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$459,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 0.45 Acres
  • 2 Car Garage
  • Updated 12 days ago
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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!

Full Property Details for 2729 Monticello Dr

General

  • Price: $459,000
  • Taxes: $5,639
  • Status: Pending
  • Type: Single Family
  • Source: Triad_MLS
  • MLS ID: 1212897
  • Updated: 3/23/2026
  • Added to Site: 16 day(s) ago

Interior

  • Number of Rooms: 13
  • Interior Features: Built-in Features, Ceiling Fan(s), Dead Bolt(s), Pantry
  • Number of Fireplaces: 3
  • Fireplace(s): Gas Log, Den, Living Room, Playroom
  • Appliances: Dishwasher, Disposal, Double Oven, Exhaust Fan, Gas Water Heater
  • Flooring: Carpet, Tile, Vinyl, Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Main Floor Baths: 2
  • Main - Full Baths: 2
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Dryer Connection, Washer Hookup

Exterior

  • Exterior Features: Garden
  • Patio/Terrace: Yes

Parking

  • Garage Description: Detached Carport
  • Garage Spaces: 2
  • Parking Features: Carport, Driveway, Detached Carport

Location

  • County: Forsyth
  • Subdivision: Buena Vista
  • Driving Directions: From N Stratford, left on Reynolda Rd. Left on Monticello. House on the right.

School Information

  • Elementary School: Whitaker
  • Middle School: Wiley
  • High School: Reynolds

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Forced Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Exterior Const.: Brick, Wood Siding
  • Basement: Yes
  • Basement Desc.: Finished, Basement
  • Drive-In Doors: Insulated Doors
  • Stories/Levels: 2.5
  • Heated/Cooled: 2,623 Sq. Ft.
  • Year Built: 1958

Additional Structures

  • Other Structures: Storage

Lot Features

  • Lot Size (Acres): 0.45
  • Road Maintenance: Public Maintained Road

Financial Considerations

  • Price Per Acre: $1,020,000
  • Tax Amount: $5,639.2

Disclosures and Reports

  • Special Conditions: Owner Sale

Listed by Leonard Ryden Burr Real Estate

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Listing agent

— 2729 Monticello Dr —

  • Leonard Ryden Burr Real Estate

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2729 Monticello Dr

School District:Forsyth County Schools
NameGradesDistance
Whitaker Elementary
2600 Buena Vista Road, Winston-Salem, NC 27104
PK-51.1 mi
Wiley Middle
1400 Northwest Boulevard, Winston-Salem, NC 27104
6-82.1 mi
Reynolds High
301 N Hawthorne Road, Winston-Salem, NC 27104
9-121.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2729 Monticello Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/19/2026
Listed
$459,000
85.08%
MLS
7/28/2009
Sold
$248,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2729 Monticello Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,231
—
$501,600
66%
2024
$4,231
5%
$301,600
—
2023
$4,038
4%
$301,600
—
2021
$3,891
-2%
$301,600
—
2022
$3,962
2%
$301,600
15%
2021
$3,891
7%
$261,200
—
2019
$3,633
5%
$261,200
—
2018
$3,450
—
$261,200
—
2017
$3,450
16%
$261,200
16%
2016
$2,974
2%
$226,000
—
2015
$2,929
3%
$226,000
—
2014
$2,840
1%
$226,000
—
2013
$2,818
—
$226,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Leonard Ryden Burr Real Estate

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2729 Monticello Drive, Winston-Salem, NC 27106 (MLS# 1212897) is a Single Family property with 5 bedrooms and 3 full bathrooms. 2729 Monticello Drive is currently listed for $459,000 and was received on March 19, 2026. Want to learn more about 2729 Monticello Drive? Do you have questions about finding other Single Family real estate for sale in Winston-Salem? You can browse all Winston-Salem real estate or contact a Coldwell Banker agent to request more information.

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