Oakland, FL Homes

/2
$1,200,000 Sold Jan 09, 2025
- 3,803 Sq Ft
- $316/SF
- 114 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2022
914 Tilden Oaks Trail, Winter Garden, FL 34787

Welcome to 914 Tilden Oaks Trail, a stunning RCB custom 5-bedroom, 3.5-bathroom residence exuding elegance and sophistication. Builders personal home. Boasting a generous 3803 square feet of living space, this home offers a luxurious lifestyle in the golf cart district of Winter Garden, FL. Upon entering, the downstairs living space features exquisite wood tile flooring, a decorative fireplace,

Matt McKee COMPASS FLORIDA LLC

914 Tilden Oaks Trail, Winter Garden, FL 34787

/2
Est $428,825 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,567 Sq Ft
13364 Pontoon Rd, Oakland, FL 34787

13364 Pontoon Rd, Oakland, FL 34787

/50
$529,900 Pending
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
17985 Adrift Rd, Oakland, FL 34787

Under contract-accepting backup offers. Better than New! Welcome to this beautifully maintained home nestled in the serene and sought-after neighborhood of Waterleigh in Horizon West. This charming property features 3 spacious bedrooms, 2.5 bathrooms, and a bright, open-concept layout perfect for both entertaining and everyday living. Enjoy a chef’s kitchen with stainless steel appliances,

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

17985 Adrift Rd, Oakland, FL 34787
/2
$634,463 Sold Jan 07, 2025
- 2,200 Sq Ft
- $288/SF
- 67 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
15173 Blue Peacock Ln Unit 86, Oakland, FL 34787

Under Construction. The Nicola II is a spacious rear-load garage home. From the 10’ ceilings to the large concept living area – this home has all the features you need packed into 2,200 square feet. As soon as you walk in you’ll see the Extra Suite with a walk-in closet, ideal for overnight guests. To the rear of the home, the open concept living is anchored by the beautiful kitchen. This kitchen

Gretta Akellino K HOVNANIAN FLORIDA REALTY

15173 Blue Peacock Ln Unit 86, Oakland, FL 34787

/30
Est $495,952 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,078 Sq Ft
2157 White Feather Loop, Winter Garden, FL 34787

2157 White Feather Loop, Winter Garden, FL 34787

/30
$389,400 Pending
- 3 Beds
- 1 Bath
- 1,159 Sq Ft
121 W Oakland Ave, Oakland, FL 34760

Under contract-accepting backup offers. Welcome to 121 W. Oakland Ave. This Charming Bungalow is in the heart of Oakland, you can walk to the Farmers Market on Thursdays, and the downtown area to include West Orange Biking trail and adorned Speer park. Situated on a corner lot, this property offers added privacy & w/ fenced in yard and wooden deck for entertaining. As you enter from the cozy

Sheri Loiacono WINDSOR REALTY GROUP INC

121 W Oakland Ave, Oakland, FL 34760
/2
$804,990 Sold Jan 05, 2025
- 3,211 Sq Ft
- $251/SF
- 62 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
9462 Emerald Berry Dr, Oakland, FL 34787

One or more photo(s) has been virtually staged. Are you looking for a home that offers space, adaptability, and style, with the convenience of a 3-car garage and ample storage space? Look no further than the Charlotte, a stunning home featuring 4 bedrooms, 3.5 bathrooms, and 3211 sq. ft. of living space. Set on a privacy homesite with beautiful wooded and pasture views, this thoughtfully designed

Bill Maltbie MALTBIE REALTY GROUP

9462 Emerald Berry Dr, Oakland, FL 34787

/23
Est $410,092 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,503 Sq Ft
2219 Gopher Tortoise Terrace, Oakland, FL 34760

2219 Gopher Tortoise Terrace, Oakland, FL 34760

/9
$853,595 Pending
- 4 Beds
- 3.5 Baths
- 3,300 Sq Ft
5320 Citrus Leaf Blvd, Oakland, FL 34787

Brand new, energy-efficient home ready NOW! No side neighbors. This functional floorplan has a spacious family room that’s open to an expansive kitchen. A combination dining and living room provides ideal space for indoor entertaining or moving the party outdoors to the private lanai. Now selling from the mid $500's, Silverleaf Reserve offers spacious open floorplan concepts fit for every

Tatiana Souza MERITAGE HOMES OF FL REALTY

5320 Citrus Leaf Blvd, Oakland, FL 34787
/2
$795,250 Sold Dec 31, 2024
- 2,923 Sq Ft
- $272/SF
- 124 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
9409 Emerald Berry Dr, Oakland, FL 34787

