A Comprehensive Guide to Retiring in Winston-Salem, North Carolina

Winston-Salem, affectionately nicknamed ‘Winston’ by residents, is a mid-sized city located in the Piedmont Triad of North Carolina. This unique location is unique as it’s situated slightly south of the Virginia border, central in the state between the Blue Ridge Mountains and the Atlantic Ocean. The community dates back to 1753 when North Carolina was first settled and in the twentieth century has been home to well-known American businesses including R.J. Reynolds Tobacco and the Hanes Companies. Winston-Salem’s leadership has been carefully planned for city growth, preventing excessive urban sprawl in order to maintain the surrounding natural beauty. To learn more, continue reading our retirement guide to Winston-Salem.

But why is Winston-Salem right for you during retirement? The low cost of living, tax benefits, small city charm, agreeable weather to settle here in retirement. If you’re considering Winston-Salem as your retirement destination, there’s a lot you’ll want to know. Use this comprehensive guide to get you started!

Tax Benefits

One of the many reasons North Carolina is a popular retirement destination for seniors is because of the tax benefits for seniors. In fact, when it comes to tax bases and the cost of living, North Carolina is one of the best states for retirees.

North Carolina is tax-friendly for seniors. Some of the tax benefits for seniors include:

  • Social Security retirement benefits from income taxes are tax exempt
  • Flat income tax rate of 5.25%
  • Moderate sales and property taxes

For those looking to retire in Winston-Salem, a retirement community is an excellent option where residents pay zero property tax altogether. The top-rated retirement community in the area is Homestead Hills. The community offers a variety of services with available cottage homes and villa apartments.

The information above should function as a starting point for your tax research but not be substituted for direct advice from a tax professional.


A mild climate is one of the many reasons people enjoy retiring in Winston-Salem. On average, temperatures range from 31°F to 41°F in January (the coldest month) and from 69°F to 88°F in July (the warmest month). Snowfall is uncommon but not rare in this region, with an average of just 6 inch of snow per year, compared to a US average of 28 inches per year. There’s an ample supply of yearly rainfall for the master gardeners to grow their favorite flowers, fruits and vegetables. There are 109 rainfall days per year and on average, the city receives 44 inches of rainfall per year, which is slightly higher than the 2019 US average of 34.7 inches.

Health & Wellness

When relocating to a new area, familiarizing yourself with local healthcare options is an important task. One of the most appealing features of Winston-Salem is the top-rated healthcare services available to all residents.

The Winston-Salem area has two premier healthcare systems, Wake Forest Baptist Health and Novant Health System. Their convenient locations and comprehensive operating hours offer a peace of mind for the city’s residents.

Healthcare Systems / Hospitals

Atrium Health – Wake Forest Baptist

Wake Forest Baptist Health is a preeminent academic health system in the area. Wake Forest Baptist’s two main components are an integrated clinical system – anchored by Wake Forest Baptist Medical Center and Wake Forest School of Medicine, a recognized leader in experiential medical education and groundbreaking research that includes Wake Forest Innovations. It is a division of Atrium Health based out of Charlotte, North Carolina.

  • Atrium Health Wake Forest Baptist Medical Center

    The hospital was ranked among the best in the nation by the U.S. News & World Report in 2015-16. Leading in seven areas: Cancer, Ear, Nose & Throat, Gastroenterology & GI Surgery, Nephrology, Neurology & Neurosurgery, Pulmonology and Urology. Among these specialities, the School of Medicine and Wake Forest Innovations continue to elevate research, procedures, and quality care.

Novant Health

Novant is an integrated system of physician practices, hospitals, outpatient centers, and more – each element committed to delivering a remarkable healthcare experience for you and your family. With world-class technology, personal connections, and care that’s easier to access and understand, Novant Health is with you every step of the way on your journey to health and wellness.

