Back to Search Results
$750,000sold price Closed

59 Middlesex Drive, Brentwood, MO, 63144

5 bd | 4 ba | 2,723 sq ft | Traditional
Subdivision: York Village Woodlands
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.

Status: Closed · MLS# 26028477 · Listing Courtesy of Compass Realty Group, [email protected]
Properties displayed may be listed or sold by various participants in the MLS.

Approximate location. Get directions

See this home with a live agent, right now

Talk to a MORE, REALTORS® agent, not a referral call center. Why that matters to what you pay

Call now
Calls may be recorded.*
How live works
Your MORE, REALTORS® agent
Trusted local partners

Facts and features

Sold Price

$ 750,000

List Price

$ 699,000

Status

Closed

Days on market

34

MLS#

26028477

Bedrooms

5

Full baths

4

Sq. Ft. Above

2,723

Subdivision

York Village Woodlands

Municipality

Brentwood

School District

Brentwood

County

St Louis

Property Type

Residential

Style

Traditional

Type

Residential

Additional Information

Property Tax (2025)

$8,414

Room Dimensions

Main level
Living Room
23 × 14 ft · 322 sq ft
Mud Room
7 × 5 ft · 35 sq ft
or Pantry
Kitchen
19 × 10 ft · 190 sq ft
Sunroom
19 × 12 ft · 228 sq ft
Screened Porch
Dining Room
14 × 12 ft · 168 sq ft
Bedroom
14 × 11 ft · 154 sq ft
or office
Bedroom 2
13 × 12 ft · 156 sq ft
Upper level
Sitting Room
17 × 7 ft · 119 sq ft
Bedroom 3
17 × 9 ft · 153 sq ft
Bedroom 4
14 × 12 ft · 168 sq ft
Bedroom 5
17 × 11 ft · 187 sq ft
Lower level
Living Room
27 × 14 ft · 378 sq ft
Office
13 × 13 ft · 169 sq ft
Bonus Room
14 × 14 ft · 196 sq ft
Laundry
17 × 8 ft · 136 sq ft

Recent Nearby Sales in 63144

Last 6 closed homes in this zip.

Address Bd/Ba SqFt List Sold Closed
1418 Oriole Place, Brentwood, MO 63144 2/1 864 $144,900 $142,000
98% of ask
Nov 10, 2026
1527 Swallow Drive, Brentwood, MO 63144 3/1 1,107 $174,900 $172,000
98.3% of ask
Nov 5, 2026
1241 Strassner Drive, 1505, Brentwood, MO 63144 2/2 1,040 $269,900 $262,500
97.3% of ask
Nov 4, 2026
8610 Rosalie Avenue, Brentwood, MO 63144 3/1 1,357 $359,900 $347,500
96.6% of ask
Oct 29, 2026
8830 Powell Avenue, Brentwood, MO 63144 4/5 1,778 $550,000 $546,000
99.3% of ask
Oct 28, 2026
2007 Parkridge Avenue, Brentwood, MO 63144 3/2 1,997 $625,000 $625,000
100% of ask
Oct 26, 2026

Price & Listing History

Listed for sale at $699,000
May 14, 2026
Sold for $750,000
Jun 17, 2026 · 107.3% of original list price · 34 days from listing to closing

Every time this home was on the market

Prior listings, expired and canceled listings, days on market, price changes and sold prices from MARIS MLS records.

Loading…

Most MLS-recorded sales near this home

Most closed sales in the last 12 months around this address, listing side and buyer side, plus this listing agent's record.

Loading…

Mortgage Estimator

Estimate your monthly payment. Adjust the sliders below.

Estimated Monthly Payment
$0
Principal & Interest: $0 · Tax: $0 · Ins: $0
Loan Amount: $0
Total Interest: $0
Total of Payments: $0
A MORE, REALTORS® agent will connect you with a trusted local lender.

Prefilled with the national 30 year fixed average, 7.11% as of Nov 12, 2026 (Freddie Mac). Your rate will differ. Estimate only. Not a loan offer. Consult a lender for an accurate quote, including HOA fees, PMI, and current rates.

Video or audio, usually in about 2 minutes. How it works

Other homes for sale nearby

In St Louis, 63144, closest in price to this one. See all in 63144 →
9328 Litzsinger Road, Rock Hill, MO, 63144 - 3 bed, 4 bath home for sale in Rock Hill, MO

$699,900

5 days on STLMLS
9328 Litzsinger Road, Rock Hill, MO, 63144
3bd|4ba|2,158sqft|$324/sqft|5 DOM|2 Story MLS#26071747
8914 W Gateway Heights, 82-503, Richmond Heights, MO, 63144 - 4 bed, 4 bath home for sale in Richmond Heights, MO

$696,900

Price drop $23,000 was $719,900
8918 Gateway Heights Avenue, 82-502, Richmond Heights, MO, 63144 - 3 bed, 4 bath home for sale in Richmond Heights, MO

$692,900

Price drop $26,000 was $718,900
8910 E Gateway Heights, 82-504, Richmond Heights, MO, 63144 - 4 bed, 4 bath home for sale in Richmond Heights, MO

$706,900

Price drop $23,000 was $729,900
8942 Gateway Heights Avenue, 77-501, Richmond Heights, MO, 63144 - 3 bed, 4 bath home for sale in Richmond Heights, MO

$739,900

30 days on STLMLS
9223 Merritt Avenue, Rock Hill, MO, 63144 - 4 bed, 3 bath home for sale in Rock Hill, MO
Pending

$745,000

299 days on STLMLS
9219 TBB Merritt Avenue, Rock Hill, MO, 63144 - 4 bed, 3 bath home for sale in Rock Hill, MO
Pending

$749,900

108 days on STLMLS
9219 TBB Merritt Avenue, Rock Hill, MO, 63144
4bd|3ba|2,275sqft|$330/sqft|108 DOM|2 Story MLS#26014972
9215 Merritt Avenue, Rock Hill, MO, 63144 - 4 bed, 3 bath home for sale in Rock Hill, MO
Pending

$757,900

8 days on STLMLS
9215 Merritt Avenue, Rock Hill, MO, 63144
4bd|3ba|2,275sqft|$333/sqft|8 DOM|2 Story MLS#26015120