Winston Hills, Hendersonville, TN Homes for Sale

Winston Hills, Hendersonville, TN Property Listings
April 21, 2024
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Winston Hills Homes

Homes in Winston Hills, Hendersonville, TN, epitomize a blend of elegance, functionality, and classic Southern charm. Nestled amidst Tennessee's natural beauty, these residences often showcase architectural elements that both reflect the region's heritage and adapt to modern tastes. From spacious colonial-inspired designs to more contemporary styles, there's a wealth of diversity in the neighborhood's architectural palette. Hardwood floors, high ceilings, and generously sized windows are but a few of the common features found in Winston Hills homes, allowing for an abundance of natural light and air, creating a warm and welcoming ambiance.

The landscaping and outdoor spaces in Winston Hills are equally compelling. Most homes in the area boast well-maintained lawns, mature trees, and verdant gardens that reflect the pride of homeownership. As the seasons change, these outdoor spaces become a kaleidoscope of colors, offering residents the pleasure of enjoying the vibrant spring blossoms, the shades of autumn, and even the occasional pristine blanket of winter snow.

Winston Hills Homes

Beyond the individual characteristics of the homes, the community of Winston Hills is an embodiment of camaraderie and a shared sense of place. The streets are pedestrian-friendly, fostering a neighborhood spirit where children can often be seen playing outside and neighbors exchange friendly greetings. This strong community bond is further cemented by frequent neighborhood gatherings, potlucks, and other social events that keep residents connected.

A significant advantage of living in Winston Hills is its proximity to various amenities in Hendersonville. This suburb of Nashville is replete with a rich historical legacy, green spaces, and recreational spots. Residents don't have to venture far to enjoy scenic walks by the Old Hickory Lake or indulge in a day of shopping and dining in the charming local establishments. The area's schools, healthcare facilities, and shopping centers are conveniently located, ensuring that the necessities of modern life are always within easy reach.

Safety and security are paramount in Winston Hills. The neighborhood has a reputation for being one of the safest areas in Hendersonville, thanks in part to the active and vigilant local community associations and the dedication of local law enforcement. The close-knit nature of the community means that residents look out for one another, making it an ideal place for families, retirees, and anyone in between.

Similar Communities

One of the neighborhoods that mirror the essence of Winston Hills in terms of price point, construction, and lifestyle is Indian Lake Peninsula. Situated not too far from the heart of Hendersonville, homes here reflect a similar attention to detail and architectural flair. Most homes in Indian Lake Peninsula exude a southern elegance, with expansive floor plans, large verandas, and meticulously crafted interiors. The closeness to Indian Lake adds an extra layer of allure, giving residents both scenic views and easy access to recreational activities like boating and fishing.

Another area echoing the sentiments of Winston Hills is the Drakes Pointe community. It's a pocket of tranquillity with a collection of homes that harmoniously blend traditional and modern elements. Much like Winston Hills, properties here tend to feature lush lawns, intricate landscaping, and a predilection for classic Southern architecture. The community spaces in Drakes Pointe are well-planned, with playgrounds and green spaces that foster a familial, tight-knit community spirit.

Cherokee Woods Homes

Mansker Farms is yet another enclave of homes that share similarities with Winston Hills. The residences in this neighborhood are a testament to fine craftsmanship, with features such as detailed masonry, high-quality woodwork, and expansive layouts that cater to the needs of the contemporary family. As with the other neighborhoods, there's a distinctive emphasis on community engagement in Mansker Farms. Seasonal events, communal spaces, and walking trails underscore the neighborhood's commitment to promoting an active and interconnected lifestyle among its residents.

Cherokee Woods, located a stone's throw away from the main avenues of Hendersonville, encapsulates a lifestyle and construction ethos comparable to Winston Hills. Homes here are often adorned with brick and stone facades, capturing a timeless aesthetic while ensuring durability. The tree-lined streets and cul-de-sacs promote a serene living environment, fostering a sense of security and belonging. Furthermore, its proximity to some of Hendersonville's top schools and recreational spots makes Cherokee Woods an appealing choice for families seeking a balance of modern convenience and suburban charm.

