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520 Smithfield Rd, Oakland
$225,000
2 Beds ⋅ 1 Baths ⋅ 1674155 MLS
Exceptional value in a desirable neighborhood near the beautiful Belgrade Lakes! This beautifully updated 1-2 bedroom, 1,056-square- foot home sits on a quiet 0.23-acre lot. Since 2018, this property has undergone massive high-ticket infrastructure improvements, giving a future owner total peace of mind. Major updates include custom hickory cabinets in the kitchen and bathroom, modern appliances, fresh flooring, updated plumbing and electrical 2018), a leach field (2019), and a drilled well (2021). Enjoy a peaceful setting with easy access to outdoor recreation and local amenities. Please note: To respect the privacy of the occupant, initial viewings are conducted via virtual tour. In-person showings will be scheduled upon an accepted offer.

520 Smithfield Rd, Oakland

Listing courtesy of Sprague & Curtis Real Estate. lori@spragueandcurtis.com

312 Briley Avenue, Oakland
$3,295,000
6 Beds ⋅ 7 Baths ⋅ O6429415 MLS
Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern luxury. Designed for both everyday living and elegant entertaining, the open-concept layout features a gourmet chef's kitchen, expansive great room, private office, loft, and spacious covered lanai. Enjoy true Florida living with an extended outdoor entertaining area complete with a resort-style pool, spa, and fully equipped summer kitchen for seamless indoor-outdoor living. Every detail reflects the exceptional craftsmanship, premium finishes, and attention to detail that define Element Home Builders. With construction just beginning, buyers have the rare opportunity to personalize select finishes and own a brand-new custom luxury home in one of Oakland's most desirable communities. Briley Farm is an exclusive enclave just minutes from historic Downtown Winter Garden, the West Orange Trail, top-rated schools, boutique shopping, dining, and major highways, offering convenient access to Downtown Orlando, Walt Disney World, and Orlando International Airport. Experience the perfect blend of luxury, privacy, and convenience in one of Central Florida's premier custom home communities.ning, and major roadways, while maintaining the privacy and charm of luxury estate living. Renderings are for illustration purposes only. Features, specifications, and finishes are subject to change without notice.

312 Briley Avenue, Oakland

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155

132 Washington St, Oakland
$239,000
3 Beds ⋅ 2 Baths ⋅ 1673925 MLS
Solid and well-maintained 3-bedroom, 2-bath home offering approximately 1,500 square feet of living space on a generous 0.50-acre lot in Oakland. Recent improvements include a newer septic system (2024), boiler, propane monitor heater, and a detached two-car garage with a recently replaced shingle roof. The home's metal roof adds to its long-term durability, while the functional layout provides flexibility for a variety of living arrangements. Conveniently located with easy access to local amenities and I-95, this property offers an excellent opportunity for an owner-occupant or investor alike. Whether you're looking for your next home or an income-producing property, this one is well worth a look.

132 Washington St, Oakland

Listing courtesy of Keller Williams Realty. nick@nickisgro.com

1603 Johns Cove Lane, Oakland
$779,000
6 Beds ⋅ 4 Baths ⋅ 1228387 MLS
PRICE REDUCED! Make this 6-bedroom, 4-bath home in gated Johns Cove your own in time for the holidays. Set on a private cul-de-sac with no rear neighbors, it offers room to gather and space to unwind. Formal living and dining rooms, a large family room, vaulted ceilings, and a double staircase welcome you inside. The kitchen features stainless steel appliances, granite countertops, an island, and a breakfast area with pond views. The first-floor primary suite overlooks the pool and includes dual vanities, a garden tub, separate shower, and walk-in closet. Upstairs offers spacious bedrooms and a dedicated movie room. Enjoy a screened saltwater pool and spa, updated full pool bath, covered lanai, and private balcony. Residents have access to a private boat ramp on Johns Lake for fishing, boating, paddleboarding, and kayaking. Near West Orange Trail, Downtown Winter Garden, Winter Garden Village, shopping, dining, and schools. Motivated sellers are ready for their next chapter!

1603 Johns Cove Lane, Oakland

Courtesy of RE/MAX Town & Country Realty

28 Belgrade Rd, Oakland
$649,900
3 Beds ⋅ 2 Baths ⋅ 1669163 MLS
Motivated Seller... and Priced far below the assessed value! Don't miss your chance to own this picturesque waterfront setting on one of Maine's most desirable lakes. On the market for the first time in many, many years, this 1865 family home has been lovingly maintained and updated while retaining its original charm. Through the years, renovations have preserved the home's warmth and character while adding modern conveniences. The spacious first floor features a well-appointed kitchen with granite countertops and newer appliances, a large dining room, and a generous living room with a hearth, and pellet stove. Sliding glass doors open to a lush backyard and waterfront views of Messalonskee Lake. Also, on the first floor is a versatile bonus room, ideal for an office or bedroom - with built-ins providing extra storage and flexible living space. The home has natural wood flooring in all of the primary rooms and kitchen. Original natural wood stairs, rails and landing add to the home's timeless appeal. Upstairs are two large bedrooms, a full bath, and finished storage space in the eaves. The primary bedroom includes its own glassed-in sun porch with electric sunshades, overlooking the yard and waterfront. Outside you'll find two decks, each with their own electric awning, a beautiful garden shed, a utility shed and well-groomed yard. Additional space over the two-car, attached garage offers potential for storage, a workshop or even future living space. A rare opportunity to own a historic, lovingly cared-for waterfront home on Messalonskee Lake. Some photos virtually enhanced.

