Front of Home - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Detached Garage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Kitchen - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Kitchen - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Living Room - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Living Room - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Primary Suite - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Primary Suite - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Primary Suite Closet - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Bedroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Primary Suite Bathroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Primary Suite Bathroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Bedroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Bedroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Bathroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Bedroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Bedroom - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Carolina Room - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Carolina Room - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Laundry Room - Main House - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
Guest Cottage - 440 E Massachusetts Avenue, Southern Pines, NC 28387
32 photos

$550,000

440 E Massachusetts Avenue, Southern Pines, NC 28387
Southern Pines, NC 28387
Listed by Samantha L Cole · La Belle Vie Realty
Bedrooms
3
Bathrooms
2
Living area
2,660 sqft
Year built
1962

About this home

***COMING SOON***SHOWINGS START SUNDAY, NOVEMBER 1ST*** Discover the charm of downtown Southern Pines living with the added benefits of a detached guest cottage and separate garage! Situated on nearly half an acre, this property offers modern updates and versatility, all within a short distance of downtown shops, restaurants, parks, and entertainment. The main residence features 3 bedrooms, 2 full bathrooms, and inviting living spaces filled with warmth and character. Beautiful wood flooring, built-in shelving, and a cozy fireplace create a welcoming atmosphere, while the updated kitchen features white cabinetry, granite countertops, stainless steel appliances, and a spacious island. French doors lead from the dining area to an enclosed sunroom, providing additional space to relax or entertain. The primary suite includes a large walk-in closet and private bathroom. Adding to the property's appeal is a detached guest cottage featuring its own living area, full kitchen, bedroom, and bathroom. The possibilities for this separate living space is abundant; guest cottage, work space or investment income, just to name a few. A detached garage provides even more versatility, with space that can serve as a traditional garage, workshop, or additional storage area. Outside, the spacious fenced backyard and mature trees create an inviting outdoor setting, all just minutes from the heart of Southern Pines. With its desirable location, thoughtful updates, detached guest cottage, and multifunctional garage, this property offers a unique opportunity to enjoy the convenience and character of Southern Pines!

Highlights

Fireplace

Property details

MLS
Hive MLS
MLS #
100613610
Property type
Single Family Residence
Subdivision
Downtown
Status
Active
Days on market
3
On market date
November 1, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
1
Parking spaces
1
Lot size
0.45 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Southern Pines Elementary
1.56 mi away · Grades -1-5
Zoned school (attendance boundary, 2015-16 data)
3.0
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: C (2025)
Enrollment
611
Student:teacher ratio
15.7:1
District
Moore County Schools
Middle
Southern Middle
2.19 mi away · Grades 6-8
Zoned school (attendance boundary, 2015-16 data)
3.0
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: C (2025)
Enrollment
630
Student:teacher ratio
15.8:1
District
Moore County Schools
High
Pinecrest High
2.7 mi away · Grades 9-12
Zoned school (attendance boundary, 2015-16 data)
3.4
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
2,219
Student:teacher ratio
21.1:1
District
Moore County Schools

Walkability

Blended score for Southern Pines's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

52
Somewhat walkable
out of 100
EPA National Walkability Index
6.7 / 20 -- Below average walkable
Google Places amenity density
80 / 100
Restaurants & cafes18
Grocery stores4
Parks3
Schools6
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in Southern Pines, from live MLS data.

On the market 3 days -- 93 fewer days than Southern Pines's current average of 96 days.
For reference, the median list price across 259 active listings in Southern Pines right now is $345,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$3,462/mo
$110,000 down
$440,000 loan
Principal & interest$2,854
Property tax (est.)$458
Home insurance (est.)$150

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Data source: Listing information provided by Hive MLS via Trestle/CoreLogic. Last updated 7 hr ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.