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1264 Ridge Lake Way, Oakland

1269 Ridge Lake Way, Oakland

Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living space with warmth and elegance. The thoughtfully designed layout flows from a formal dining room into an eat-in kitchen with a breakfast nook — perfect for everything from quiet mornings to lively gatherings. Two dedicated laundry rooms add a level of everyday convenience rarely found at any price point. Outside your door, golf-cart your way to Downtown Winter Garden's shops and restaurants— this is Florida living at its finest.

4 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living space with warmth and elegance. The thoughtfully designed layout flows from a formal dining room into an eat-in kitchen with a breakfast nook — perfect for everything from quiet mornings to lively gatherings. Two dedicated laundry rooms add a level of everyday convenience rarely found at any price point. Outside your door, golf-cart your way to Downtown Winter Garden's shops and restaurants— this is Florida living at its finest.

1204 Water Maple Drive, Oakland

$2,045,357

Pre-Construction. To be built. Nestled within the exclusive Grove community in the heart of Oakland and Winter Garden's coveted golf cart district, this bespoke pre-construction residence is a rare opportunity to own something truly one-of-a-kind. Five bedrooms, five full bathrooms, a powder room, and a gracious loft unfold across 3,725 square feet of living space where timeless architecture and modern sophistication coexist effortlessly — every detail considered, every finish deliberate. Element Home Builders has built its reputation on craftsmanship that doesn't cut corners and design that doesn't follow trends — because the Clementine wasn't designed to be fashionable. It was designed to be unforgettable. Step outside and you're two minutes from the West Orange Trail and just a short golf cart ride from the vibrant energy of Downtown Winter Garden — boutique shopping, acclaimed dining, weekend farmers markets, and the kind of small-town charm that's increasingly impossible to find this close to the city. This isn't just a home. It's a lifestyle you'll never want to leave.

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community in the heart of Oakland and Winter Garden's coveted golf cart district, this bespoke pre-construction residence is a rare opportunity to own something truly one-of-a-kind. Five bedrooms, five full bathrooms, a powder room, and a gracious loft unfold across 3,725 square feet of living space where timeless architecture and modern sophistication coexist effortlessly — every detail considered, every finish deliberate. Element Home Builders has built its reputation on craftsmanship that doesn't cut corners and design that doesn't follow trends — because the Clementine wasn't designed to be fashionable. It was designed to be unforgettable. Step outside and you're two minutes from the West Orange Trail and just a short golf cart ride from the vibrant energy of Downtown Winter Garden — boutique shopping, acclaimed dining, weekend farmers markets, and the kind of small-town charm that's increasingly impossible to find this close to the city. This isn't just a home. It's a lifestyle you'll never want to leave.

1225 Water Maple Drive, Oakland

$619,999

NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and low-maintenance living. Don’t miss the opportunity to own a move-in-ready home in Oakland, conveniently located near parks, trails, and local amenities. Schedule your private showing today!

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and low-maintenance living. Don’t miss the opportunity to own a move-in-ready home in Oakland, conveniently located near parks, trails, and local amenities. Schedule your private showing today!

38 S Pollard Street, Oakland

$683,000

Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated single-story ranch home features a bright, open layout with the kitchen flowing seamlessly into the living room. The renovated kitchen includes quartz countertops, updated cabinetry, and a large island with eat-in seating, creating a great space for everyday living and entertaining. The living room is warm and inviting with a wood-burning fireplace and plenty of natural light. Recent improvements include a new kitchen, updated bathrooms, new flooring, new windows, interior and exterior paint, gutters, and a resurfaced pool and paver pool deck. A spacious enclosed Florida room with large windows and a slider that overlooks the backyard and pool, providing additional living space filled with natural light. The home also features a very large indoor utility room that could easily function as a home office, flex space, or additional storage. Outside, you’ll find a large in-ground pool and a fully fenced backyard, perfect for relaxing or entertaining. Located just minutes from downtown Oakland, the West Orange Trail, and Plant Street in downtown Winter Garden, offering easy access to restaurants, shops, and community events. Updated pool homes with no hoa in this area are very rare.