28 Belgrade Rd, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

72 Cedar Village Pl, Oakland
$699,000
2 Beds ⋅ 2 Baths ⋅ 1668380 MLS
Experience the best of Maine lakefront living with this charming 2-bedroom home on sought-after Messalonskee Lake in Oakland, Maine. Offering stunning water views, a sandy beach, and direct lake access, this year-round home is the perfect retreat for relaxing, entertaining, and enjoying all that lake life has to offer. Conveniently located just minutes from downtown Oakland and close to I-95, this property allows convenient easy access to everything Central Maine has to offer. Whether you enjoy fishing, swimming, sunbathing or water sports, this can be your year-round home or seasonal retreat. Just minutes from the Waterville Country Club and fine restaurants, enjoy a round of golf, dinner and still make it home in time to watch the breathtaking sunsets from your deck. Come see why the Belgrade Lakes Region is one of the most desirable after regions in Maine.

72 Cedar Village Pl, Oakland

Listing courtesy of Coldwell Banker Plourde Real Estate.

78 Ten Lots Rd, Oakland
$299,900
3 Beds ⋅ 2 Baths ⋅ 1663560 MLS
Set on over an acre in Oakland, this classic 1800s farmhouse blends historic New England character with thoughtful modern improvements. Offering over 2,100 square feet of living space, this 3-bedroom home features the warmth and charm expected from a property of this era, combined with the practical updates today's buyers are looking for. The home has been exceptionally maintained and includes a newer roof, vinyl siding, updated exterior improvements, and a recently added oversized garage providing tremendous utility for vehicles, storage, hobbies, or workshop space. Inside, you'll find generous living areas filled with natural light, multiple heat sources including wood stoves and a fireplace, and the timeless feel that only a historic Maine farmhouse can provide. The acreage offers privacy, flexibility, and room to enjoy country living while remaining conveniently close to town amenities, schools, and I-95 access. Whether you're looking for a primary residence with space to spread out, a hobby farm setting, or simply a home with authentic character and substance, this property presents a rare opportunity in today's market. A unique combination of history, land, practicality, and charm in one of Central Maine's most desirable communities.

78 Ten Lots Rd, Oakland

Listing courtesy of Keller Williams Realty. nick@nickisgro.com

Lot 15 Autumn, Oakland
$614,305
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.

113 & 121 High St, Oakland
$1,249,000
1656690 MLS
Exceptional Commercial and Residential Investment Opportunity in Prime Oakland Location! Looking for the perfect space to launch or grow your business, add to your portfolio, or live on site while you work? This rare offering includes both 113 and 121 High Street in Oakland, presenting a unique blend of commercial functionality and residential comfort. At 121 High Street, you'll find a 57x53 heated commercial garage, fully equipped with a lift, tools, and half bath, ideal for trades, storage, or auto work. A second 29x25 garage, additional outbuildings, and a separate office space provide even more versatility. There are three RV hookups, a fenced garden, and fruit bearing plum, apple, and blueberry trees. The 3.68 acre lot offers potential for future development, such as a mobile home park or tiny home community where affordable housing is much needed in the desirable Oakland area. A never used junkyard permit can also transfer with the property. All just minutes from downtown Oakland and the public boat launch at Messalonskee Lake, and under 10 minutes to Waterville's colleges, hospital, and airport. Next door, 113 High Street features an updated home with over 2,700 square feet of finished space. It includes a sleek kitchen with black granite countertops, modern bathrooms with a tiled shower, a spacious family room, and a cozy den with a built-in bar. The layout is ideal for adding bedrooms or converting part of the home into a business office. The basement offers additional space, and the attached garage includes a rear office. Outside, enjoy the stamped concrete patio and well maintained backyard on 0.50 acres. Whether you're an investor, entrepreneur, or buyer seeking a versatile live/work setup, this unique opportunity checks all the boxes! Home could easily be converted to a 3-4 Bedroom home. Seller would entertain having that done with an acceptable offer!

113 & 121 High St, Oakland

Listing courtesy of Real Broker.

Lot 8 Autumn, Oakland
$552,945
3 Beds ⋅ 2 Baths ⋅ 1663285 MLS
The Amherst model offers beautifully designed single-level living with 3 bedrooms, 2 bathrooms, and approximately 1,535± square feet of thoughtfully planned space. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating the perfect setup for entertaining or everyday life. The spacious kitchen features a large center island, quartz countertops, painted cabinetry, and plenty of storage, including a walk-in pantry. The private primary suite offers a walk-in closet and an oversized bath with double vanities, while two additional bedrooms and a second full bath provide flexibility for guests, family, or home office space. Additional features include a dedicated utility room, abundant natural light, and a functional layout designed for comfort and convenience. This home is fully customizable, allowing buyers to tailor finishes, colors, and details to match their style and needs. Want to see the layout in person? The Amherst model is available to walk through at our sales center in Chelsea. Reach out today for more information on the process and timeline to completion.

Lot 8 Autumn, Oakland

Listing courtesy of Summit Real Estate.

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal,noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.

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