Homes for Sale with a Pool in Oviedo, FL

8 Beds ⋅ 5 Baths ⋅ N/A SubDv. ⋅ 32765 Zip Code

One or more photo(s) has been virtually staged. Welcome to Oak Hollow Manor, a rare 20-acre gated equestrian estate and private family compound tucked into one of Oviedo’s most desirable acreage corridors. Set deep within the property and surrounded by mature trees, open pasture, and high-and-dry usable land, this Southern ranch-style estate offers a unique combination of privacy, flexibility, and lifestyle opportunity just minutes from Oviedo, Winter Park, UCF, and Central Florida’s major conveniences. Built in 1985, the main residence features 6 large traditional bedrooms, 4.5 bathrooms, two large bonus rooms (that can be large bedrooms as well), comes fully furnished and has approximately 5,737 square feet of living space designed for comfortable estate living, multigenerational households, entertaining, working from home, or simply enjoying room to spread out. The downstairs primary suite includes a spacious bedroom, sitting area, and his-and-her closets, while the flexible floor plan also allows for a potential second downstairs primary-style suite with direct access to a full bathroom. Warm and inviting living spaces, generous room sizes, and timeless Southern estate character create a welcoming atmosphere while still offering the next owner opportunities to personalize and modernize to their taste. The land itself is one of the property’s most exceptional features. With approximately 5 fully fenced acres currently dedicated to horse grazing, A-1 zoning, and wide-open usable acreage, the property is ideally suited for equestrian enthusiasts, boutique farm operations, hobby farmers, bonfire gatherings, agricultural use, or buyers seeking long-term land value, privacy, and lifestyle flexibility in a highly sought-after Central Florida location. Major recent improvements provide additional value and peace of mind, including a new roof installed in 2022, a permitted 2,500+ square-foot metal barn with electric completed in 2022, and a newly constructed resort-style saltwater in-ground pool completed in 2026 and luxury vinyl plank flooring installed in 2025. Other recent improvements completed between 2022 - 2024 are kitchen updates, bathroom updates, interior and exterior paint, lighting and fixtures. The barn offers exceptional flexibility as an equestrian barn, workshop, hobby space, equipment storage building, or future entertainment pavilion. Two additional storage buildings provide even more utility and functionality. Out back, the newly completed pool creates a peaceful private retreat overlooking scenic acreage and mature natural surroundings, offering the feel of a secluded countryside estate while remaining close to everyday conveniences. Despite its private setting, the property is surrounded by established and desirable communities, including neighboring Aloma Woods. Additional features include three HVAC systems, with two replaced in 2021, no HOA, and zoning for top-rated Seminole County schools including Evans Elementary, Tuskawilla Middle, and Lake Howell High School. Trinity Prep is located just minutes away. With 20 acres and A-1 zoning, the property may also offer future flexibility for additional accessory structures or a potential accessory dwelling unit up to approximately 1,000 square feet, subject to Seminole County approval, permitting requirements, setbacks, and buyer verification.

5750 Oak Hollow Lane, Oviedo

$1,300,000

4 Beds ⋅ 3 Baths ⋅ Deep Lake Homesites SubDv. ⋅ 32765 Zip Code

Special opportunity to own a breathtaking, very private three-acre lakefront estate. This stunning property offers a park-like setting with expansive flower beds, gardens, an edible food forest with citrus, tropical fruit, figs, mulberries, blackberries, and majestic live oaks overlooking a beautiful ski lake. Located on Deep Lake in Oviedo, this 42-acre lake has an excellent water-quality rating, 239 feet of waterfront, two docks, and a double boathouse. The ranch-style home has been impeccably maintained with newer flooring, roof, A/C, pool resurfacing and equipment, primary bath, plantation shutters, and fresh interior and exterior paint. Enjoy water sports on the lake or relax beside the oversized, screened, solar-heated lap pool. Gardeners will appreciate the private potting shed, while hobbyists will enjoy the workshop connected to the extra-large detached two-car garage. Come see this exceptional home, offering pride of ownership, top-rated schools, and convenient access to the 417 Expressway, restaurants, and shopping.

