Wynnewood Homes under $250,000

Welcome to Wynnewood, Oklahoma – a hidden gem nestled in the heart of southern Oklahoma! Known for its warm community spirit and picturesque landscapes, Wynnewood is a charming small town that offers the perfect blend of friendly neighbors and serene living. With its rich history and vibrant culture, this delightful city is an ideal place for families, retirees, and everyone in between.

One of the most appealing aspects of Wynnewood is its affordability. Here, you can find a variety of charming homes priced under $250,000, making it an excellent choice for first-time homebuyers or those looking to downsize without compromising on comfort or style. These homes often feature spacious yards, cozy interiors, and the kind of character that makes a house feel like a true home. Whether you're searching for a quaint cottage or a family-friendly residence, Wynnewood has something to suit every taste and budget.

Beyond its affordable housing, Wynnewood boasts a range of local amenities, including parks, schools, and shops that cater to your everyday needs. The community is also known for its welcoming atmosphere, where neighbors become friends and everyone feels a sense of belonging. Plus, with easy access to nearby attractions like the Chickasaw National Recreation Area and the bustling city of Ardmore, residents can enjoy the tranquility of small-town living while being just a short drive away from more urban conveniences.

Discover the charm and affordability of Wynnewood, Oklahoma, where your dream home awaits!

Newest Wynnewood Homes under $250,000

$219,000

3 Beds ⋅ 3 Baths ⋅ 1250867 MLS

This beautifully remodeled 3-bedroom, 3-bath home combines character, modern updates, and plenty of space inside and out. Situated on a fully fenced .51-acre corner lot, the property features a durable metal roof, detached garage, and storm shelter. Inside, the spacious open kitchen is designed for gathering, featuring abundant cabinetry, generous counter space, stainless appliances, and an oversized island with plenty of room for seating. A walk-in pantry with a dedicated coffee bar adds even more storage and functionality. Large windows throughout the home provide abundant natural light and complement the updated finishes. The primary suite is a standout, offering plenty of room for a sitting area or cozy reading nook, plus its own private exit to the adjoining deck. The attached primary bath features a large walk-in shower, while a spacious walk-in closet provides excellent storage. The roomy laundry area goes beyond the basics with a utility sink, countertop workspace, cabinetry, and additional storage. With open living spaces, thoughtful updates, and functional storage throughout, this home offers a layout designed for comfortable everyday living. Outside, enjoy the privacy and possibilities of the fully fenced half-acre lot, outdoor deck space, detached garage, and storm shelter. Call or text today to schedule your private showing and see everything this property has to offer!

509 N Taylor Avenue, Wynnewood

$115,900

3 Beds ⋅ 2 Baths ⋅ 1249907 MLS

Fantastic opportunity for investors or buyers looking to bring their vision to life. This property offers an abundance of living space with 3 separate living areas [or 2 living areas and 1 formal dining]. One living room features a wood burning fireplace. All 3 bedrooms are large enough to fit a king size bed. This home already has a 2 car- carport. This home sits on a generously sized lot with mature trees and plenty of room to enjoy. Room for a garden, pets, or kids to run!

1205 E Indianola Street, Wynnewood

$195,000

3 Beds ⋅ 2 Baths ⋅ 1248396 MLS

Welcome to 506 E Schmid Street—a beautifully remodeled brick home offering room to live, work, and unwind on a spacious .4821-acre corner lot. Inside, you’ll find 3 bedrooms, 2 bathrooms, a comfortable living room, dedicated dining area, and versatile bonus room. One of the three bedrooms is currently arranged as an office, demonstrating the flexibility of the floor plan. The refreshed kitchen features newly installed quartz countertops, a crisp subway tile backsplash, generous cabinetry, and updated flooring that continues into the dining and utility areas. Both bathrooms have been tastefully updated, while modern lighting and thoughtful finishes add a fresh feel throughout. The roomy utility area provides additional cabinetry and countertop space for everyday organization. Outside, the fully fenced yard offers nearly half an acre with mature shade trees, a back patio, and plenty of room for outdoor enjoyment. An attached carport and a detached carport with additional storage provide covered parking for up to four vehicles—a standout feature for anyone needing extra space for vehicles, equipment, or hobbies. Updated, versatile, and ready for its next owner, this Wynnewood property deserves a closer look. Schedule your private showing today!

