Homes for Sale Near Chiles Middle in Oviedo - 50 homes

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: Under contract-accepting backup offers. Welcome to this beautifully appointed 4-bedroom, 3-bathroom home nestled in Oviedo’s highly sought-after Riverside community. Ideally located just a short walk or bike ride to Partin Elementary and Chiles Middle Schools, this home combines convenience with exceptional versatility. From the moment you arrive, you’ll appreciate the inviting curb appeal, enhanced by fresh landscaping, new exterior paint, and a spacious two-car garage. Inside, a bright and open floorplan greets you with luxury vinyl flooring, fresh neutral paint, and abundant natural light pouring through large windows. The formal living and dining areas sit just off the entry, creating an ideal space for entertaining, while the living room offers peaceful patio views and direct access for effortless indoor-outdoor living. At the heart of the home, the kitchen and family room combination is perfectly designed for both daily life and gatherings. The kitchen boasts ample cabinetry, generous counter space, a breakfast bar, all-new stainless steel appliances, and a large pantry. The adjacent family room overlooks the backyard and also provides patio access, while a spacious under-stair storage closet adds extra functionality. The split floorplan ensures privacy, with the primary suite tucked away on the left side of the home. This relaxing retreat features private sliding glass door access to the pool, a walk-in closet, and an en-suite bathroom complete with a double-sink vanity, linen storage, and a large shower/garden tub combination. On the right side of the home, two generously sized secondary bedrooms offer large closets and sliding doors, and share an updated bathroom with a single-sink vanity and an oversized walk-in shower. Upstairs, accessible via a staircase equipped with a built-in chair lift, is an impressive bonus room with full wet bar—perfect for a man cave, kid’s game room, multi-generational living, extended guests, or a private apartment setup. This expansive space includes a full kitchen, living and dining areas, and access to a private balcony. The oversized bathroom features a double-sink vanity, water closet, and a large walk-in tile shower. Beyond the bathroom, you’ll find two walk-in closets—one with a custom system—leading into a massive bedroom that could easily be reconfigured into two separate rooms if desired. Step outside to your private backyard oasis, where a covered patio overlooks a large, open pool and above-ground spa with Bluetooth speakers—perfect for relaxing or entertaining year-round. The expansive pool deck provides plenty of space for lounging, dining, or gathering around a firepit, while the fully fenced yard still offers room for a playset, pets, or additional outdoor features. With its flexible layout, thoughtful updates, and rare in-law suite, this home offers the perfect blend of space, comfort, and functionality in one of Oviedo’s most desirable communities.

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

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

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)

Remarks: Welcome home to this charming 4-bedroom, 2-bath single-family home in Oviedo, located in a desirable, family-friendly neighborhood just minutes from Oviedo on the Park. This well-maintained home offers a functional layout with spacious bedrooms and comfortable living areas ideal for everyday living. Enjoy Florida living in the fully fenced backyard, perfect for entertaining, pets, or relaxing evenings around the wood-burning fire pit. The outdoor space offers privacy and flexibility for future enhancements. Zoned for top-rated Seminole County schools, this home is conveniently located near parks, shopping, dining, and major roadways. A rare opportunity to own a move-in ready home in one of Oviedo’s most sought-after areas.

Listing is courtesy of: ALIGN REAL ESTATE LLC (305-389-2922)

Listing Agent: Aarohi Shah (407-399-6496)

Remarks: One or more photo(s) has been virtually staged. Welcome! This delightful 4-bedroom, 3-bathroom pool home enjoys a tranquil cul-de-sac setting and a versatile one-story floor plan, resulting in a cozy environment for daily living and a home ready for life’s ever-changing needs. The split-bedroom floor plan offers great privacy forever, while the dedicated living spaces, glistening in-ground pool, and beautiful chef’s kitchen are there to bring everyone together. High ceilings, recessed lighting, fresh interior/exterior paint, and no carpet add to the appeal of this move-in-ready home. For added convenience, the property features a large brick paver driveway and a split three-car garage, providing ample parking and added flexibility. Use the separate one-car garage for more parking, as a workshop, or whatever your mind can envision. Whether it is a normal day or a special occasion, this functional home thrives. The community is moments from modern amenities and activities, offering outstanding convenience while set amid Florida’s natural beauty. Within the neighborhood, a resort-like community pool/splash pad, clubhouse, fitness center, parks, and sports courts await. Nearby, residents will find the Oviedo Mall, Publix at Riverside Landing, and a variety of other dining and shopping options at your fingertips. For nature enthusiasts, Riverside Park and Little Big Econ State Forest/canoe launch offer immediate outdoor adventures. At the same time, golfers will appreciate the proximity to Twin Rivers Golf Club for convenient rounds. Don't miss the chance to make this beautiful home yours – schedule your private showing today.

