Oakland, FL Homes

/2
$565,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,206 Sq Ft
14111 Frasier St, Oakland, FL 34787

We present this beautiful new bungalow-style home, located in the Highland Ridge condominium, in Winter Garden – one of the most valued and desired areas to live in.With a charming façade and a welcoming porch at the entrance, this residence combines comfort, elegance and functionality in one place.The project has an open-concept floor plan, perfectly integrating the kitchen with an island with

Erika Castellani WRA BUSINESS & REAL ESTATE

14111 Frasier St, Oakland, FL 34787
/2
$538,491 Sold Feb 27, 2025
- 1,836 Sq Ft
- $293/SF
- 0 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
16465 Hamlin View St, Oakland, FL 34787

Under Construction. SAMPLE IMAGES!!! Builder offers phenomenal incentives including interest rate promotions, and closing cost assistance with the use ofa preferred lender. The Brantley floorplan is designed to impress, featuring 3 spacious bedrooms, 2.5 baths, and a versatile loft perfect for anoffice, child's playroom, or additional entertainment space. This home exudes a sense of

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

16465 Hamlin View St, Oakland, FL 34787

/64
Est $589,760 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,502 Sq Ft
17167 Writing Alley, Oakland, FL 34787

17167 Writing Alley, Oakland, FL 34787

/2
$498,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,836 Sq Ft
Brantley, Oakland, FL 34787

Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

Dream Finders Homes

Brantley, Oakland, FL 34787
/2
$730,000 Sold Feb 26, 2025
- 3,059 Sq Ft
- $239/SF
- 92 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2020
1404 High Springs Ln, Winter Garden, FL 34787

***MAJOR PRICE IMPROVEMENT***. Step into this exquisite 4-bedroom, 3.5-bath home in the highly desired community of LongLeaf at Oakland, where every detail has been carefully considered. The home features 4 spacious bedrooms, each offering a peaceful retreat for rest and relaxation. A perfectly designed jack and jill bathroom joins two of the three upstairs bedrooms while the fourth bedroom

Kaitlin LaMacchia DENIZ REALTY PARTNERS LLC

1404 High Springs Ln, Winter Garden, FL 34787

/54
Est $716,760 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,722 Sq Ft
11072 Robert Frost Dr, Oakland, FL 34787

11072 Robert Frost Dr, Oakland, FL 34787

/15
$1,975,000 New Construction
- 5 Beds
- 5.5 Baths
- 3,596 Sq Ft
1149 Dr, Oakland, FL 34787

Pre-Construction. To be built. Welcome to the Clementine Floorplan by Element Home Builders – A Stunning New Home in Oakland's Premier Community!Discover your dream home with the Clementine Floorplan, a thoughtfully designed residence nestled in Oakland's newest, most sought-after community. This spacious, modern home combines elegance, functionality, and comfort to create the perfect

Blaine Dooley REGENCY REAL ESTATE LLC

1149 Dr, Oakland, FL 34787
/2
$285,000 Sold Feb 26, 2025
- 1,019 Sq Ft
- $280/SF
- 135 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1986
527 W Herriott Ave, Oakland, FL 34760

Nestled in the quaint Town of Oakland enjoy this 3 bedroom 2 bath home on a quiet street with oversized lot. Home offers a new roof 8/2024, HVAC 3/2024, and a hot water heater in 8/2024. Interior remodeled with new drywall, engineered hardwood flooring, fixtures and new doors. Home is close to Oakland Nature Preserve, West Orange Trail, Oakland Farmers Market, and the public park.

W. Channing Harrison LAKESIDE REALTY WINDERMERE INC

527 W Herriott Ave, Oakland, FL 34760

/44
Est $634,608 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,704 Sq Ft
8186 Sayings Dr, Oakland, FL 34787

8186 Sayings Dr, Oakland, FL 34787

/59
$600,000 Pending
- 3 Beds
- 2.5 Baths
- 1,995 Sq Ft
1740 Standing Rock Cir, Oakland, FL 34787

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Exceptional POOL HOME with SOLAR PANELS and Many Other ENERGY-EFFICIENT FEATURES!Welcome to a home that truly impresses from the moment you arrive. As you step inside, you’re greeted by seamless WOOD PLANK TILE FLOORING that flows throughout the home, creating a warm and cohesive aesthetic. The heart