506 E Schmid Street, Wynnewood

$209,900

4 Beds ⋅ 2 Baths ⋅ 1237130 MLS

Welcome to 9408 Joy Road in Wynnewood, Oklahoma — a spacious and thoughtfully designed 4-bedroom home offering comfort, flexibility, and room to enjoy a quieter country setting. Built in 2022 and situated on approximately 1.95 acres, this home blends modern finishes with the peaceful feel of rural living, all while remaining within the Wynnewood School District. Inside, the home features a bright and open layout with attractive wood-look flooring, neutral finishes, and plenty of natural light. The kitchen is a standout with white cabinetry, stainless appliances, a farmhouse-style sink, a large center island, black countertops, and a warm reclaimed-wood-style backsplash that gives the space character and charm. The open kitchen and dining area create a comfortable gathering space for everyday living, meals, and entertaining. The home offers 4 bedrooms plus an additional bonus room with a closet, giving buyers valuable flexibility. This extra room could serve as a second living area, home office, playroom, guest room, or potential 5th bedroom depending on the buyer’s needs. The primary suite includes a spacious bathroom with a double vanity, soaking tub, separate shower, and a clean modern feel. Outside, the acreage provides room to spread out, enjoy the outdoors, add a shop, garden, or create the country lifestyle many buyers are looking for. The setting offers privacy and open space while still being close to town conveniences in Wynnewood, with easy access to nearby communities such as Pauls Valley, Davis, and Sulphur. The surrounding area is known for outdoor recreation and small-town charm. Buyers can enjoy nearby attractions such as the Arbuckle Mountains, Turner Falls, Chickasaw National Recreation Area, and the Lake of the Arbuckles, offering opportunities for hiking, fishing, boating, swimming, camping, and weekend getaways. Reach out to schedule a showing today.

9408 Joy Road, Wynnewood

$38,000

2 Beds ⋅ 1 Baths ⋅ 1236772 MLS

Opportunity awaits with this 2-bedroom, 1-bath home that's already well on its way to becoming a great investment or personal residence. Remodeling has been started, with the kitchen appearing to be completed and the bathroom already underway—just bring your finishing touches to complete the project. Choose your own flooring to add your personal style and complete the home's transformation. A newer roof, installed around 2020, provides added value and peace of mind. Conveniently located near the Wynnewood Refinery, this property offers strong potential for investors, rental income, or buyers looking to build equity. With much of the hard work already started, this is your chance to customize the final details and unlock this home's full potential. Don't miss this value-packed opportunity!

406 E Colbert Street, Wynnewood

$110,000

2 Beds ⋅ 1 Baths ⋅ 1236328 MLS

Investor opportunity with upside potential! This 2-bedroom, 1-bath home sits on two lots and offers the perfect combination of immediate rental income potential and future value growth. Featuring a newer roof and updated closet doors, just a few small improvements could have this property rent-ready in no time. Conveniently located near the Wynnewood Refinery, this property is well-positioned to attract tenants seeking proximity to major local employers. The oversized lot configuration provides exciting possibilities for expansion, allowing a future owner to add square footage, additional bedrooms, and bathrooms to maximize value and rental returns. Whether you're looking to start your investment portfolio, add a cash-flowing asset, or capitalize on a property with room to grow, this is a rare opportunity to secure a home with both immediate potential and long-term upside. Bring your vision and unlock the possibilities!

501 N Taylor Street, Wynnewood

$85,000

2 Beds ⋅ 1 Baths ⋅ 1232288 MLS

Welcome to this charming home built in 1950. Situated on a spacious corner lot, this 3 bedroom, 1 bath home offers a comfortable space to call home. Inside you will find a large kitchen with plenty of space for cooking, gathering, and entertaining. Two large bedrooms with walk-in closets provide ample storage. A third bonus area could be used as a third bedroom or office. Outside enjoy the large, fenced backyard and storage building. This home is full of possibilities and is too cute to miss!

807 E Kean Street, Wynnewood

$99,500

2 Beds ⋅ 1 Baths ⋅ 1232260 MLS

Step into the charm of yesteryear with this adorable 1950s home full of character and timeless appeal. Featuring 2 bedrooms and 1 bathroom, this inviting property has so many cool features from coved ceilings to custom display cabinets. You can peace of mind with easy to maintain vinyl flooring and a brand-new roof. Situated on a large corner lot the property is shaded by beautiful mature trees that provide both curb appeal and a relaxing outdoor setting. An outbuilding offers extra outdoor storage, or a home for hobbies. Whether a first-time buyer, looking to downsize, or an investor, this home provides opportunity for all. Give us a call today to make this home your own.

405 S Clayton Avenue, Wynnewood

$45,000

5 Beds ⋅ 3 Baths ⋅ 1195686 MLS

INVESTMENT OPPORTUNITY in Wynnewood, Oklahoma! This 4–5 bedroom, 3-bath home offers approximately 2,480 square feet (MOL) of potential, situated on just under a 1/5-acre lot (MOL). While the property does need repairs, it presents a great opportunity to renovate, add value, and build equity. Don’t miss your chance to invest in a quiet Oklahoma community with room to grow. Homeowner does not have insurance. Please use caution when entering the properties and houses. Seller/brokerage not liable for accidents. Title work has been completed at Garvin County Abstract.

200 E Juanita Street, Wynnewood

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