5701 Cross Fox Lane, Oviedo

$1,100,000

5 Beds ⋅ 4 Baths ⋅ Live Oak Reserve Unit Three SubDv. ⋅ 32766 Zip Code

Virtually Staged. Luxury 5-Bedroom Pool Home on an Oversized Conservation Lot in Live Oak Reserve | Oviedo, Florida Welcome to an exceptional opportunity to own a beautifully updated home in Live Oak Reserve, one of Oviedo, Florida’s highly sought-after communities. Situated on an oversized lot backing to conservation, this impressive 5-bedroom, 4.5-bathroom home with a private solar-heated pool and spa offers a rare combination of elegant living, modern comfort, privacy, and an exceptional Central Florida lifestyle. Inside, the thoughtfully designed floor plan offers generous space for everyday living and entertaining, featuring five spacious bedrooms, 4.5 bathrooms, a dedicated home office, and a versatile loft. At the heart of the home is a beautifully updated kitchen featuring stylish cabinetry, upgraded countertops, modern appliances, LED lighting, and a reverse osmosis water filtration system with a dedicated tap for fresh, purified drinking water. Designed for both everyday living and entertaining, the kitchen offers a welcoming and functional gathering space for family and friends. The spacious primary suite provides a private retreat with a built-in vanity, while the beautifully remodeled primary bathroom creates a refined and relaxing space. Throughout the home, numerous updates and thoughtful improvements enhance the property’s comfort, functionality, and appeal. Major improvements include a roof replacement in 2019, both A/C units replaced in 2020, and a new water heater in 2020. Sonos speakers throughout the house add a premium whole-home entertainment experience. The outdoor living space is truly a standout feature. Enjoy Florida’s year-round lifestyle from the large screened-in lanai featuring a private pool and spa. Whether you’re entertaining guests, relaxing poolside, or enjoying a quiet evening outdoors, this private backyard provides an exceptional extension of the home’s living space. The oversized conservation lot offers a peaceful natural backdrop, added privacy, and a serene setting surrounded by nature. Residents of Live Oak Reserve enjoy an impressive array of community amenities, including a resort-style swimming pool with splash pad, fitness center, clubhouse, basketball courts, tennis courts, and playgrounds. Surrounded by beautiful wooded conservation areas, the community offers a tranquil setting while remaining conveniently connected to everything Oviedo and Central Florida have to offer. The location is exceptional, with convenient access to UCF, Research Park, Seminole State College, hospitals, restaurants, shopping, entertainment, and major highways. Families will also appreciate the property’s proximity to highly regarded schools, adding to the appeal of this desirable Oviedo location. Combining beautifully updated interiors, a private saltwater pool and spa, oversized conservation homesite, spacious 5-bedroom floor plan, dedicated office, loft, remodeled primary bathroom, reverse osmosis drinking water system, whole-house Sonos audio, and outstanding community amenities, this Live Oak Reserve residence offers an exceptional opportunity to experience the best of Oviedo, Florida living. Luxury, privacy, resort-style amenities, and a private saltwater pool, all set against a beautiful conservation backdrop in one of Oviedo’s most desirable communities.

2710 Regal Pine Trail, Oviedo

$1,099,999

5 Beds ⋅ 5 Baths ⋅ Oviedo Gardens - A Rep SubDv. ⋅ 32765 Zip Code

Located inside the gated community of Oviedo Gardens on a quarter-acre lot, this home offers rare park and pond views with no rear neighbors. The open-concept layout features soaring 2-story ceilings and tons of natural light, creating a bright, spacious feel the moment you walk in. A standout feature is the dual primary suites, both designed as private retreats with large windows, spa-style bathrooms, soaking tubs, walk-in showers, and custom cabinetry. Perfect for an in-law suite. The gourmet kitchen includes stainless steel appliances, granite countertops, and custom cabinets, opening directly to the main living and dining areas — perfect for entertaining. Upstairs you’ll also find a private theater room, ideal for movie nights or game days. Step outside to a screened-in pool and landscaped backyard overlooking the park and pond — a rare combination of privacy and view. Located near top-rated schools including Hagerty High School, with quick access to shopping, dining, and major roads. 2024 UPDATES the following upgrades were completed! 17.3 SEER AC units on every level, fresh interior paint, crown molding throughout, and a redesigned office with custom 8-ft French doors. Homes with these upgrades, views, and dual primary suites in Oviedo Gardens don’t last