Melissa Vance MAINFRAME REAL ESTATE

1740 Standing Rock Cir, Oakland, FL 34787
/2
$800,000 Sold Feb 24, 2025
- 2,587 Sq Ft
- $309/SF
- 229 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2023
16261 Point Rock Dr, Oakland, FL 34787

Beautifully designed home ideal for both entertaining and everyday living. The gourmet kitchen features cabinets, a built-in oven and microwave, a cooktop, and others. The property has a spacious front porch, rear porch, and driveway. One bedroom and a full bathroom are situated on the first floor, while the remaining four bedrooms, a large loft/second living room, and a laundry room are located

Jose Fernandes CELEBRITY GLOBAL REALTY LLC

16261 Point Rock Dr, Oakland, FL 34787

/10
Est $495,195 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
11307 Great Rock St, Winter Garden, FL 34787

11307 Great Rock St, Winter Garden, FL 34787

/36
$645,000 Pending
- 3 Beds
- 2.5 Baths
- 2,060 Sq Ft
2390 Standing Rock Cir, Oakland, FL 34787

Under contract-accepting backup offers. Stunning 3-Bedroom Home with Upgraded Outdoor Oasis in Oakland TrailsWelcome to this immaculate 3-bedroom, 2.5-bathroom home nestled in the highly sought-after Oakland Trails community in Oakland, Florida steps away from the West Orange Trail. Boasting a beautifully maintained living space, this move-in-ready home combines comfort, elegance, and

Francisco Chavez, Jr DENIZ REALTY PARTNERS LLC

2390 Standing Rock Cir, Oakland, FL 34787
/2
$1,600,000 Sold Feb 21, 2025
- 3,920 Sq Ft
- $408/SF
- 5 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2024
10081 Atwater Bay Dr, Oakland, FL 34787

Under Construction. Waterleigh presents the North Haven. This two-story Emerald Series home contains elevated designs, elegant exteriors and high-end features. The spacious all concrete block construction home features 5 bedrooms, 3.5 baths, flex space and a game room. A beautiful porch welcomes you, as you enter the foyer, you’ll find a flex room perfect for work or play and a powder room. The

Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

10081 Atwater Bay Dr, Oakland, FL 34787

/12
Est $471,972 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
11301 Great Rock St, Oakland, FL 34787

11301 Great Rock St, Oakland, FL 34787

/41
$812,421 Pending
- 5 Beds
- 4 Baths
- 2,866 Sq Ft
16195 Point Rock Dr, Oakland, FL 34787

Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find a flex room perfect for work or play and downstairs powder room. The well-appointed kitchen overlooking the

Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

16195 Point Rock Dr, Oakland, FL 34787
/2
$1,050,000 Sold Feb 14, 2025
- 2,711 Sq Ft
- $387/SF
- 129 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
1056 Sadler Oaks Way, Oakland, FL 34787

Discover this stunning 4-bedroom, 3-bath home in Oakland Park, offering 2,711 sqft of custom-designed elegance. Set on a private lot with no rear neighbors and just steps from the West Orange Trail, this residence provides serene living and unique charm. Located in the golf cart district, you'll enjoy easy access to local amenities and a convenient lifestyle. The thoughtful layout features 3

Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

1056 Sadler Oaks Way, Oakland, FL 34787

/2
Est $512,938 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,788 Sq Ft
12338 Bracco St, Oakland, FL 34787

12338 Bracco St, Oakland, FL 34787

/36
$520,000 Pending
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
1877 Standing Rock Cir, Oakland, FL 34787

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 1877 Standing Rock Circle, a warm and inviting 3-bedroom, 2.5-bathroom home tucked into the desirable Oakland Trails community. This home offers a thoughtful layout with comfortable living spaces filled with natural light. Inside, you’ll find upgraded luxury vinyl plank flooring that’s both stylish

James Goodyear REAL BROKER, LLC

1877 Standing Rock Cir, Oakland, FL 34787
/2
$468,000 Sold Feb 13, 2025
- 1,579 Sq Ft
- $296/SF
- 159 Days On Market
- 2 Beds
- 2 Baths
- Built 2024
13460 Princess St, Oakland, FL 34787

The gorgeous Ellenwood villa by Del Webb boasts tons of useful space and natural light throughout its open floor plan. This home features 2 bedrooms, 2 bathrooms, a combined kitchen, café and gathering room, a screened, covered lanai, upgraded laundry room, refrigerator, window blinds, and a 2-car garage. Upon entry, you are greeted by a formal foyer which offers a stunning view back to the

Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

13460 Princess St, Oakland, FL 34787

/25
Est $547,801 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,239 Sq Ft
1775 Standing Rock Cir, Oakland, FL 34787

1775 Standing Rock Cir, Oakland, FL 34787

/52
$939,900 Pending
- 4 Beds
- 3.5 Baths
- 3,267 Sq Ft
9068 Sonoma Coast Dr, Oakland, FL 34787

Under contract-accepting backup offers. Welcome to your dream home in the highly sought-after Waterleigh community of Horizon West! This beautifully upgraded Sea Cliff model sits on one of the largest lots in the neighborhood, offering the perfect blend of luxury, comfort, and convenience.The well-thought-out floor plan features a first-floor primary suite, while upstairs you’ll find three

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

9068 Sonoma Coast Dr, Oakland, FL 34787
/2
$1,224,660 Sold Feb 10, 2025
- 3,653 Sq Ft
- $335/SF
- 0 Days On Market
- 4 Beds
- 5 Baths
- Built 2024
15252 Canopy Cover Dr, 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

Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

15252 Canopy Cover Dr, Oakland, FL 34787

/5
Est $949,633 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,653 Sq Ft
Unlisted Address

Unlisted Address

/13
$385,140 Pending
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
5840 Meditation Dr, Oakland, FL 34787

Under Construction. Refresh your lifestyle with the Wilshire! This magnificent townhome covers two stories and includes three bedrooms, two and one-half bathrooms and a two-car rear load garage. 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 enticing patio.

Ben Goldstein LENNAR REALTY

5840 Meditation Dr, Oakland, FL 34787
/2
$410,000 Sold Feb 07, 2025
- 1,759 Sq Ft
- $233/SF
- 13 Days On Market
- 4 Beds
- 2 Baths
- Built 2001
1171 Railside Way, Oakland, FL 34787

**Take advantage of a seller paid promotion. The seller will credit the buyer $8,398 towards their closing costs and prepaid items at closing, which could include a rate buy down, on any full price offer accepted by 12/31/24.**Charming 4-bedroom, 2-bathroom home with 1,759 sqft, located in Historic Oakland, just minutes from the Florida Turnpike, West Orange Bike Trail, and Downtown Winter

Mark D'Italia PROPERTY LOGIC RE

1171 Railside Way, Oakland, FL 34787

/21
Est $583,093 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,060 Sq Ft
2120 Standing Rock Cir, Oakland, FL 34787

2120 Standing Rock Cir, Oakland, FL 34787

/51
$875,000 Pending
- 4 Beds
- 3 Baths
- 3,290 Sq Ft
413 MacChi Ave, Oakland, FL 34787

Under contract-accepting backup offers. RARE OPPORTUNITY in the highly desirable Winters Landing community – golf cart accessible to downtown Winter Garden and steps to the tree-shaded, 22 mile long West Orange Trail! Upon entering this David Weekly-designed home, you’ll be captivated by the inviting nature of this single-story property loaded with upgrades. No stone has been left unturned,

Sophia Ferrara COLDWELL BANKER REALTY

413 MacChi Ave, Oakland, FL 34787
/2
$695,000 Sold Feb 03, 2025
- 2,179 Sq Ft
- $319/SF
- 48 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
14219 Spring Garden Dr, Oakland, FL 34787

Under Construction. Under Construction- Brand New-One story 4 bedroom 3 bath single family home by Toll Brothers in Winter Garden-Westhaven at Ovation.This home features a gourmet kitchen with 42 inch cabinets, quartz counter tops and natural gas cook top. Move-in by early 2025.

George Weiss ORLANDO TBI REALTY LLC

14219 Spring Garden Dr, Oakland, FL 34787

/28
Est $1,038,908 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,914 Sq Ft
1266 Civitas Way, Oakland, FL 34787

1266 Civitas Way, Oakland, FL 34787

/76
$850,000 Pending
- 3 Beds
- 2.5 Baths
- 2,720 Sq Ft
3182 Sailing Pier Ave, Oakland, FL 34787

***Motivated Sellers just reduced more than $50K BELOW RECENT APPRAISAL!!!*** Welcome home to this 2024 built custom Pulte luxury pool home nestled within the highly desirable gated community of Estates at Lakeview Preserve in Winter Garden. This practically brand new 3 bedroom, 2.5 bathroom, with office/flex room, home offers an impressive array of features that combine elegance and comfort.

