34760 Zip Code FL Real Estate, Homes with No HOA Fee for Sale

521 W Herriott Avenue, Oakland

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

Virtually Staged. Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and timeless appeal. Surrounded by mature landscaping and stately oak trees, this property offers a serene escape with no HOA to limit your creativity. Quiet dirt roads wind through the neighborhood, adding a touch of rural nostalgia, while the vibrant shops and cafes of Oakland’s quaint downtown are just a short stroll away. Inside, the home welcomes you with a warm and inviting layout. The living room, filled with natural light, provides a cozy space for relaxing or entertaining. It connects seamlessly to a well-appointed kitchen, featuring stainless steel appliances, granite countertops, and plenty of cabinetry for storage—ideal for home-cooked meals. The primary bedroom offers a peaceful retreat with a standard closet and an en-suite bathroom boasting dual vanities and a luxurious soaking tub. Two additional bedrooms, each with standard closets, provide versatile space for family, guests, or a home office, with a second full bathroom conveniently nearby. The exterior is a true highlight, with mature landscaping creating a private, tranquil setting. Towering oak trees provide shade and beauty, complemented by colorful, well-kept gardens. The spacious backyard is perfect for barbecues, gardening, or simply soaking in the calm of your own oasis. A charming front porch invites you to enjoy morning coffee while greeting neighbors on the peaceful dirt road. Located in the heart of Oakland, this home blends small-town charm with modern convenience. Enjoy local events, dining, and community spirit just steps away, with easy access to highways for commuting. With no HOA, you have the freedom to make this property your own.

409 E Gulley Avenue, Oakland

$1,125,000

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

SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, Oakland

$629,999

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

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

38 S Pollard Street, Oakland

$683,000

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

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

$395,000

34760 Zip Code

Sold Data Entry.

329 E Gulley Avenue, Oakland

$395,000

Oakland Heights SubDv. ⋅ 34760 Zip Code

Looking for the best little town near Orlando? Oakland has so much character and charm. New construction in all around up to 4M. You now have the chance to build your custom dream home.

321 E Gulley Avenue, Oakland

$1,250,000

6 Beds ⋅ 8 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code

PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

620 N Tubb Street, Oakland

$360,000

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

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

$450,000

Town/Oakland SubDv. ⋅ 34760 Zip Code

Discover this rare 0.31-acre residential lot in the heart of Oakland, one of the most charming and fastest-growing towns in Central Florida. Tucked just a few blocks from downtown Oakland, you’ll find yourself surrounded by the area’s signature tree-lined unpaved and stone roads, giving the neighborhood a warm, small-town character that’s hard to find today. Oakland continues to grow with new, luxurious communities, yet opportunities like this, a vacant lot with no HOA in the downtown core, are truly uncommon. From here, you’re just minutes to Plant Street in downtown Winter Garden, with its award-winning restaurants, local shops, and vibrant events, while still enjoying the peaceful lakeside setting Oakland is known for along the shores of Lake Apopka, one of Florida’s largest lakes. This property blends charm, convenience, and location, an ideal setting to build your dream home in a community that feels both timeless and connected.

N Daniels Street, Oakland

$390,000

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

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

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

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

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

$410,000

Town/Oakland SubDv. ⋅ 34760 Zip Code

Discover this RARE 0.31-acre residential lot located in the charming town of Oakland, one of the most desirable and rapidly appreciating areas in West Central Florida. Just a few blocks from Oakland’s historic downtown, this property is set on picturesque unpaved and stone roads, adding a unique character and peaceful atmosphere to the neighborhood. Oakland is known for its warm community feel, seasonal events, and its privileged location along the shores of Lake Apopka, one of Florida’s largest lakes. Additionally, it borders the sought-after area of Winter Garden, renowned for its vibrant historic downtown, local restaurants, excellent infrastructure, and appeal as a top destination for Central Florida residents. This lot offers the perfect blend of serenity and convenience, ideal for building your dream home in a location that combines nature, culture, and close access to everything you need. Bonus: The seller already has a custom home project available, featuring 4 bedroom suites, 6 bathrooms, 2 offices, a den, and a bonus room. The planned layout includes 3,850 sqft of air-conditioned space and a total construction area of 5,024 sqft, offering a spacious and well-designed floor plan ready to be brought to life.

