Oakland | Luxury Homes for Sale & Real Estate

$2,295,000

1244 WATER MAPLE Dr, Oakland, FL

6 br5 ba, 1 half ba4,859 sf

virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC, ALEXIS ANDERSON - 561-670-5901

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wine Storage, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Dining room, Fireplace, Interior, Living room, Wooden Beams, Wooden Ceilings, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Wood Texture Flooring

Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Pendant Lights, Recessed Lighting

Bathroom, Free Standing Baths, Glass Shower, Interior

Interior, Recessed Lighting, Walk-in Closets, Wood Texture Flooring

$2,200,000

110 W Railway Ave, Oakland, FL

5 br4 ba, 1 half ba3,876 sf

Listing Courtesy of REGENCY REAL ESTATE LLC, HEATHER SPIRAZZA - 407-757-6022

$2,175,000

1256 WATER MAPLE Dr, Oakland, FL

5 br5 ba, 3 half ba4,433 sf

virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC, ALEXIS ANDERSON - 561-670-5901

$2,150,000

1250 WATER MAPLE Dr, Oakland, FL

5 br5 ba, 1 half ba4,388 sf

virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC, HEATHER SPIRAZZA - 407-757-6022

contract signed

$2,098,500

1112 Sarah Mathews Dr, Oakland, FL

5 br4 ba, 2 half ba3,956 sf

virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC, ALEXIS ANDERSON - 561-670-5901

Attached, Exterior, Facade, Brick Facade, Farmhouse

$1,996,500

1258 Ridge Lake Way, Oakland, FL

4 br4 ba4,557 sf

virtual tour

Listing Courtesy of COMPASS FLORIDA LLC, MATTHEW MCKEE - 407-948-0658

$1,975,000

1149 PRADO LANE Dr, Oakland, FL

5 br5 ba, 1 half ba3,596 sf

virtual tour

Listing Courtesy of REGENCY REAL ESTATE LLC, BLAINE DOOLEY - 321-277-0933

contract signed

Backyard, Exterior, Facade, Queen Anne Victorian

Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances

Chandelier, Dining room, Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wooden Beams, Wood Texture Flooring

Fireplace, Interior, Living room, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Fireplace, Interior, Living room, Stone Walls, Wooden Beams, Wood Texture Flooring

Dining room, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Interior, Living room, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Chandelier, Dining room, Interior, Wood Texture Flooring

Bathroom, Interior, Wood Texture Flooring

Bedroom, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Free Standing Baths, Glass Shower, Interior, Marble Walls, Recessed Lighting, Wood Texture Flooring

Bathroom, Free Standing Baths, Interior, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Recessed Lighting

Interior, Living room, Recessed Lighting, Wood Texture Flooring

Bedroom, Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Interior, Recessed Lighting, Wood Texture Flooring

Bedroom, Fitness Equipment, Interior, Recessed Lighting, Wood Texture Flooring

Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Chandelier, Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Chandelier, Interior, Pendant Lights, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Marble, Marble Walls

Fireplace, Interior, Living room, Pendant Lights, Stone Walls, Wood Texture Flooring

Fireplace, Interior, Living room, Pendant Lights, Stone Walls, Wooden Beams, Wood Texture Flooring

$1,925,000

625 CHEEKWOOD Aly, Oakland, FL

6 br4 ba, 1 half ba3,796 sf

virtual tour

Listing Courtesy of BHHS FLORIDA REALTY, ASHLEY BOYD - 321-209-5540

$1,895,000

511 Briley Ave, Oakland, FL

5 br4 ba, 1 half ba3,862 sf

virtual tour

Listing Courtesy of CORCORAN PREMIER REALTY, MATTHEW BURKS - 407-257-5347

Interior, Kitchen, Stainless Steel Appliances, Wood Texture Flooring

Interior, Kitchen, Marble Walls, Stainless Steel Appliances, Wood Texture Flooring

