Refine Search
Map
Sort by
402 N Pollard Street, Oakland
$3,495,000
5 Beds ⋅ 6 Baths ⋅ O6405707 MLS
Luxury new construction model home by Element Home Builders located in the exclusive custom home community of Briley Farm in Oakland. This thoughtfully designed residence offers approximately 4,900 square feet of elevated living space with 5 bedrooms, 5.5 bathrooms, and a spacious 3-car garage. Designed for both everyday living and entertaining, the home features soaring ceilings, expansive open-concept living areas, designer finishes, and seamless indoor-outdoor flow. The chef’s kitchen is the centerpiece of the home with premium appliances, custom cabinetry, oversized island, generous prep and storage space, and a fully equipped back kitchen designed for seamless entertaining and everyday functionality. The luxurious primary suite offers a spa-inspired bath and oversized walk-in closet, while additional guest suites, flex spaces, and entertaining areas provide comfort and functionality throughout. Outdoor living is equally impressive with a resort-style pool, covered lanai, and beautifully designed entertaining spaces perfect for enjoying Florida living year-round. Professionally furnished by Arhaus, the home showcases elevated designer selections and a warm modern aesthetic throughout. Located just minutes from downtown Winter Garden, top-rated schools, restaurants, shopping, the West Orange Trail, and major highways, Briley Farm offers a rare combination of privacy, luxury, and convenience. This professionally designed model home is available with a lease-back opportunity from the builder, offering a unique investment opportunity with immediate income potential. A rare opportunity to own one of Central Florida’s premier luxury model homes in one of the area’s most desirable custom home communities.

402 N Pollard Street, Oakland

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155
620 N Tubb Street, Oakland
$1,250,000
6 Beds ⋅ 8 Baths ⋅ O6362142 MLS
Under contract-accepting backup offers. 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

Listing courtesy of OAKSTRAND REALTY. 888-912-5258
16 Oakland Pointe Circle, Oakland
$795,999
5 Beds ⋅ 3 Baths ⋅ TB8513260 MLS
Under contract-accepting backup offers. 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
38 S Pollard Street, Oakland
$619,000
4 Beds ⋅ 3 Baths ⋅ O6394442 MLS
Under contract-accepting backup offers. 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
410 E, Oakland
$549,000
4 Beds ⋅ 3 Baths ⋅ 1677284 MLS
Welcome home to effortless modern living in one of the area's most desirable neighborhoods. Nestled in a peaceful, established community with a welcoming suburban feel, this newly built home offers the perfect blend of privacy, convenience, and quality craftsmanship. Step inside to discover a bright, open floor plan filled with natural light, warm wood-look flooring, recessed lighting, and tasteful finishes throughout. The spacious living area flows seamlessly into the kitchen, creating an ideal space for both everyday living and entertaining. The thoughtfully designed layout features generously sized bedrooms, including a spacious primary suite complete with a walk-in closet and an elegant en-suite bath featuring a double vanity. A breezeway between the home and the 2 car garage will make the perfect mudroom. The unfinished walkout basement offers incredible potential to increase your living space, whether you envision a family room, home gym, workshop, or additional bedrooms. Outside, enjoy the serenity of a wooded setting while being part of a neighborhood where neighbors wave, evening walks are the norm, and the streets invite bike rides, dog walks, and outdoor enjoyment. This is the kind of community buyers dream about--a true neighborhood atmosphere with the space and tranquility of suburban living. If you've been searching for a move-in-ready brand new home that combines modern finishes, room to grow, and an exceptional neighborhood, this one is not to be missed.

410 E, Oakland

Listing courtesy of Signature Homes Real Estate Group, LLC.