  • Novant Health Forsyth Medical Center

    Novant Health Forsyth Medical Center is a Winston-Salem hospital providing emergency services, medical services, surgical services, rehabilitation and behavioral health services. Our centers of excellence include Novant Health Rehabilitation, Maya Angelou Women’s Health & Wellness Center, Heart & Vascular Institute, Derrick L. Davis Cancer Center, Stroke & Neurosciences Center, Orthopedic Center and Behavioral Health.

Fitness Centers and Nutritionists

Keeping active is one of the best ways to maintain health and wellness. While it’s easy to find a nearby gym through a quick Google search, there’s no guarantee that the first one you find will meet your needs. To aid in your search, we recommend using this tool to find age-friendly fitness locations in Winston-Salem.

Senior Living Communities

You have earned your retirement, now enjoy it and let someone else handle your daily responsibilities! Senior living communities are found throughout Winston-Salem and each of them offer different quality of services and amenity features. To plan for the future, a community like Winston-Salem’s top-rated senior living community, Homestead Hills, is a great choice as they offer industry-best services and amenities. These services include Active Adult Living, Independent Living, Assisted Living, Memory Care, Skilled Nursing, Rehabilitation, and Respite Care. If you’re interested in maintenance-free living, upscale amenities and a close-knit community of peers, Homestead Hills may be a good fit. To learn more about Homestead Hills, click here.

Food & Drink

A melting pot of unique fare and libations, Winston-Salem offers a wide range of options for residents. From authentic southern cuisine and smoked barbeque to asian-fusion and oyster bars, there’s a lot to choose from. Here are the top rated restaurants and drinks in Winston-Salem.

Top-Rated Restaurants in Winston-Salem:

Sweet Potatoes

607 Trade St NW, Winston-Salem, NC 27101

Owned by Vivián Joiner and Stephanie Tyson, this award-winning restaurant is located in the Downtown Arts District of Winston-Salem. They are serving up unique, southern inspired uptown, down-home cooking.

Mozelle’s Fresh Southern Bistro

878 W 4th St, Winston-Salem, NC 27101

Owned by Jennifer Smith since 2008, their goal has been to represent the flavors of Winston-Salem. Their ingredients are sourced locally to create a variety of southern comfort foods that can be made gluten-friendly, vegetarian and vegan menu items.

Young Cardinal Cafe

424 4th St NW, Winston-Salem, NC 27101

Young Cardinal Cafe and Co. is Downtown Winston-Salem’s latest spot for classic and simple breakfast and lunch. Their menu goes back to basics with modern twists and fresh ingredients.

Hops Burger Bar

901 Reynolda Rd, Winston-Salem, NC 27104

Hops is a salt of the earth restaurant that features only the finest ingredients. They serve a great blend of angus beef, a unique selection of craft beers and other american pub fare with locally grown ingredients.


121 W 9th St, Winston-Salem, NC 27101

Earl’s is a whiskey bar with live country and good times. Their traditional American / Southern fare is available for brunch through late-night meals.

Top-Rated Drinks in Winston-Salem:

Vintage Sofa Bar

1001 Burke St, Winston-Salem, NC 27101

A grown-folks lounge near downtown Winston-Salem, with craft cocktails, fine wine and creative cuisine created by a chef of national renown. Sofas for lounging, quiet table sports and a patio for watching the world go by. It’s known as a great place to hangout.

Wise Man Brewing

826 Angelo Bros Ave, Winston-Salem, NC 27101

Opened in January 2017, Wise Man Brewing was years of experimentation, competitions, and love for beer from Sam, Jason, and Mike. Today they brew an incredible lineup of beers for everyone to enjoy.

Fair Witness Fancy Drinks

290 4th St E, Winston-Salem, NC 27101

Fair Witness is a friendly neighborhood cocktail bar located conveniently across from Bailey Park in Downtown Winston-Salem.

