Homes for Sale Near Chiles Middle in Oviedo - 48 homes

Remarks: Under contract-accepting backup offers. Discover the perfect blend of comfort, style, and location in this beautifully maintained 4-bedroom, 2.5-bath home located in the highly desirable Alafaya Woods community in Oviedo. Perfectly positioned on a spacious corner lot, this property combines functionality, charm, and modern upgrades. From the moment you arrive, you’ll appreciate the pride of ownership and the many valuable improvements throughout the home. Inside, you’ll find an inviting and versatile layout featuring a formal living room, dining room, and an oversized family room designed for both everyday living and entertaining. The home showcases beautifully remodeled bathrooms, brand-new luxury vinyl flooring throughout the home, and a bright, welcoming atmosphere with plenty of natural light flowing throughout the living spaces. The kitchen is thoughtfully positioned overlooking the main living areas, creating a seamless connection ideal for gatherings, family time, and entertaining guests. The spacious family room provides endless possibilities for relaxing, hosting celebrations, movie nights, or creating the perfect flex space to fit your lifestyle. Major improvements provide peace of mind for future homeowners, including a roof replaced in 2016, updated windows installed in 2019, a brand-new A/C system in 2025, and a water heater replaced in 2024. These significant updates make this home move-in ready while adding long-term value and efficiency. Step outside and enjoy the oversized backyard with ample space to create your ideal outdoor retreat, add a pool, entertain, garden, or simply enjoy Florida living year-round. The corner lot location provides additional privacy, curb appeal, and extra outdoor space rarely found in similar homes. Location is everything, and this home truly delivers. Conveniently located near top-rated Seminole County schools, shopping, dining, parks, and major highways, residents enjoy quick access to everything Central Florida has available. Just minutes from University of Central Florida, Research Park, Siemens, Lockheed Martin, and major employers, this property is ideal for families, professionals, and investors alike. Enjoy nearby outdoor recreation at Oviedo on the Park, trails, sports complexes, and multiple community parks, while still being within easy reach of Downtown Orlando, Orlando International Airport, and world-famous attractions. This is an exceptional opportunity to own a beautifully updated home in one of Oviedo’s most established and sought-after communities. Schedule your private showing today and experience everything this incredible property has available.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Fatima Pereira De Araque (407-861-0800)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Nestled on a quiet cul-de-sac in Oviedo’s sought-after The Sanctuary community, this beautifully maintained 3-bedroom, 2.5-bath home with a private office offers peaceful pond and conservation views along with access to incredible neighborhood amenities, including a community pool, clubhouse, fitness center, basketball and tennis courts, playgrounds, and more. Ideally located within walking distance to Chiles Middle School, this home combines comfort, convenience, and an unbeatable location. Inside, neutral paint and flooring paired with large windows create a bright and inviting atmosphere filled with natural light. The spacious great room serves as the heart of the home, seamlessly blending the family room, dining area, and kitchen for easy everyday living and entertaining. Sliding glass doors in the family room open to the covered and screened patio, creating effortless indoor-outdoor living. The dining space is tucked just off the main living area with direct kitchen access and picturesque pond views. The updated kitchen is designed to impress with stainless steel appliances, miles of granite countertop space, 42-inch cabinetry, a closet pantry, breakfast bar, and a sunny dinette overlooking the conservation and pond. Just off the dining area, double doors lead to a private office, ideal for working from home or creating a quiet flex space. A convenient half bath is located nearby for guests. The split-bedroom floorplan provides privacy, with the spacious primary suite tucked away at the back of the home. Enjoy tranquil conservation views, dual closets, and a well-appointed en-suite bath featuring double vanities, a large shower, garden tub, and private water closet. Both secondary bedrooms are generously sized with large closets and ceiling fans, while the secondary bathroom offers a single-sink vanity and shower/tub combination. Step outside to a large covered and screened patio overlooking the pie-shaped backyard with plenty of room to play, garden, or relax — all backed by conservation for added privacy and serenity. Additional highlights include a 2025 roof and water heater, as well as built-in automatic storm shutters for peace of mind. Whether you’re enjoying the peaceful views, entertaining family and friends, or taking advantage of The Sanctuary’s exceptional amenities, this home offers the perfect blend of comfort, privacy, and Oviedo living.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Jean Scott (407-759-5320)

