Oakland Homes for Sale

Oakland Homes for Sale

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Oakland, Maine offers a diverse housing market, appealing to a wide range of preferences and lifestyles. From charming historic homes with character to newly constructed residences boasting modern amenities, there's something for everyone seeking to settle in this welcoming community. The town's desirable location, combined with a strong sense of community, makes it an attractive destination for families, young professionals, and retirees alike.

The real estate market in Oakland benefits from the town's proximity to larger urban centers while maintaining its peaceful, rural atmosphere. Residents enjoy easy access to both outdoor recreation and essential services, creating a balanced and fulfilling lifestyle. With a variety of property types available, prospective homeowners can find the perfect space to suit their individual needs and budget, whether it's a cozy starter home or a spacious property with room to grow.

Investing in Oakland's housing market provides the opportunity to become part of a vibrant and thriving community. The town's commitment to preserving its natural beauty and fostering a strong sense of belonging makes it a truly special place to call home. Whether you're drawn to the scenic landscapes, the friendly neighbors, or the convenient location, Oakland offers a unique blend of small-town charm and modern convenience that's hard to resist.

This website features the best Oakland real estate search for homes available. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®'s database every 15 minutes.

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Curious about what's happening in the Oakland area? You can view a custom market report to see what's active, under contract, and sold in Oakland!

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Oakland Homes for Sale

$289,000
2 Beds ⋅ 2 Baths ⋅ 1670027 MLS
New Construction!! 2 bed/1.5 bath Condos to be built! Public water & sewer will be connected. Call us today for additional information!

28 Jacques Ln Unit 4, Oakland

Listing courtesy of Hoang Realty.

$289,000
2 Beds ⋅ 2 Baths ⋅ 1670025 MLS
New Construction!! 2 bed/1.5 bath Condos to be built! Public water & sewer will be connected. Call us today for additional information!

28 Jacques Ln Unit 2, Oakland

Listing courtesy of Hoang Realty.

$250,000
1669311 MLS
Investors Take Notice: Situated on 35 private acres, this unique property is being offered primarily for its land value. Includes 3 existing dwellings with limited value, 3 septic systems, and 3 wells. With ample space, privacy, and existing infrastructure, the possibilities are numerous. Buyers are encouraged to verify potential uses and consult with the town regarding any applicable zoning and code enforcement requirements. Conveniently located approximately one mile from the Messalonskee Lake Oakland Town Beach and Boat Landing, offering easy access to outdoor recreation.

30 Porter Dr, Oakland

Listing courtesy of Home At Last Realty.

$699,000
3 Beds ⋅ 2 Baths ⋅ 1669163 MLS
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.

$79,900
3 Beds ⋅ 2 Baths ⋅ 1669102 MLS
**A Turn Key opportunity!** Welcome to 37 Olivia Avenue in Oakland, Maine -- a beautifully maintained home tucked away at the end of a quiet cul-de-sac offering privacy, comfort, and numerous recent updates. Inside, you'll find stylish laminate flooring throughout much of the home, complemented by new carpeting that adds warmth and comfort to the living spaces. The upgraded kitchen provides a modern and functional space for cooking and entertaining, while the remodeled bathrooms feature updated finishes that today's buyers are looking for. Outside, the property truly shines with attractive landscaping, established gardens, and inviting front decks that create exceptional outdoor living spaces and impressive curb appeal. Additional improvements include an efficient heat pump for year-round comfort, a cozy wood stove for supplemental heat during Maine winters, and a whole-home Generac generator that provides peace of mind no matter the weather. As an added bonus, the seller is willing to include much of the home's furnishings, making this an excellent turnkey opportunity for buyers seeking a move-in-ready home in a desirable Oakland neighborhood. Don't miss your chance to own this thoughtfully updated and meticulously cared-for property in a peaceful setting close to local amenities, schools, and recreation.

37 Olivia Ave, Oakland

Listing courtesy of Coldwell Banker Realty.

$369,000
1668880 MLS
Recent Price Reduction! Exceptional 2014 SF professional office building at Central Maine's First Park. Prior medical offices of Surgi-Care. Full basement for expansion of storage. First Park is located just off I-95 Exit 127 and is coinvenient to Waterville and ALL of Central Maine. Attractive moderen building with ample parking. eing offered ''For Sale' or 'For Leasae'.

10 Evergreen Dr, Oakland

Listing courtesy of Venture Real Estate & Asset Management.

$749,000
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.

$289,000
1667607 MLS
This premier commercial building just outside Oakland Village offers an exceptional turnkey investment opportunity, pairing high-visibility placement with an adaptable layout engineered for immediate business scaling. The architecture features a bright, welcoming storefront or reception entry that transitions into an expansive rear footprint, allowing owner-users to easily configure the space for high-capacity storage or an expanded retail showroom. Outside, a massive private driveway ensures seamless logistics with dedicated parking stalls for both staff and clients, while professionally curated landscaping and mature fruit trees deliver premium curb appeal. Strategically positioned to maximize local presence, this property provides the ultimate structural flexibility and market visibility required to accelerate your commercial venture's growth and return on investment.

152 Fairfield St, Oakland

Listing courtesy of Portside Real Estate Group.

$799,999
5 Beds ⋅ 3 Baths ⋅ TB8513260 MLS
Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

16 Oakland Pointe Circle, Oakland

Listing courtesy of JACK KELLER INC. 727-586-1497
$489,000
1664109 MLS
Recent Price Reduction! Prior MGHC professional medical building with 3440 SF. Perfect reuse for Corporate or Business office space. First Park location just off I-95 and convenient to Waterville and ALL of Central Maine. Modern attrac tive building with 35+/- parking spaces, ample reception area, 5 exam/private offices, proceedure room or possible conference room, break room, and multi rack IT room. Electrical and mechanical are all in top shape. Ready to go for medical use or easily re-fitted to most any business. ALSO AVAILABLE FOR 'LEASE' !!

11 Evergreen Dr, Oakland

Listing courtesy of Venture Real Estate & Asset Management.

$325,000
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
$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.

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