1250 Red Haven Lane, Oviedo

$1,075,000

4 Beds ⋅ 4 Baths ⋅ Red Ember North SubDv. ⋅ 32765 Zip Code

Virtually Staged. Built in late 2022 and UPGRADED THROUGHOUT, this 4 bedroom, 3.5 bath Tradewinds model by M/I Homes offers 4,234 square feet of beautifully designed living space, a RESORT STYLE POOL, dedicated office, expansive media room and 3 car garage in the gated Red Ember North community of Oviedo, Florida. MOVE IN READY and thoughtfully finished from top to bottom, this POOL HOME combines generous living space, elevated design and exceptional indoor and outdoor living. The pool, landscaping, custom finishes and outdoor spaces are already complete, allowing buyers to move in and immediately enjoy the home without a long list of projects or improvements still to tackle. The fully screened, SOLAR HEATED POOL was added in 2023 and creates a true backyard retreat with water fountains, FIRE BOWLS, an extended paver patio, wired tiki torches, upgraded landscaping and bamboo privacy screening. Designed for year round Florida living, this private outdoor setting is ideal for relaxing, entertaining and enjoying evenings by the pool. Inside, the OPEN CONCEPT floor plan is filled with natural light and showcases WOOD LOOK PLANK TILE FLOORING, upgraded cabinetry and countertops, 8 foot interior doors, crown molding, designer lighting and custom accent walls. The family room is anchored by a dramatic STACKED STONE FEATURE WALL with built in electric fireplace. The dining room features a coffered ceiling, while the kitchen offers upgraded cabinetry, sleek countertops, pendant lighting and a striking backsplash extended to the ceiling. Glass French doors open to a DEDICATED OFFICE, while the EXPANSIVE MEDIA ROOM with slat wall paneling and built in ceiling speakers provides an impressive additional living space for movie nights, entertaining, hobbies or guests. The MAIN FLOOR PRIMARY SUITE offers a peaceful retreat with a spa inspired bath featuring fully tiled walls, a freestanding soaking tub and seamless glass enclosed walk in shower. With 4 bedrooms PLUS a dedicated office and large media room, 3.5 baths and a 3 car garage, the flexible floor plan provides exceptional space for working from home, entertaining, hosting guests and everyday living. Located in RED EMBER NORTH in Oviedo, this GATED COMMUNITY offers convenient access to Hagerty High School, UCF, Research Park, Lockheed Martin, Siemens, Oviedo on the Park, shopping, dining and nearby trails. Hagerty High School is within walking distance, offering added convenience for buyers who value school proximity. For buyers also considering nearby new construction, this home offers a compelling advantage: a COMPLETED RESORT STYLE POOL, extensive upgrades, finished landscaping, generous living spaces and outdoor entertaining areas already in place. NO CONSTRUCTION WAIT. NO POST CLOSING POOL PROJECT. NO LENGTHY UPGRADE LIST. Schedule your private tour and experience this NEARLY NEW OVIEDO HOME, completely turnkey, beautifully finished and ready to enjoy from the moment you move in.

