Pittsylvania, VA Homes

• 

  

  

  /45

  $229,900

  • 4 Beds
  • 2 Baths
  • 3,025 Sq Ft

  246 N Main St, Chatham, VA 24531

  Charming historic home looking for a new owner to bring it back to it's original beauty. Original hardwood floors, and moldings throughout. Pocket doors on the main level, DR is being used as a main floor bedroom. Property adjoins Hargrave Military Academy. Priced at $229,900 due to the needed updates. Some contents is available for purchase. This property may not meet VA & FHA appraisal

  

  Donna Gibson

  WILKINS & CO., REALTORS, INC.

  (434) 442-6008

  246 N Main St, Chatham, VA 24531
• 

  

  

  /12

  $975 - $1,195 per month

  Chatham Lofts

  1 Bed

  315 S Main St, Chatham, VA 24531

  Chatham Lofts is the charming, historic home with lots of amenities that you have been looking for! And these apartments are pet-friendly!Chatham Lofts is a clever renovation of a 1920's school and offers open floor plans, modern kitchens, and large windows that overlook 10 beautiful acres! Escape the big city and enjoy small town life! Chatham lofts is just a few steps away from SAFE and

  315 S Main St, Chatham, VA 24531
• 

  

  

  /11

  $31,000 Sold Jul 28, 2025

  • Land
  • 2.50 Acres
  • $12,400 per Acre

  • 106 Days On Market

  3298 Sago Rd, Chatham, VA 24531

  Welcome to your dream homesite on 2.5 acres of picturesque landscape, offering a stunning backdrop of mountain views. With over 400 feet of road frontage, ideal for building your forever home. The driveway is already in place, leading to a cleared area at the front with serene woods at the rear, ensuring privacy & tranquility. Enjoy the freedom of NO RESTRICTIONS, allowing you the flexibility to

  Kimberly Fowlkes KELLER WILLIAMS

  3298 Sago Rd, Chatham, VA 24531
• 

  

  

  /25

  Est $146,759 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  892 Sheva Rd, Chatham, VA 24531

  892 Sheva Rd, Chatham, VA 24531
• 

  

  

  /21

  $379,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft

  2348 Anderson Mill Rd, Chatham, VA 24531

  Rare opportunity to own 23+ acres of serene countryside, paired with a beautifully restored log home. Near To Smith Mtn Lake, Homeplace Vineyards, Olde Dominion Agricultural Complex, Hargrave Military Academy, Chatham Hall, and just 20 minutes to Caesars in Danville - this property offers both convenience and seclusion. Featuring exposed beams, classic chinking, and a stunning double-sided river

  Genna Dickinson RAMSEY YEATTS & ASSOCIATES, REALTORS

  2348 Anderson Mill Rd, Chatham, VA 24531
• 

  

  /19

  $96,440 Sold Jul 25, 2025

  • Land
  • 8 Acres
  • $11,619 per Acre

  • 78 Days On Market

  8.3 ac Cherrystone Rd, Chatham, VA 24531

  Beautiful 8.3+/- acres just outside the town of Chatham with mostly open fields and beautiful views for your new construction home! Not another tract of land like this on the market ! First time this property has been for sale since 1938 with long family history of ownership! Easy access to US 29 with public water and sewer available. Home site secluded with long road frontage and entrance

  Ramsey Yeatts RAMSEY YEATTS & ASSOCIATES, REALTORS

  8.3 ac Cherrystone Rd, Chatham, VA 24531
• 

  

  /14

  Est $296,587 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1188 Sheva Rd, Chatham, VA 24531

  1188 Sheva Rd, Chatham, VA 24531
• 

  

  /55

  $1,050,000

  • Land
  • 100 Acres
  • $10,500 per Acre

  4031 Marion Rd, Chatham, VA 24531

  Income Producing Property! 20,000 sqft chicken house operation and large free span litter shed! WILLING TO SUBDIVIDE CHICKEN OPERATION FROM FARM. 40 acres in pasture. 4,060ft of frontage on Marion Rd and 670 on Irish Rd. 4,000ft of Lick Branch running through 20 acres of mature hardwoods. 10 acres in 20 year old planted pines. 1950 farm house heated by a central boiler wood stove, ideal for farm

  Micah Woodall Mast Realty Estates and Farms

  4031 Marion Rd, Chatham, VA 24531
• 

  

  /18

  $255,420 Sold Jul 17, 2025

  • Land
  • 38 Acres
  • $6,750 per Acre

  • 266 Days On Market

  000 Cherrystone Lake Rd, Chatham, VA 24531

  Waterfront Property in Pittsylvania County. This 37.84 Acres is located on Cherrystone Lake Rd. The back side of the property fronts Roaring Fork Lake. This property offers incredible views of the lake as well as seclusion. This would be the perfect property to build your primary home or consider building a vacation get-away cabin in the woods overlooking the lake. This is a great price on this

  Diron Clements WILKINS & CO., REALTORS, INC.

