Oakland 5 Bedroom Homes for Sale

Oakland 5 Bedroom Homes for Sale

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Oakland 5 Bedroom Homes for Sale

$2,595,000
5 Beds ⋅ 8 Baths ⋅ O6413035 MLS
Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated. Five generously sized bedrooms, each with its own private ensuite bath, provides unmatched comfort and privacy for family and guests alike. Two additional powder baths serve the main living areas, while a dedicated pool bath keeps the outdoor experience seamless. At the heart of the home, a dramatic double island kitchen commands attention — equal parts showpiece and hardworking hub — crowned by soaring coffered ceilings that lend architectural depth and timeless elegance throughout. Step outside to your own private resort, where a sparkling pool and spa, summer kitchen, and covered lanai with roll-down screens create the ultimate Florida lifestyle — open-air breezes or a fully enclosed retreat, all at the touch of a button. Beyond your front door, The Grove places you steps from The Harvest District's boutique shops and restaurants, with exclusive access to the resort amenities at nearby Briley Farm — all reachable by foot or golf cart.

1134 Prado Lane, Oakland

Listing courtesy of REGENCY REAL ESTATE LLC. 407-469-5021
$878,000
5 Beds ⋅ 2 Baths ⋅ 1669553 MLS
Looking for a waterfront home with a rare, grandfathered setting right at the shoreline that you cannot replicate today? The main home sits less than 15 feet from the water, an irreplaceable advantage that defines this legacy property. Come experience the best of Maine at this stunning 5-bedroom, 2 full bath contemporary home nestled on 3.5 surveyed acres with 336 feet of private shoreline on stunning East Pond. With 2,608 sq ft in the main home and an additional 600 sq ft in a separate finished ranch, this one-of-a-kind property offers unmatched flexibility for guests, rental income, or your creative retreat. Step inside to soaring cathedral ceilings, sun-drenched skylights, and a spacious layout perfect for entertaining or peaceful lakeside living. The main home features a large family room, an inviting living room with a dramatic stone fireplace, and a standing seam metal roof for lasting durability. Four bedrooms and a full bath are conveniently located on the first floor, while the second-floor great room and screened-in porch provide panoramic lake views and a peaceful escape. Just a few feet from the water's edge, the massive front deck invites you to relax and unwind in a quiet cove ideal for sandy-bottom swimming, sunset watching, and listening to loons call at dusk. Nature lovers will be in awe of the bald eagles, ospreys, and owls that frequently visit. Enjoy easy access to kayaking, paddleboarding, boating, and fishing--all from your own dock and ladder. The finished ranch-style guest house, built in 1984, adds over 600 sq ft of heated living space--ideal for Airbnb potential, extended stays, or a private home office or studio. Lovingly owned by the same family since 1939, the original camp was rebuilt in 1962, with the second floor added in 1994. This is more than a home--it's a legacy, a lifestyle, and a rare opportunity! Located just 20 minutes from the vibrant downtowns of Waterville and Augusta. Docks, Swim Platform & mooring included.

20 & 21 Bass Cv, Oakland

Listing courtesy of OWN REAL ESTATE.

$799,999
5 Beds ⋅ 3 Baths ⋅ TB8513260 MLS
Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

16 Oakland Pointe Circle, Oakland

Listing courtesy of JACK KELLER INC. 727-586-1497
$389,000
5 Beds ⋅ 3 Baths ⋅ 1654744 MLS
Set along the peaceful banks of Messalonskee Stream, this move-in ready ranch offers the kind of space and setting that's hard to find. With 5 bedrooms and 2.5 bathrooms across 2,460 square feet, there's room here to grow, gather, and truly feel at home. Inside, you'll find a bright, open layout designed for connection--where the kitchen flows easily into the main living space, and natural light fills the rooms throughout the day. Whether it's quiet mornings or lively evenings, this home adapts effortlessly to the rhythm of everyday life. Step out onto the back deck and take in the calming water views--an ideal spot for morning coffee, unwinding at the end of the day, or simply enjoying the beauty of your surroundings. With flexible space that could accommodate guests or extended family, plus a two-car garage, the home offers both comfort and versatility. Located just minutes from Colby College, local shops, and I-95, you'll enjoy the perfect balance of privacy and convenience. This is more than a home--it's a place to settle in, spread out, and stay awhile.

88 County Rd, Oakland

Listing courtesy of The Maine Real Estate Experience.

$1,900,000
5 Beds ⋅ 5 Baths ⋅ 1663344 MLS
This phenomenal home is sitting on over 28 acres w/ horse stalls, riding pens & a stocked trout pond. You'll always have something fun to do here. This gorgeous home offers lots of space, 5-6 bedrooms, & beautiful finishes. Lovely landscaping & white fences. Large garage for 4 cars w/radiant heat, & a pull thru overhead door to the back. Beautiful deck w/ pergola looks out to the back acreage, perfect for watching wildlife. Inside you are greeted w/ a large family room w/ lots of windows. 180x 320 ft riding arena, w/ announcer booth/ tree stand for hunters. The well-appointed kitchen features a stone island, double pantries, & a cozy sunroom off the rear to watch Sunday games or simply to enjoy the gas fireplace. First floor laundry & a beautiful formal living room w/ built in cabinets. First floor primary bedroom w/ a gorgeous en suite bath w/ tile steam shower, soaking tub, & double vanities. Upstairs there is a fantastic family room, perfect for games, a theater, office or workout space & a large bonus room. In the daylight basement is an additional kitchen, full bath w/ laundry, & 3 additional rooms. Stand by generator. This property also features modern barn venue, which could also be used for many other business & activities. Beautiful grounds include a fountain, hardscaping, & lovely gardens. This building has an upscale finish w/ rustic flair. Generous parking in the rear. High ceilings give a spacious feel to the 7,200 sq ft main floor. Next to the main floor is an additional space that includes a kitchen area w/ commercial fridges, a bar area, & multiple bathrooms including a handicap accessible bathroom. Upstairs is a room that was used for a bridal suite, but it could be used as a conference space as well. Outdoor seating under pergolas & garden lights. Beautiful setting for photographs. Separate 5 car garage & mobile home for storage. Generator on site. So many possibilities with this property.

78 98 Hussey Hill Rd, Oakland

Listing courtesy of Sprague & Curtis Real Estate. tyler@spragueandcurtis.com
$1,975,000
5 Beds ⋅ 6 Baths ⋅ O6375487 MLS
Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1106 Sarah Mathews Drive, Oakland

Listing courtesy of REGENCY REAL ESTATE LLC. 407-469-5021
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