This Baldwin floorplan by Hartizen Homes offers 4 bedrooms, 3.5 bathrooms beautifully accented with a home office, complete with barn doors, loft & extended covered lanai. Privacy homesite with no rear neighbors! The gourmet kitchen showcases a built-in oven/microwave, smooth cooktop and vent hood with soft-close cabinetry, 42” uppers, contrasting island cabinetry and quartz countertops. An

Bill Maltbie MALTBIE REALTY GROUP

9409 Emerald Berry Dr, Oakland, FL 34787

/30
Est $436,040 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,560 Sq Ft
6159 Juneberry Way, Oakland, FL 34787

6159 Juneberry Way, Oakland, FL 34787

/40
$645,000 Pending
- 5 Beds
- 3 Baths
- 2,458 Sq Ft
410 E Gulley Ave, Oakland, FL 34760

Charming 1959 Gem in the Town of Oakland with In-Law Suite. Find where timeless character meets small town charm in the heart of Oakland, FL. This beautifully maintained 4-bedroom, 2-bath, plus the Multi-generational suite home offers almost 2,500 square feet of living space, blending vintage appeal with the comfort and flexibility today's buyers are seeking. Nestled on a quiet street just

Keith Packey RE/MAX TITANIUM GROUP

410 E Gulley Ave, Oakland, FL 34760
/2
$776,995 Sold Dec 30, 2024
- 2,950 Sq Ft
- $263/SF
- 28 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
16225 Silver Brook Way, Oakland, FL 34787

Under Construction. Brand new, energy-efficient home available by Oct 2024! Photos are of builder model home. The main floor features an open kitchen island work area overlooking the dining room and spacious family room. Enjoy outdoor living on the covered porch or back lanai. First floor den and hobby room offer great workspaces. Silverleaf Reserve offers spacious open floorplan concepts fit for

Tatiana Souza MERITAGE HOMES OF FL REALTY

16225 Silver Brook Way, Oakland, FL 34787

/54
Est $650,813 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,089 Sq Ft
11078 Robert Frost Dr, Oakland, FL 34787

11078 Robert Frost Dr, Oakland, FL 34787

/19
$405,040 Pending
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
5832 Meditation Dr, Oakland, FL 34787

Under Construction. Welcome to the light & bright Landcaster! This elegant townhome covers two stories and includes three bedrooms, two and one-half bathrooms with a two-car rear load garage. The front door opens onto the spacious open concept combination living room and dining room. There is also a laundry room with washer and dryer and a fully equipped kitchen that leads to an beautiful patio.

Ben Goldstein LENNAR REALTY

5832 Meditation Dr, Oakland, FL 34787
/2
$700,000 Sold Dec 26, 2024
- 2,282 Sq Ft
- $307/SF
- 129 Days On Market
- 4 Beds
- 3 Baths
- Built 1979
305 W Briley Ave, Oakland, FL 34760

NO HOA | Golf cart district | 624 sqft ADU | 1-block from WEST ORANGE TRAIL | walking distance Speer Park | Blocks away from Lake Apopka. Welcome to this charming 4 bed 3 bath WITH GUEST SUITE WITH FULL KITCHEN, BATHROOM, WASHER AND DRYER (additional 624 sqft of living space) ranch-style home in the heart of historic Oakland, ideally located on a spacious corner lot in the highly desired Golf

Kristy Cook EXP REALTY LLC

305 W Briley Ave, Oakland, FL 34760

/70
Est $901,265 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,414 Sq Ft
613 Cheekwood Alley, Winter Garden, FL 34787

613 Cheekwood Alley, Winter Garden, FL 34787

/79
$1,800,000 Pending
- 6 Beds
- 5 Baths
- 3,911 Sq Ft
102 Hammock Preserve Loop, Oakland, FL 34787

Under contract-accepting backup offers. Welcome to 102 Hammock Preserve Loop—a beautifully crafted custom, J&J Home tucked away in the heart of Oakland Park, one of Winter Garden's most sought-after communities. Owners never fully moved into this new home due to change in family circumstances. This spacious corner-lot property is framed by mature oak trees that make you feel like you're living in

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

102 Hammock Preserve Loop, Oakland, FL 34787
/2
$628,000 Sold Dec 26, 2024
- 2,830 Sq Ft
- $222/SF
- 10 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2024
15049 Summer Harvest St, Oakland, FL 34787

Pre-Construction. To be built. MLS#O6205174 REPRESENTATIVE PHOTOS ADDED. December Completion! The Newberry bungalow floor plan epitomizes modern living and is the ideal space for all your entertainment needs. This two-story, 2305 sq. ft. home features 4 bedrooms, 4.5 bathrooms, and a 2-car detached garage. From the foyer, step into the expansive gathering room, passing one of the secondary

Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

15049 Summer Harvest St, Oakland, FL 34787

/2
Est $451,080 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,992 Sq Ft
13958 Title Way, Winter Garden, FL 34787

13958 Title Way, Winter Garden, FL 34787

/40
$444,590 Pending
- 3 Beds
- 2.5 Baths
- 1,846 Sq Ft
6678 Juneberry Way, Oakland, FL 34787

Ready to MOVE-IN, this completed new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,846 sq. ft. As you enter this home through the 8' entry-door, you are welcomed with an open spacious foyer with immediate access to your open flex room. As you continue up, you

Adam Schott DRB GROUP REALTY, LLC

6678 Juneberry Way, Oakland, FL 34787
/2
$848,885 Sold Dec 23, 2024
- 3,899 Sq Ft
- $218/SF
- 5 Beds
- 4.5 Baths
- Built 2024
16465 Silver Brook Way, Oakland, FL 34787

Beautiful 5-bedroom, 4.5-bath home in the heart of Winter Garden! Enjoy an open kitchen overlooking the family room, walk-in closets in every secondary bedroom, an oversized 2-car garage, and a versatile first-floor study. Located in the desirable Silverleaf Reserve community.

Stellar Non-Member Agent Stellar Non-Member Office

16465 Silver Brook Way, Oakland, FL 34787

/65
Est $392,317 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,472 Sq Ft
1502 Sweet Apple St, Oakland, FL 34787

1502 Sweet Apple St, Oakland, FL 34787

/19
$404,990 Pending
- 3 Beds
- 2.5 Baths
- 1,647 Sq Ft
2907 Transformation Way, Oakland, FL 34787

Under Construction. The Westwood is timeless and built to last. The Great Room and kitchen share a convenient open floorplan on the first floor of this two-story home, with sliding glass doors that lead to the lanai. All three bedrooms occupy the second level, including the owner’s suite which is comprised of a restful bedroom, en-suite bathroom and walk-in closet. With “Everything’s Included”,

Ben Goldstein LENNAR REALTY

2907 Transformation Way, Oakland, FL 34787
/2
$799,000 Sold Dec 20, 2024
- 2,247 Sq Ft
- $356/SF
- 21 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2024
1215 Wilder Oaks Way, Oakland, FL 34787

Under Construction. Luxurious new home by RockWell Homes features covered front porch, covered back yard patio, elegant exterior design and 8ft doors. Kitchen features island, large pantry, solid surface countertops, stainless steel appliances, gas cooktop, oven, microwave, dishwasher, upgraded cabinets, upgraded flooring, ceramic tile backsplash and Moen faucet. Living-Dining area

Abigail Belchick OLYMPUS EXECUTIVE REALTY INC

1215 Wilder Oaks Way, Oakland, FL 34787

/4
Est $82,866 Not Listed For Sale
Unlisted Address

Unlisted Address

/22
$604,334 Pending
- 4 Beds
- 4.5 Baths
- 2,904 Sq Ft
16198 Honey Harvest St, Oakland, FL 34787

Under contract-accepting backup offers. Under Construction. MLS# REPRESENTATIVE PHOTOS ADDED. New Construction - August Completion! Welcome to the Baldwin, a new home at Harvest at Ovation, where thoughtful design meets effortless living. Step inside and find a secondary bedroom with a full bath just off the foyer. The formal dining room flows seamlessly into the gathering room, kitchen, and

Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

16198 Honey Harvest St, Oakland, FL 34787
/2
$449,530 Sold Dec 20, 2024
- 1,579 Sq Ft
- $285/SF
- 5 Days On Market
- 2 Beds
- 2 Baths
- Built 2024
13437 Princess St, Oakland, FL 34787

All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis will offer an abundance of resort-style

Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

13437 Princess St, Oakland, FL 34787

/43
Est $698,015 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,117 Sq Ft
9418 Bolero Rd, Oakland, FL 34787

9418 Bolero Rd, Oakland, FL 34787

/14
$415,000 Pending
- Land
- 0.27 Acre
- $1,537,037 per Acre
15738 E Oakland Ave, Oakland, FL 34787

Under contract-accepting backup offers. Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood

Alexis Anderson REGENCY REAL ESTATE LLC

15738 E Oakland Ave, Oakland, FL 34787
/2
$380,000 Sold Dec 18, 2024
- 1,472 Sq Ft
- $258/SF
- 1 Day On Market
- 2 Beds
- 2.5 Baths
- Built 2020
2226 Gopher Tortoise Terrace, Oakland, FL 34760