  000 Cherrystone Lake Rd, Chatham, VA 24531
• 

  

  /34

  Est $242,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  440 Sheva Rd, Chatham, VA 24531

  440 Sheva Rd, Chatham, VA 24531
• 

  

  /74

  $349,900 Open Wed 5PM - 7PM

  • 4 Beds
  • 2 Baths
  • 2,018 Sq Ft

  227 Catalpa Dr, Chatham, VA 24531

  OPEN HOUSE - Wednesday, Aug 6th 5-7pm! Immaculate, one of a kind 4 BR / 2 BA Cape Cod updated inside & out! The main level features a pretty living room with a wood burning fireplace, beautifully remodeled kitchen with a granite island which flows into a spacious dining room with a second fireplace. This home has many upgrades - too many to list here. Pretty hardwood floors and main level

  Lolly Baker Mark A. Dalton & Co., Inc.

  227 Catalpa Dr, Chatham, VA 24531
• 

  

  /9

  $170,000 Sold Jul 16, 2025

  • 1,458 Sq Ft
  • $117/SF
  • 83 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1964

  201 Rison St, Chatham, VA 24531

  Lovely, move-in ready cottage on a quiet street, with fresh paint and refinished floors, just waiting for your touch! Excellent workmanship in this home, fenced back and front yards. Cozy sunporch will be where you spend all your time! Third bedroom could easily be home office. Easy maintenance!

  Alisa Davis WILKINS & CO., REALTORS, INC.

  201 Rison St, Chatham, VA 24531
• 

  

  /33

  Est $345,639 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,641 Sq Ft

  5009 Chalk Level Rd, Chatham, VA 24531

  5009 Chalk Level Rd, Chatham, VA 24531
• 

  

  /60

  $340,000

  • 5 Beds
  • 2 Baths
  • 3,320 Sq Ft

  111 N Main St, Chatham, VA 24531

  Charming and spacious 5-bedroom, 2-bath home located on Main Street in the heart of Chatham! Enjoy the convenience of a main-level primary suite with en-suite bath, high ceilings, gorgeous moldings and beautiful hardwood floors throughout. The living room features a cozy fireplace with gas logs and built-in bookshelves. The kitchen offers a built-in desk, a large eating area, & appliances that

  Kimberly Fowlkes KELLER WILLIAMS

  111 N Main St, Chatham, VA 24531
• 

  

  /35

  $260,000 Sold Jun 30, 2025

  • 1,557 Sq Ft
  • $167/SF
  • 432 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  1673 Chalk Level Rd, Chatham, VA 24531

  Very well maintained home, over 4 acres of level land, large 40 x 50 shop with 200 amp electricity, large dog lot with 4 pins w/water & electric, family room with fp/ gas logs, replacement windows, new generator less than 2 years old, metal roof, single garage in the back, hardwood flooring, unfinished basement. Also there is a underground oil tank that has been filled in by code.

  Kelli Hauser HAUSER REALTY GROUP

  1673 Chalk Level Rd, Chatham, VA 24531
• 

  

  /68

  Est $312,219 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,788 Sq Ft

  273 Catawba Dr, Chatham, VA 24531

  273 Catawba Dr, Chatham, VA 24531
• 

  

  /23

  $325,000

  • 4 Beds
  • 2 Baths
  • 3,132 Sq Ft

  238 N Main St, Chatham, VA 24531

  Beautiful two story home in the Town of Chatham. Huge dining room, study area and living room. Bedroom on the first level with bath. Enclosed sun room off of eat in kitchen. Huge bedrooms upstairs with full bath. Home is being sold as is. Seller to make no repairs.

  Nikki Dodson DODSON REALTY

  238 N Main St, Chatham, VA 24531
• 

  /2

  $32,500 Sold Jun 20, 2025

  • Land
  • 6 Acres
  • $5,078 per Acre

  • 7 Days On Market

  6.4 AC Brandon Rd, Chatham, VA 24531

  Nice road frontage and large open field with multiple home sites.

