Winona Homes with Two Levels

Welcome to Winona, Texas – a hidden gem nestled in the heart of Smith County! This charming city is a delightful blend of small-town warmth and vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful yet engaging lifestyle. With its picturesque landscapes, friendly neighbors, and a rich tapestry of local history, Winona invites you to discover the joys of Southern living.

One of the standout features of Winona is its inviting real estate market, particularly for those interested in two-level homes. These spacious residences offer the perfect balance of comfort and functionality, providing ample room for families to grow and thrive. Imagine coming home to a beautifully designed two-story house, where you can enjoy the luxury of separate living spaces, making it easy to entertain guests or find a quiet nook for relaxation.

The two-level homes in Winona often feature charming architectural details, modern amenities, and generous outdoor spaces perfect for family gatherings or peaceful evenings under the stars. Whether you’re drawn to the cozy charm of a traditional home or the sleek lines of a contemporary design, you’ll find a variety of options that cater to your unique style and needs.

Living in Winona means you’re just a short drive away from the bustling city of Tyler, while still enjoying the tranquility of a close-knit community. With its excellent schools, local parks, and a strong sense of community, Winona is not just a place to live – it’s a place to call home. Come explore the possibilities and discover your dream two-level home in this enchanting Texas town!

Newest Winona Homes with Two Levels

$335,000

3 Beds ⋅ 3 Baths ⋅ 26013216 MLS

This 3 bed 2.5 bath homestead features a classic red brick farm house exterior with a real log cabin all wood interior! Renovated kitchen in October 2025 with granite countertops and a huge farmhouse sink. Gas range and stainless steel appliances with a large eat in dining area. Plenty of kitchen storage with 2 food pantries and extra built in’s. Included with the house is a 21.3 cu ft GE standup freezer. The master bedroom is your cabin oasis with large windows overlooking the garden. Attached updated full bath with fresh paint and new vanity in November 2025. Two extra bedrooms upstairs with a built in custom window seat. With a half bath to share. Downstairs, main living room is large and well lit with wall to wall windows providing great views of the property. Large stone fireplace centers the living room. With built in shelves and a large foyer. You will have more than enough land to fulfill all your gardening and food growing desires. This 2 acres is cleared and built out with dozens of growing spaces (raised and in ground). You will enjoy the thoughtfully designed landscape including a massive stone fire pit, picnic tables, fenced back yard, built in chicken coop and yard. A unique variety of mature trees and several new additions including a fruit orchard. As well as a 20x12 shop and a potting storage shed. This home is situated at the top of the neighborhood fully fenced with a combination of pipe fence and barbed wire. Surrounded by larger properties on both sides create an even bigger feel and a peaceful sanctuary. Conveniently located within 30 minutes of Tyler and Longview but just far enough that you get that peaceful country living.

11408 County Road 3168, Winona

Listing Courtesy of: with Listing Results, LLC. info@listingresults.com

$1,700,000

3 Beds ⋅ 26011255 MLS

Spanning approximately 137± acres in northeastern Smith County, just northwest of Winona and approximately 15 miles from Tyler, this versatile farm and ranch property offers an exceptional combination of rolling pasture, mature timber, abundant water, recreational opportunities and existing improvements. With two areas of frontage along FM 16, the property features multiple elevated areas, broad open pastures, wooded drainages and approximately 315–380 feet of elevation, creating beautiful views. A 4± acre pond serves as a focal point of the property, while East Mill Creek runs along much of the western side. The diverse landscape of open pasture, mature timber, creek frontage and water provides opportunities for cattle, hunting, fishing, trail riding and other outdoor recreation. Fencing and cross fencing are reported throughout the property, and an agricultural exemption is currently in place. Situated on elevated ground overlooking the pond is an approximately 3,151 sq ft home featuring 3 bedrooms, 2.5 baths and an attached 2-car garage. An in-ground pool and expansive concrete patio extend the outdoor living space and take advantage of the peaceful water views. The home offers an opportunity to renovate and customize as a primary residence, guest house or ranch manager's quarters. Additional improvements include an approximately 40x60 all-steel barn with open equipment storage and an enclosed portion with concrete flooring. Conveniently located approximately 5 miles from SH 155 and I-20, this property offers the space and privacy of an East Texas ranch while remaining within easy reach of Tyler. A rare opportunity to own substantial acreage with pasture, timber, water and improvements all in one property.

