Oakland, FL Homes

/62
$1,674,999

$50K PRICE DROP
- 6 Beds
- 5 Baths
- 4,104 Sq Ft
1101 Eagles Pass Way, Oakland, FL 34787

Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown

Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

1101 Eagles Pass Way, Oakland, FL 34787
/2
$1,949,000

Sold Jun 02, 2026

511 Briley Ave, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,862 Sq Ft
- Built 2026
Last Sold Summary
- $505/SF
- 56 Days On Market
Last Listing Agent Carolina Dumit CORCORAN PREMIER REALTY

511 Briley Ave, Oakland, FL 34787

/2
Not Listed For Sale

Unlisted Address
- 4 Beds
- 5 Baths
- 3,794 Sq Ft
- Built 2025
Unlisted Address

Last Sold Summary

/3
$548,000

New Construction $20K PRICE DROP Pending
- 3 Beds
- 2.5 Baths
- 2,062 Sq Ft
12911 Westhaven Oak Dr, Oakland, FL 34787

Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2

Dayene Grubert ORLANDO TBI REALTY LLC

12911 Westhaven Oak Dr, Oakland, FL 34787
/2
$445,999

Sold Mar 23, 2026

12748 Brodlove Ln, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,796 Sq Ft
- Built 2022
Last Sold Summary
- $248/SF
- 30 Days On Market
Current Estimated Value $447,012

Last Listing Agent Mayra Rivas Acevedo CASA SOL REALTY LLC

12748 Brodlove Ln, Oakland, FL 34787

/46
Est $625,807

Not Listed For Sale

13007 Tollcross Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,160 Sq Ft
- Built 2024
13007 Tollcross Way, Oakland, FL 34787

/25
$699,490

New Construction
- 3 Beds
- 2 Baths
- 2,166 Sq Ft
4620 Scenic Woods Dr, Oakland, FL 34787

Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home.Step into the Garnet, a single-story home offering 3 spacious bedrooms, 2 beautifully appointed

Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

4620 Scenic Woods Dr, Oakland, FL 34787
/2
$828,296

Sold Sep 29, 2025

16146 Point Rock Dr, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,225 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $257/SF
- 48 Days On Market
Current Estimated Value $826,000

Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

16146 Point Rock Dr, Oakland, FL 34787

/2
Est $793,377

Not Listed For Sale

9462 Emerald Berry Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,211 Sq Ft
- Built 2024
9462 Emerald Berry Dr, Oakland, FL 34787

Last Sold Summary
- 62 Days On Market

/3
$844,000

New Construction $20K PRICE DROP Pending
- 4 Beds
- 3.5 Baths
- 3,005 Sq Ft
12916 Westhaven Oak Dr, Oakland, FL 34787

Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion Summer 2026- Welcome home to this beautifully designed open-concept residence featuring a sought-after primary suite on the main level. The light-filled two-story foyer creates an impressive first impression and flows seamlessly into spacious living and entertaining areas. Thoughtful layout,

Dayene Grubert ORLANDO TBI REALTY LLC

12916 Westhaven Oak Dr, Oakland, FL 34787
/2
$633,000

Sold May 05, 2026

847 Cura Ct, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 3,000 Sq Ft
- Built 2002
Last Sold Summary
- 2% Below List Price
- $211/SF
- 104 Days On Market
Current Estimated Value $632,384

Last Listing Agent Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

847 Cura Ct, Oakland, FL 34787

/2
Est $848,820

Not Listed For Sale

5590 Orange Orchard Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,853 Sq Ft
- Built 2021
5590 Orange Orchard Dr, Oakland, FL 34787

Last Sold Summary
- 3 Days On Market

/35
$766,000

$59K PRICE DROP Pending
- 4 Beds
- 4 Baths
- 2,831 Sq Ft
931 Kylee Aly, Winter Garden, FL 34787

Under contract-accepting backup offers. ***Seller to offer up to $17,000 toward buyer's closing cost & or rate buy down.*** There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place.

Matt McKee COMPASS FLORIDA LLC

931 Kylee Aly, Winter Garden, FL 34787
/2
$389,000

Sold Dec 23, 2025

2218 Gopher Tortoise Terrace, Oakland, FL 34760
- 2 Beds
- 2.5 Baths
- 1,472 Sq Ft
- Built 2020
Last Sold Summary
- $264/SF
- 36 Days On Market
Last Listing Agent Chelsea Eckert LISA REALTY PARTNERS

2218 Gopher Tortoise Terrace, Oakland, FL 34760

/2
Est $758,805

Not Listed For Sale

14205 Lanyard Way, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,076 Sq Ft
- Built 2024
14205 Lanyard Way, Oakland, FL 34787

