Located in the highly sought-after York Village, this charming home sits in one of Brentwood’s most beloved neighborhoods—known for its energy, warmth, and strong sense of community. From cozy firepit nights to festive Halloween parties, life here is filled with connection, tradition, and fun. Picture manicured lawns, blooming flower pots, and friendly neighbors who truly make this street feel like home. Lovingly cared for by its owners for nearly 5 decades, this home is ready for its next chapter—offering a wonderful opportunity to bring your vision to life. Inside, you’ll find fabulous sun-filled spaces, oversized windows, and hardwood floors throughout. The main floor features a rare and desirable layout with two bedrooms and a full bathroom. Enjoy a spacious XL family room with fireplace, a dining room with French doors that open to a large porch, and a kitchen with walk-in pantry and convenient access to the attached two-car garage. Upstairs offers three additional generously sized bedrooms, a versatile flex space perfect for work or play, and a full bathroom. The finished lower level adds even more living spaces and bonus rec room and half bath. Set on an XL corner lot, the outdoor space is just as impressive—featuring a beautiful patio and expansive front and side yards. All of this in an incredible Brentwood location close to everything.
Closed
Listed by: Compass Realty Group • Lizzy Dooley • Contact: 314-680-1426
Bought with: ReeceNichols Real Estate
Price Unknown
59 Middlesex Dr, Saint Louis, MO 63144
5beds
2,723sqft
Single Family Residence
Built in 1946
0.42 Acres Lot
$753,600 Zestimate®
$--/sqft
$4,436 Estimated rent
Home value
$753,600
$708,000 - $799,000
$4,436/mo
Zestimate® history
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List your homeWhat's special
Xl corner lotLarge porchRare and desirable layoutHardwood floors throughoutManicured lawnsBlooming flower potsOversized windows
Zillow last checked:
Listing updated:
Listed by:
Lizzy Dooley 314-680-1426,
Compass Realty Group
Bought with:
Erik C Petersen, 2016041156
ReeceNichols Real Estate
Source: MARIS,MLS#: 26028477
Originating MLS: St. Louis Association of REALTORS
Originating MLS: St. Louis Association of REALTORSFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 2
- 1/2 bathrooms: 2
- Main level bathrooms: 2
- Main level bedrooms: 2
Bedroom
- Description: or office
- Features: Floor Covering: Wood
- Level: Main
- Area: 154
- Dimensions: 14x11
Bedroom 2
- Features: Floor Covering: Wood
- Level: Main
- Area: 156
- Dimensions: 13x12
Bedroom 3
- Features: Floor Covering: Wood
- Level: Upper
- Area: 153
- Dimensions: 17x9
Bedroom 4
- Features: Floor Covering: Wood
- Level: Upper
- Area: 168
- Dimensions: 14x12
Bedroom 5
- Features: Floor Covering: Wood
- Level: Upper
- Area: 187
- Dimensions: 17x11
Bonus room
- Features: Floor Covering: Vinyl
- Level: Basement
- Area: 196
- Dimensions: 14x14
Dining room
- Features: Floor Covering: Wood
- Level: Main
- Area: 168
- Dimensions: 14x12
Kitchen
- Features: Floor Covering: Wood
- Level: Main
- Area: 190
- Dimensions: 19x10
Laundry
- Features: Floor Covering: Vinyl
- Level: Basement
- Area: 136
- Dimensions: 17x8
Living room
- Features: Floor Covering: Wood
- Level: Main
- Area: 322
- Dimensions: 23x14
Living room
- Features: Floor Covering: Carpeting
- Level: Basement
- Area: 378
- Dimensions: 27x14
Mud room
- Description: or Pantry
- Features: Floor Covering: Wood
- Level: Main
- Area: 35
- Dimensions: 7x5
Office
- Features: Floor Covering: Carpeting
- Level: Basement
- Area: 169
- Dimensions: 13x13
Sitting room
- Features: Floor Covering: Wood
- Level: Upper
- Area: 119
- Dimensions: 17x7
Sunroom
- Description: Screened Porch
- Features: Floor Covering: Wood
- Level: Main
- Area: 228
- Dimensions: 19x12
Heating
- Forced Air, Natural Gas
Cooling
- Ceiling Fan(s), Central Air, Electric
Appliances
