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$1,495,000
4 Beds ⋅ 4 Baths ⋅ O6440357 MLS
FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking in the peaceful surroundings and views of the West Orange Trail just beyond your front door. Step inside to soaring spaces, abundant natural light, and architectural details that immediately make an impression. A grand staircase leads to a striking bridge-style balcony overlooking the family room, while a beautiful brick gas-burning fireplace anchors the living space and creates a warm, inviting centerpiece for gathering and entertaining. Designed with both everyday living and flexibility in mind, the spacious floor plan features a formal dining room, dedicated office, bonus room, and enclosed sunroom offering even more space to relax and enjoy the Florida lifestyle year-round. A generously sized walk-in closet provides exceptional storage, while thoughtful features such as a central vacuum system add everyday convenience. Roof Replacement in 2025 and HVAC replacement in 2022 add peace of mind for years to come. Located within Oakland's golf cart district, this home offers extra garage space for your golf cart, bikes, and moreWhether you're enjoying coffee on the porch swing, relaxing beside the fireplace, or simply taking in the peaceful small-town atmosphere, this home offers a wonderful combination of space, character, and location in sought-after Oakland. Come experience the charm and lifestyle that make this community such a special place to call home!

137 Petris Avenue, Oakland

Listing courtesy of REGENCY REAL ESTATE LLC. 407-469-5021
$289,900
4 Beds ⋅ 2 Baths ⋅ 1678117 MLS
Some houses ask you to move in. This one asks you to move forward, into the life you've been imagining, on your own terms. Set on a surveyed 0.39-acre corner lot in Oakland, this classic New England farmhouse gives you 2,484± sq. ft., 4 bedrooms, 2 full baths, and something rare: 22± feet of owned frontage on Messalonskee Lake, Not shared access, yours, running the parcel to the water. This is your chance to combine a true renovation project with genuine Maine lakefront ownership, at a price point waterfront rarely offers. Step inside and you can feel what's waiting: spacious rooms, hardwood floors, tall windows, substantial trim, a traditional staircase, built-ins, a decorative mantel, a pantry, and first-floor laundry. Every detail is a starting point, not a finished thought. The attached one-car garage/barn adds storage, workspace, and even more room to make this place your own. This is not a turnkey home, offered as-is as part of an estate, it will require substantial renovation. But if you're the kind of buyer who'd rather create than compromise, who's been searching for a farmhouse fixer-upper, a restoration project, an investment opportunity, or simply an affordable way onto Messalonskee Lake, this is the one worth seeing in person. Public water and sewer. An in-town Oakland location near shopping, recreation, and the public boat landing. Restore the farmhouse. Rework the rooms. Bring back the character. Keep the lake. Make it unmistakably yours.

2 Old Belgrade Ave, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

$449,900
4 Beds ⋅ 2 Baths ⋅ 1677714 MLS
Welcome Home! This well-maintained 4 bedroom, 2 full bath Maine farmhouse, beautifully situated on 10 acres of peaceful, private land. Thoughtfully cared for and updated over the years, this home blends classic farmhouse charm with the comforts and conveniences today's buyers are looking for. The beautifully updated kitchen offers a welcoming space for everyday living and entertaining, while the first-floor laundry adds valuable convenience. A true Maine must-have, the spacious mud room provides the perfect spot to kick off boots, hang coats, and keep life organized through every season. Outside, enjoy your own private retreat with an in-ground pool, perfect for summer gatherings, relaxing, and making memories. With 10 acres to explore, there's plenty of room for gardening, recreation, animals, or simply enjoying the peace and privacy of country living. A wonderful combination of character, updates, usable acreage, and outdoor enjoyment, this farmhouse is ready to welcome its next owners home.

241 Belgrade Rd, Oakland

Listing courtesy of Portside Real Estate Group.

$569,000
4 Beds ⋅ 4 Baths ⋅ 1670036 MLS
New Construction!! Duplex to be built! Public water & sewer will be connected. Call us today for additional information!

28 Jacques Ln Unit 1 & 2, Oakland

Listing courtesy of Hoang Realty.

$569,000
4 Beds ⋅ 4 Baths ⋅ 1670037 MLS
New Construction!! Duplex to be built! Public water & sewer will be connected. Call us today for additional information!

28 Jacques Ln Unit 3 & 4, Oakland

Listing courtesy of Hoang Realty.

$569,000
4 Beds ⋅ 4 Baths ⋅ 1670041 MLS
New Construction!! Duplex to be built! Public water & sewer will be connected. Call us today for additional information!

28 Jacques Ln Unit 9 & 10, Oakland

Listing courtesy of Hoang Realty.

$569,000
4 Beds ⋅ 4 Baths ⋅ 1670038 MLS
New Construction!! Duplex to be built! Public water & sewer will be connected. Call us today for additional information!

28 Jacques Ln Unit 5 & 6, Oakland

Listing courtesy of Hoang Realty.

$569,000
4 Beds ⋅ 4 Baths ⋅ 1670040 MLS
New Construction!! Duplex to be built! Public water & sewer will be connected. Call us today for additional information!

28 Jacques Ln Unit 7 & 8, Oakland

Listing courtesy of Hoang Realty.

$594,900
4 Beds ⋅ 3 Baths ⋅ 1663280 MLS
Skip the construction loan and step into a beautifully designed new construction Colonial offering approximately 1,870± square feet of thoughtfully crafted living space. This 4-bedroom, 2.5-bath home blends timeless style with modern functionality, creating the perfect space for everyday living and entertaining. The first floor features a spacious open-concept kitchen and living area centered around a large island, along with a dedicated dining room, convenient utility/laundry room, and half bath. Upstairs, you'll find four generously sized bedrooms including a private primary suite complete with a walk-in closet and full bath with double vanities and a custom shower. This home features quartz countertops, painted cabinetry, and durable click-lock flooring throughout the main living spaces, creating a clean and modern feel from top to bottom. Please note: garage is not included in the offering price. Want to experience the layout in person? This model is available to walk through at our sales center in Chelsea. Reach out today to learn more about the process and timeline to completion.

Lot 15 Autumn, Oakland

Listing courtesy of Summit Real Estate.

$1,049,000
4 Beds ⋅ 3 Baths ⋅ G5110973 MLS
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

Listing courtesy of COAST TO COAST REAL ESTATE PRO. 352-296-8930
$619,999
4 Beds ⋅ 3 Baths ⋅ O6394442 MLS
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

Listing courtesy of MS LAND & BUILDING LLC. 407-466-7000

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