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Back 2729 Monticello Drive
Off Market

2729 Monticello Drive

Winston-Salem NC 27106

5
3
2
3377 sq. ft.
0.45 ac.
Single-Family
Last sold for $450,000
Jason BraggJason Bragg, last sold this property on 20 April 2026 after 31 days on market.

Overview

Amazing opportunity in the ever-beautiful Buena Vista neighborhood! This stunning 5-bedroom, 3-bath home at 2729 Monticello is filled with charm and versatility. The main level features a welcoming living room with a beautiful bay window, a stylish kitchen with bar seating, and a spacious dining area flowing into a cozy keeping room—perfect for everyday living and entertaining. The lower level offers a warm and inviting den, laundry room, and an expansive primary bedroom complete with a walk-in closet and spa-like en suite with a soaking tub. The basement apartment adds incredible flexibility with its own kitchenette, full bath, and bedroom; ideal for guests, rental income, or multi-generational living. A rare find full of possibilities! Don’t miss it, schedule your showing today!

Features

5 bedrooms
3 bathrooms
2 carspaces
2 garage spaces
3377 sq. ft. floor area
0.45 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Winston-Salem over the last 12 months, the estimated median property value of 2729 Monticello Drive is $678.5k.

Median value
$678.5k
Estimated value range
$270k - $1.8m
Median days on market
38
Estimated value trend
-25%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Winston-Salem. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 2729 Monticello Drive

2026
Sold
$450,000
20 Apr 2026 by Jason Bragg, of Leonard Ryden Burr Real Estate

Happy sellers in Winston-Salem

68%
68% of sellers in Winston-Salem reported that their sale price either exceeded or met their price expectations.

Winston-Salem stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 8 reviews in Winston-Salem over the last 12 months.

Local market activity for 5 bedroom single-family properties in Winston-Salem

In the last 12 months, 64 five-bedroom single-family properties similar to 2729 Monticello Drive, have been sold.

This represents a 5% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winston-Salem

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Lane Young

Lane Young is a recommended agent for Winston-Salem.  They have 3 local sales and collected 2 local reviews across the last 12 months.

  •   5   (6 reviews)
  •  2 Reviews in Winston-Salem
  •  3 Sales in Winston-Salem
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Zachary Jarvis

Zachary Jarvis is a recommended agent for Winston-Salem.  They have 2 local sales and collected 2 local reviews across the last 12 months.

  •   5   (4 reviews)
  •  2 Reviews in Winston-Salem
  •  2 Sales in Winston-Salem
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Wendy Taylor

Wendy Taylor is an award winning recommended agent for Winston-Salem.  They have 5 local sales and collected 1 local review across the last 12 months.

  •   4.9   (12 reviews)
  •  1 Review in Winston-Salem
  •  5 Sales in Winston-Salem
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Emily Phipps

Emily Phipps is a recommended agent for Winston-Salem.  They have 4 local sales and collected 1 local review across the last 12 months.

  •   5   (3 reviews)
  •  1 Review in Winston-Salem
  •  4 Sales in Winston-Salem
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