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated single-story ranch home features a bright, open layout with the kitchen flowing seamlessly into the living room. The renovated kitchen includes quartz countertops, updated cabinetry, and a large island with eat-in seating, creating a great space for everyday living and entertaining. The living room is warm and inviting with a wood-burning fireplace and plenty of natural light. Recent improvements include a new kitchen, updated bathrooms, new flooring, new windows, interior and exterior paint, gutters, and a resurfaced pool and paver pool deck. A spacious enclosed Florida room with large windows and a slider that overlooks the backyard and pool, providing additional living space filled with natural light. The home also features a very large indoor utility room that could easily function as a home office, flex space, or additional storage. Outside, you’ll find a large in-ground pool and a fully fenced backyard, perfect for relaxing or entertaining. Located just minutes from downtown Oakland, the West Orange Trail, and Plant Street in downtown Winter Garden, offering easy access to restaurants, shops, and community events. Updated pool homes with no hoa in this area are very rare.

310 E Gulley Avenue, Oakland

$88,000

An exceptional opportunity to build your dream residence in the charming and highly desirable Town of Oakland, Florida. This beautiful homesite offers the perfect canvas for a custom home surrounded by the character, tranquility, and small-town elegance that Oakland is known for. Ideally positioned near the scenic West Orange Trail, residents enjoy easy access to miles of biking and walking trails, picturesque natural surroundings, and a vibrant outdoor lifestyle. The property is also just minutes from the historic charm, dining, and boutique shopping of nearby Winter Garden, Florida. With convenient access to major roadways including Florida State Road 50 and Florida's Turnpike, commuting to the greater Orlando, Florida area, world-class attractions, shopping, and dining is effortless. As a courtesy to the Buyer(s) Seller is providing copy of the Survey to the Buyer(S). The survey is for informational purposes only. It is not current and may not reflect recent changes. Buyer(s) is responsible for verifying all property boundaries and obtaining an updated survey if required. Buyer(s) may have a discount showing this courtesy survey to the company Buyer(s) choose to get an update survey,

Oakland Town SubDv. ⋅ 34760 Zip Code

An exceptional opportunity to build your dream residence in the charming and highly desirable Town of Oakland, Florida. This beautiful homesite offers the perfect canvas for a custom home surrounded by the character, tranquility, and small-town elegance that Oakland is known for. Ideally positioned near the scenic West Orange Trail, residents enjoy easy access to miles of biking and walking trails, picturesque natural surroundings, and a vibrant outdoor lifestyle. The property is also just minutes from the historic charm, dining, and boutique shopping of nearby Winter Garden, Florida. With convenient access to major roadways including Florida State Road 50 and Florida's Turnpike, commuting to the greater Orlando, Florida area, world-class attractions, shopping, and dining is effortless. As a courtesy to the Buyer(s) Seller is providing copy of the Survey to the Buyer(S). The survey is for informational purposes only. It is not current and may not reflect recent changes. Buyer(s) is responsible for verifying all property boundaries and obtaining an updated survey if required. Buyer(s) may have a discount showing this courtesy survey to the company Buyer(s) choose to get an update survey,

406 W Herriott Avenue, Oakland

$360,000

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!

507 W Oakland Avenue, Oakland

$57,000

If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

Oakland Town SubDv. ⋅ 34760 Zip Code

If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

121 S Nixon Street, Oakland

$375,000

Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home. Set in the illustrious community of The Grove, Lot 41 is a generously sized corner lot ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal location. Access to modern amenities, including walking trails, parks, and recreational areas. Close proximity to top-rated schools, shopping, dining, and entertainment. Easy access to major highways, ensuring seamless connectivity to Orlando and surrounding areas. This homesite is your chance to become part of a vibrant and growing community while enjoying the privacy and comfort of a custom-built home tailored to your lifestyle. Don’t miss this opportunity to secure your spot in one of Oakland’s most desirable locations.