3336 Lone Cypress Point, Oviedo

$1,024,000

7 Beds ⋅ 5 Baths ⋅ Ellingsworth SubDv. ⋅ 32765 Zip Code

Virtually Staged. Experience true luxury living in this stunning 7-bedroom, 5-bath former model home, perfectly situated within the sought-after Seminole County school district and just a short walk to both the elementary and high school. Exterior paint in 2026. Upon entering, you’ll find the formal dining room to one side and a living room—or flexible additional space—on the other. Double doors off the living room open into a charming office or multipurpose room, offering even more versatility. Toward the back of the home, a chef’s kitchen awaits, equipped with premium KitchenAid appliances, 42-inch wood cabinetry, and gorgeous granite countertops. This impressive kitchen provides abundant storage, extensive prep space, and a seamless connection to the dinette and family room, all overlooking the breathtaking backyard and pool. A spacious pantry and a butler’s pantry with glass-front cabinets and additional lower storage create an ideal coffee, tea, or serving area conveniently adjoining the formal dining room. The home features two primary suites—one on each floor—perfect for comfort and flexibility, including multi-generational living. Both oversized suites offer large walk-in closets and luxurious bathrooms with dual sinks, a soaking tub, a walk-in shower, and a private water closet. The first floor also includes a second bedroom with a full bath that doubles as a convenient pool bath. Upstairs, you’re welcomed into an expansive loft with a bar equipped with a sink and refrigerator, ideal for entertaining. A dedicated theater room sets the stage for movie nights. In addition to the upstairs primary suite, four more generously sized bedrooms and two full baths complete the second level. Three of these bedrooms are located on the opposite side of the home from the primary suite, offering added privacy. The outdoor area is a true retreat, featuring a gorgeous screened-in custom pool with a sun shelf, built-in seating, and a grotto. Elegant travertine pavers elevate the space, while the covered lanai hosts a fully equipped summer kitchen with a gas grill, side burner, sink, and separate bar area. As an added bonus, the home includes Tesla solar panels which cover most of the monthly electricity costs—paid off at closing! Home water treatment system. This exceptional home has everything you’ve been looking for. Call today to schedule your private tour. Pool (2021) Solar Panels (2020) Both HVACs (2021)

2356 Kelbrook Court, Oviedo

$997,500

4 Beds ⋅ 4 Baths ⋅ Preserve At Black Hammock Rep SubDv. ⋅ 32765 Zip Code

Set within the gated Preserve at Black Hammock, this exceptional pool home offers 4 bedrooms, 4 bathrooms, and a thoughtfully designed layout ideal for multigenerational living and entertaining; featuring two primary suites—one on the main level and one upstairs—along with a dedicated office, expansive upstairs family room, and a large bonus/media room complete with roll-down screen, projector, and receiver, this home seamlessly blends comfort and functionality. The chef’s kitchen showcases quartz countertops, stainless steel appliances, double ovens, an exterior-vented hood, and abundant prep space, all opening to a spacious great room highlighted by a custom stone feature wall and striking electric fireplace, while automatic electric blinds enhance the downstairs primary suite, kitchen, and great room. Step outside to a stunning custom heated pool completed in 2020 with misting system and a panoramic screen enclosure offering unobstructed water views, creating a true backyard retreat; additional highlights include an oversized garage with ample storage, 80-gallon water heater (2021), new roof (2023), and energy-efficient A/C (2017). Ideally located in highly desirable Oviedo with top-rated schools and convenient access to major highways, dining, shopping, Orlando International Airport, downtown Orlando, and Florida’s world-famous beaches and attractions, this home offers the perfect blend of luxury, location, and lifestyle.

1185 Stellar Drive, Oviedo

$990,000

5 Beds ⋅ 4 Baths ⋅ Brighton Park At Carillon Ph 2 SubDv. ⋅ 32765 Zip Code

Welcome to this beautifully updated home in the highly sought-after Brighton Park community of Carillon, perfectly positioned to overlook the peaceful waters of Lake Kensington. From breathtaking sunsets to the beauty of nature and local wildlife, this home offers a tranquil setting that is truly special. Whether you’re enjoying your morning coffee by the pool or unwinding at the end of the day, the picturesque water views create a relaxing backdrop for everyday living. Thoughtfully designed for both comfortable living and effortless entertaining, this spacious residence features an inviting floor plan filled with natural light and generous gathering spaces. The updated kitchen serves as the heart of the home, featuring abundant cabinetry, generous counter space, and an open flow into the family room, making it ideal for hosting family and friends. The first-floor primary suite provides a private retreat with direct access to the outdoor living area, allowing you to enjoy the peaceful surroundings just steps from your bedroom. Upstairs, you’ll find spacious secondary bedrooms that provide comfort, privacy, and flexibility for family and guests. Step outside to your private screened pool and covered patio, thoughtfully designed for both relaxation and entertaining. Whether hosting family and friends, enjoying an outdoor meal, or taking a refreshing swim, this inviting outdoor living space provides the perfect setting to create lasting memories. Located in one of Oviedo’s most desirable communities, Carillon is known for its tree-lined streets, beautiful surroundings, and top-rated Seminole County schools. Residents enjoy convenient access to parks, shopping, dining, Oviedo on the Park, UCF, Research Park, Siemens, and SR-417, providing easy access throughout Central Florida. This exceptional waterfront home offers the perfect blend of comfort, privacy, and natural beauty in one of Oviedo’s most desirable communities. Don’t miss the opportunity to make it yours. Schedule your private showing today.