Bar Piña

770 Liberty View Ct #200, Winston-Salem, NC 27101

Winston-Salem’s only rooftop bar featuring a variety of tasty cocktails, spirits, and views. Located downtown, this trendy spot has an incredible atmosphere, views and creative drinks for locals and tourists alike to enjoy.

The Tap

473 W End Blvd, Winston-Salem, NC 27101

A local favorite, the tap has darts, beer, and a variety of mixed drinks available. It’s got a great atmosphere, friendly bartender, an interior area and outdoor deck that is dog-friendly.


For those who enjoy shopping, Winston-Salem has a variety of shopping destinations. Whether you prefer strolling through big shopping malls, finding a killer deal or browsing local boutiques, you’re sure to find somewhere that meets your retail needs. Here’s the breakdown of the top places to shop in Winston-Salem:

Downtown Arts District

An ultra-hip area of downtown, the Downtown Arts District is an eclectic collection of working studios, galleries, shops, residences, restaurants, and nightlife.

Hanes Mall

3320 Silas Creek Pkwy, Winston-Salem, NC 27103

Hanes Mall was North Carolina’s largest enclosed shopping center until 2004 (now held by Southpark Mall in Charlotte, NC). The mall has 1,558,860 square feet with 3 anchor stores and over 200 tenants in all. It is located off I-40 on Hanes Mall Boulevard, the road named after the mall. The area has become very high traffic with over 250 businesses stretching over 2.9 miles.

Thruway Shopping Center

300 S Stratford Rd, Winston-Salem, NC 27103

Thruway Center, with convenient store front parking, the wide variety of shops, and things to do, is a lifestyle shopping experience. Where else can you do your banking, buy pet supplies, select a new outfit, have a spa day, pick up something for your home, enjoy a meal, or grocery shop? That’s the Thruway experience.

Reynolda Village

2201 Reynolda Rd, Winston-Salem, NC 27106

Reynolda Village, once the dairy barn and cottages of the working Reynolds family estate, has been converted to specialty boutique shops and restaurants for shopping and exploring.


While there aren’t any Major League sports teams in the area, residents of Winston-Salem are rooting for Carolina based teams like the Carolina Panthers (NFL), Charlotte Hornets (NBA), and Carolina Hurricanes (NHL). Winston-Salem based sports teams include:

Winston-Salem Dash (MiLB)

The Dash have been a proud High-A East affiliate of the Chicago White Sox since 1997. Winston-Salem has been home to various baseball teams since 1905 and currently, The Dash, have been a farm team of the Chicago White Sox since 1997. They currently play in Truist Stadium which opened in 2010.

Winston-Salem Wolves (ECBL)

Founded in 2018, the Winston-Salem Wolves are a professional minor league basketball franchise currently playing in the East Coast Basketball League (ECBL).

Carolina Thunderbirds (FPHL)

Founded in 2016 by Barry Soskin, the Thunderbirds are a minor league professional hockey team and play in the Federal Prospects Hockey League. Their home arena is located at the Winston-Salem Fairgrounds Annex. The Thunderbirds won the league’s championship in the 2018-19 season.

Collegiate Teams

While there aren’t many professional teams in the area, collegiate sports reign supreme. Locals continually cheer for Carolina-based teams like UNC Chapel Hill, Duke University, and North Carolina State. Additionally, area residents enjoy attending Winston-Salem based sporting events from local favorites, the Wake Forest University Demon Deacons.

Wake Forest University

Based in Winston-Salem, the Wake Forest Demon Deacons of the ‘Deacs’ compete in the Atlantic Coast Conference and FBS Division I. Wake Forest is sometimes referred to as being a part of “Tobacco Road” or “The Big Four”, terms that refer to the four North Carolina schools that compete heatedly against each other within the ACC; these include Duke University, North Carolina, and North Carolina State, as well as Wake Forest. As the local favorite college team, Wake Forest has over 15 men’s and women’s varsity sports to enjoy. Men’s and Women’s sports at Wake Forest include Baseball, Basketball, Crew, Cross Country, Fencing, Field Hockey, Football, Golf, Gymnastics, Ice Hockey, Lacrosse, Sailing, Softball, Squash, Swimming & Diving, Tennis, Volleyball, and more.