Last Sold Summary
- 0 Days On Market

/42
$599,000

$80K PRICE DROP Pending
- 4 Beds
- 3.5 Baths
- 2,743 Sq Ft
12554 Westhaven Oak Dr, Oakland, FL 34787

This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

Adriana PL Franzoi WRA BUSINESS & REAL ESTATE

12554 Westhaven Oak Dr, Oakland, FL 34787
/2
$2,050,000

Sold Apr 09, 2026

9008 Morgana Ct, Oakland, FL 34787
- 5 Beds
- 5 Baths
- 4,934 Sq Ft
- Built 2022
Last Sold Summary
- 7% Below List Price
- $415/SF
- 76 Days On Market
Current Estimated Value $2,047,730

Last Listing Agent Bent Danholm DANHOLM COLLECTION

9008 Morgana Ct, Oakland, FL 34787

/2
Est $782,311

Not Listed For Sale

1404 High Springs Ln, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 3,059 Sq Ft
- Built 2020
1404 High Springs Ln, Winter Garden, FL 34787

Last Sold Summary
- 92 Days On Market

/4
$2,395,000

New Construction Pending
- 5 Beds
- 5.5 Baths
- 4,527 Sq Ft
1137 Prado Ln, Oakland, FL 34787

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, and a spacious loft across 3,712 square feet of elegantly

Alexis Anderson REGENCY REAL ESTATE LLC

1137 Prado Ln, Oakland, FL 34787
/2
$520,000

Sold Aug 29, 2025

1877 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
- Built 2018
Last Sold Summary
- $259/SF
- 9 Days On Market
Current Estimated Value $497,878

Last Listing Agent James Goodyear COMPASS FLORIDA LLC

1877 Standing Rock Cir, Oakland, FL 34787

/2
Est $801,748

Not Listed For Sale

9516 Emerald Berry Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,211 Sq Ft
- Built 2024
9516 Emerald Berry Dr, Oakland, FL 34787

Last Sold Summary
- 13 Days On Market

/46
$724,900

$25K PRICE DROP
- 4 Beds
- 4 Baths
- 2,852 Sq Ft
2017 Boss Hewett St, Oakland, FL 34787

Virtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously maintained 2,852 sq ft home built in 2022, with owned rooftop solar that keeps utility costs well below the Florida norm for a home this size. Four bedrooms, four full baths, and a two-car garage, all just minutes from historic Winter Garden's shops, restaurants, and Saturday farmers market.All four

Peter Biskup CHARLES RUTENBERG REALTY ORLANDO

2017 Boss Hewett St, Oakland, FL 34787
/2
$645,000

Sold Feb 28, 2026

2139 Bay Line Rd, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,281 Sq Ft
- Built 2020
Last Sold Summary
- 1% Below List Price
- $283/SF
- 17 Days On Market
Current Estimated Value $644,173

Last Listing Agent Ryan Barnett MARKET CONNECT REALTY LLC

2139 Bay Line Rd, Oakland, FL 34787

/2
Est $589,728

Not Listed For Sale

12891 Westhaven Oak Dr, Oakland, FL 34787
- 3 Beds
- 3.5 Baths
- 1,908 Sq Ft
- Built 2024
12891 Westhaven Oak Dr, Oakland, FL 34787

Last Sold Summary

/55
$2,075,000

$275K PRICE DROP Pending
- 5 Beds
- 4.5 Baths
- 4,436 Sq Ft
9014 Morgana Ct, Oakland, FL 34787

Under contract-accepting backup offers. This is more than a house ~ Lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare

Jennifer Wemert WEMERT GROUP REALTY LLC

9014 Morgana Ct, Oakland, FL 34787
/2
$530,000

Sold Oct 15, 2025

8001 Sayings Dr, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 2,552 Sq Ft
- Built 2022
Last Sold Summary
- 8% Below List Price
- $208/SF
- 66 Days On Market
Current Estimated Value $524,267

Last Listing Agent Shanta Navarro KELLER WILLIAMS ADVANTAGE III

8001 Sayings Dr, Winter Garden, FL 34787

/21
Est $436,393

Not Listed For Sale

2261 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,753 Sq Ft
- Built 2019
2261 Standing Rock Cir, Oakland, FL 34787

Last Sold Summary
- 136 Days On Market

/55
$525,000
- 3 Beds
- 2.5 Baths
- 2,152 Sq Ft
2241 White Feather Loop, Oakland, FL 34787

Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, style, and location. Built in 2018, the home features a bright, open-concept floor plan with spacious living areas, a modern kitchen, and plenty of room for both everyday living and entertaining. Step outside and enjoy all the amenities