  Ramsey Yeatts RAMSEY YEATTS & ASSOCIATES, REALTORS

  6.4 AC Brandon Rd, Chatham, VA 24531
• 

  

  /17

  Est $235,651 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft

  261 Catawba Dr, Chatham, VA 24531

  261 Catawba Dr, Chatham, VA 24531
• 

  

  /83

  $285,000

  • 4 Beds
  • 2 Baths
  • 1,420 Sq Ft

  1433 Chalk Level Rd, Chatham, VA 24531

  Come check out this completely renovated cute bungalow in the town of Chatham. New everything. New LVP flooring, new kitchen with new stainless steel appliances and granite countertops, new under cabinet lighting, new bathrooms, new roof, new furnace, new garage doors and garage door openers, even the paved driveway was newly sealed. Convenient one level living floor plan with 4 bedrooms and 2

  Jeremy Phillips BHHS Dawson Ford Garbee-Forest

  1433 Chalk Level Rd, Chatham, VA 24531
• 

  

  /19

  $185,000 Sold Jun 19, 2025

  • 1,525 Sq Ft
  • $121/SF
  • 83 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1955

  608 Oakland Dr, Chatham, VA 24531

  Nestled in the charming town of Chatham, Virginia, this delightful three-bedroom, one-bath brick ranch exudes warmth and comfort. As you step inside, you'll be greeted by beautiful hardwood floors that flow throughout the home, leading you to a cozy living room complete with a welcoming fireplace—perfect for those chilly evenings. The eat-in kitchen is both functional and inviting, offering

  Chuck Eskey ESKEY & ASSOCIATES REALTY

  608 Oakland Dr, Chatham, VA 24531
• 

  

  /20

  Est $173,613 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,752 Sq Ft

  117 Robin Ct, Chatham, VA 24531

  117 Robin Ct, Chatham, VA 24531
• 

  

  /43

  $299,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  Unlisted Address

  Welcome to 1545 Chalk Level Rd. in Chatham, VA! This charming three-bedroom, two-bath home features real hardwood floors beneath the carpeting and sits on an expansive 5.93-acre lot. Over the years this home has been maintained with the best if care! The property offers a full unfinished basement, providing excellent potential for future living space or storage. Enjoy the great yard space,

  Shannon Sims Keller Williams

  Unlisted Address
• 

  

  /19

  $275,000 Sold Jun 09, 2025

  • 1,622 Sq Ft
  • $170/SF
  • 41 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1938

  220 Catalpa Dr, Chatham, VA 24531

  A southern classic in Chatham!! This adorable cottage boasts hardwood floors, Spacious living room with fireplace, formal dining, Kitchen has ample prep space and storage. Primary bedroom has private bath with tile. Guest bedrooms and hall bath. Laundry room located on enclosed porch. Permanent steps to attic which could be future living space. Unfinished basement for storage. Single car

  Elizabeth Ware ELIZABETH WARE REALTORS

  220 Catalpa Dr, Chatham, VA 24531
• 

  

  /25

  Est $150,152 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft

  1488 Mill Creek Rd, Chatham, VA 24531

  1488 Mill Creek Rd, Chatham, VA 24531
• 

  

  /41

  $259,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,902 Sq Ft

  107 Woodlawn Heights, Chatham, VA 24531

  This is an updated, remodeled home with an added back wood deck and side porch, enclosed sunroom, new vinyl siding, and additional living room space. Within the past 3 years: New roof, new HVAC, painted cabinets, and new granite countertops. New insulation, electrical, and plumbing. Composite decking on front porch and new windows, new doors, and new drywall. All new tiled bathrooms. Come see

  Samantha Aaron Keller Williams

  107 Woodlawn Heights, Chatham, VA 24531
• 

  

  /29

  $43,000 Sold Apr 04, 2025

  • 988 Sq Ft
  • $44/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  800 Mitchell Rd, Chatham, VA 24531

  Charming 2-bedroom, 1-bath cottage-style home situated on a 2.55-acre lot with a peaceful creek running along the back of the property. This cozy home features a finished attic for extra space and several wall-mounted heaters for warmth (no central Heat or A/C). A perfect retreat for those seeking a quiet, natural setting! Needs TLC. Sold as is, where is- seller will make no repairs

  Kimberly Fowlkes KELLER WILLIAMS

  800 Mitchell Rd, Chatham, VA 24531
• 

  

  /5

  Est $256,980 Not Listed For Sale

  • 3 Beds

  677 Strader Rd, Chatham, VA 24531

  677 Strader Rd, Chatham, VA 24531
• 

  

  /50

  $259,900 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft

  501 Climax Rd, Chatham, VA 24531

  If you are seeking rural beauty and charm, look no further. This lovely home provides an open view of living/dining/kitchen along with 2 BR, 2BA and Office on the main level. Attached one car garage with laundry. Downstairs is a full, unfinished basement, perfect for expansion, storage or just a fun space. There is an out building with lean to for extra storage. Full house Generac generator

  Debra Fugate RAMSEY YEATTS & ASSOCIATES, REALTORS

  501 Climax Rd, Chatham, VA 24531
• 

  