18 Fieldstone Dr, Oakland
$439,500
3 Beds ⋅ 3 Baths ⋅ 1680788 MLS
Within Fieldstone Landing's desirable 55+ community , this well-maintained and spacious three-bedroom, two-and-a-half-bath home makes for an ideal living experience. Upon entering is the beautiful dining room and a well designed kitchen, featuring cherry cabinets that makes cooking enjoyable and efficient. This space seamlessly flows into the living room and beyond it lies the large four-season sunroom. This sunroom is a perfect retreat, offering ample natural light and easy access to the deck, making it an excellent spot for morning coffee or evening relaxation. The primary bedroom is a standout feature of the home with a well-appointed bathroom that includes double sinks and a pocket door, providing privacy for the walk-in shower and toilet area. Equipped with heat pumps in both the primary and living rooms, the home remains cozy in the winter months and refreshingly cool during the summer with minimal use of the oil furnace. Extra blown-in insulation in the attic contributes to energy efficiency, making heating and cooling both economical and effective. This property's two additional rooms can serve as bedrooms, a home office, or a hobby room. The half bath is conveniently located with a laundry area discreetly tucked behind bifold doors. The attached two-car garage includes an upstairs area for additional storage. The neighborhood is located on a dead-end private drive, making it perfect for leisurely walks and socializing with neighbors. Fieldstone Landing is not only about comfortable living but also about accessibility. The proximity to Waterville provides residents with a wealth of shopping options, restaurants, and health facilities. With easy access to I-95, commuting is a breeze, while nearby golf courses and the beautiful Belgrade Lakes chain offer recreational opportunities for outdoor enthusiasts. Generator Included.

18 Fieldstone Dr, Oakland

Listing courtesy of Lakehome Group Real Estate. info@lakehomegroup.com
49 Mayland St, Oakland
$390,000
3 Beds ⋅ 2 Baths ⋅ 1683782 MLS
Discover the perfect combination of privacy, convenience, and classic ranch-style living in this inviting home nestled in a desirable, established neighborhood! Perfectly positioned as the last home on a dead-end street, this property enjoys a peaceful, private setting while remaining just minutes from shopping, dining, schools, recreational trails, highway access, and all the amenities that make everyday living easy. Step inside and experience a home designed with comfort and functionality in mind. The classic ranch-style layout provides an inviting atmosphere with practical living spaces that are equally suited for quiet evenings, everyday routines, and entertaining family and friends. Whether you're looking to settle into a comfortable home or create a space that reflects your personal style, this property provides an excellent foundation. One of the home's standout features is its abundance of storage! With ample storage options throughout the house and garages, you'll have plenty of room to keep belongings organized, store seasonal equipment, and accommodate hobbies and recreational gear. Adding even more value and peace of mind is a Generac generator, providing an additional level of preparedness during unexpected power outages. Outside, enjoy the rare combination of an established neighborhood and the added privacy that comes with being tucked away at the end of the street. With no through traffic passing your home, you can appreciate a quieter residential setting without sacrificing accessibility to everything the surrounding area has to enjoy. From its desirable location and private setting to its functional layout, generous storage, garage space, and generator, this property brings together features that make a house feel like home. Come discover the possibilities and see why this charming ranch could be the perfect place for your next chapter!

49 Mayland St, Oakland

Listing courtesy of NextHome Experience.

41 Mary Ln, Oakland
$325,000
3 Beds ⋅ 2 Baths ⋅ 1681370 MLS
Easy, efficient, and thoughtfully laid out, this single-level home offers comfortable living in a quiet neighborhood close to schools, recreation, and everyday amenities. Whether you're just starting out, looking to simplify, or hoping to enjoy the ease of one-floor living, this home offers a lot to appreciate. Inside, the painted kitchen features warm wood countertops, an island for added prep and gathering space, and an easy flow into the living and dining areas. A pellet stove adds extra warmth and coziness to the living room, while the back porch extends the living space and offers a great spot to relax and enjoy the surroundings. Down the hall, you'll find a dedicated utility and laundry room, a conveniently located half bath, and three bedrooms. One bedroom features its own full bath, creating a comfortable primary bedroom setup with added privacy. With everything you need on one level, an efficient footprint, and a peaceful neighborhood setting close to desirable schools and outdoor recreation, this home offers a simple and comfortable way to settle in and make it your own.

41 Mary Ln, Oakland

Listing courtesy of Portside Real Estate Group.