Blue Ridge, with its sweeping vistas and upscale homes, stands as another worthy mention in the vicinity of Winston Hills. While it offers a slightly more secluded feel, the quality of construction and the lifestyle it promotes are undeniably on par. Residents here can often be seen taking leisurely strolls, enjoying the natural surroundings, or participating in community-organized activities, making it another gem in the tapestry of Hendersonville's upscale neighborhoods.

Food Scene

The Rudder at Anchor High Marina! This lakeside dining spot is an absolute favorite among many, and it's easy to see why. Beyond its appetizing seafood offerings, the establishment offers breathtaking views of Old Hickory Lake, especially during sunset. Diners can enjoy a casual yet intimate ambiance, with the gentle sounds of water setting a peaceful backdrop to their meals.

For those with a penchant for Italian, there’s Avanti Gourmet. It’s not just a restaurant; it's an experience. Their menu boasts traditional Italian dishes, with each plate narrating a story of age-old family recipes and fresh ingredients. The tiramisu, in particular, has quite the reputation, often being dubbed by regulars as a slice of heaven.

Then there’s Sax Deli & Grill, a spot that feels like Hendersonville's little secret. Tucked away from the hustle and bustle, this eatery specializes in sandwiches, but not just any sandwiches. Think generously stuffed, thoughtfully seasoned, and perfectly toasted. It’s a laid-back place where locals can grab a quick bite or linger over a late lunch, chatting away with friends.

For those seeking flavors from the East, Kohana Japanese Restaurant doesn’t disappoint. This establishment has mastered the art of sushi, sashimi, and other Japanese specialties. The ambiance is calm and inviting, with subtle touches of Japanese decor enhancing the dining experience. Kohana’s dedication to freshness is evident, with sushi aficionados often praising the quality and presentation of their rolls.

And of course, no mention of Hendersonville's dining scene would be complete without a nod to the city's homestyle eateries and barbecue joints. Establishments like Center Point Barbecue have entrenched themselves in the hearts of locals. With its smoky, tender meats and classic Southern sides, it’s a place that embodies the soul of Tennessee dining.

Residents around Winston Hills and Hendersonville, in general, are spoilt for choice when it comes to dining. Whether seeking gourmet experiences, international flavors, or the simple joys of comfort food, the area ensures no palate goes unsatisfied.


For music enthusiasts, the Hendersonville Performing Arts Company serves as a local gem. They frequently host musicals, plays, and live performances that showcase both local talent and touring artists. The intimate setting of the theater allows for an immersive experience, where audiences can truly connect with the performers. And considering Hendersonville's proximity to Nashville, the Music City itself, it's not uncommon for residents to make the short drive to immerse themselves in the world-famous music scene, be it country, blues, or any genre in between.

When it comes to sports, Drakes Creek Activity Center is a hive of activity. From soccer and baseball fields to tennis courts, the facility is often buzzing with local leagues, training sessions, and friendly matches. The sight of families cheering on young athletes on weekends or friends competing in a spirited tennis match on a sunny afternoon is a testament to the community's love for sports and outdoor activity. Plus, the Old Hickory Lake nearby is not just for tranquility and picnics; it's a hub for water sports. Whether you're into kayaking, paddleboarding, or simply watching the boats sail by, the lake ensures there's never a dull moment.

Film buffs have a special spot in their hearts for The Streets of Indian Lake. Beyond its shopping allure, the center's cinema offers a wide array of films, from the latest Hollywood blockbusters to indie gems. The comfortable seating and top-notch audio-visual quality make movie nights a favorite pastime for many Winston Hills residents.

Moreover, the local festivals and events peppered throughout the year add another dimension to entertainment in the area. From seasonal celebrations to art showcases, there's a communal spirit that shines through, bringing folks together in joyous harmony.

The Winston Hills vicinity in Hendersonville brims with life, offering a plethora of entertainment and sporting avenues. Whether one is a spectator or an active participant, there’s no shortage of avenues to dive into and enjoy.