Remarks: Under contract-accepting backup offers. Welcome to this fully updated Oviedo pool home located at 1008 Moccasin Run Rd in the highly desirable Twin Rivers area, just minutes from UCF, Oviedo on the Park, and SR-417. If you’ve been searching for a move-in ready home in Oviedo with a pool, modern upgrades, and no major expenses, this one stands out. This 3-bedroom, 2-bath home features a split floor plan with high ceilings, a formal dining room, and a spacious family room with a tri-tier sliding glass door opening to an enclosed porch, ideal for indoor-outdoor living and entertaining. The remodeled kitchen offers solid wood cabinetry, quartz countertops, stainless steel appliances (2025), a breakfast bar, and a pass-through to the dining area. The primary suite includes a beautifully remodeled bathroom with a garden tub, newly tiled shower with upgraded glass enclosure, and dual vanities. The guest bathroom has also been updated and provides convenient access to the pool area. Enjoy a large vinyl-fenced backyard with a private pool and enclosed porch, perfect for Florida living. Additional features include an oversized laundry room with utility sink and ample storage, epoxy-coated garage floor, and numerous interior upgrades throughout. Major updates include: roof (2024), replumb (2019), tankless water heater (2021), HVAC (2017), windows (2013), luxury vinyl flooring and baseboards (2024), interior paint (2024), gutters (2025), stucco and exterior paint (2025), and updated lighting, blinds, and exterior doors (2025). Kitchen appliances were replaced in 2025, and a disposal was installed in 2026. Conveniently located near top-rated Seminole County schools, shopping, dining, parks, and major highways, this home offers both convenience and lifestyle. Schedule your private showing today to see this Oviedo home for sale in person.

Listing is courtesy of: PARK VIEW REALTY INC (321-663-0905)

Listing Agent: Casey Irwin (321-609-1589)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Alafaya Woods community in Oviedo. Step inside to an open and inviting floor plan featuring a spacious living, dining, and kitchen combination with a desirable split-bedroom layout for added privacy. The kitchen features an oversized sink, plenty of counter space, and sliding glass doors that lead to the large backyard — perfect for entertaining or relaxing outdoors. Recent updates include a new vinyl fence, fresh exterior paint, a 2019 roof, and a 2018 A/C system, giving you peace of mind for years to come. Nestled in a quiet, established neighborhood with low HOA fees, this home is conveniently located just 10 minutes from UCF and close to Oviedo on the Park, Waterford Lakes Town Center, shopping, dining, and local favorites. With easy access to SR-417, commuting to downtown Orlando, the airport, and Florida’s beautiful beaches is a breeze. Come see all this home has to offer and make it your own!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Franki Gonzalez (954-918-4665)

Remarks: Under contract-accepting backup offers. This Stunning 5-bedroom, 3-bathroom pool home in a newer gated community offers the perfect blend of luxury, comfort, and functionality-designed with every detail in mind. From the moment you arrive, you'll be impressed by the well-manicured yard and extended driveway, providing both curb appeal and convenient parking. The welcoming front porch with a charming space for a swing sets the tone for the warmth and elegance that awaits inside. Step through the grand entryway adorned with beautiful wainscoting and into a thoughtfully designed layout with amazing wood-look tile. The formal dining room features matching wainscoting and is perfect for hosting gatherings. The gourmet kitchen is a chef's dream, complete with a large center island with pendant lights, granite countertops, stainless steel appliances, double ovens, a walk-in pantry and a spacious casual dining area. The kitchen flows seamlessly into a generously sized family room featuring an electric fireplace, creating an inviting space for everyday living and entertaining. A guest bedroom and full bath are conveniently located on the first floor, along with a spacious laundry room that includes a built-in storage bench for added functionality. Upstairs, a beautiful wood staircase with wrought-iron railings leads to an expansive loft-ideal as a media room, home office, or playroom. Three secondary bedrooms all feature walk-in closets, while the luxurious primary suite impresses with a double-door entry, a spa-like bathroom with a garden tub, seamless glass shower, dual vanities, and an enormous walk-in closet. Step outside to your private backyard oasis. The saltwater pool features color-changing LED lights and a sun shelf for lounging or play. A panoramic screen enclosure offers uninterrupted views of the lush conservation area beyond the enclosure which has an extended roof for an added entertainment area. The fenced yard and landscaped borders provide added privacy. Additional features include a 3-car tandem garage, 2 AC units for zoned comfort, Brita Pro whole-house water filter and softener system, updated lighting, and a Simply Safe Security System that covers the doors and windows downstairs. Located in one of Seminole County's most sought after areas-zoned for top-rated schools and conveniently located near Siemens, Lockheed Martin, Research Park and easy access to SR-417. This is more than a home-It's A Lifestyle. Don't miss your chance to own this beautifully upgraded, move-in-ready retreat!