152 Fairfield St, Oakland
$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.

30 Porter Dr, Oakland
$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.

87 Summer St, Oakland
$199,900
2 Beds ⋅ 2 Baths ⋅ 1682536 MLS
Have you been looking for an affordable, updated home with the convenience of one-level living? This Oakland home could be just what you've been waiting for! Step inside to an updated kitchen with newer appliances and plenty of cabinet space to keep everything organized. Just off the kitchen, the spacious living room offers plenty of room to get comfortable and unwind after a long day. The two good-sized bedrooms are located on opposite ends of the home for added privacy. One has an attached half bath, while the other offers generous closet space and a full bathroom right next door. Newer flooring throughout gives the home a fresh, welcoming feel, and the laundry area off the kitchen keeps everyday living convenient. An enclosed porch gives you another spot to relax, enjoy your morning coffee, or settle in with a good book. Outside, there's plenty to appreciate, too! The yard offers room for gardening, outdoor activities, or a cookout with friends. A paved driveway, large two-car garage, and separate storage shed give you plenty of space for parking, tools, and outdoor gear. Located on a quiet road in desirable Oakland, you're just a half mile from Messalonskee Lake's public boat launch and beach, with easy access to the highway and downtown Waterville. Whether you're buying your first home, looking to downsize, or simply ready for the ease of one-level living, this one is worth a look. Come see it before it's gone!

87 Summer St, Oakland

Listing courtesy of Real Broker.

320 W Sadler Avenue, Oakland
$199,000
2 Beds ⋅ 1 Baths ⋅ O6436879 MLS
Under contract-accepting backup offers. Hot Oakland opportunity. Motivated seller, bring all offers. This two-bed, one-bath on a no HOA lot puts you minutes to John’s Lake boat access and the West Orange Trail, plus a short hop to downtown Winter Garden dining and shops. Fix and flip, hold as a rental, or tear down and build new. The upside is real and the seller is ready. Quiet small-town setting with outdoor perks and growth around you. Don’t wait. Opportunities at this price and location move fast.

320 W Sadler Avenue, Oakland

Listing courtesy of OFFERPAD BROKERAGE FL LLC. 813-534-6326
510 Oak St, Oakland
$189,500
3 Beds ⋅ 2 Baths ⋅ 1682772 MLS
Stop paying rent and start building equity. This 1997 double-wide sits on a level, tree-lined lot in Oakland, where property taxes stay reasonable and help keep monthly costs down. The open floor plan connects the kitchen, dining room, and living room. Because the home faces east, the kitchen fills with morning light. The primary bedroom has a walk-in closet and a full bath, with a privacy door separating the shower and toilet from the vanity. A large front deck gives you outdoor space from day one. The back deck needs repair, which is an opportunity to add value with your own work. The home is set on a concrete slab with tie-downs and is within easy reach of Waterville's jobs, shopping, dining, and the arts. It's an affordable first step into ownership and it comes with a cozy woodburning fireplace to top it all off!

510 Oak St, Oakland

Listing courtesy of EXP Realty.

327 Middle Rd, Oakland
$167,900
2 Beds ⋅ 1 Baths ⋅ 1673243 MLS
**BACK ON THE MARKET THROUGH NO FAULT OF THE SELLER -- NOW OFFERED AT AN ATTRACTIVE NEW PRICE!** A fresh opportunity to own this Oakland property. Set on a landscaped 1.03± acre lot, this **2-bedroom, 1-bath manufactured home** offers affordable one-floor living with plenty of potential. The home has been **relocated from its original site**, an important consideration for buyers and lenders when determining financing options. With cosmetic updating and personal touches, this property could become a comfortable and inviting year-round home. The level lot combines open lawn with mature trees, providing space for gardening, outdoor activities, or simply enjoying the peaceful setting. Inside, the practical layout includes first-floor laundry, two bedrooms, living room, kitchen, and a spacious three-season sunroom. A large deck adds outdoor living space, while the metal roof provides added durability. A major feature is the **heated, oversized two-car garage** with a fully subfloored second level and cedar closet--excellent space for vehicles, a workshop, hobbies, equipment, and storage. A separate shed adds even more utility. Conveniently located near downtown Oakland and Waterville, with easy access to shopping, restaurants, healthcare, Colby College, Thomas College, Messalonskee Lake, and year-round recreation. I-95 is nearby for convenient travel throughout central Maine. **With its new price reduction, 327 Middle Road offers an appealing combination of land, garage space, location, and the opportunity to update the home to your own style.**

327 Middle Rd, Oakland

Listing courtesy of True North Realty, Inc..