Health and Wellness

The Winston Hills area of Hendersonville is not just a hub for community and culture; it's also a haven for those in pursuit of health and wellness. The neighborhood and its surroundings resonate with options that cater to a holistic approach to well-being, ensuring that residents have ample opportunities to nurture both body and mind.

A cornerstone in the community’s wellness scene is the Sumner County YMCA. More than just a fitness center, the 'Y' is a vibrant gathering spot that offers a plethora of programs for all ages. From swimming lessons in their indoor pool to yoga and spin classes, residents can tailor their fitness regimen according to their preferences. Additionally, the sense of camaraderie among the members makes working out feel more like a communal activity rather than a solitary pursuit.

For those who lean towards holistic and alternative treatments, several wellness centers and spas in the vicinity specialize in services like massage therapy, acupuncture, and meditation sessions. These establishments are not only sanctuaries for relaxation but also play a crucial role in helping individuals manage stress and find inner balance.

Nature itself is one of the best wellness assets in Hendersonville. The green trails, particularly around Drakes Creek Park, beckon residents to take long walks, jog, or simply meditate amidst nature. Old Hickory Lake's serene expanse offers another sanctuary for peace-seekers, allowing individuals to engage in paddleboarding, fishing, or simply taking a tranquil lakeside stroll.

Nutrition and diet, crucial components of a balanced lifestyle, are well-served by local organic stores and farmer's markets. Fresh, locally-sourced produce, dairy, and other essentials are readily available, allowing families to incorporate wholesome and nutritious meals into their daily routines. Moreover, several local cafes and eateries prioritize health-conscious menus, making it easier for residents to make nutritious choices even while dining out.

For those moments when medical care is needed, the vicinity boasts top-tier healthcare facilities. With advanced medical services, experienced practitioners, and a commitment to patient well-being, residents can rest assured that their health is in capable hands.

The environment around Winston Hills in Hendersonville effortlessly marries the realms of recreation and health. Whether one's path to wellness involves a rigorous fitness regime, a connection with nature, or a blend of holistic practices, the area ensures that the journey is both fulfilling and accessible.

Outdoor Lifestyle

One of the most iconic natural retreats in the area is Old Hickory Lake. Beyond its shimmering waters that glisten under the Tennessee sun, the lake provides a host of recreational opportunities. Kayaking, fishing, or simply picnicking along its shores are just a few of the favorite pastimes for Winston Hills residents. The lake also features several designated walking trails, perfect for those early morning jogs or leisurely evening strolls.

Then there's Drakes Creek Park, a treasure trove of outdoor amenities spread across its vast expanse. Families, sports enthusiasts, and nature lovers alike frequent this park. Kids revel in the playgrounds, while adults might be spotted in spirited matches on the tennis or volleyball courts. The park’s green spaces are often dotted with picnickers, dog walkers, and yoga enthusiasts, making it a hub of activity and relaxation.

Veterans Park, aptly named as a tribute to those who've served, is another slice of green paradise in Hendersonville. With its well-maintained soccer and baseball fields, it often hosts local leagues and tournaments. But beyond sports, its winding trails surrounded by verdant trees and chirping birds offer a peaceful escape for nature lovers.

For the avid golfers, the local courses blend the love of sport with the beauty of nature. These manicured greens set against the backdrop of rolling hills and clear blue skies make for a delightful way to spend a morning or afternoon.

Winston Hills residents also enjoy the proximity to the many community gardens in the area. These spots are not only a testament to the city's commitment to green living but also provide a therapeutic space for those who wish to indulge in some gardening, cultivating both plants and a sense of community.

The natural beauty and outdoor spaces around Winston Hills, Hendersonville, provide a compelling invitation to embrace an active, outdoor-centric lifestyle. Whether it's through sports, relaxation, or simple appreciation of the environment, there’s a slice of nature waiting to be explored and cherished by all.


For families residing in the Winston Hills region of Hendersonville, the quality and diversity of education options play a pivotal role in making the neighborhood a preferred residential choice. The commitment to fostering a robust educational environment is palpable, and it's reflected in the array of both public and private institutions that cater to the community.