Ron Howell, II EXP REALTY LLC

3182 Sailing Pier Ave, Oakland, FL 34787
/2
$645,000 Sold Jan 19, 2025
- 2,281 Sq Ft
- $283/SF
- 79 Days On Market
- 4 Beds
- 3 Baths
- Built 2022
1328 Foltz Loop, Oakland, FL 34787

***MOTIVATED SELLER - EASY TO SHOW - PRICED TO SELL***Welcome to your dream home in the heart of beautiful Oakland. This stunning two-year-old, one-story residence boasts four spacious bedrooms and three luxurious baths, all designed in an open floor plan that complements modern living. On a serene conservation lot in a peaceful cul-de-sac, this home offers unparalleled privacy with a private

Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

1328 Foltz Loop, Oakland, FL 34787

/12
Est $495,700 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
11343 Great Rock St, Oakland, FL 34787

11343 Great Rock St, Oakland, FL 34787

/17
$423,190 Pending
- 3 Beds
- 2.5 Baths
- 1,795 Sq Ft
5693 Meditation Dr, Oakland, FL 34787

Under Construction. Welcome to the refreshing Autumn, that includes three bedrooms, two and a half baths, with a two-car garage. This is a modern classic two-story home with a detached rear load garage. The kitchen has a large island, fabulous panty and opens to the elegant dining room and spacious family room. There is a laundry room with washer and dryer and a half bathroom on the first floor.

Ben Goldstein LENNAR REALTY

5693 Meditation Dr, Oakland, FL 34787
/2
$425,000 Sold Jan 17, 2025
- 1,626 Sq Ft
- $261/SF
- 6 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2022
16467 Prairie School Dr, Oakland, FL 34787

This picture-perfect, MOVE-IN READY, 3 BEDROOM/2.5 BATH, Arcadia model townhome by Mattamy Homes in the popular HAWKSMOOR neighborhood of HORIZON WEST is ready for its new owner. Barely lived in, the home features a great OPEN FLOOR PLAN on the main level and thoughtful UPGRADES throughout. Entering the front door, you’re immediately greeted by the LIGHT & AIRY feel of the MASSIVE entertaining

Carlos Machiavello LAKESIDE REALTY

16467 Prairie School Dr, Oakland, FL 34787

/51
Est $408,507 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,620 Sq Ft
1400 Planted Pine St, Oakland, FL 34760

1400 Planted Pine St, Oakland, FL 34760

/36
$439,990 Pending
- 3 Beds
- 2.5 Baths
- 1,753 Sq Ft
2405 Standing Rock Cir, Oakland, FL 34787

Under contract-accepting backup offers. Beautifully maintained 3-bedroom, 2.5-bath home featuring inviting outdoor and indoor living spaces. Enjoy the convenience of a garage, providing ample parking and storage options. The second floor offers a large, versatile area ideal for a family room, home office, playroom, or media space. Inside, you'll find a comfortable and functional layout with a

Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

2405 Standing Rock Cir, Oakland, FL 34787
/2
$700,000 Sold Jan 16, 2025
- 2,425 Sq Ft
- $289/SF
- 76 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2022
930 Auction Alley, Winter Garden, FL 34787

Discover your dream home in the sought after community of Oakland Park! Only 2 YEARS NEW, this IMMACULATE and beautifully maintained, MODERN home features 4 bedrooms, 3.5 baths. It’s the perfect blend of convenience and charm. Featuring LOW MAINTENANCE LIVING with HOA-managed landscaping, sprinklers, and fencing. Enjoy your WALKABLE NEIGHBORHOOD or relax on your FRONT PORCH overlooking the

Sandy Jones CLOCK TOWER REALTY

930 Auction Alley, Winter Garden, FL 34787

/85
Est $494,543 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
15779 Water Spring Blvd, Winter Garden, FL 34787

15779 Water Spring Blvd, Winter Garden, FL 34787

/19
$422,240 Pending
- 3 Beds
- 2.5 Baths
- 1,647 Sq Ft
5689 Meditation Dr, 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

5689 Meditation Dr, Oakland, FL 34787

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