Brynn Munro CORCORAN PREMIER REALTY

2241 White Feather Loop, Oakland, FL 34787
/2
$850,000

Sold Apr 06, 2026

501 E Oakland Ave, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 3,448 Sq Ft
- Built 2007
Last Sold Summary
- 11% Below List Price
- $247/SF
- 104 Days On Market
Current Estimated Value $855,581

Last Listing Agent Erica Diaz HOMEVEST REALTY

501 E Oakland Ave, Winter Garden, FL 34787

/2
Est $1,169,392

Not Listed For Sale

1112 Hull Island Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,562 Sq Ft
- Built 2021
1112 Hull Island Dr, Oakland, FL 34787

Last Sold Summary
- 49 Days On Market

/60
$997,000

$38K PRICE DROP Pending
- 5 Beds
- 3.5 Baths
- 3,910 Sq Ft
9549 Bolero Rd, Oakland, FL 34787

Under contract-accepting backup offers. The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home

Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

9549 Bolero Rd, Oakland, FL 34787
/2
$599,200

Sold Sep 25, 2025

4727 Forest Haven Way, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,935 Sq Ft
- Built 2025
Last Sold Summary
- $310/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

4727 Forest Haven Way, Oakland, FL 34787

/2
Est $672,849

Not Listed For Sale

2157 Bay Line Rd, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,274 Sq Ft
- Built 2020
2157 Bay Line Rd, Oakland, FL 34787

Last Sold Summary
- 69 Days On Market

/63
$3,495,000

New Construction Pending
- 5 Beds
- 5.5 Baths
- 5,001 Sq Ft
402 N Pollard St, Oakland, FL 34787

Luxury new construction model home by Element Home Builders located in the exclusive custom home community of Briley Farm in Oakland. This thoughtfully designed residence offers approximately 4,900 square feet of elevated living space with 5 bedrooms, 5.5 bathrooms, and a spacious 3-car garage. Designed for both everyday living and entertaining, the home features soaring ceilings, expansive

Carolina Dumit CORCORAN PREMIER REALTY

402 N Pollard St, Oakland, FL 34787
/2
$495,000

Sold Feb 18, 2026

2755 Bobcat Chase Blvd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,822 Sq Ft
- Built 2020
Last Sold Summary
- 7% Below List Price
- $272/SF
- 203 Days On Market
Current Estimated Value $491,985

Last Listing Agent Tania Matthews KELLER WILLIAMS ELITE PARTNERS III REALTY

2755 Bobcat Chase Blvd, Oakland, FL 34787

/2
Est $576,849

Not Listed For Sale

2050 Standing Rock Cir, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 2,596 Sq Ft
- Built 2019
2050 Standing Rock Cir, Oakland, FL 34787

Last Sold Summary
- 5 Days On Market

/45
$639,000
- 4 Beds
- 3 Baths
- 2,650 Sq Ft
529 Johns Landing Way, Oakland, FL 34787

Welcome home to this stunning 4-bedroom, 3-bathroom pool home tucked inside a sought-after gated community! Offering 2,650 square feet of thoughtfully designed living space, this home is perfect for both everyday comfort and entertaining. The versatile 4th bedroom is ideal as a mother-in-law suite, guest quarters, or home office — perfect for multi-generational living. The spacious primary suite

Denise Pellegrino REAL BROKER, LLC

529 Johns Landing Way, Oakland, FL 34787
/2
$865,000

Sold Jul 25, 2025

70 Millholland St, Oakland, FL 34760
- 5 Beds
- 3 Baths
- 2,534 Sq Ft
- Built 2009
Last Sold Summary
- 15% Below List Price
- $341/SF
- 261 Days On Market
Current Estimated Value $882,100

Last Listing Agent Ashley Boyd BHHS FLORIDA REALTY

70 Millholland St, Oakland, FL 34760

/2
Est $536,517

Not Listed For Sale

1763 White Feather Loop, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,152 Sq Ft
- Built 2017
1763 White Feather Loop, Oakland, FL 34787

Last Sold Summary
- 51 Days On Market

/49
$1,050,000

Pending
- 4 Beds
- 3.5 Baths
- 2,667 Sq Ft
1219 Saddleback Dr, Winter Garden, FL 34787

Welcome to what may be the most impeccably maintained and beautifully upgraded home in Oakland Park! This stunning 4-bedroom, 3.5-bath residence showcases designer-inspired finishes throughout, featuring soaring ceilings, modern color palettes, and countless custom enhancements that make it truly one of a kind. Built just four years ago and nestled on a quiet street directly across from green

Lynette Piontek CENTRAL FLORIDA PRIME REAL ESTATE LLC

1219 Saddleback Dr, Winter Garden, FL 34787

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