On the public education front, Hendersonville boasts a number of highly-rated schools. Hendersonville High School, for instance, has a longstanding reputation for academic excellence and offers a comprehensive curriculum. The school is known for its robust athletics program, a thriving arts scene, and a myriad of extracurricular activities, ensuring that students receive a well-rounded education. Additionally, schools like Nannie Berry Elementary and Hendersonville Middle School stand as testaments to the area's commitment to fostering a strong foundation in the early and middle academic years. These institutions, supported by Sumner County Schools, focus on creating nurturing environments where students are encouraged to explore, inquire, and grow.

For families considering private education, Hendersonville doesn't disappoint. The Merrol Hyde Magnet School is one such institution that garners attention. While technically a public school, its magnet status means its curriculum is geared towards academically advanced programs, particularly in the realms of foreign languages and STEM. Additionally, Hendersonville Christian Academy offers an education grounded in faith-based principles, combined with a rigorous academic program. From preparatory classes to spiritual programs, the academy seeks to develop not just the mind but also the character of its students.

For those seeking alternative educational approaches, Montessori schools and other specialized institutions provide options that cater to specific teaching philosophies and methodologies. These schools often emphasize individualized learning, ensuring each student's unique needs and potential are acknowledged and nurtured.

The educational landscape around Winston Hills is as diverse as it is impressive. The blend of public, private, and alternative institutions ensures that families have a plethora of choices, allowing them to find the best fit for their children's growth and development.

Shopping and Retail

A particularly standout destination in the area is The Streets of Indian Lake. Beyond being just a shopping complex, this hub combines retail, dining, and entertainment, creating a holistic experience. As you wander its walkways, you'll encounter a delightful blend of fashion boutiques, home decor stores, and gadget outlets. But what many appreciate is its open-air concept; it’s not merely a mall but a place to enjoy a leisurely afternoon, pausing perhaps for a cup of coffee or catching a movie at the cinema.

For those who have a penchant for local finds, Hendersonville's Main Street is a must-visit. It's the kind of place where you're likely to discover a rare vintage piece in an antique shop, or perhaps a handcrafted trinket that speaks of the area's artistry and heritage. The street is dotted with family-owned businesses, and the warm greetings you receive when you step into these stores remind you of the tight-knit community that forms the essence of Hendersonville.

Of course, for the everyday essentials, the town boasts several large department stores and supermarkets. From fresh groceries to the latest in tech and electronics, these establishments ensure residents don't have to venture far for their daily needs.

Seasonal pop-up markets and farmers' markets are also a staple in the area. Not only do they offer fresh, locally-sourced produce, but they also become community gathering spots where stories are exchanged, and friendships are kindled over the aroma of fresh bread and blooms.

The shopping experience around Winston Hills mirrors the broader Hendersonville ethos – a marriage of the old and the new, the global and the local, all served with a generous dose of Southern warmth. Whether you're on the hunt for the latest fashion trend or a piece of artisanal craftwork, you're bound to find it here.

Business and Economy

Around the Winston Hills area in Hendersonville, the local economy is buoyed by a diverse mix of businesses and industries. These not only provide a foundation for the region's economic well-being but also reflect the unique character and growth trajectory of the community.

Retail and commerce play a significant role in shaping the area's economic landscape. The Streets of Indian Lake, for instance, stands out as a premier shopping, dining, and entertainment destination. This commercial hub houses an array of boutique shops, national retail chains, and local businesses, making it a frequent spot for residents and visitors alike. It's not just a place of business; it’s a symbol of the community's vibrancy and growth.

Healthcare is another sector that supports the local economy. Hendersonville is home to several top-tier medical facilities that offer a range of services, from primary care to specialized treatments. These establishments not only serve the health needs of the community but also provide significant employment opportunities, further anchoring the city's economic stability.