  /35

  $295,000 Sold Mar 27, 2025

  • Land
  • 35 Acres
  • $8,347 per Acre

  • 142 Days On Market

  2297 Tight Squeeze Rd, Chatham, VA 24531

  Long frontage on Tightsqueeze Rd, 25 acres fenced into 3 pastures. Each pasture has its own watering system (new with separate well) Numerous outbuildings. Currently operating as a cattle farm. Includes 3BR,2B double wide with great room and huge deck. Wood stove. Also includes a single wide mobile home rented ($550 m), 2242 Tightsqueeze on same property. Whole house generator. Wonderful mini

  Chris Dunlap HAUSER REALTY GROUP

  2297 Tight Squeeze Rd, Chatham, VA 24531
• 

  

  /11

  Est $133,551 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  613 N Main St, Chatham, VA 24531

  613 N Main St, Chatham, VA 24531
• 

  

  /23

  $189,000

  • 4 Beds
  • 2 Baths
  • 1,754 Sq Ft

  439 Peach St, Chatham, VA 24531

  This lovely, well-kept, 4 bedroom, 2 bath home sits on a gorgeous .42 acre corner lot in charming Chatham. Whether you are downsizing, aging in place, or just starting out, this home offers comfortable living on one level, with one fireplace and a lovely sun porch, as well as a generous utility room for crafting or other activities. Enjoy grilling or just chilling on the back deck. Don't miss the

  Alisa Davis WILKINS & CO., REALTORS, INC.

  439 Peach St, Chatham, VA 24531
• 

  

  /61

  $395,000 Sold Mar 12, 2025

  • 3,680 Sq Ft
  • $107/SF
  • 110 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1912

  135 Reid St, Chatham, VA 24531

  Experience a blend of history & modern living in this stunning 1912 home. This 5 bedroom, 3 bath residence features a durable metal roof & wood siding, both painted in 2019. The property is enhanced by elegant wrought iron fencing salvaged from the Floyd County Courthouse. Inside, enjoy spacious bedrooms, including a primary suite with en suite bathroom & walk-in closet. The cozy wood-paneled den

  Kimberly Fowlkes KELLER WILLIAMS

  135 Reid St, Chatham, VA 24531
• 

  

  /25

  Est $143,177 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,262 Sq Ft

  206 Hurt St, Chatham, VA 24531

  206 Hurt St, Chatham, VA 24531
• 

  

  /35

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  1953 Anderson Mill Rd, Chatham, VA 24531

  Remarkably well maintained home loaded with extras with a double garage with additional room/kitchen. All on a garden like setting with beautiful flower beds. Private setting in the countryside. Just around the corner from Cedars Country Club & Golf Coarse. Almost 56 adjoining acres for sale.

  Justin Johnson ESKEY & ASSOCIATES REALTY

  1953 Anderson Mill Rd, Chatham, VA 24531
• 

  

  /23

  $180,000 Sold Mar 07, 2025

  • Land
  • 40 Acres
  • $4,502 per Acre

  • 44 Days On Market

  00 Callands Rd, Chatham, VA 24531

  Beautiful tract of land that has so much to offer. With 342 ft of road frontage, +/- 16 acres of open crop land, +/- 5 AC planted loblolly pine (15+ years old), 804 ft of frontage on the Bannister River and a pond, this makes for a unique property. If you are looking for a place in a private setting to build your dream home this offers possibilities. If you are looking for working cropland or an

  Kevin Amos ELIZABETH WARE REALTORS

  00 Callands Rd, Chatham, VA 24531
• 

  

  /31

  Est $198,512 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,270 Sq Ft

  17 Lanier Ave, Chatham, VA 24531

  17 Lanier Ave, Chatham, VA 24531
• 

  

  /18

  $224,900

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  2130 Riddle Rd, Chatham, VA 24531

  Very nice home in move in condition. Beautiful hardwood floors in a somewhat open floor space. Large family room. Situated in the country with a large lot suitable for gardening. This is a must see at this price

  Jim Houser WILKINS & CO., REALTORS, INC.

  2130 Riddle Rd, Chatham, VA 24531
• 

  

  /18

  $50,000 Sold Jan 16, 2025

  • 135 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  301, 329 Wayne Robertson Rd, Chatham, VA 24531

  Attention all INVESTORS!! This property has TWO rentals properties on one parcel of land! Located near the town of Chatham and convenient to HWY 29. There are two single-wide trailers on the property along with two storage sheds. Homes need TLC and repairs. Seller is willing to repair back deck on one. Homes and property will be cleaned out before closing - otherwise sold as-is. Potential for

  Samantha Aaron KELLER WILLIAMS

  301, 329 Wayne Robertson Rd, Chatham, VA 24531
• 

  

  /39

  Est $311,620 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,384 Sq Ft

  18 Lanier Ave, Chatham, VA 24531

  18 Lanier Ave, Chatham, VA 24531

Showing Results 1 - 40, Page 1 of 18