N Daniels Street, Oakland

$795,000

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

Experience the charm of Oakland living in this beautifully updated custom built home located in the heart of town—just minutes to Downtown Winter Garden, Plant Street Market, the West Orange Trail, the Lake Apopka boat ramp/dock and so much more! This move-in ready home is situated on a .27-acre corner lot with no HOA. When entering this 4-bedroom, 3-bathroom home, you’re welcomed by a spacious front patio, beautiful foyer and open floor plan, perfect for entertaining. The flex space to the left of the front entryway offers a great space for an office, secondary dining area or den. The living room overlooks the breathtaking kitchen and exterior screened in patio with beautiful views of the private backyard. The downstairs bedroom and full bath offer flexibility, while the spacious upstairs includes a stunning primary suite with dual closets, and an en suite bath. There are two additional bedrooms upstairs with a shared Jack and Jill bathroom, as well as, a large laundry room with a stackable washer & dryer, sink and plenty of cabinet and countertop space. This home boasts countless updates throughout, including, but not limited to, New Taj Mahal quartzite countertops + backsplash (2024), brand new kitchen sink, hardware and faucet (2024), High end appliances and a brand new gas stove (2025) perfect for the chef at heart! The office features new custom built-in shelving (2024), and the entire interior has been freshly painted (2024). Stylish new fixtures, mirrors, and an updated fireplace façade add to the elegant aesthetic (2024). Move in stress free with upgrades such as a Newer Metal Roof (2022), Shingle Roof (2014), consistent servicing of the HVAC system, Double-Pane Windows throughout and new Plumbing & Electric (2014). Enjoy Florida living in your gorgeous backyard oasis—complete with new sod (2024), lush landscaping, a paver patio, hot tub, and a spacious screen-enclosed brick paver patio with an outdoor kitchen area. This home is truly turn-key and perfectly positioned for nature lovers, golf cart enthusiasts and downtown living alike. Don’t miss this rare opportunity to own this wonderful home in the sought-after Oakland neighborhood—schedule your private showing today!

101 W Oakland Avenue, Oakland

$530,000

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

DOUBLE LOT .55 - GREAT LOCATION!- NO HOA - GOLF CART FRIENDLY COMMUNITY - ACCESS TO WINTER GARDEN'S HISTORICAL DOWNTOWN - CLOSE TO WEST ORANGE TRAIL - Spacious 3 Bedroom 1 Bathroom home. Open Concept Living with High Ceilings - Wood Floors - Plenty of Natural Light - Oversized Lot Offering Ample Room to Expand or Build New. Large Storage Shed - Newer Roof and A/C - Take Advantage of this Rare Opportunity to Make This Property Your Own in the Charming Community of Oakland. Call Today for a Private Showing!!

321 E Gulley Avenue, Oakland

$571,000

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

Located in the heart of Downtown Oakland, this well-built and meticulously maintained CBS construction ranch house offers a perfect blend of comfort, style, and convenience. Located on a spacious corner lot, under heritage oak trees, the home features an open and airy split floor plan with high ceilings and sky lights, creating a bright and inviting atmosphere. With numerous updates and renovations, to its roof, double pane, windows, wood flooring, fully renovated kitchen and primary bathroom with steam shower, PVC shutters, fresh interior, and exterior paint, HVAC system and more, ensure a move-in-ready experience. Living in Oakland is like stepping back in time to a more relaxed Florida lifestyle, where canopy tree-lined streets, historic charm, and a strong sense of community create a peaceful setting to call home. Just a short walk to the Lake Apopka pier and one block from the West Orange Trail, along with the Oakland Nature Preserve, .8 miles away, it offers endless outdoor activities. Plus, it’s only minutes from Historic Downtown Winter Garden, Oakland’s sister city, known as the area’s hub for entertainment, dining, shopping, the famed farmers market, a local brewery, and a thriving business district. This prime location catty-corner from Oakland's Speer Park, with tennis, pickle ball and BB courts and playground, this home is a rare find, offering both small-town charm and modern conveniences nearby!