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)

Listing Agent: Joseph Doher (407-203-0007)

Remarks: Under contract-accepting backup offers. Move-in ready and beautifully updated, this home in the highly sought-after Alafaya Woods community in Oviedo checks all the boxes. Zoned for top-rated schools, the property features a brand new roof and AC (2025), fresh interior paint, and stylish upgrades throughout. The kitchen and bathrooms have been thoughtfully renovated, complemented by modern light fixtures and clean knockdown ceilings for a contemporary feel. The spacious split-bedroom floorplan offers both privacy and functionality, ideal for families or guests. Step outside to enjoy a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings at home. Located just minutes from shopping, dining, and everything the greater Orlando area has to offer, this home delivers the perfect combination of comfort, convenience, and value. Don’t miss your opportunity to own in one of Oviedo’s most desirable neighborhoods!

Listing is courtesy of: ADAMUS REALTY GROUP, INC (407-620-6608)

Listing Agent: Jon Adamus (407-620-6608)

Remarks: Location, Location, Location! Less than 4 miles from UCF, 3 miles from Hagerty High School, and 2 miles from Seminole State College, this beautifully updated 4-bedroom, 3-bathroom single-story pool home perfectly combines comfort, style, and functionality. Nestled on an oversized lot in the highly sought-after Big Oaks community, this property offers privacy, space, and peace of mind with numerous recent upgrades. Step inside to a bright, open floor plan that seamlessly connects the living, dining, and kitchen areas ideal for everyday living and entertaining. The expansive master suite boasts soaring ceilings and a newly renovated spa-inspired bathroom with elegant, modern finishes your own private retreat. The chef’s kitchen is a true highlight, featuring granite countertops, a stylish backsplash, an oversized island with added cabinetry, and a cozy breakfast nook for casual meals. Enjoy true Florida living in your outdoor oasis: a covered lanai, sparkling private pool, and an extended patio perfect for BBQs, family gatherings, or simply soaking up the sun. The spacious backyard offers additional green space for pets, play, or even a future garden. A unique bonus is the flexible In-Law Suite with a private entrance, bedroom, full bath, kitchenette, and living area ideal for multi-generational living and/or guests. Recent Upgrades Include: New Roof in 2023 Updated A/C System Fresh Exterior Paint Families will love being zoned for top-rated schools, including Hagerty High School just minutes away. The location couldn’t be better close to shopping, dining, medical centers, and major employers like Lockheed Martin, UCF, and Valencia College. With easy access to 417, 434, and 426, you’re just a short drive from Disney, Universal, and Central Florida’s beautiful beaches. This is more than a home, it’s a lifestyle upgrade. Don’t wait—schedule your private showing today!!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Monica Cuervo (407-701-3095)

Remarks: Welcome to this well-maintained 3-bedroom, 2.5 bathroom single-family home in the highly sought-after Twin Rivers community in Oviedo. Featuring formal living and dining rooms, this home offers a functional layout ideal for both everyday living and entertaining. The main living area is highlighted by a cozy fireplace, while the large screened porch provides the perfect space to relax or host gatherings year-round. Conveniently located near Oviedo on the Park, Twin Rivers Golf Course, UCF, and a variety of shopping and dining options, this home offers both comfort and accessibility in one of Oviedo’s most desirable neighborhoods.

Listing is courtesy of: LUKER & CO REAL ESTATE LLC (321-244-2542)

Listing Agent: Tom Luker (407-415-2821)

Remarks: Welcome to this charming 3-bedroom, 2-bath home located in the Riverside at Twin Rivers community in Oviedo. With 1,305 square feet of living space, this home offers a bright and open layout designed for comfortable everyday living. Upon entering, you are greeted by high vaulted ceilings that enhance the living space and create an open connection between the living room, kitchen, and dining area. The kitchen features stainless steel appliances, a beautiful modern backsplash, and an eat-in dining area. Just off the kitchen, a sliding glass door provides natural light and convenient access to the backyard. The primary bedroom offers a private retreat with its own sliding glass door leading directly to the patio. The en-suite bathroom includes a shower and tub combination. Step outside to the covered, screened-in lanai overlooking the fully fenced backyard, providing a comfortable space to relax or enjoy the outdoors. This home is conveniently located near a variety of restaurants, shopping, and the mall, while also offering easy access to major highways for commuting to Downtown Orlando and surrounding areas. With its open layout, thoughtful features, and desirable location, this home presents a wonderful opportunity to enjoy all that Oviedo has to offer.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: David Bollet (407-927-4595)