The Grove SubDv. ⋅ 34760 Zip Code

Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home. Set in the illustrious community of The Grove, Lot 41 is a generously sized corner lot ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal location. Access to modern amenities, including walking trails, parks, and recreational areas. Close proximity to top-rated schools, shopping, dining, and entertainment. Easy access to major highways, ensuring seamless connectivity to Orlando and surrounding areas. This homesite is your chance to become part of a vibrant and growing community while enjoying the privacy and comfort of a custom-built home tailored to your lifestyle. Don’t miss this opportunity to secure your spot in one of Oakland’s most desirable locations.

1225 Water Maple Drive, Oakland

$390,000

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 front porch, you are captivated by the spacious living room with vaulted ceilings and Hardwood flooring with a stunning Brick wood burning fireplace. The primary bedroom and the other 2 bedrooms all have hardwood flooring as well. The kitchen is appointed with lots of counter space and natural sunlight overlooking the backyard. For added convenience, the dining area is just off the kitchen. NO HOA>>>>Oaklands quaint town is a stones throw away from Bustling Winter Garden, Clermont, and Disney can be found within 25-30 mins drive. Convenient to all major Arteries & shopping too. Schedule your private showing today and experience the beauty of this "one of a kind" home.

3 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

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 front porch, you are captivated by the spacious living room with vaulted ceilings and Hardwood flooring with a stunning Brick wood burning fireplace. The primary bedroom and the other 2 bedrooms all have hardwood flooring as well. The kitchen is appointed with lots of counter space and natural sunlight overlooking the backyard. For added convenience, the dining area is just off the kitchen. NO HOA>>>>Oaklands quaint town is a stones throw away from Bustling Winter Garden, Clermont, and Disney can be found within 25-30 mins drive. Convenient to all major Arteries & shopping too. Schedule your private showing today and experience the beauty of this "one of a kind" home.

121 W Oakland Avenue, Oakland

$480,000

Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs + half kitchen upstairs — possibilities of in-law suite, rental potential, or multi-generational living - 14' x 12' elevated deck / covered patio — outdoor entertaining or private oasis - Optional furnished sale for a move-in ready experience - 10' gate to access backyard— boat, RV, or trailer storage - 18' x 22' carport as well as 12' x 30' gravel lot offers ample parking - Roof estimates available—opportunity for buyers to personalize or negotiate Outdoor Appeal: A spacious backyard offers room to expand patios, garden, or build additional outdoor amenities. The elevated deck and gated access make it both functional and private—perfect for Florida living. Location: Enjoy small-town charm with easy access to major highways, schools, parks, and the community of Oakland. Zoned for top-rated schools and close to everything Central Florida has to. Don't miss your chance to own this energy-efficient, flexible-use property in a sought-after location.

4 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs + half kitchen upstairs — possibilities of in-law suite, rental potential, or multi-generational living - 14' x 12' elevated deck / covered patio — outdoor entertaining or private oasis - Optional furnished sale for a move-in ready experience - 10' gate to access backyard— boat, RV, or trailer storage - 18' x 22' carport as well as 12' x 30' gravel lot offers ample parking - Roof estimates available—opportunity for buyers to personalize or negotiate Outdoor Appeal: A spacious backyard offers room to expand patios, garden, or build additional outdoor amenities. The elevated deck and gated access make it both functional and private—perfect for Florida living. Location: Enjoy small-town charm with easy access to major highways, schools, parks, and the community of Oakland. Zoned for top-rated schools and close to everything Central Florida has to. Don't miss your chance to own this energy-efficient, flexible-use property in a sought-after location.