Welcome to this inviting 2-bedroom, 2.5-bathroom townhouse in Oakland, offering 1,472 sq ft of thoughtfully designed living space. Upon entering, you’ll be greeted by an open layout on the first floor, where the living room, dining room, and kitchen seamlessly blend together with abundant natural light and modern finishes that add warmth and style. A convenient half bathroom is located

Cristina Ireland DENIZ REALTY PARTNERS LLC

2226 Gopher Tortoise Terrace, Oakland, FL 34760

/36
Est $1,089,354 Not Listed For Sale
- 6 Beds
- 6 Baths
- 4,674 Sq Ft
3175 Sailing Pier Ave, Oakland, FL 34787

3175 Sailing Pier Ave, Oakland, FL 34787

/39
$600,000 Pending
- 4 Beds
- 2.5 Baths
- 1,811 Sq Ft
1119 Bobcat Chase Blvd, Oakland, FL 34760

Prepare to be captivated by this enchanting 4-bedroom, 2.5-bath pool home, nestled amidst mature oaks that lend an air of timeless charm. Located in the idyllic community of Long Leaf, this home boasts the best lot in the neighborhood—complete with a cozy fire pit that begs for evening gatherings under the stars.Step inside to discover a kitchen adorned with tasteful taupe cabinetry,

Erica Diaz HOMEVEST REALTY

1119 Bobcat Chase Blvd, Oakland, FL 34760
/2
$695,000 Sold Dec 18, 2024
- 2,350 Sq Ft
- $296/SF
- 26 Days On Market
- 4 Beds
- 2 Baths
- Built 2021
13534 Parkfield Way, Oakland, FL 34787

One or more photo(s) has been virtually staged. Welcome to your dream home in the sought-after community of Winter Garden! This beautiful 4-bedroom, 2-bathroom residence offers an open floor plan, perfect for both everyday living and entertaining. Enjoy natural light flooding the spacious living areas, and the modern kitchen that overlooks the family room, creating a seamless flow throughout.Step

Jonathan Olinger JASON MITCHELL REAL ESTATE FLO

13534 Parkfield Way, Oakland, FL 34787

/2
Est $471,557 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,567 Sq Ft
13304 Pontoon Rd, Oakland, FL 34787

13304 Pontoon Rd, Oakland, FL 34787

/2
$788,500 Sold Dec 18, 2024
- 2,240 Sq Ft
- $352/SF
- 162 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
1221 Wilder Oaks Way, Oakland, FL 34787

Under Construction. Luxurious new home with 4 bedrooms, 3 bathrooms, 3 car garage, covered front porch, covered back yard patio and elegant exterior design. Open concept kitchen-living area with solid surface countertops, stainless steel appliances, cooktop, oven, microwave, dishwasher, vent hood, ceramic tile backsplash, upgraded flooring, upgraded cabinetry, and walk in pantry.

Jasmine Martz OLYMPUS EXECUTIVE REALTY INC

1221 Wilder Oaks Way, Oakland, FL 34787

/48
Est $973,833 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,265 Sq Ft
15311 Arcadia Bluff Loop, Oakland, FL 34787

15311 Arcadia Bluff Loop, Oakland, FL 34787

/2
$557,000 Sold Dec 18, 2024
- 2,477 Sq Ft
- $225/SF
- 170 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2018
16140 Harbor Mist Alley, Oakland, FL 34787

**THE BEST PRICED CLEARDEN MODEL IN WATERLEIGH**$60,000 PRICE ADJUSTMENT**We are pleased to bring to market this one owner estate home in Waterleigh! Built in 2018 and featuring 4 bedrooms, 3 full bathrooms and 1 half bathroom. This incredible open floor plan offers a downstairs suite for guests with en suite bathroom and walk in closet. The first floor has an open floor plan with tile floors,

Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

16140 Harbor Mist Alley, Oakland, FL 34787

/30
Est $1,877,444 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,340 Sq Ft
1091 Eaglecrest Dr, Oakland, FL 34787

1091 Eaglecrest Dr, Oakland, FL 34787

/2
$820,100 Sold Dec 17, 2024
- 2,254 Sq Ft
- $364/SF
- 135 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2024
1197 Wilder Oaks Way, Oakland, FL 34787

Under Construction. Luxurious new home with 3 bedrooms, 2.5 bathrooms, Home Office, 3 car garage, covered front porch, covered back yard patio and elegant exterior design. Open concept kitchen-living area with solid surface countertops, stainless steel appliances, cooktop, oven, microwave, dishwasher, vent hood, ceramic tile backsplash, upgraded flooring, upgraded cabinetry, and walk in pantry.

Jasmine Martz OLYMPUS EXECUTIVE REALTY INC

1197 Wilder Oaks Way, Oakland, FL 34787

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