Parks & Recreation

Winston-Salem’s proximity mid-climate and quick access to the Blue Ridge Mountains makes it a great place to live if you enjoy the outdoors. The city is home to countless parks, recreation facilities and public venues for residents to enjoy year-round. Here are some of the most popular spots that locals love:

  • Winston-Salem Greenway System

    Winston-Salem has 25 miles of greenways, incorporating paved and unpaved trails, boardwalks, and bridges. Some greenways connect to each other, enabling longer excursions.

  • Pilot Mountain State Park

    1792 Pilot Knob Park Road, Pinnacle, North Carolina 27043

    Located just 20 minutes from Mount Airy, Pilot Mountain is a treasured North Carolina state park. The park centers around the iconic geologic knob that serves as a beacon to the surrounding Piedmont, inviting outdoor enthusiasts to a vast array of activities. Pilot Mountain offers miles of winding trails to take in stunning views year-round. Enjoy hiking, biking and rock climbing/rappelling.

  • Hanging Rock State Park

    1790 Hanging Rock Park Rd, Danbury, NC 27016

    Created in the 1930s as a part of the Civilian Conservation Corps project, Hanging Rock State Park has offered the best of a traditional outdoor experience with 73-site campground, picnic grounds, stocked lake for swimming and canoe rentals and more than 20 miles of hiking trails that climb onto spectacular views and weave alongside clear streams and waterfalls. Twisted pathways lead to awe-inspiring waterfalls at Hanging Rock State Park, located just 40 minutes from downtown Winston-Salem.

  • Tanglewood Park

    4201 Manor House Circle, Clemmons, NC 27012

    Tanglewood Park is the former estate of Will and Kate Reynolds. Now a public park, Tanglewood offers fishing on two stocked lakes, pedal boats, tennis courts, an Aquatic Center, picnic shelters, rental venues, trail systems, horse stables, gardens, golf and more. The Arboretum and Garden at Tanglewood showcases plant varieties from around the world. During the holiday season, they host the Tanglewood Festival of Lights, a drive-through holiday light show! The Festival of Lights is a community tradition complete with lights, gift shop/village, and visits with Santa Claus.

Arts & Entertainment


Each corner of Winston-Salem is filled with history and a number of the museums in the area reflect the settlers and heritage of the city. In addition to the historical museums, there are some newer facilities that reflect contemporary art, science and more. Local museums that are frequented by residents and visitors alike include:

  • Old Salem Museum and Gardens

    600 S Main St, Winston-Salem, NC 27101

    Old Salem is a historic district that was originally settled by the Moravian community in 1766. This small city features a living history museum that interprets the restored Moravian community. The non-profit organization began its work in 1950, although some private residents had restored buildings earlier. As the Old Salem Historic District, it was declared a National Historic Landmark in 1966 and expanded in 2016. The district showcases the culture of the Moravian settlement in North Carolina during the 18th and 19th centuries, communal buildings, churches, houses, and shops.

  • Reynolda House Museum of American Art

    2250 Reynolda Rd, Winston-Salem, NC 27106

    Reynolda House Museum displays a premiere collection of American art ranging from the colonial period to the present. Built in 1917 by Katharine Smith Reynolds and her husband R.J. Reynolds, founder of the R.J. Reynolds Tobacco Company, the house originally occupied the center of a 1,067-acre estate. It opened to the public as an institution dedicated to the arts and education in 1965, and as an art museum in 1967. The house holds one of the country’s finest collections of American paintings.