201 Briley Avenue, Oakland

$85,000

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

**8MULTIPLE OFFERS***The asset manager has requested a 'HIGHEST AND BEST' response from the outstanding buyer(s) for the following property: 537 WEST HERRIOTT AVENUE, OAKLAND, FL 34760 BY 3:00 PM October 2,2024*** Quarter of an acre ,end of the street lot close to Downtown Winter Garden walking distance to the neighborhood Park . There is a structure in the lot that might need removal to build your dream home here. ***No access to the structure***

537 W Herriott Avenue, Oakland

$285,000

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

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

$570,000

5 Beds ⋅ 5 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Looking for a bit of Oakland History - NOW available 525 N Tubb! Property includes the main house, an apartment and a workshop. The house is a 3500 square foot home with three bedrooms, three baths, powder bathroom, large kitchen, large living room, dining room and much more. There are ten-foot ceilings throughout, and all appliances remain. Attached to the main house is a screened breeze way, a two-car garage, a 1300 square foot workshop and storage room. An amazing feature of this house is a 629 square foot apartment with a two-car carport and deck. This attached area can be a rental or an in-law suite. This circa 100-year-old home sits on 3/4 acre filled with various fruit and flowering trees and shrubs and giant oaks. The wiring, plumbing has been updated and the roof replaced in March of 2020.

525 N Tubb Street, Oakland

$365,000

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

One or more photo(s) has been virtually staged. Welcome to beautiful 524 W Oakland, a charming updated home nestled in the heart of Oakland, FL! You'll be delighted by this 3-bedroom, 1.5-bathroom home on an OVERSIZED PRIVATE Lot that is perfectly positioned just minutes from the vibrant Historic Downtown Winter Garden and along the scenic W Orange Trail, where you have immediate access to the Oakland Nature Preserve, Lake Apopka & more! This location is one of a kind! Inside you will discover a fresh and inviting interior featuring new flooring and windows throughout. The open living area is ideal for both relaxation and entertaining. The spacious primary bedroom boasts a walk-in closet for your convenience and En-Suite Bath. A large bonus room off the kitchen offers endless possibilities—perfect as a family room, home office, or bedroom. Additional highlights include an inside laundry area and an oversized corner lot that provides ample space for outdoor enjoyment and potential expansion. Don’t miss your chance to own this lovely home in a serene yet conveniently located neighborhood just 30 minutes from the Airport & 30 minutes from Disney! Schedule a showing today!

524 W Oakland Avenue, Oakland

$575,000

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

Welcome home to the charming historic district of downtown Oakland. This beautiful .4304 Acre single family home sits directly across from Speer Park, .3 miles (2.5 blocks) away from the quaint and charming downtown Oakland, the West Orange Trail connection, and the Healthy West Orange Arts and Heritage Center at the town of Oakland. The Oakland Farmers Market is held every 2nd Thursday. Speer park offers, tennis courts, basketball, pickleball, playgrounds, a pavilion with picnic tables, and charming gazebo anchoring at the center. The public Tubb Street Fishing peer overlooking Lake Apopka is just .3 miles away. The property is approved to subdivide into 3 lots, per the town of Oakland. The area is now also open to the golf cart district to the historic downtown Winter Garden. This home features, 1320 SF, 1 story, block construction, above ground pool, fruit trees, a shed and RV hookups.