312 W Hull Avenue, Oakland

$450,000

Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

310 E Gulley Avenue, Oakland

$367,500

One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed living space and NO HOA restrictions! You’ll fall in love with the bright, clean, and welcoming feel throughout with brand-new flooring and fresh interior paint. The heart of the home is the completely renovated chef’s kitchen, featuring all-new cabinets, sleek countertops, and modern appliances—perfect for anyone who loves to cook or entertain. Enjoy the flexibility of a main-level bedroom and full bathroom, ideal for guests, multigenerational living, or a private home office. Upstairs, you’ll find two additional bedrooms and another full bathroom, offering comfort and privacy for the whole family. Set on a peaceful, nature-filled corner lot with attached an garage plus plenty of parking Residents of the 34760 zip code enjoy the unique charm of mail pickup at the historic Oakland Post Office, where you’ll also find the latest issue of the Orange Observer and a quaint Little Free Library out front. Oakland also hosts a variety of beloved community events, including Heritage Day, Santa meet-and-greets, Easter egg drops, and weekly farmers markets in-front of the Heritage Center, an ever changing art gala. The town is a scenic rest stop along the West Orange Bike Trail and is home to numerous parks and landmarks. Speer Park features two playgrounds, tennis, pickleball, and basketball courts. The Jake Voss public fishing pier provides a peaceful spot for watching sunsets on Lake Apopka. Prairie House Coffee serves local coffee, baked goods, floral arrangements, and gifts inside a charming 1860s residence. Disney enthusiasts will love Recycling the Magic, which offers an eclectic shopping experience filled with Walt Disney World props, resort decor, and memorabilia. Just 3.5 blocks from the upcoming boutique district at 300 S. Tubb Street, this location offers walkability to a future hub of shopping, dining, and community spaces—modeled after Winter Garden’s beloved Plant Street. Nearby, luxury estate communities like Briley Farm and The Grove are bringing multi-million-dollar homes to Oakland, setting the stage for strong equity growth. This is your chance to own a move-in ready gem in Oakland at an affordable value!

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed living space and NO HOA restrictions! You’ll fall in love with the bright, clean, and welcoming feel throughout with brand-new flooring and fresh interior paint. The heart of the home is the completely renovated chef’s kitchen, featuring all-new cabinets, sleek countertops, and modern appliances—perfect for anyone who loves to cook or entertain. Enjoy the flexibility of a main-level bedroom and full bathroom, ideal for guests, multigenerational living, or a private home office. Upstairs, you’ll find two additional bedrooms and another full bathroom, offering comfort and privacy for the whole family. Set on a peaceful, nature-filled corner lot with attached an garage plus plenty of parking Residents of the 34760 zip code enjoy the unique charm of mail pickup at the historic Oakland Post Office, where you’ll also find the latest issue of the Orange Observer and a quaint Little Free Library out front. Oakland also hosts a variety of beloved community events, including Heritage Day, Santa meet-and-greets, Easter egg drops, and weekly farmers markets in-front of the Heritage Center, an ever changing art gala. The town is a scenic rest stop along the West Orange Bike Trail and is home to numerous parks and landmarks. Speer Park features two playgrounds, tennis, pickleball, and basketball courts. The Jake Voss public fishing pier provides a peaceful spot for watching sunsets on Lake Apopka. Prairie House Coffee serves local coffee, baked goods, floral arrangements, and gifts inside a charming 1860s residence. Disney enthusiasts will love Recycling the Magic, which offers an eclectic shopping experience filled with Walt Disney World props, resort decor, and memorabilia. Just 3.5 blocks from the upcoming boutique district at 300 S. Tubb Street, this location offers walkability to a future hub of shopping, dining, and community spaces—modeled after Winter Garden’s beloved Plant Street. Nearby, luxury estate communities like Briley Farm and The Grove are bringing multi-million-dollar homes to Oakland, setting the stage for strong equity growth. This is your chance to own a move-in ready gem in Oakland at an affordable value!

500 W Oakland Avenue, Oakland

$604,000

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 minutes from the West Orange Trail and the scenic beauty of Lake Apopka, this unique property is perfect for those who appreciate the warmth and personality of a home with history. This mid-century home residence showcases many of its original features—from the striking parquet style ceiling in the living room along with the built-in shelving, to the exposed beams in the dining room, this home is inviting and full of character. The home’s thoughtful layout includes the spacious in-law suite that includes a private entrance and an ADA accessible bathroom, prime for multigenerational living, hosting guests, or creating a private work-from-home retreat. Step inside and discover generously sized bedrooms and a living space that flows effortlessly through the dining space overlooking your outdoor oasis. Step out onto the vaulted ceiling, screened-in lanai that overlooks a spacious backyard—perfect for relaxing evenings, lively gatherings, or enjoying Oakland’s peaceful atmosphere. Whether you’re looking for a forever home with vintage charm or an opportunity to personalize a home with great bones, this is your canvas. Don't miss your chance to own a piece of Oakland's history! Schedule your private showing today and experience firsthand the character, comfort and community this home has to offer.