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: Melinda Jarzynka (407-694-3655)

Remarks: Under contract-accepting backup offers. Location. Lifestyle. Luxury. Welcome to an extraordinary, beautifully appointed 4-bedroom, 2-bath pool residence nestled in the highly coveted and established Twin Rivers community of Oviedo. Gracefully positioned on a rare and expansive .44-acre conservation homesite with no rear neighbors, this property offers exceptional privacy, tranquil natural views, and an enviable sense of space — all in an unbeatable, highly desirable location. From the moment you enter, soaring vaulted ceilings and abundant, natural light create an airy, welcoming, and sophisticated ambiance. The elegant formal living and dining spaces blend seamlessly, enhanced by gorgeous luxury vinyl plank flooring that flows throughout the main living areas, striking the perfect balance between warmth, durability, and modern refinement. At the heart of the home lies a stunning, thoughtfully renovated chef-inspired kitchen designed for both comfortable everyday living and effortless entertaining. Expansive tiled countertops and backsplash, sleek newer appliances, generous bar seating, and a charming sunlit eat-in area make this space as functional as it is stylish — ideal for peaceful morning coffee, festive holiday gatherings, or intimate evenings with friends. The desirable split floor plan offers privacy and comfort, with a spacious and serene primary suite tucked away as a true retreat. Dual walk-in closets, a beautifully updated tiled shower, relaxing garden tub, new frameless glass enclosure, and contemporary lighting elevate the space into a spa-like sanctuary. The secondary bath has also been tastefully remodeled with clean, modern finishes, ensuring comfort and style for family or guests. Additional thoughtful upgrades include a newer AC system, refreshed pool features, and an enhanced sprinkler system for easy, efficient maintenance. Step outside and discover your own private, resort-style Florida oasis. A generous 20x12 covered and screened patio creates the perfect setting for relaxed outdoor living, whether hosting lively celebrations or enjoying quiet sunset evenings. The impressive 7-foot-deep saltwater pool features a unique underwater table with built-in seating and umbrella sleeve — an inviting and distinctive touch perfect for long, sun-drenched afternoons. A raised, heated spa and sleek aluminum accent fencing add architectural elegance, while the expansive fenced yard still provides abundant green space, including a charming, colorful corner flower garden. Fresh, lush St. Augustine sod in both the front and back yards enhances the home’s manicured curb appeal, and the property line extends well beyond the rear fence (see survey), offering even greater privacy, flexibility, and possibility. And then there’s the location — truly exceptional. Walking distance to Carillon Elementary and Hagerty High School, and just minutes from Twin Rivers Golf Club, the Oviedo Skate Park, UCF, Siemens, Lockheed Martin, Waterford Town Center, SR 417, and Downtown Orlando — convenience, community, and connectivity come together effortlessly. This is more than a home — it is a refined lifestyle opportunity in one of Oviedo’s most desirable and well-loved neighborhoods. Opportunities of this caliber are rare. Come experience the comfort, privacy, and understated luxury for yourself — and let’s get you to closing.