  • The Winston Cup Museum

    1355 N Martin Luther King Jr Dr, Winston-Salem, NC 27101

    Originally opened in 2005, the Winston Cup Museum tells the story of stock car racing during the legendary Winston Cup Series era of NASCAR. As you walk through, you will see exhibits and photos that capture the 33 years that R.J. Reynolds Tobacco Company sponsored NASCAR’s premier series.


  • Kaleideum North

    400 W Hanes Mill Rd, Winston-Salem, NC 27105

    There are multiple Kaleideum museums throughout the city but Kaleideum North has 25,000 square feet of exhibits, and a 17-acre Science and Environmental Park.

  • Historic Bethabara Park

    2163 Bethabara Rd, Winston-Salem, North Carolina 27106

    Known as the “Birthplace of Winston-Salem” and founded in 1753 by German-speaking Moravians, Bethabara was the first European settlement in the North Carolina Piedmont. A National Historic Landmark and Local Historic District, historic Bethabara Park encompasses 183 acres of preserved wildlife, historic buildings and grounds, walking and birding trails, and protected wetlands.

  • Graylyn Estate

    1900 Reynolda Rd, Winston-Salem, NC 27106

    The Graylyn Estate was built by Bowman and Nathalie Lyons Gray in XXXX. Bowman Gray was the son of the founder of Wachovia Bank and Trust Co. He began work as a salesman for R.J. Reynolds Tobacco Co. and eventually rose to the Chairman of the Board. The Gray family moved into the completed Graylyn Estate in 1932. The home had approximately 60 rooms, the house was one of the largest in North Carolina, second only to George Vanderbilt’s “Biltmore” in Asheville.

Music Venues

The sounds of music create a vibrant lifestyle within a city; from small clubs to large venues there’s something for everyone. Attending local and national acts is easy to do in Winston-Salem with a variety of venues to choose from. Some of the top locations in Winston-Salem to see your favorite performers are:

  • The Ramkat

    170 W 9th St, Winston-Salem, NC 27101

    The Ramkat is a two-level, 11,670- square-foot, 1,000-person-capacity live music venue, handicap-accessible, and operates three bars serving a wide variety of beer, wine, spirits and non-alcoholic beverages. The Ramkat continues to build on the long legacy of live music in Winston-Salem.

  • Lawrence Joel Veterans Memorial Coliseum

    2825 University Parkway, Winston-Salem, NC 27105

    Opened in 1989, the Lawrence Joel Veterans Memorial Coliseum (LJVM Coliseum) is a 14,407-set multi-purpose arena. It is currently home to the Wake Forest University Demon Deacons men’s and women’s basketball teams. The arena has hosted a variety of concerts since it’s opening including AC/DC, The Beach Boys, Elton John, Dolly Parton, Phish, Rascal Flatts, and more.

  • Elberson Fine Arts Center

    Located on the grounds of Salem College, Elberson Fine Arts Center hosts countless acts, shows, recitals, and exhibitions in Winston-Salem. Their goal is to be able to share the magic and imaginative wonder of world-class artists and performers with the local community.

  • The Quiet Pint Tavern

    The Quiet Pint Tavern is your down-to-earth hangout with patio tables and live music throughout the week. They are your spot to grab a drink, kick back, and enjoy local live music.

  • Krankies Coffee

    211 East 3rd Street, Winston-Salem, NC 27101

    Krankies is an open, inclusive community focused coffee and food venture founded in 2003. In addition to an excellent menu, they welcome live music and performers throughout the month. This helps to sustain the culture and vitality of the communities that they are a part of.


Public Transportation

The public transit system in the Winston-Salem area is called Winston-Salem Transit Authority (WSTA). The local bus routes make frequent stops to connect a variety of different towns. The bus system provides options for those who want to use shuttles, express bus rides, or need connecting routes.