Fireplace, Interior, Living room, Marble Walls, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, Wood Texture Flooring

Interior, Walk-in Closets, Wood Texture Flooring

Dining room, Interior, Stainless Steel Appliances

$1,675,000

166 HAMMOCK PRESERVE Loop, Winter Garden, FL

4 br4 ba3,186 sf

virtual tour

Listing Courtesy of CORCORAN PREMIER REALTY, A.J. LASH - 407-913-1324

Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Chandelier, Dining room, Interior, Living room, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Chandelier, Dining room, Interior, Pendant Lights, Wood Texture Flooring

Interior, Kitchen, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting, Walk-in Closets

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting, Walk-in Closets, Wood Texture Flooring

Bathroom, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

$1,650,000

921 BRADENVILLE Ln, Winter Garden, FL

4 br4 ba3,468 sf

virtual tour

Listing Courtesy of RE/MAX PRIME PROPERTIES, RONALD ZIOLKOWSKI - 407-592-7653

Backyard, Exterior, Facade, French Provincial

Attached, Backyard, Exterior, Facade, Ranch

Dining room, Interior, Living room, Pendant Lights, Recessed Lighting, Stone Walls, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Recessed Lighting

Fireplace, Interior, Living room, Pendant Lights, Recessed Lighting, Stone Walls, Wood Texture Flooring

Fireplace, Interior, Living room, Recessed Lighting, Stone Walls, Wood Texture Flooring

Dining room, Fireplace, Interior, Living room, Pendant Lights, Recessed Lighting, Stone Walls, Wood Texture Flooring

Glass Ceilings, Interior, Pool, Sun Room, Wood Texture Flooring

Glass Ceilings, Interior, Pool, Sun Room, Water

Interior, Kitchen, Pendant Lights, Recessed Lighting

Fireplace, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stone Walls, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Glass Ceilings, Interior, Pool, Sun Room, Water, Wood Texture Flooring

Glass Ceilings, Interior, Pool, Sun Room

Bedroom, Fireplace, Interior, Recessed Lighting

Dining room, Glass Ceilings, Interior, Pool, Stone Walls, Sun Room, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Free Standing Baths, Glass Shower, Interior, Recessed Lighting

Bathroom, Bedroom, Interior, Tile Countertops

Glass Ceilings, Interior, Sun Room, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Wood Texture Flooring

Glass Ceilings, Interior, Sun Room, Water

$1,599,900

141 MILLHOLLAND St, Oakland, FL

4 br3 ba, 1 half ba3,920 sf

virtual tour

Listing Courtesy of CLOCK TOWER REALTY, MATTHEW MATIN - 321-948-5857

contract signed

Dining room, Glass Ceilings, Interior, Sun Room

Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Water, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Water, Wood Texture Flooring

Home Office, Interior, Wood Texture Flooring

Bedroom, Interior, Recessed Lighting, Water, Wood Texture Flooring

Bathroom, Free Standing Baths, Glass Shower, Interior, Recessed Lighting

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Recessed Lighting

Bedroom, Home Office, Interior, Wood Texture Flooring

Fitness Equipment, Interior, Wood Texture Flooring

Dining room, Glass Ceilings, Interior, Sun Room, Water

$1,300,000

1112 Hull Island Dr, Oakland, FL

4 br3 ba, 1 half ba3,562 sf

virtual tour

Listing Courtesy of HOMEVEST REALTY, KELLY ZANNINI - 407-970-6298

Backyard, Exterior, Facade, Mediterranean

Attached, Backyard, Exterior, Facade, Modern

Dining room, Interior, Kitchen, Marble, Recessed Lighting

Dining room, Interior, Kitchen, Living room, Marble, Pendant Lights, Recessed Lighting, Stainless Steel Appliances

Chandelier, Dining room, Interior, Kitchen, Living room, Marble, Pendant Lights, Recessed Lighting, Stainless Steel Appliances

Dining room, Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting, Stainless Steel Appliances

