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Homes for sale under $5 million in Winston Salem, NC

Winston SalemUp to $5MHomeCondominiumTownhomeDuplex

Homes for Sale in Winston Salem

5400 Dartmoor Street #246, Winston Salem, NC 27106$1.7MActive

5400 Dartmoor Street #246, Winston Salem, NC 27106

4 Bed · 5 Bath · 5,309 Sqft

Single Family Residence · Built 1984 · 5-Car Garage

MLS# CAR4392717

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2051 Royall Drive, Winston Salem, NC 27106$650,000Active Under Contract

2051 Royall Drive, Winston Salem, NC 27106

4 Bed · 4 Bath · 4,262 Sqft

Single Family Residence · Built 1967 · 2-Car Garage

MLS# CAR4381495

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5005 Mayberry Lane, Winston Salem, NC 27106$625,000Active

5005 Mayberry Lane, Winston Salem, NC 27106

4 Bed · 4 Bath · 3,309 Sqft

Single Family Residence · Built 1993 · 2-Car Garage

MLS# CAR4365094

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337 Petree Road, Winston Salem, NC 27106$439,900Active

337 Petree Road, Winston Salem, NC 27106

5 Bed · 3 Bath · 2,976 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4394954

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2858 Eland Drive, Winston Salem, NC 27127$436,900Active

2858 Eland Drive, Winston Salem, NC 27127

4 Bed · 4 Bath · 2,591 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4426027

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436 Peace Haven Road, Winston Salem, NC 27103$414,900Active

436 Peace Haven Road, Winston Salem, NC 27103

4 Bed · 3 Bath · 2,661 Sqft

Single Family Residence · Built 1978 · 1-Car Garage

MLS# CAR4416574

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624 Brentwood Court, Winston Salem, NC 27104$409,900Active

624 Brentwood Court, Winston Salem, NC 27104

5 Bed · 3 Bath · 3,006 Sqft

Single Family Residence · Built 1962

MLS# CAR4411661

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106 Miller Pointe Way, Winston Salem, NC 27106$390,000Active

106 Miller Pointe Way, Winston Salem, NC 27106

3 Bed · 2 Bath · 1,820 Sqft

Townhouse · Built 1999 · 2-Car Garage

MLS# CAR4425145

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821 Watson Avenue, Winston Salem, NC 27103$390,000Active

821 Watson Avenue, Winston Salem, NC 27103

3 Bed · 2 Bath · 1,811 Sqft

Single Family Residence · Built 1921

MLS# CAR4384198

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2314 Broad Street, Winston Salem, NC 27127$382,900Active

2314 Broad Street, Winston Salem, NC 27127

3 Bed · 3 Bath · 1,635 Sqft

Single Family Residence · Built 1940

MLS# CAR4405936

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3447 Robindale Drive, Winston Salem, NC 27107$379,900Active

3447 Robindale Drive, Winston Salem, NC 27107

3 Bed · 3 Bath · 2,060 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4295140

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186 O Farrell Street, Winston Salem, NC 27107$379,900Active

186 O Farrell Street, Winston Salem, NC 27107

3 Bed · 2 Bath · 1,515 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4409327

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3453 Robindale Drive, Winston Salem, NC 27107$373,900Active

3453 Robindale Drive, Winston Salem, NC 27107

3 Bed · 3 Bath · 2,060 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4295134

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3416 Robindale Drive, Winston Salem, NC 27107$369,900Active

3416 Robindale Drive, Winston Salem, NC 27107

3 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4360016

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1046 Jonestown Road, Winston Salem, NC 27127$366,900Active

1046 Jonestown Road, Winston Salem, NC 27127

4 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4314067

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3410 Robindale Drive, Winston Salem, NC 27107$365,900Active

3410 Robindale Drive, Winston Salem, NC 27107

3 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4359987

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4815 Sterling Brooke Lane, Winston Salem, NC 27103$365,000Active