The flexibility in airport options makes it easy to host incoming friends and family as well as head out of town from Winston-Salem. Just 30 minutes outside of Winston-Salem is the Piedmont Triad International Airport (PTI). Each year there are over 50,000 empanelments at PTI on 7 different airlines to over 15 different destinations. The top two destinations from PTI are regional airline hubs Charlotte, North Carolina and Atlanta, Georgia. Other top destinations include Dallas/Fort Worth, Texas; Chicago, Illinois; Washington District of Columbia; Philadelphia, Pennsylvania and more.

For a wider selection of direct flights, Winston-Salem residents can drive less than two hours and fly out of larger airports including:

  • Charlotte Douglas International Airport (CLT)

    Located in Charlotte, North Carolina, CLT is the 11th-busiest airport in the United States and fifth-busiest by aircraft movements. (2019) It was the sixth-busiest airport in the world ranked by aircraft movements. They handle around 50 million passengers annually on over 13 airlines with approximately 178 nonstop destinations around the globe. Top destinations from CLT include Orlando, Florida; Dallas/Fort Worth, Texas; Miami, Florida; Cancún, Mexico; Montego Bay, Jamaica; London, England; Munich, Germany and more.

  • Raleigh-Durham International Airport (RDU)

    Located in Raleigh-Durham, RDU handles around 14 million passengers annually on 10 different airlines. The airport currently has service to 57 cities with over 400 average daily departures. Top destinations from RDU include larger regional hubs like Atlanta, Georgia and Charlotte, North Carolina as well as Denver, Colorado; Orlando, Florida; Dallas/Fort Worth, Texas; Chicago, Illinois; and Fort Lauderdale, Florida.

Retirement Neighborhoods

According to Realtor.com, the median listing home price in Winston-Salem is $219k, while the median sold home price is $225k. The median listing home prices ate $126 per square foot.

Winston-Salem is one of the best places to retire in North Carolina. Living in Winston-Salem offers residents a suburban feel in a close-knit community. There are a lot of restaurants, coffee shops, and parks in the area for residents to enjoy. It’s a great suburban town for many young professionals and retirees alike. Some of the best areas in and around Winston-Salem to lay down roots are:

Atwood / Atwood Acres

The Atwood and Atwood Acres Neighborhood is located southwest of Winston-Salem, but is just minutes from the city. The area is mainly suburban with low crime and mature neighborhoods. Its location offers quick access to interstate 40 and you won’t have to search far for a plethora of unique shopping, dining and entertainment.


Ardmore is the largest and newest historic district in Winston-Salem. It is a popular Winston-Salem neighborhood for young families and medical students, as it is located between Atrium Health Wake Forest University Baptist Medical Center and Novant Health Forsyth Hospital. This area hosts one of the largest parks in the city – Miller Park.

Oak Ridge

This is a quaint town located in Guilford County, which is known for the Old Mill of Guilford and Oak Ridge Military Academy. You’ll be surrounded by beautiful mountain ranges and foothills making it an ideal place to settle down.

Old Salem

Dating back to 1766, the historic area of Old Salem is a preserved Moravian planned community. The cobblestone streets are surrounded by gardens, historical building and are known for their tourism – historical tours, classes and staff in period dress.

Bermuda Run

Situated in Davie County, Bermuda Run is an upscale, fully-gated town located just off of Interstate 40. The community of 1,500 is adjacent to Tanglewood Park and is home to Bermuda Run private country club, and golf course.

Winston-Salem Awaits

Winston-Salem is a historical city primed for your perfect retirement. The city’s low cost of living, tax benefits, moderate climate, culinary scene, universities, and hospitals make it an excellent choice. You’ll wonder why you didn’t move here earlier.

Other Top Cities For Retirement:

Mt. Airy, North Carolina
Charlotte, North Carolina
Tega Cay, South Carolina
Lexington, South Carolina
Columbia, South Carolina
Greenville, South Carolina
Spartanburg, South Carolina
Charleston, South Carolina
Myrtle Beach, South Carolina
Pawleys Island, South Carolina
St. Simons Island, Georgia
Amelia Island, Florida
Carmel, Indiana
North Branford, Connecticut