Wood deck
- Concrete patio
- Flat lot
- Traditional style
- Hardwood floors
- Accent wall
- Mixed-finish hardware
- Beige walls
- Carpet
- Attached garage
Is this your home?
Claim this home to get your HouseLoop Home Valuation & Buyer Demand Report — real-time buyer demand and an up-to-date value for your home. Free, no obligation, about 3 minutes.
Estimated Sales Range
HouseLoop Home Value History
Property Details
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Full bathrooms: 4
- 1/2 bathrooms: 1
Heating
- Heating: Natural Gas
Cooling
- Cooling: Electric
Appliances
- Included: Dishwasher, Disposal, Microwave, Refrigerator, Electric Range
- Laundry: Main Level
Features
- Features: Ceiling Fan(s), Custom Cabinets, Pantry, Stained Cabinets, Vaulted Ceiling(s), Walk-In Closet(s)
- Flooring: Carpet, Wood
- Basement: Basement BR, Finished, Full, Walk-Out Access
- Fireplace features: Living Room
- Other rooms: Breakfast Room, Entry, Family Room, Great Room, Main Floor Primary Bedroom, Recreation Room
Interior area
- Finished area above ground: 4,294 sqft
- Total interior livable area: 4,294 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Door Opener, Garage Faces Front
Lot
- Size: 0.41 Acres
- Features: Adjoin Greenspace, Estate Lot, Level, Many Trees
- Patio & porch: Deck, Porch
Construction
Type & style
- Home type: Residential
- Architectural style: Single Family Residence
Materials
- Materials: Brick/Mortar
Condition
- Year built: 1999
- Age: 21-30 Years
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Highlights
Outdoor & Lot
- Deck
- Covered Patio
- Mature Trees
- Acreage
- Adjoins Greenspace
Kitchen
- Walk-in Pantry
Interior
- Hardwood Floors
- Tall Ceilings
- Two-Story Living Room
Layout
- Main Floor Primary
- Basement
- Finished Basement
- Walk-out Basement
- In-law Suite
- Bonus Room
Garage & Parking
- Attached Garage
HOA and Amenities
No HOA on this home.
Nearby schools
GreatSchools rating
- 6Pleasant Hill Intermediate School
- 6Pleasant Hill Middle School
- 7Pleasant Hill High School
Schools provided by the listing agent
- District: Pleasant Hill
- Elementary: Pleasant Hill Prim
- Middle: Pleasant Hill
- High: Pleasant Hill
Price history
Tax
- Annual tax amount: $4,042 / yr
Property tax history
| Year | Property tax | Assessed value |
|---|---|---|
| 2025 | $4,042 | $63,300 |
| 2024 | $4,040 | $56,020 |
| 2023 | $4,011 | $56,020 |
| 2022 | $3,496 | $47,920 |
| 2021 | $3,400 | $47,920 |
| 2020 | — | $40,340 |
| 2019 | — | $40,340 |
| 2018 | $2,508 | $36,200 |
| 2017 | $2,508 | $36,200 |
| 2016 | $2,399 | $34,480 |
| 2015 | $2,399 | $34,480 |
| 2014 | $2,439 | $34,480 |
Similar listings and the Pleasant Hill market
Look throughout Pleasant Hill, Missouri
There are currently 81 homes for sale in Pleasant Hill, with 17 under contract. Homes here sell for a median of $365,000 and go under contract in a median of 26 days. This home is priced $130,000 above the Pleasant Hill median.
Pleasant Hill sits in Jackson County, which covers 51 zip codes and 2,939 homes for sale. Nearby Lee's Summit runs a higher median at $410,000; Kansas City is lower at $299,950 with more inventory.
This home's area
Popular searches in Pleasant Hill, MO
Search nearby cities
Pleasant Hill, MO 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 ReeceNichols Shewmaker
Listed May 05, 2026 02:00 PM · Source: Heartland MLS as distributed by MLS GRID · MLS #2618421
HouseLoop last checked:
Listing updated:
Insights on 1508 Winchester Drive
This 1999 single-family home in Hunters Ridge took 36 days to go under contract, slightly outpacing typical market velocity for the subdivision. Strong engagement—4,000 page views and 200 saves—reflected genuine buyer interest, driven by HouseLoop's AI detection of standout features including a deck, fireplace, and pool amenities alongside the home's spacious 4,294 square feet and flat lot. The combination of luxury finishes, desirable condition, and outdoor living appeal resonated with the local buyer pool, signaling solid demand for this property type in the neighborhood.
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|---|---|
| 523 Brookwood Lane | Eagle Glen |
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| 7210 E 165th Street | Richmond Park |
| 1500 Whispering Ridge | Sugarland at Whispering Ridge |
| 4612 SW Gull Point Drive | Raintree Lake |
Frequently asked questions
How much did 1508 Winchester Drive sell for?
1508 Winchester Drive was listed at $495,000 and sold in Jul 2026. Individual sold prices aren't published here, but the surrounding data tells the story: it featured Covered front porch, Finished basement, Traditional style per HouseLoop Vision.
How fast did 1508 Winchester Drive sell?
It went under contract in 36 days.
What features did this home have?
HouseLoop Vision detected: Covered front porch, Finished basement, Traditional style, Tall ceilings, Fireplace, Deck, Open floor plan, Main-floor primary bedroom.
What schools serve 1508 Winchester Drive?
This home is in the Pleasant Hill school district (Pleasant Hill High School). Verify the exact attendance boundary for this address before relying on it.