1746 Carillon Park Drive, Oviedo

$950,000

6 Beds ⋅ 5 Baths ⋅ Sanctuary Ph 1 Village 4 SubDv. ⋅ 32766 Zip Code

Welcome to this beautifully maintained 6-bedroom, 4.5-bath home in The Sanctuary, Oviedo. Situated on a .26-acre homesite with a wooded backdrop, this spacious 4,332-square-foot residence offers an exceptional blend of comfort and functionality. Highlights include soaring ceilings, abundant natural light, plantation shutters, a well-appointed kitchen with Corian countertops and a walk-through Butler's Pantry, formal living and dining rooms, a versatile loft, and a spacious primary suite with a sitting area, two walk-in closets, and a luxurious ensuite bath. Enjoy year-round outdoor living in the expansive screened enclosure with paver flooring. Additional features include two separate 2-car garages and access to outstanding community amenities, including a clubhouse, fitness center, resort-style pool, splash pad, tennis, basketball, volleyball, playground, and more. Schedule your private showing today!

3405 Heirloom Rose Place, Oviedo

$930,000

6 Beds ⋅ 5 Baths ⋅ Ellingsworth SubDv. ⋅ 32765 Zip Code

Six bedrooms, five baths, two primaries, and a floor plan that has an answer for just about everything. Welcome to Ellingsworth, one of Oviedo's premier gated communities. The Mediterranean exterior, tile roof, and fresh paint make a strong first impression, and the soaring ceilings inside give the home an immediate sense of scale that the floor plan fully backs up. Flexibility is its biggest asset. The ground floor is built for living and hosting in equal measure. A flex room and formal dining anchor the entry, opening into a kitchen and living area designed to keep everyone connected. A full primary suite with a massive walk-in closet sits on one end of the home, a second bedroom and full bath on the other — a true split layout that gives everyone their own corner. Two laundry areas, one on each floor, mean nobody is hauling anything up or down stairs. Upstairs is where this home really separates itself. An oversized loft anchors the second level and spills into two generous bonus rooms ready to become a theater, a craft room, a home office, or all three. Four additional bedrooms surround it, including a second full primary suite with its own walk-in closet that rivals most dedicated dressing rooms. Five full baths across both floors means the morning routine never becomes a negotiation. Step outside and the screened enclosure frames a long lap-style pool, with mature palms rising just beyond the screen creating a natural privacy wall that makes the whole space feel intentional and secluded. The covered lanai and expansive deck give you room to host a crowd or simply decompress after a long week. Add a three-car tandem garage, fresh paint inside and out, and this one is ready the day you close. Oviedo consistently ranks among the best places to live in Florida, and it's easy to see why. You're minutes from the Oviedo on the Park town center, local favorites like Whalers Brewing and Domu Oviedo, and the weekly Farmers Market. UCF is ten minutes away, SR-417 puts you on the way to the airport or downtown Orlando in under 30, and the beaches are just about an hour out. Room to grow into. Room to work from. Room to entertain on your own terms.This one was built for all of it.

