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745 N May Street

Southern Pines, NC 28387
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Bed 3

Bed

Bath 2

Bath

SqFt1,341

Sqft

Acres0.38

Acre(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $585,000

AD Id : 76315732

MLS Id : 100561615

Beds : 3

Lot Size : 0.38 Acre

Living Area Size : 1,341

Year Built : 1925

County : Moore

Subdivision: Downtown

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Feature Features

  • Bedroom Information

    Total beds: 3

    Bathroom Information

    Total Baths: 2 Full Baths: 2

    Room Information

    Rooms Total: 6 Has Basement: Yes Basement: Interior Entry, Unfinished
  • Flooring Information

    Tile, Wood
  • Roofing Information

    Metal
  • Interior Features

    Master Downstairs, Kitchen Island, Pantry Roof: Metal Appliances: Electric Oven, Electric Cooktop, Washer, Refrigerator, Dryer, Dishwasher, Water Purifier, Gas Water Heater, Tankless Water Heater Laundry Features: Washer Hookup, Laundry Room
  • Heating & Cooling

    Has Heating: Yes Heating: Electric, Forced Air, Heat Pump, Natural Gas Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 1925 Building Area Total: 1341 Construction Materials: Vinyl Siding, Frame Patio And Porch Features: Enclosed, Patio, Porch Private Pool: No View: See Remarks

  • Lot Information

    Lot Dimensions: 121.84x150.94x70.94x72x100 Main Square Feet: 0.38 Acres Lot Size Acres: 0.38 Lot Size Square Feet: 16553 Lot Description: Interior Lot

    Property Information

    Subdivision: Downtown Source Property Type: Residential Property SubType: Single Family Residence Levels: Two Property Age: 101

  • Listing Price Information

    Listing Price: $585000 Original Price: $619000 Cash, Conventional, FHA, USDA Loan, VA Loan

  • Tax Information

    Parcel Number: 00037339 Tax Year: 2024 Annual Tax: $2910.7

  • Parking Information

    Additional Parking, Gravel, On Site

  • School Information

    Elementary School: Southern Pines Primary
    Junior High School: Crain's Creek Middle
    Senior High School: Pinecrest High
  • Utility Information

    Sewer Available, Water Available
  • Location Information

    Direction: House is located on N May Street between E New Jersey and E Delaware Ave. WaterSource: Public Security Features: Smoke Detector(s)
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
668 Chambers Drive, Southern Pines, NC, 28387 $372,000 3 3 1,551 1,551 SqFt
640 Chambers Drive, Southern Pines, NC, 28387 $368,900 3 3 1,551 1,551 SqFt
656 Chambers Drive, Southern Pines, NC, 28387 $407,900 4 3 1,906 1,906 SqFt
620 Chambers Drive, Southern Pines, NC, 28387 $367,900 3 3 1,551 1,551 SqFt
628 Chambers Drive, Southern Pines, NC, 28387 $407,900 4 3 1,906 1,906 SqFt
608 Chambers Drive, Southern Pines, NC, 28387 $407,900 4 3 1,906 1,906 SqFt
292 Bump A Long Lane, Southern Pines, NC, 28387 $2,150,000 4 4 3,443 3,443 SqFt
212 Skyline Manor Road, Southern Pines, NC, 28387 $235,000 2 3 2,337 2,337 SqFt
130 Horseshoe Drive, Southern Pines, NC, 28387 $349,000 3 2 1,500 1,500 SqFt
132 Tower Street, Southern Pines, NC, 28387 $599,998 3 3 1,531 1,531 SqFt

The data relating to real estate on this website comes in part from the Internet Data Exchange program of Hive MLS. All information is deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal. Neither listing broker(s) nor ByOwner shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. Copyright ©2026 Hive MLS LLC. All Rights Reserved.

ByOwner last updated this listing 06/25/2026 @ 02:54

MLS: 100561615 LISTED BY: Kristi Snyder, Everything Pines Partners LLC SOURCE: Hive MLS (North Carolina Regional)

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