- Included: Dishwasher, Disposal, Microwave, Electric Oven, Electric Range
- Laundry: In Basement
Features
- Bookcases, Ceiling Fan(s), Pantry, Separate Dining, Walk-In Closet(s)
- Flooring: Carpet, Hardwood
- Basement: Partially Finished,Full,Walk-Out Access
- Number of fireplaces: 2
- Fireplace features: Basement, Gas, Living Room
Interior area
- Total structure area: 2,723
- Total interior livable area: 2,723 sqft
- Finished area above ground: 2,723
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage, Garage Faces Front
- Attached garage spaces: 2
Features
- Levels: One and One Half
- Patio & porch: Patio, Rear Porch, Screened
Lot
- Size: 0.42 Acres
- Dimensions: 154 x 120
- Features: Corner Lot, Level
Details
- Parcel number: 20K130042
- Special conditions: Listing As Is
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Brick
Condition
- Year built: 1946
Utilities & green energy
- Electric: Ameren
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Community & HOA
Community
- Subdivision: York Village Woodlands
HOA
- Has HOA: Yes
- Amenities included: None
- Services included: Common Area Maintenance
- HOA fee: $500 annually
- HOA name: York Village
Location
- Region: Saint Louis
Financial & listing details
- Tax assessed value: $682,900
- Annual tax amount: $8,414
- Date on market: 5/14/2026
- Cumulative days on market: 3 days
- Listing terms: Cash,Conventional,Other
- Ownership: Private
- Electric utility on property: Yes
Price history
| Date | Event | Price |
|---|---|---|
| 6/17/2026 | Sold | -- |
Source:  MARIS #26028477 Report a problem | ||
| 5/17/2026 | Pending sale | $699,000$257/sqft |
Source: MARIS #26028477 Report a problem | ||
| 5/14/2026 | Listed for sale | $699,000$257/sqft |
Source: MARIS #26028477 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,414 +1.1% | $129,760 +7.1% |
| 2024 | $8,325 +2.8% | $121,130 |
| 2023 | $8,095 +1.7% | $121,130 +8.1% |
| 2022 | $7,963 +0.8% | $112,040 |
| 2021 | $7,899 -3.5% | $112,040 -2.6% |
| 2020 | $8,190 +12.4% | $115,080 |
| 2019 | $7,290 | $115,080 +21.5% |
| 2018 | $7,290 | $94,700 |
| 2017 | $7,290 +2.5% | $94,700 +24% |
| 2016 | $7,113 +17.5% | $76,380 |
| 2015 | $6,053 | $76,380 +14% |
| 2014 | $6,053 +14.3% | $66,990 |
| 2013 | $5,295 | $66,990 -27% |
| 2012 | -- | $91,770 |
| 2011 | -- | $91,770 -5.5% |
| 2010 | $6,121 +12.4% | $97,090 |
| 2009 | $5,444 -10.3% | $97,090 -14% |
| 2008 | $6,068 +23.7% | $112,860 |
| 2007 | $4,907 | $112,860 +34.4% |
| 2006 | $4,907 -1.2% | $83,970 |
| 2005 | $4,965 +36% | $83,970 +21.9% |
| 2003 | $3,650 -20.8% | $68,900 +4.3% |
| 2002 | $4,611 +49% | $66,050 -21% |
| 2001 | $3,095 | $83,630 |
Find assessor info on the county website
Neighborhood: 63144
Nearby homes
- $711,1003 bd2 ba2.1k sqft12 York Hills Dr, Saint Louis, MO 63144Off Market
- $898,7004 bd5 ba2.8k sqft55 Middlesex Dr, Saint Louis, MO 63144Off Market
- $844,7003 bd3 ba3k sqft60 Middlesex Dr, Saint Louis, MO 63144Off Market
- $662,8003 bd2 ba2k sqft11 York Hills Dr, Saint Louis, MO 63144Off Market
- $799,1004 bd2 ba3.4k sqft54 Middlesex Dr, Saint Louis, MO 63144Off Market
- $659,1003 bd3 ba1.9k sqft13 York Hills Dr, Saint Louis, MO 63144Off Market
- $687,4004 bd2 ba2.6k sqft26 Southcote Rd, Saint Louis, MO 63144Off Market
- $797,4004 bd2 ba2.7k sqft47 Middlesex Dr, Saint Louis, MO 63144Off Market
Nearby schools
GreatSchools rating
- 9/10McGrath Elementary SchoolGrades: K-5Distance: 0.5 mi
- 9/10Brentwood Middle SchoolGrades: 6-8Distance: 0.4 mi
- 9/10Brentwood High SchoolGrades: 9-12Distance: 0.4 mi
Schools provided by the listing agent
- Elementary: Mcgrath Elem.
- Middle: Brentwood Middle
- High: Brentwood High
Source: MARIS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$753,600
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Estimated market value
$753,600
- Missouri
- Saint Louis County
- Brentwood
- 63144
- 59 Middlesex Dr
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