5 Beds ⋅ 3 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

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 minutes from the West Orange Trail and the scenic beauty of Lake Apopka, this unique property is perfect for those who appreciate the warmth and personality of a home with history. This mid-century home residence showcases many of its original features—from the striking parquet style ceiling in the living room along with the built-in shelving, to the exposed beams in the dining room, this home is inviting and full of character. The home’s thoughtful layout includes the spacious in-law suite that includes a private entrance and an ADA accessible bathroom, prime for multigenerational living, hosting guests, or creating a private work-from-home retreat. Step inside and discover generously sized bedrooms and a living space that flows effortlessly through the dining space overlooking your outdoor oasis. Step out onto the vaulted ceiling, screened-in lanai that overlooks a spacious backyard—perfect for relaxing evenings, lively gatherings, or enjoying Oakland’s peaceful atmosphere. Whether you’re looking for a forever home with vintage charm or an opportunity to personalize a home with great bones, this is your canvas. Don't miss your chance to own a piece of Oakland's history! Schedule your private showing today and experience firsthand the character, comfort and community this home has to offer.

410 E Gulley Avenue, Oakland

$285,000

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.

3 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

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.

527 W Herriott Avenue, Oakland

$600,000

This home has been beautifully remodeled with a warm, cozy mid-century modern feel. This 3 bedroom, 2 bath home boasts many amazing upgrades including luxury vinyl flooring through out.You will find solid wood cabinets, solid surface countertops, and premium tile in both the Kitchen and the bathrooms. Modern light fixtures and plantation shutters add the perfect touch to this recently painted interior. The block exterior was refurbished with concrete siding and custom wood detail. A new garage was built this year keeping with the mid-century look. The pitched roof was designed for extra storage above the 2 car bay. Enjoy gazing at your own fruit trees in this quiet,quaint town from the covered front porch or the wrap around back deck with gazebo. This home sits on a .25 acre newly custom frenced lot and is close to the West Orange Trail. Oakland is a golf cart friendlytown with access to Winter Garden's Historical Downtown. This turn-key home is a must see for anyone looking for the charm of old Oakland.

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

This home has been beautifully remodeled with a warm, cozy mid-century modern feel. This 3 bedroom, 2 bath home boasts many amazing upgrades including luxury vinyl flooring through out.You will find solid wood cabinets, solid surface countertops, and premium tile in both the Kitchen and the bathrooms. Modern light fixtures and plantation shutters add the perfect touch to this recently painted interior. The block exterior was refurbished with concrete siding and custom wood detail. A new garage was built this year keeping with the mid-century look. The pitched roof was designed for extra storage above the 2 car bay. Enjoy gazing at your own fruit trees in this quiet,quaint town from the covered front porch or the wrap around back deck with gazebo. This home sits on a .25 acre newly custom frenced lot and is close to the West Orange Trail. Oakland is a golf cart friendlytown with access to Winter Garden's Historical Downtown. This turn-key home is a must see for anyone looking for the charm of old Oakland.

418 E Gulley Avenue, Oakland

$261,000

Welcome to this beautifully renovated 2-bedroom, 1-bathroom home at 412 W Herriot Ave, Oakland, FL. With 1,015 sq ft of modern living space, this home has been completely updated. As you enter, you'll notice the spacious open living area, perfect for gatherings and everyday living. The modern kitchen features new stainless steel appliances, elegant countertops, and custom cabinetry. Both bedrooms are comfortable with ample natural light and closet space. The stylish bathroom has been fully updated with modern fixtures, a chic vanity, and a luxurious tub/shower combo. This home also includes energy-efficient upgrades like new windows and a central air conditioning system, ensuring comfort and savings on energy costs. Situated in a quiet neighborhood, it's conveniently close to schools, parks, and shopping centers, with easy access to major highways.