Interior, Kitchen, Marble, Recessed Lighting, Stainless Steel Appliances

Chandelier, Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting

Chandelier, Dining room, Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting

Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting, Stainless Steel Appliances

Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting

Chandelier, Dining room, Interior, Kitchen, Living room, Marble, Pendant Lights, Recessed Lighting

Interior, Kitchen, Marble, Pendant Lights, Stainless Steel Appliances

Dining room, Glass Ceilings, Interior, Pool, Sun Room

Dining room, Interior, Living room, Sun Room

Bathroom, Glass Shower, Interior, Marble Walls

Bathroom, Dual Sink Vanities, Interior, Marble Walls

Attached, Backyard, Exterior, Facade, Farmhouse

$1,150,000

627 LARGOVISTA Dr, Oakland, FL

4 br3 ba3,800 sf

virtual tour

Listing Courtesy of DALTON WADE INC, HEIDI PFEFFER-MORGAN - 407-408-6101

price reduced

Interior, Pendant Lights, Wood Texture Flooring

Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Bathroom, Bedroom, Interior, Pendant Lights, Wooden Ceilings, Wood Texture Flooring

Bedroom, Interior, Recessed Lighting, Wooden Ceilings, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Pendant Lights, Wood Texture Flooring

Bathroom, Interior, Utility Closets, Washer

$1,049,000

936 ALLENDALE Ln, Winter Garden, FL

4 br3 ba2,711 sf

virtual tour

Listing Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY, KEN POZEK - 407-717-0197

$1,010,000

0000 SOUTHERN RAILWAY, Oakland, FL

3,000 sf

virtual tour

Listing Courtesy of THE MARKS GROUP REALTY, LLC, WYATT MARKS - 352-432-8678

contract signed | price reduced

Dining room, Interior, Recessed Lighting

Home Office, Interior, Recessed Lighting

Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Empty room, Interior, Wood Texture Flooring

Empty room, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

$999,000

301 S TUBB St G1 & G2, Oakland, FL

2,670 sf

Listing Courtesy of THE REAL ESTATE COLLECTION LLC, ERICA SADELFELD - 407-427-0398

contract signed | price reduced

Dining room, Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stone Walls, Wood Texture Flooring

Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Living room, Stone Walls

Dining room, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting

Dining room, Fireplace, Interior, Wood Texture Flooring

Fireplace, Interior, Living room, Stone Walls, Wood Texture Flooring

Interior, Living room, Pendant Lights, Piano, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Recessed Lighting, Washer, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Wood Texture Flooring

Bathroom, Bedroom, Glass Shower, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior

Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Game Room, Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Game Room, Interior, Living room, Recessed Lighting, Wood Texture Flooring

$915,000

70 MILLHOLLAND St, Oakland, FL

5 br3 ba2,534 sf

virtual tour

Listing Courtesy of BHHS FLORIDA REALTY, ASHLEY BOYD - 321-209-5540

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Luxury listings for sale in Oakland

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1244 WATER MAPLE Dr, Oakland, FL

110 W Railway Ave, Oakland, FL

1256 WATER MAPLE Dr, Oakland, FL

1250 WATER MAPLE Dr, Oakland, FL

1112 Sarah Mathews Dr, Oakland, FL

1258 Ridge Lake Way, Oakland, FL

1149 PRADO LANE Dr, Oakland, FL

625 CHEEKWOOD Aly, Oakland, FL

511 Briley Ave, Oakland, FL

166 HAMMOCK PRESERVE Loop, Winter Garden, FL

921 BRADENVILLE Ln, Winter Garden, FL

141 MILLHOLLAND St, Oakland, FL

1112 Hull Island Dr, Oakland, FL

627 LARGOVISTA Dr, Oakland, FL

936 ALLENDALE Ln, Winter Garden, FL

0000 SOUTHERN RAILWAY, Oakland, FL

301 S TUBB St G1 & G2, Oakland, FL

70 MILLHOLLAND St, Oakland, FL