12251 Fm 16 E, Winona

Listing Courtesy of: with Dwell Realty. davidkurtz903@gmail.com

$239,900

4 Beds ⋅ 4 Baths ⋅ 26008586 MLS

Two properties for this price - you can't beat this deal. 104 S Tyler St. is a lot that is included in this listing. It could be built on or sold separately. Zoned commercial and residential, this historic downtown Winona property offers many possibilities as either a large residential home or home for a non-profit organization, ministry, offices, church or community facility. Built as a church in 1926, this property has been an important part of the history of this town. History lovers would be interested in the sea level marker located on its sidewalk. The property is made up of 6 lots and the back part of the property has electric, water, and sewage hook ups for RV or another build site. The rooms are very large and offer many options for use. Absolutely enormous kitchen with tons of counter space and cabinetry and a huge pantry would be ideal for a church or community center or a big family. Walls downstairs are 14.25" thick with 3 layers of brick and regular studded walls. Highlights include newer roof, new pex water lines throughout, gas fixtures and a 20x20 covered deck. All electrical has been inspected. Remodeled Kitchen, front bedroom (new carpet) and paint. Living room fresh paint. New flooring in kitchen, downstairs bathrooms and office. New vanities in downstairs bathrooms. New dishwasher and garbage disposal. Downstairs features 2 bedrooms and 2 full and one half bath. Upstairs offers 2 additional bedrooms and another half bath that is ready for tub/shower to be installed making it a full bath. Priced well below recent appraisal for a quick sale. *Some photos virtually staged

110 Church St, Winona

Listing Courtesy of: with Leslie Cain Realty, LLC. lesliecainsells@gmail.com

$789,900

4 Beds ⋅ 2 Baths ⋅ 26007079 MLS

HGTV FEATURED HOME! You can always appreciate when a piece of history is preserved — and this breathtaking 1910 home is the perfect example. Lovingly restored and exceptionally maintained, this property blends classic charm with modern comfort in all the best ways. Inside, the home offers two bedrooms and two baths downstairs, plus two additional bedrooms upstairs, giving plenty of space for everyone. You’ll also appreciate the abundant storage throughout, along with a spacious shop and 4 car garage ideal for additional storage, hobbies, and parking. This beautiful home is nestled on just over 18 acres, offering peaceful country scenery and endless possibilities. Enjoy the Koi pond from your welcoming front porch, or spend your afternoons fishing in the stocked back pond, complete with catfish, crappie, and perch. There is also a cabin pad near the back pond with full RV hookups, including septic — perfect for guests, a future tiny home, or a private retreat. This property is truly something special. From the history to the acreage to the thoughtful updates, you’re going to fall in love with every bit of its charm. Don't miss this rare opportunity! Call today!

15198 E Fm 16, Winona

Listing Courtesy of: with Century 21 First Group - Lindale. century21firstgroup@gmail.com

$430,000

3 Beds ⋅ 2 Baths ⋅ 26003916 MLS

Discover this one-of-a-kind 3-bedroom, 2-bath home with a 3-car carport, perfectly set on 4.149 beautiful acres. From the moment you step inside, you’ll notice the incredible craftsmanship and character that make this home truly stand out. Beautiful wood paneling flows through the main living areas, adding warmth and timeless charm throughout the home. The spacious living room is the heart of the home—anchored by a grand stone fireplace that instantly draws your attention and surrounded by large windows that fill the space with natural light. The kitchen and dining areas offer plenty of room for gathering, while each bedroom and bathroom provides generous space and comfort for everyday living. Upstairs, you’ll find a second-floor retreat complete with its own balcony and exterior staircase—perfect for enjoying peaceful country views. The third bedroom is exceptionally large and even features its own fireplace, making it an inviting and versatile space that can be used as a primary suite, guest quarters, or entertainment area. Recent updates include a new roof in 2020, freshly painted upstairs bedrooms in 2024, and a new A/C unit for added peace of mind. Outside, a storage shed provides extra space for all your tools, hobbies, or outdoor equipment. With over 4 acres of land, timeless details, and thoughtful updates, this property offers endless possibilities and a true sense of home.

13240 County Road 353, Winona

Listing Courtesy of: with RE/MAX Professionals. ben@tylerhousehunters.com

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The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) of the Greater Tyler Association of REALTORS Multiple Listing Service. The IDX logo indicates listings of other real estate firms that are identified in the detailed listing information. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This information is deemed reliable, but not guaranteed.