2 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Welcome to this beautifully renovated 2-bedroom, 1-bathroom home at 412 W Herriot Ave, Oakland, FL. With 1,015 sq ft of modern living space, this home has been completely updated. As you enter, you'll notice the spacious open living area, perfect for gatherings and everyday living. The modern kitchen features new stainless steel appliances, elegant countertops, and custom cabinetry. Both bedrooms are comfortable with ample natural light and closet space. The stylish bathroom has been fully updated with modern fixtures, a chic vanity, and a luxurious tub/shower combo. This home also includes energy-efficient upgrades like new windows and a central air conditioning system, ensuring comfort and savings on energy costs. Situated in a quiet neighborhood, it's conveniently close to schools, parks, and shopping centers, with easy access to major highways.

412 W Herriott Avenue, Oakland

$575,000

Discover the charm of this custom-built home, completed in 2020, with no HOA! Situated just minutes from downtown Winter Garden, this stunning, four-year-old residence is ready to welcome you. Featuring 3 spacious bedrooms, 2.5 bathrooms, an office, and a generous loft, this home is thoughtfully designed with premium features throughout; including electrical plug in the front yard that can be used to charge Electric Vehicles! Step onto the expansive front porch and into the inviting entryway, showcasing a glass staircase railing, luxury vinyl flooring, and an open view of the main living area. To your immediate right, you'll find a half bath and an office with custom glass doors, perfect for use as a guest room, playroom, or TV room. The kitchen is a chef’s delight with a gas stove and an oversized island adorned with custom lighting. Adjacent to the kitchen is a mudroom leading to a large laundry room, and access to the side entry and extended driveway. The kitchen opens to a spacious family room that connects to the primary bedroom, featuring French doors to a private deck. The primary bathroom offers double sinks, a walk-in shower, and a custom closet with a barn door that is sure to impress. From the family room, large tandem sliding doors lead to an amazing outdoor space perfect for entertaining. The oversized patio, with wood wall and ceiling, is prepped for a summer kitchen and offers covered access to the garage and fenced-in long driveway. Upstairs, you'll find 2 additional large bedrooms and an oversized loft with a wood beam ceiling, along with a hookup for a stackable washer and dryer! Conveniently located near the turnpike and within close proximity to all that Winter Garden has to offer, such as Downtown Winter Garden and its famously known for Farmers Market, Winter Garden Trail, shopping, dining, and entertainment. In addition to great public schools, this home is also near the TOP rated Oakland Avenue Charter School while enjoying quick access to the 429, 408, and the Turnpike. This home has it all and a must-see! Don’t miss out on this exceptional opportunity and schedule your showing today!

3 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Discover the charm of this custom-built home, completed in 2020, with no HOA! Situated just minutes from downtown Winter Garden, this stunning, four-year-old residence is ready to welcome you. Featuring 3 spacious bedrooms, 2.5 bathrooms, an office, and a generous loft, this home is thoughtfully designed with premium features throughout; including electrical plug in the front yard that can be used to charge Electric Vehicles! Step onto the expansive front porch and into the inviting entryway, showcasing a glass staircase railing, luxury vinyl flooring, and an open view of the main living area. To your immediate right, you'll find a half bath and an office with custom glass doors, perfect for use as a guest room, playroom, or TV room. The kitchen is a chef’s delight with a gas stove and an oversized island adorned with custom lighting. Adjacent to the kitchen is a mudroom leading to a large laundry room, and access to the side entry and extended driveway. The kitchen opens to a spacious family room that connects to the primary bedroom, featuring French doors to a private deck. The primary bathroom offers double sinks, a walk-in shower, and a custom closet with a barn door that is sure to impress. From the family room, large tandem sliding doors lead to an amazing outdoor space perfect for entertaining. The oversized patio, with wood wall and ceiling, is prepped for a summer kitchen and offers covered access to the garage and fenced-in long driveway. Upstairs, you'll find 2 additional large bedrooms and an oversized loft with a wood beam ceiling, along with a hookup for a stackable washer and dryer! Conveniently located near the turnpike and within close proximity to all that Winter Garden has to offer, such as Downtown Winter Garden and its famously known for Farmers Market, Winter Garden Trail, shopping, dining, and entertainment. In addition to great public schools, this home is also near the TOP rated Oakland Avenue Charter School while enjoying quick access to the 429, 408, and the Turnpike. This home has it all and a must-see! Don’t miss out on this exceptional opportunity and schedule your showing today!

