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$599,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,341 Sq. Ft.
  • 0.38 Acres
  • Updated 13 hours ago
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Charming cottage in the heart of downtown Southern Pines, complete with a detached apartment and an oversized in-town lot. The main home offers 1,341 square feet with three bedrooms and two full bathrooms, while the separate 664-square-foot apartment features one bedroom and one full bath, ideal for guests, a private retreat, or income-producing potential. Full of classic Southern Pines charm, this inviting property welcomes you with cheerful yellow siding and a timeless white picket fence. Inside, the main cottage features a bright, open living and kitchen area with a breakfast bar, dedicated dining space, and a cozy enclosed front porch that is perfect for morning coffee or relaxing in the evening. The main level includes two guest bedrooms and a full bath with a charming clawfoot tub, while the private primary suite is tucked upstairs with its own full bath. Outside, a spacious patio nestled between the main home and apartment creates the perfect setting for entertaining, complete with a large pergola and fire pit. The detached apartment includes its own kitchen, living area, private bedroom, and full bath, offering excellent flexibility and privacy. Beautiful renovations paired with original character, highlighted by classic brick details and rich wood flooring, create a warm and inviting atmosphere. This one-of-a-kind downtown property is a rare find.

Full Property Details for 745 N May St

General

  • Price: $599,000
  • Taxes: $2,910 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 2253
  • MLS ID: 100561615
  • Updated: 5/13/2026
  • Added to Site: 55 day(s) ago

Interior

  • Number of Rooms: 6
  • Interior Features: Master Downstairs, Kitchen Island, Pantry
  • Appliances: Electric Oven, Electric Cooktop, Washer, Refrigerator, Dryer, Dishwasher, Water Purifier
  • Flooring: Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Living Area

Other Rooms

  • Laundry: Dryer Hookup, Washer Hookup, Laundry Room

Additional Information

  • Security/Safety: Smoke Detector(s)

Exterior

  • Porch/Patio/Deck: Open, Enclosed, Patio, Porch

Parking

  • Parking Features: Additional Parking, Gravel, On Site

Location

  • County: Moore
  • Subdivision: Downtown
  • Driving Directions: House is located on N May Street between E New Jersey and E Delaware Ave.

School Information

  • High School District: Moore County Schools
  • Elementary School: Southern Pines Primary
  • Middle School: Crain's Creek Middle
  • High School: Pinecrest High

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Air
  • Heating Type: Electric, Forced Air, Heat Pump, Natural Gas

Utilities

  • Sewer: Municipal Sewer, Town of Southern Pines
  • Water: Public
  • Utility Description: Sewer Available, Water Available

Structural Information

  • Structure Type: Wood Frame, Stick Built
  • Construction: Vinyl Siding, Wood Frame
  • Basement Desc.: Interior Entry, Unfinished2
  • Roof: Metal
  • Entry Floor Number: 1
  • Square Feet: 1,341
  • Year Built: 1925

Additional Structures

  • Other Structures: Pergola

Lot Features

  • Lot Size (Acres): 0.38
  • Lot Size (Sq. Ft.): 16,553
  • Lot Dimensions: 121.84 x 150.94 x 70.94 x 72 x 100
  • Frontage: City Street, State Road, Paved, Paved
  • Lot Features: Interior Lot
  • Zoning: RS-1
  • Fencing (Description): Fenced2

Financial Considerations

  • For Sale: Yes
  • Price Per Sq. Ft.: $446.68
  • Assessment Amount: $456,580
  • Tax Amount: $2,910.7
  • Tax Year: 2024
  • Terms: Cash, Conventional, FHA, USDA Loan, VA Loan

Disclosures and Reports

  • Special Conditions: Standard
  • Legal Description: LOT B
  • Property ID: 37339

Listed by Everything Pines Partners LLC, Kristi Snyder

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Listing agent

— 745 N May St —

  • Kristi Snyder

    Everything Pines Partners LLC

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 745 N May St

School District:Moore County Schools
NameGradesDistance
Crain's Creek Middle School
4631 Union Church Road, Carthage, NC 28327
6-88.6 mi
Pinecrest High School
250 Voit Gilmore Lane, Southern Pines, NC 28387
9-123.1 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 745 N May St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/20/2026
Listed
$599,000
76.18%
MLS
1/23/2019
Sold
$340,000
—
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 745 N May St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,842
-5%
$456,580
—
2023
$3,002
6%
$456,580
49%
2022
$2,838
-3%
$306,820
—
2021
$2,915
1%
$306,820
—
2020
$2,881
-1%
$306,820
66%
2019
$2,915
80%
$184,880
—
2016
$1,618
—
$184,880
—
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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NMLS#: 1598647

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Listed by Everything Pines Partners LLC, Kristi Snyder

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745 N May Street, Southern Pines, NC 28387 (MLS# 100561615) is a Single Family property with 3 bedrooms and 2 full bathrooms. 745 N May Street is currently listed for $599,000 and was received on March 20, 2026. Want to learn more about 745 N May Street? Do you have questions about finding other Single Family real estate for sale in Highland Trails? You can browse all Highland Trails real estate or contact a Coldwell Banker agent to request more information.

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