4815 Sterling Brooke Lane, Winston Salem, NC 27103

3 Bed · 3 Bath · 2,248 Sqft

Townhouse · Built 2007 · 2-Car Garage

MLS# CAR4387273

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3441 Robindale Drive, Winston Salem, NC 27107$363,900Active

3441 Robindale Drive, Winston Salem, NC 27107

4 Bed · 3 Bath · 2,002 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4295095

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3411 Robindale Drive, Winston Salem, NC 27107$363,900Active

3411 Robindale Drive, Winston Salem, NC 27107

3 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4359965

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1072 Russell Drive, Winston Salem, NC 27127$359,900Active

1072 Russell Drive, Winston Salem, NC 27127

4 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4273528

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1041 Russell Drive, Winston Salem, NC 27127$359,900Active

1041 Russell Drive, Winston Salem, NC 27127

4 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4273519

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1059 Russell Drive, Winston Salem, NC 27127$359,900Active

1059 Russell Drive, Winston Salem, NC 27127

4 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4271018

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3423 Robindale Drive, Winston Salem, NC 27107$357,900Active

3423 Robindale Drive, Winston Salem, NC 27107

3 Bed · 3 Bath · 1,800 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4337255

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3446 Robindale Drive, Winston Salem, NC 27107$351,900Active

3446 Robindale Drive, Winston Salem, NC 27107

3 Bed · 2 Bath · 1,552 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4353131

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3435 Robindale Drive, Winston Salem, NC 27107$351,900Active

3435 Robindale Drive, Winston Salem, NC 27107

3 Bed · 3 Bath · 1,700 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4321834

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1355 Leheigh Court, Winston Salem, NC 27103$350,000Active

1355 Leheigh Court, Winston Salem, NC 27103

4 Bed · 3 Bath · 1,711 Sqft

Single Family Residence · Built 1956 · 3-Car Garage

MLS# CAR4394268

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3434 Robindale Drive, Winston Salem, NC 27107$347,900Active

3434 Robindale Drive, Winston Salem, NC 27107

3 Bed · 2 Bath · 1,552 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4387755

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1900 Austin Place Lane, Winston Salem, NC 27127$347,000Active

1900 Austin Place Lane, Winston Salem, NC 27127

3 Bed · 2 Bath · 1,538 Sqft

Single Family Residence · Built 1999 · 2-Car Garage

MLS# CAR4390396

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3417 Robindale Drive, Winston Salem, NC 27127$346,900Active

3417 Robindale Drive, Winston Salem, NC 27127

3 Bed · 3 Bath · 1,548 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4359962

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1076 Jonestown Road, Winston Salem, NC 27103$343,900Active

1076 Jonestown Road, Winston Salem, NC 27103

3 Bed · 3 Bath · 2,238 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4314083

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3428 Robindale Drive, Winston Salem, NC 27127$341,900Active

3428 Robindale Drive, Winston Salem, NC 27127

3 Bed · 2 Bath · 1,552 Sqft

Single Family Residence · Built 2025 · 2-Car Garage

MLS# CAR4321828

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3458 Robindale Drive, Winston Salem, NC 27127$341,900Active

3458 Robindale Drive, Winston Salem, NC 27127

3 Bed · 2 Bath · 1,552 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4321829

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865 Winterside Lane, Winston Salem, NC 27107$329,900Active

865 Winterside Lane, Winston Salem, NC 27107

4 Bed · 3 Bath · 2,052 Sqft

Single Family Residence · Built 2017 · 2-Car Garage

MLS# CAR4418707

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2274 Darwick Road, Winston Salem, NC 27127$329,900Active

2274 Darwick Road, Winston Salem, NC 27127

4 Bed · 2 Bath · 1,800 Sqft

Single Family Residence · Built 2026

MLS# CAR4411764

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792 Reaford Road, Winston Salem, NC 27104$324,900Active

792 Reaford Road, Winston Salem, NC 27104

3 Bed · 3 Bath · 2,074 Sqft

Single Family Residence · Built 1984 · 2-Car Garage

MLS# CAR4397982

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421 Robindale Court, Winston Salem, NC 27107$317,900Active