Given Hendersonville's proximity to the famed Music City, it's no surprise that the music and entertainment industries leave their imprint on the local economy. Numerous recording studios, music academies, and venues for live performances can be found here. These institutions not only nurture the region’s rich musical heritage but also contribute to the influx of tourism and associated revenue streams.

Real estate and construction have seen a consistent surge in the area, reflecting Hendersonville's growing appeal as a residential and commercial destination. From plush residential communities like Winston Hills to commercial establishments, the construction boom is indicative of the city's forward momentum.

Additionally, the local agricultural sector, though not as vast as some of the other industries, remains a staple in the economy. Farmers' markets and organic produce stands are regular sights, echoing the community's commitment to sustainable living and local produce.

The businesses and industries near Winston Hills underscore the multifaceted nature of Hendersonville's economy. The balance of traditional sectors with emerging industries ensures that the city remains both rooted in its heritage and poised for future growth.

Hotels and Lodging

Among the notable accommodations is the Hyatt Place Nashville/Hendersonville, known for its comfortable rooms and top-notch service. It's a favorite for business travelers and families alike, given its range of amenities and proximity to local attractions. Their hearty breakfast spread, featuring a mix of local and international delights, is often praised by guests, setting the tone for a day of exploration or work.

For travelers seeking a more intimate experience, Hendersonville boasts a selection of bed and breakfasts that exude character and warmth. These establishments, often set in historic homes or scenic locales, offer a personalized touch to one's stay. Picture waking up in a beautifully restored Victorian-era home, the aroma of freshly baked muffins wafting through the air, and the innkeeper sharing stories of the town's history and suggesting hidden gems to explore. That's the kind of experience these bed and breakfasts aim to provide.

A mention also goes to the many budget-friendly lodging options around the area. Chain hotels like the Holiday Inn Express & Suites or the Fairfield Inn & Suites by Marriott offer reliable accommodations with a touch of local flavor. These establishments often surprise visitors with their commitment to ensuring a comfortable stay, be it through their room service, local food recommendations, or their knowledge about nearby attractions.

For those who prefer a more home-like environment during their travels, the surge in vacation rentals has been a boon. Platforms like Airbnb feature listings in Hendersonville, ranging from lakefront properties to quaint cottages, providing travelers with the option to live like a local.

The Winston Hills vicinity and greater Hendersonville area understand the diverse needs of its visitors. Whether it's the sophistication of a branded hotel, the charm of a bed and breakfast, or the convenience of a budget stay, the locale ensures every traveler feels right at home.

Travel and Transportation

The Winston Hills neighborhood in Hendersonville is strategically positioned to provide its residents with relatively easy access to essential transportation hubs. When it comes to air travel, the convenience of having Nashville International Airport (BNA) nearby is hard to overstate. Located just a short drive away, usually around 25 to 30 minutes under typical traffic conditions, the airport serves as a major gateway for both domestic and international travelers. From here, residents can catch flights to virtually any major city in the U.S. and numerous international destinations. The airport itself is constantly evolving, with modern facilities, an array of dining and shopping options, and a touch of Nashville's iconic music scene with live performances now and then.

Regarding public transportation, while Hendersonville has its own local options, many residents find themselves leaning on the broader services provided by the Metropolitan Transit Authority (MTA) of Nashville. MTA's bus services have routes that connect various parts of the Nashville metropolitan area, including stops in Hendersonville. These services are particularly beneficial for those who commute to downtown Nashville for work or leisure, offering a stress-free alternative to driving. Additionally, ride-sharing services like Uber and Lyft are widely used in the area, providing an additional layer of convenience for those who prefer not to drive or don't have access to a vehicle.

Another noteworthy mention is the Music City Star, a commuter rail service that connects Nashville with several of its eastern suburbs, including a stop in Hendersonville. It's a favorite among many locals, not only because it's a picturesque way to travel alongside the region's waterways, but it also eases the commute during peak traffic times.

For those residing in or visiting the Winston Hills area, navigating to and from the neighborhood, whether by air or ground, is made considerably smoother thanks to these transportation options. They not only connect residents to the broader Tennessee region but also play a crucial role in knitting together the fabric of the community itself.