306 W Hull Avenue, Oakland

$255,000

Welcome to a promising canvas awaiting your personal touch! This 3 bedroom, 1.5-bathroom home presents a wonderful opportunity for those with a vision for transforming a space into their dream residence. In need of light rehab, this property allows you to infuse your unique style while creating a comfortable and personalized haven.

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Welcome to a promising canvas awaiting your personal touch! This 3 bedroom, 1.5-bathroom home presents a wonderful opportunity for those with a vision for transforming a space into their dream residence. In need of light rehab, this property allows you to infuse your unique style while creating a comfortable and personalized haven.

411 W Hull Avenue, Oakland

$535,000

Welcome to this like-new home in the intimate community of Hull Island. This split floorplan 3 bedroom 2 bathroom home has been lovingly updated. As you step inside through the foyer, you are drawn to the two well-appointed secondary bedrooms, sharing a stylishly designed hall bath at the front of the house. Beautiful wood-look tile spreads throughout the home - no carpet here! The L-shaped kitchen is a culinary enthusiast's dream, featuring an abundance of 42” maple cabinets crowned with modern LED under-cabinet lighting that accentuates the backsplash, and luxurious quartz countertops. Not to mention a gas range! The island provides not only a quick spot for on-the-go meals but also a spacious prep area for the family chef. The generously sized walk-in pantry is your ideal companion for all of those bulk shopping trips. Adjacent to the kitchen, a tech-savvy desk area serves as a versatile hub for sorting mail, charging devices, or exploring your next Pinterest-worthy recipe. The primary suite, tucked away for privacy at the rear of the home, is bathed in natural light through its expansive windows and features an elegant tray ceiling. The deluxe ensuite bath is a sanctuary of comfort, showcasing a dual-sink quartz-topped vanity, an oversized shower adorned with upgraded subway tile and a river rock floor, a semi-frameless enclosure, an enclosed water closet, and a spacious walk-in closet. Step out onto the covered lanai and enjoy the privacy of a fenced-in backyard. Other upgrades include an interior laundry room with a utility sink, blinds on all windows, a tankless gas hot water heater, and an additional pavered area in the backyard. All appliances convey, making this a truly move-in ready home! Hull Island offers a community pool with a cabana area, a bark park, picnic trails, and a viewing dock off of Lake Apopka. Minutes away from downtown Winter Garden, the Florida Turnpike, and walking distance to the West Orange Trail. Schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34760 Zip Code

Welcome to this like-new home in the intimate community of Hull Island. This split floorplan 3 bedroom 2 bathroom home has been lovingly updated. As you step inside through the foyer, you are drawn to the two well-appointed secondary bedrooms, sharing a stylishly designed hall bath at the front of the house. Beautiful wood-look tile spreads throughout the home - no carpet here! The L-shaped kitchen is a culinary enthusiast's dream, featuring an abundance of 42” maple cabinets crowned with modern LED under-cabinet lighting that accentuates the backsplash, and luxurious quartz countertops. Not to mention a gas range! The island provides not only a quick spot for on-the-go meals but also a spacious prep area for the family chef. The generously sized walk-in pantry is your ideal companion for all of those bulk shopping trips. Adjacent to the kitchen, a tech-savvy desk area serves as a versatile hub for sorting mail, charging devices, or exploring your next Pinterest-worthy recipe. The primary suite, tucked away for privacy at the rear of the home, is bathed in natural light through its expansive windows and features an elegant tray ceiling. The deluxe ensuite bath is a sanctuary of comfort, showcasing a dual-sink quartz-topped vanity, an oversized shower adorned with upgraded subway tile and a river rock floor, a semi-frameless enclosure, an enclosed water closet, and a spacious walk-in closet. Step out onto the covered lanai and enjoy the privacy of a fenced-in backyard. Other upgrades include an interior laundry room with a utility sink, blinds on all windows, a tankless gas hot water heater, and an additional pavered area in the backyard. All appliances convey, making this a truly move-in ready home! Hull Island offers a community pool with a cabana area, a bark park, picnic trails, and a viewing dock off of Lake Apopka. Minutes away from downtown Winter Garden, the Florida Turnpike, and walking distance to the West Orange Trail. Schedule your showing today!