68 High St, Oakland
$155,000
3 Beds ⋅ 2 Baths ⋅ 1671352 MLS
Well-maintained home situated on a private, manageable lot in the heart of Oakland. The open-concept kitchen and living area creates a functional and inviting layout. The primary bedroom with en suite bath and bonus room, currently used as a laundry space, are located on one end of the home, while two additional bedrooms and a full bath are situated on the opposite end for added privacy. Conveniently located just minutes from downtown Oakland, highway access, local amenities, and the many lakes and recreational opportunities of the Belgrade Lakes Region. A great opportunity for those seeking comfortable, low-maintenance living in a desirable Central Maine location.

68 High St, Oakland

Listing courtesy of Portside Real Estate Group.

007-019-2 Mulberry Ln, Oakland
$115,000
1673867 MLS
*Fox Ridge Subdivision* A beautifully situated vacant residential lot in a subdivision of executive homes in the heart of Oakland, Maine, this parcel offers a rare blend of privacy, convenience, and natural charm. Located just minutes from Messalonskee Lake, local schools, and downtown amenities, Lot 007-019-2 provides an ideal canvas for your future home or investment build. The land features a peaceful wooded setting, gentle terrain, and ample road access--perfect for designing a retreat that balances quiet living with everyday practicality. Whether you envision a cozy year-round residence, a modern build, or a nature-inspired getaway, this property delivers the space and flexibility to bring your plans to life. Oakland's welcoming community, strong school system, and easy access to Waterville and Augusta make this location especially appealing for homeowners seeking both comfort and convenience. Key Highlights Prime Oakland location -- close to lakes, trails, schools, and town services Wooded privacy with natural surroundings Flexible building potential for a variety of home styles Easy access to major routes connecting to Waterville & Augusta A great opportunity for new construction, investment, or future development

007-019-2 Mulberry Ln, Oakland

Listing courtesy of Brookewood Realty.

30 Oak St Unit 39, Oakland
$30,000
3 Beds ⋅ 2 Baths ⋅ 1679321 MLS
OPEN HOUSE MONDAY OCT. 19th 4:30 -6:00PM and Massive PRICE ADJUSTMENT!! What are you waiting for? Affordable Maine Living in the Heart of the Belgrade Lakes Region! Welcome to Oakland, Maine—where small-town charm, four-season recreation, and convenient access to Central Maine come together. If you're looking to live in a community with a genuine small-town atmosphere while still being close to the amenities and employment centers of Waterville and Augusta, then this is the home for you. This well-sized 3-bedroom, 2-bath offers comfortable living space and an opportunity to enjoy the best of the Oakland lifestyle without giving up everyday convenience. The 1,078-square-foot floor plan offers comfortable living without the maintenance and expense often associated with a larger home. Oakland is a community where you can enjoy the outdoors without being far from the things you need. Located in the heart of the Belgrade Lakes Region, Oakland is surrounded by four major bodies of water—Messalonskee Lake, East Pond, McGrath Pond, and Salmon Lake—creating endless opportunities for boating, fishing, swimming, kayaking, hiking, and enjoying Maine's spectacular four-season scenery. It's also a remarkably convenient place to live, with daily necessities, cafes, restaurants and shopping nearby. Oakland sits just minutes from Waterville and approximately 18 miles from Augusta, while convenient access to I-95 makes commuting throughout Central Maine and beyond much easier. If you're looking for an affordable way to put down roots in Central Maine, enjoy four-season recreation and be close to the Belgrade Lakes, Waterville and Augusta, this Oakland home is worth a look.

30 Oak St Unit 39, Oakland

Listing courtesy of Breakwater Realty Group, LLC.

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.

This information is provided exclusively for consumers' personal, non-commerical use and may not be used for any purpose other than to identify prospective properties consumers may be intrested in purchasing.

Privacy Policy

Your privacy on the Internet is important to us. This Privacy Statement is to inform you that we will not provide your personal information to any third parties except as required by law or expressly authorized by you. We do not sell, trade, barter, or share information obtained from use of this site with any other businesses or people. All information gathered from a visitor to this web site is used solely by this office and/or its affiliated licensee(s). For additional information, please contact this office.

How much is your home worth?

Get instant property value now!