20 W Vick Ave, Oakland

$261,000

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

$700,000

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

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 Cart District. Under the majestic canopy oak trees, this 2,282 sqft home offers the perfect Florida lifestyle with a great sense of community with NO HOA. Just a few blocks away from the West Orange Trail, Lake Apopka's dock, pickleball courts, and Spear Park, outdoor activities are right at your doorstep. Inside, the open and spacious layout, this well-designed floor plan features a cozy living room, a dedicated office space, and a kitchen perfect for large gatherings. One of the home's UNIQUE FEATURES is the above the garage GUEST SUITE. Complete with its own private bathroom, kitchenette, washer and dryer, and a separate entrance. Perfect for guests, in-laws, private workspace or man cave! Oakland’s downtown area retains its historical charm with preserved buildings and a community-centric layout. The town has a rich history from the late 19th century and maintains its small-town feel. Nearby, the Oakland Nature Preserve offers walking trails, educational programs, and lovely views of Lake Apopka. Hop on your golf cart and you’re minutes away from Historic Downtown Winter Garden, full of restaurants, shops, an award-winning farmers market, and tons of family activities. This home is also conveniently located just minutes away from the Turnpike and SR 429 for easy access to Downtown Orlando and Disney World. Don’t miss out on this awesome opportunity to own a piece of paradise in a prime location. Schedule your private showing today and see for yourself!

305 Briley Ave, Oakland

$730,000

5 Beds ⋅ 4 Baths ⋅ Starr Gardens Oakland SubDv. ⋅ 34760 Zip Code

Escape to your own private oasis in this stunning pool home nestled in sought after GOLF CART COMMUNITY in Oakland FL between Clermont and Winter Garden! This property boasts, not only a beautiful main house, but also a detached guest house, AND a detached office/mancave.NO HOA is a BIG PLUS. Immediately you'll be charmed by the mature landscaping and inviting front porch. Inside, the fully renovated kitchen in 2022 cabinets, upgraded appliances, subway tile backsplash, and oversized walk-in pantry is a chef's dream. The open-concept layout allows natural light to flow throughout the spacious living areas, creating a perfect atmosphere for entertaining. The split floor plan offers ultimate privacy for the master suite, complete with a massive walk-in closet and a luxurious bathroom.The elegant French doors in the master bedroom add a touch of sophistication and allows you to step outside to your sparkling screened-in pool with a block wall surround, perfect for enjoying the Florida sunshine. A convenient poolside bathroom means guests won't need to enter the main house. The detached guest house is a dream come true for visitor or In-Laws. It features a full kitchen with granite countertops, a great room, a dining area, and a flexible room that can be used as a bedroom or office. Upstairs, a spacious bedroom with a full bathroom and laundry hookups provides a peaceful retreat. This meticulously maintained property boasts an extensive list of recent upgrades, ensuring you can move right in and start living your Florida dream. There is also a THIRD STRUCTURE! This one room building could be your dream office, She-shed or man cave! Upgrades include new AC units, new flooring throughout, fresh interior and exterior paint, a French drain, pool resurfacing, new stoves in both the main house and guest house, upgraded insulation, new landscaping, a privacy fence, a new waterfall pump for the pool, new fans and light fixtures, and even a treehouse for all ages! BUT WAIT, there's more! This incredible property also features a solar system with a transferable lease, so you can enjoy significant energy savings on top of your veteran tax savings the owner has for the year. BONUS: RIDING MOWER INCLUDED IN THE SALE! Don't miss this incredible opportunity – schedule your private tour today!

410 E Henschen Avenue, Oakland

$575,000

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

$652,000

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

****MULTIPLE OFFERS....HIGHEST & BEST BY 5/6/2024 BY 2PM**** Welcome to this beautifully renovated 4-bedroom, 2-full bath home located at 200 Mather Smith Dr in the charming town of Oakland, Florida with NO HOA!! This stunning property has been completely transformed and boasts exquisite upgrades throughout. As you step inside, you'll be greeted by the spacious and open floor plan that seamlessly connects the living, dining, and kitchen areas. The tastefully designed kitchen features modern stainless-steel appliances, custom cabinetry, sleek countertops, and ample storage space, making it a chef's dream. The four bedrooms are generously sized and offer plenty of natural light, creating a serene and inviting atmosphere. The bathrooms have been meticulously upgraded with stylish fixtures and finishes, providing a spa-like experience. The huge backyard includes a large patio that is perfect for entertaining friends & family and a shed with shelving for plenty of storage. The 2-car garage has new paint, epoxy floor, and wooden storage shelves. This home is the perfect location for outdoor enthusiasts and those seeking the vibrant downtown Oakland experience & events. Situated just steps away from the West Orange Trail, you'll have easy access to miles of scenic biking, walking, and jogging paths in addition you will be walkable to Oakland Avenue Charter School Golf cart path to Downtown Winter Garden where you can explore the vibrant shops, boutiques, and restaurants, or take part in the various community events and festivals held throughout the year. Schedule a showing today and envision yourself living in this renovated gem!