421 Robindale Court, Winston Salem, NC 27107

3 Bed · 2 Bath · 1,172 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4321840

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469 Sunset Drive, Winston Salem, NC 27107$310,000Active

469 Sunset Drive, Winston Salem, NC 27107

3 Bed · 2 Bath · 1,865 Sqft

Single Family Residence · Built 1961 · 3-Car Garage

MLS# CAR4420990

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3743 Crosland Road, Winston Salem, NC 27106$299,900Active

3743 Crosland Road, Winston Salem, NC 27106

4 Bed · 2 Bath · 2,044 Sqft

Single Family Residence · Built 1955 · 1-Car Garage

MLS# CAR4360986

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427 Inlet Place Drive, Winston Salem, NC 27127$299,000Active

427 Inlet Place Drive, Winston Salem, NC 27127

3 Bed · 3 Bath · 2,376 Sqft

Single Family Residence · Built 2015 · 2-Car Garage

MLS# CAR4384907

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509 1st Street, Winston Salem, NC 27101$275,000Active

509 1st Street, Winston Salem, NC 27101

6 Bed · 2 Bath · 744 Sqft

Single Family Residence · Built 1923

MLS# CAR4406821

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4627 Shattalon Drive, Winston Salem, NC 27106$275,000Active

4627 Shattalon Drive, Winston Salem, NC 27106

3 Bed · 3 Bath · 1,632 Sqft

Single Family Residence · Built 2023 · 2-Car Garage

MLS# CAR4407534

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103 Briar Ridge Circle, Winston Salem, NC 27104$274,900Active

103 Briar Ridge Circle, Winston Salem, NC 27104

3 Bed · 2 Bath · 1,524 Sqft

Single Family Residence · Built 1984 · 1-Car Garage

MLS# CAR4421455

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946 Waterworks Road, Winston Salem, NC 27101$268,888Active

946 Waterworks Road, Winston Salem, NC 27101

4 Bed · 3 Bath · 2,014 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4387200

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926 Waterworks Road, Winston Salem, NC 27101$264,888Active

926 Waterworks Road, Winston Salem, NC 27101

4 Bed · 3 Bath · 1,774 Sqft

Single Family Residence · Built 2026 · 2-Car Garage

MLS# CAR4397668

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1900 Peachtree Street, Winston Salem, NC 27107$259,900Active

1900 Peachtree Street, Winston Salem, NC 27107

3 Bed · 2 Bath · 1,792 Sqft

Single Family Residence · Built 1947 · 2-Car Garage

MLS# CAR4426125

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373 Sailway Road, Winston Salem, NC 27127$259,900Active

373 Sailway Road, Winston Salem, NC 27127

3 Bed · 3 Bath · 1,523 Sqft

Single Family Residence · Built 2004 · 1-Car Garage

MLS# CAR4406802

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5757 Fox Ridge Lane, Winston Salem, NC 27104$248,500Active

5757 Fox Ridge Lane, Winston Salem, NC 27104

3 Bed · 2 Bath · 1,537 Sqft

Townhouse · Built 2005

MLS# CAR4406995

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1150 Red Sage Road, Winston Salem, NC 27127$239,900Active

1150 Red Sage Road, Winston Salem, NC 27127

3 Bed · 2 Bath · 1,021 Sqft

Single Family Residence · Built 2015 · 1-Car Garage

MLS# CAR4364862

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4040 Burnham Court, Winston Salem, NC 27105$230,000Active

4040 Burnham Court, Winston Salem, NC 27105

3 Bed · 2 Bath · 1,048 Sqft

Single Family Residence · Built 1970

MLS# CAR4409615

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2254 lula Street, Winston Salem, NC 27101$229,900Active

2254 lula Street, Winston Salem, NC 27101

3 Bed · 3 Bath · 1,462 Sqft

Single Family Residence · Built 2026

MLS# CAR4416956

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There are currently 72 homes for sale in Winston Salem, NC priced under $5M. Prices range from $85,000 to $1.7M with a median of $313,950.

Listings courtesy of Canopy MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 09/20/2026, 06:53:52 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website.

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