Listing is courtesy of: BEAR TEAM REAL ESTATE (407-228-1112)

Listing Agent: Bethanne Baer (407-228-1112)

Remarks: Under contract-accepting backup offers. Welcome to your dream home in the highly sought-after Oviedo community of Live Oak Reserve, where luxury upgrades, modern design, and an unbeatable location come together. Perfectly positioned on a premium oversized fenced corner lot, this move-in-ready residence showcases standout curb appeal with a paver driveway, a split three-car garage and elegant double etched-glass French doors that create an unforgettable first impression. Step inside to a bright, open-concept floor plan featuring soaring 10-foot ceilings, rich crown molding, upgraded 5.5-inch baseboards, and a seamless blend of laminate and tile flooring throughout, complemented by luxury tile plank in the bedrooms. Every inch of this home has been thoughtfully maintained, delivering a refined yet comfortable living experience. The gourmet kitchen is ideal for both entertaining and everyday living, offering Corian countertops, abundant 40-inch cabinetry, upgraded appliances, and an effortless flow into the spacious family room. The primary suite serves as a true retreat with a relaxing garden tub, generous walk-in closets, and a dedicated vanity space designed for convenience and comfort. Three additional bedrooms provide exceptional flexibility, perfect for overnight guests, a home office, or creative spaces tailored to your lifestyle. Outside, you’ll find a screened-in patio that seamlessly extends your living space outdoors, along with a sparkling, heated, saltwater pool that creates the perfect setting for year-round relaxation and entertaining. Imagine starting your summer mornings with refreshing laps in the pool, unwinding in the Florida sunshine poolside, and hosting unforgettable evenings grilling and gathering with friends. Designed with both function and peace of mind in mind, this home includes new roof (2024), HVAC (2025), whole-home noise-reduction insulation, Cat 5 high-speed wiring, ceiling fans with remote controls, Pentair pool heater and a full security and irrigation system. Living in Live Oak Reserve means enjoying resort-style amenities and access to top-rated schools, just minutes from University of Central Florida, Siemens, Research Park, premier shopping and dining, and convenient access to the commuter routes. This is a rare opportunity to own a fully upgraded, meticulously maintained home in one of Oviedo’s most desirable communities, offering the perfect blend of style, comfort, and convenience. Do not wait, call today to learn more!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Thomas Mcnamara, Jr (407-754-6412)

Remarks: One or more photo(s) has been virtually staged. Experience elevated living in this beautifully updated pool home located in the highly sought-after Live Oak Reserve community in Oviedo. Thoughtfully designed with both comfort and style in mind, this residence features a spacious, open-concept layout enhanced by fresh interior paint, creating a bright and refined atmosphere throughout. The main living areas are filled with natural light and flow effortlessly, with multiple sliding glass doors opening to a private screened-in pool and patio—offering a true indoor-outdoor lifestyle ideal for entertaining or unwinding in your own backyard retreat. At the heart of the home, the kitchen is appointed with granite countertops, stainless steel appliances, and a breakfast nook overlooking the pool, blending functionality with everyday elegance. A first-floor bedroom and full bath provide a versatile space for guests, extended family, or a private home office. Upstairs, the home continues to impress with generously sized bedrooms and a well-appointed primary suite featuring dual walk-in closets and a spacious ensuite bath designed for comfort and relaxation. Recent upgrades include fresh interior paint (2026), exterior paint (2025), resurfaced pool area (2025), updated luxury vinyl stairs (2025), new oven (2025), dual A/C systems (2016 & 2018), and a variable-speed pool pump. Buyer incentives you don’t want to miss—this home qualifies for a 1% lender credit, offering additional value and flexibility for qualified buyers. Residents enjoy access to resort-style amenities including a clubhouse, fitness center, community pool, tennis and basketball courts, sports fields, and playgrounds. Ideally located within a highly regarded school zone and just minutes from UCF, Siemens, Oviedo on the Park, shopping, dining, and major highways.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Timur Kapanov (646-701-2332)