200 Mather Smith Drive, Oakland

$1,696,482

5 Beds ⋅ 5 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Custom Home Sold Off Market.

21 Daniels Street, Oakland

$725,000

4 Beds ⋅ 4 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code

Discover the charm of this 4-bedroom, 3.5-bathroom single-family home in Oakland, Florida, boasting 2836 sq ft and a 2-car attached garage with NO HOA. Recently painted inside and out, this beautiful home features a new roof and numerous elegant updates throughout. Inside, an open floor plan includes a formal dining room (or office space) and breakfast nook, with the master suite conveniently located on the 1st floor, featuring a bath with double vanities and a walk-in shower. Two additional bedrooms, a full bathroom, and a half bathroom for guests are also on the 1st floor, while the 2nd floor offers a versatile bonus room suitable for various needs, along with the fourth bedroom and third full bathroom. Enjoy outdoor relaxation on the screened back porch. Located in the Golf Cart District just minutes from Historic Downtown Winter Garden, hop in your golf cart and enjoy local restaurants, shops, and a weekly farmers market with ease. Enjoy a morning or evening walk or run on the West Orange Trail located just a block away, or stroll down to Historic Downtown Oakland, where you can enjoy a large community park and playground, have a scoop of ice cream and other treats from Oakland General, see the seasonal community art at the Healthy West Orange Arts and Heritage Center, take in stunning Lake Apopka views at the nearby pier, or partake in the numerous community events put on by this charming small town, including holiday events, block parties, and local farmers’ markets. Don't forget to enjoy Florida's natural beauty at the Oakland Nature Preserve. Take advantage of the proximity to desirable schools, including Oakland Charter School and the international magnet program at Tildenville Elementary. This home is nestled among the historic oak trees of Oakland but conveniently located just minutes away from the Turnpike and SR 429 for easy access to Downtown Orlando and Disney World. Don't miss out on the opportunity to make this home your own—schedule a showing today!

206 Mather Smith Drive, Oakland

$842,500

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

Oh, what an amazing area Oakland is!! Even more amazing is this three-bedroom home with two and half baths featuring a massive 25x15 loft over garage. New Fresh Look the owners gave it, now we are up to new build standards and beyond. Impressive dental crown in the living areas. With the Recently completed Kitchen Renovation, walls were removed to open the floor plan to give you a spacious feel. Kitchen features a Wolf induction stove with a commercial grade hood with lights and a multitude of fan speeds. Z-Line dishwasher cabinet front. KitchenAid refrigerator, Huge farm sink sits in the middle of the quartz island that has additional deep cabinets below so you won’t need a ladder to get whatever it is you have stored. Over the Top quiet close cabinets deep for all your pots and pans with the coolest hardware for handles. All adorned with quartz backsplash. Two huge pantries that have pull out drawers and fully equipped with electricity for those appliances you want out of sight. French doors lead out back to a tropical paradise. With its lush landscaping you wouldn’t know you had neighbors. Just installed motorized awnings to prolong your days out back enjoying the pool area. Enjoy yearlong soaking in the upgraded led lights and heated pool. Your days will be perfect for recreation and relaxation. After your morning walk or run on the West Orange trail. You won’t be able to contain yourself thinking of the COMPLETE PRIVACY your Lot offers. When you get back to take a dip in your private oasis pool. Let's don’t forget to mention your magical side entrance. Stroll through the courtyard with pavers, fenced in along with beautiful hedges surrounding its perimeter giving the privacy desired. A second outdoor getaway location to be enjoyed! The Oversized garage is Nestled amongst the majestic oaks of Downtown Oakland and Winter Garden. Beautifully appointed in one of Oakland’s most sought-after neighborhoods. This residence is strategically positioned in the highly desired Golf Cart District. Just jump on your golf cart and in minutes you are in Historic Downtown Winter Garden. Also enjoy preferred enrollment & walking distance to renowned Oakland Charter School. Nestled just a stone's throw away from the West Orange Trail, this property provides easy golf cart access to the vibrant Downtown Winter Garden, brimming with an array of restaurants, shops, a weekend farmers market, and an abundance of family activities. Enjoy 22.26 miles of paved Trail from the Orange/Lake County line, the town of Killarney and Oakland, the city of Winter Garden, across U.S. 441, through downtown Apopka to Welch Road. Stop and enjoy the butterfly garden at the Tildenville outpost!