1808 Western Trailway Drive, Oakland

$309,000

If you are looking for a great starter home, or even a great investment property at an excellent price, in a great location, then look no further! This charming home is located on a corner lot in beautiful Oakland, Florida. The home offers an open floor plan that flows seamlessly from the kitchen to the great room. The kitchen features wood cabinets, laminate countertops, and stainless steel appliances with an adjacent laundry room. There are fans in the bedrooms for extra comfort. The flooring in the home is laminate and ceramic throughout. This property is located just two miles from downtown Winter Garden which offers a variety of shopping, restaurants, breweries and more! The home is located just 2 blocks from the West Orange Trail, half a mile to Lake Apopka access/dock, and 1 mile to the Oakland Nature Preserve! This location also boasts quick access to major roads such as the 429, Florida Turnpike and the 408, making for an easy commute and travel to Orlando and all of Central Florida.

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

If you are looking for a great starter home, or even a great investment property at an excellent price, in a great location, then look no further! This charming home is located on a corner lot in beautiful Oakland, Florida. The home offers an open floor plan that flows seamlessly from the kitchen to the great room. The kitchen features wood cabinets, laminate countertops, and stainless steel appliances with an adjacent laundry room. There are fans in the bedrooms for extra comfort. The flooring in the home is laminate and ceramic throughout. This property is located just two miles from downtown Winter Garden which offers a variety of shopping, restaurants, breweries and more! The home is located just 2 blocks from the West Orange Trail, half a mile to Lake Apopka access/dock, and 1 mile to the Oakland Nature Preserve! This location also boasts quick access to major roads such as the 429, Florida Turnpike and the 408, making for an easy commute and travel to Orlando and all of Central Florida.

500 W Oakland Avenue, Oakland

$305,000

Welcome to your dream home in the charming community of Oakland, FL! This 2-bedroom, 2-bathroom cottage is a haven of modern comfort, with a newer roof, HVAC, and water heater all installed in 2020. Nestled on a generous, fenced lot, this property offers the perfect backdrop for outdoor gatherings or serene solitude. Step inside to discover a cozy, open floor plan and tastefully updated bathrooms and kitchen that make everyday living a breeze. Conveniently located, you're just minutes away from Oakland's quaint parks, local shopping, and delightful dining options. This home is more than just a place to live—it's a lifestyle.

2 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Welcome to your dream home in the charming community of Oakland, FL! This 2-bedroom, 2-bathroom cottage is a haven of modern comfort, with a newer roof, HVAC, and water heater all installed in 2020. Nestled on a generous, fenced lot, this property offers the perfect backdrop for outdoor gatherings or serene solitude. Step inside to discover a cozy, open floor plan and tastefully updated bathrooms and kitchen that make everyday living a breeze. Conveniently located, you're just minutes away from Oakland's quaint parks, local shopping, and delightful dining options. This home is more than just a place to live—it's a lifestyle.

210 S Pollard Street, Oakland

$65,000

PRICE IMPROVEMENT!! Don't let this amazing opportunity pass you by! Your chance to build a dream house on this quiet and very desirable lot in the town of Oakland. Walking distance to playgrounds, park and picnic areas.

Oakland Town SubDv. ⋅ 34760 Zip Code

PRICE IMPROVEMENT!! Don't let this amazing opportunity pass you by! Your chance to build a dream house on this quiet and very desirable lot in the town of Oakland. Walking distance to playgrounds, park and picnic areas.

528 W Hull Avenue, Oakland