2330 Kelbrook Court, Oviedo

$925,000

6 Beds ⋅ 4 Baths ⋅ Terralago SubDv. ⋅ 32765 Zip Code

Welcome to this stunning luxury home located on a private cul-de-sac in the highly desirable gated community of Terralago. Showcasing exceptional curb appeal with a Spanish-style tile roof, extended paver driveway, and spacious three-car garage, this beautifully upgraded residence offers the perfect blend of elegance, comfort, and functionality. Step inside to a grand foyer with soaring ceilings, crystal chandeliers, and formal living and dining spaces designed to impress. The gourmet kitchen features shaker-style cabinetry, granite countertops, pendant lighting, newer stainless steel appliances, tile flooring, a large pantry, and a cozy breakfast nook with French door access to the screened lanai and resort-style pool area. The spacious family room offers beautiful wood flooring, breathtaking pool views, and an in-ceiling speaker system ideal for entertaining. The first floor also includes a private bedroom, full pool bath, and a large office or bonus room with double-door entry, perfect for guests or multi-generational living. Upstairs, enjoy a versatile loft space with a walk-in closet for additional storage. The luxurious primary suite features a designer chandelier, dual vanities, soaking tub, glass-enclosed shower, and custom walk-in closet built-ins. Four additional oversized bedrooms and two guest bathrooms provide ample space for family and visitors. Step outside to your private backyard oasis featuring a covered lanai, screened-in swimming pool, and citrus tree, creating the ultimate Florida lifestyle experience. Recent upgrades include a new AC system, pool heater, fresh interior and exterior paint, newer appliances with warranties, and an expanded driveway accommodating up to six vehicles. Conveniently located near SR-417, UCF, Orlando International Airport, top-rated schools, Publix, Target, shopping, dining, golf courses, Oviedo Mall, Lake Jesup, and endless entertainment options. Experience luxury living in one of Central Florida’s most sought-after communities — schedule your private showing today!

450 Terravista Place, Oviedo

$915,000

5 Beds ⋅ 3 Baths ⋅ Pickett Downs Unit 4 SubDv. ⋅ 32766 Zip Code

UPDATED! NEW FULLY EQUIPPED SUMMER KITCHEN INSTALLED! Welcome to your private retreat in the highly sought-after Chuluota area—this beautifully renovated 5-bedroom, 3-bath home sits on 1.07 acres and includes deeded access to the exclusive 760-acre Lake Pickett. Designed for both everyday living and entertaining, the home showcases expansive multi-panel stacking glass doors that open seamlessly to a screened-in pool, creating the perfect indoor-outdoor lifestyle. Inside, you’ll find a fully renovated interior featuring new flooring throughout, updated lighting, new 5-inch baseboards, and a custom faux fireplace feature wall with shiplap and built-in shelving. The stunning kitchen has been completely redesigned with a large granite island, farmhouse sink, pot filler, KitchenAid built-in microwave and wall oven, three-rack dishwasher, pull-out spice rack, and a charming breakfast banquette with under-seat storage. A wine and coffee bar adds an extra touch of luxury and convenience. The spacious primary suite offers a spa-like bathroom complete with a clawfoot soaking tub, dual showerheads with hand shower, and custom closet systems. All bathrooms have been renovated, and major components throughout the home have been thoughtfully upgraded. A heated and cooled bonus room—perfect for a home office or gym—has been converted from part of the garage, while still allowing for ample workshop and storage space. Significant system upgrades include a 2016 roof, whole-house re-pipe, two newer HVAC systems, new water heater, updated well components, new windows, and more—providing peace of mind for years to come. Step outside to enjoy the screened pool with recently upgraded equipment, expanded driveway, added sidewalks, boat parking, and a large 3-car-size storage shed. The property has been cleared and landscaped to enhance both usability and privacy, with frequent deer sightings adding to the serene, natural setting. Additional features include a buried 200-gallon gas tank servicing the pool and a pre-plumbed, paid connection for a future summer kitchen. Enjoy exclusive access to Lake Pickett, offering a private dock, boat and trailer parking, swimming area, and endless opportunities for boating, skiing, wakeboarding, fishing, and more. This is a rare opportunity to own a fully upgraded home with acreage and private lake access—combining luxury, functionality, and the best of Florida living.

2461 Wassum Trail, Oviedo

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