207 Mather Smith Drive, Oakland

$730,000

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

This custom built home is on the market for the first time and is nestled in the heart of Oakland! Sitting on just under a half acre of land, this delightful property offers a perfect blend of comfort, style, and convenience, making it an ideal place to call home. As you enter this meticulously maintained residence you will be greeted by a spacious living area, perfect for relaxing or entertaining guests. The well-appointed kitchen features modern appliances, sleek stone countertops, and ample storage space, making meal preparation a breeze. This home boasts 4 bedrooms and 2 bathrooms split plan, providing plenty of space for the whole family. The master suite offers a peaceful retreat with a luxurious en-suite bathroom and a walk-in closet, ensuring privacy and comfort. Outside, you'll find a beautifully landscaped yard, ideal for enjoying the Florida sunshine and hosting outdoor gatherings with friends and family. The property also includes a 3-car garage with plenty of storage space and large driveway for your convenience. Located in the desirable Oakland area, this home offers easy access to Oakland Nature Preserve, The West Orange Trail, shopping and dining in nearby Downtown Winter Garden and is close to major roadways, making commuting a breeze. Schedule a showing to see your next home today.

112 W Sadler Avenue, Oakland

$255,000

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

$309,000

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

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

$769,000

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

Small town living in nature-filled Oakland. Bring your golf cart! No HOA!! This 2-story custom home proudly stands on a .27-acre corner lot, just 2 blocks to the 20+ mile West Orange Trail, half a mile to Lake Apopka access/dock, and 1 mile to Oakland Nature Preserve! On days you want a break from exploring Florida’s wild beauty, this magazine-worthy property can accommodate. The 4 bedroom, 3 bathroom floor plan keeps 1 bedroom/bathroom downstairs, while the upstairs holds the primary bedroom/bathroom with dual closets, and 2 secondary bedrooms with a shared bath. The open-concept gathering areas share a gas fireplace for cozy evenings, and the formal but versatile dining room can be transformed to meet any other living space needs. Outdoors, the fenced backyard offers a screen-enclosed porch with outdoor kitchen area, and beyond the screen is another patio area with firepit and 6-person spa, completely open to Florida’s night sky. Over $60K in upgrades have been completed within the past 2 years to ensure an elegant living experience inside and out. Bonus: The oversized garage has room for 2 cars and your golf cart, plus the attic has flooring for storage. This Oakland treasure is located less than a half mile to Speer Park for playground, picnics & tennis. Convenient roadways West Colonial Dr and FL Turnpike are nearby, both which can start your journey to wherever you may need to go. Two miles to downtown Winter Garden with shopping, restaurants, breweries and more! Schedule a showing today!

101 W Oakland Avenue, Oakland

$65,000

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

$410,000

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

Beautiful oversized corner lot in charming Oakland. Nice open floor plan. Workshop is in the Garage and offers tons of storage. There is no HOA, so bring your boats and RV's to this property that has plenty of room to park/store them. This house has been under renovation, so requires work including a new roof. However, the property offers many possibilities to suit your vision of a dream home.

202 W Oakland Avenue, Oakland

34760 Zip Code Real Estate & Homes with No HOA Fee

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