Map location of
Fairoaks, Maitland, FL, USA

Maitland, Florida, United States

Homes for sale near Fairoaks, Maitland, FL, USA

Address Bed / Bath Listing Price
Picture of 105 TANGELO COURT
105 TANGELO COURT
Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finis
MAITLAND, FL
Living Area: 3203 Sqft.
5 Beds, 5 Baths
$1,799,000
Picture of 1231 GLASTONBERRY ROAD
1231 GLASTONBERRY ROAD
One or more photo(s) has been virtually staged. Don’t miss this beautifully updated 3-bedroom, 2-bathroom English Estates pool home with a versatile bonus room that can serve as a 4th bedroom, office, gym, or playroom—complete with its own private entrance. Priced below appraised value, this hom
MAITLAND, FL
Living Area: 1753 Sqft.
3 Beds, 2 Baths
$525,000
Picture of 360 LAKE SEMINARY CIRCLE
360 LAKE SEMINARY CIRCLE
Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansiv
MAITLAND, FL
Living Area: 6466 Sqft.
5 Beds, 8 Baths
$4,999,000
Picture of 10 MINNEHAHA CIRCLE
10 MINNEHAHA CIRCLE
Welcome to this beautifully refined 4-bedroom, 3-bath POOL HOME in the highly sought-after Minnehaha Shores community of Maitland. Situated on a prominent corner lot with picturesque views of Minnehaha Park, this residence offers thoughtful enhancements, generous indoor–outdoor living, and exclusi
MAITLAND, FL
Living Area: 1995 Sqft.
4 Beds, 3 Baths
$679,000
Picture of 1511 E HORATIO AVENUE
1511 E HORATIO AVENUE
Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, 3-bathroom residence is a perfect blend of modern comfort and timeless elegance. Total Living Area 2760 Sq Ft. As you step inside, you'll be greeted by an inviting foyer that leads to a spacious open-concept li
MAITLAND, FL
Living Area: 2676 Sqft.
4 Beds, 3 Baths
$699,900
Picture of 2270 DELORAINE TRAIL
2270 DELORAINE TRAIL
This beautifully updated 4-bedroom, 2-bath pool home offers 2,000 square feet of inviting living space on a spacious corner lot in highly desirable Maitland. The open living, kitchen, and dining area features a striking limestone fireplace, crown molding, custom built-ins, laminate wood flooring, an
MAITLAND, FL
Living Area: 2000 Sqft.
4 Beds, 2 Baths
$850,000
Picture of 2167 MOHAWK TRAIL
2167 MOHAWK TRAIL
One or more photo(s) has been virtually staged. Celebrate the holidays in this charming 3 bedroom, 2 bath home nestled in one of Maitland’s most sought-after communities. As you step onto the inviting front porch and enter the foyer, you’re greeted by a sense of home, a perfect ambiance for fe
MAITLAND, FL
Living Area: 2162 Sqft.
3 Beds, 2 Baths
$625,000
Picture of 135 ROOSEVELT PLACE
135 ROOSEVELT PLACE
This charming home boasts a wealth of valuable upgrades and improvements, making it an enticing opportunity for anyone seeking a move-in ready property The roof was replaced in 2024, ensuring long-lasting durability. A significant renovation in 2024 Both Bathrooms FULLY REMODELED, New AC inside and
MAITLAND, FL
Living Area: 2426 Sqft.
4 Beds, 2 Baths
$564,900
Picture of 731 BUCHER ROAD
731 BUCHER ROAD
Welcome! This well-maintained ranch-style home features a functional single-level design with a newer roof (2024) encompassing 1,523 square feet of living space, plus you get to enjoy an additional 255ft' of expanded living space on the enclosed florida room which is under AC. The main living area i
MAITLAND, FL
Living Area: 1523 Sqft.
3 Beds, 2 Baths
$445,000
Picture of 216 OBRIEN ROAD
216 OBRIEN ROAD
One or more photo(s) has been virtually staged. Seller may consider seller contribution! Come see this beautiful renovated home offering the perfect blend of comfort and style. Nestled in a neighborhood with no HOA! This 4 bedroom and 2 bathroom move-in ready home boasts a bright and open floor plan
CASSELBERRY, FL
Living Area: 1432 Sqft.
4 Beds, 2 Baths
$335,000
Picture of 791 SEQUOIA TRAIL
791 SEQUOIA TRAIL
Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecti
MAITLAND, FL
Living Area: 4144 Sqft.
5 Beds, 4 Baths
$1,299,000
Picture of 505 LAKE SHORE DRIVE
505 LAKE SHORE DRIVE
Imagine mornings with the sunrise shimmering across Lake Faith, directly across the street from your front door. Coffee by the crackling wood-burning fireplace makes Florida feel like fall in New England (Yes, even in Florida we like to imagine it gets cold), and evenings end with sunset strolls and
MAITLAND, FL
Living Area: 2317 Sqft.
4 Beds, 2 Baths
$570,000
Picture of 604 MINNEHAHA LANE
604 MINNEHAHA LANE
The Winter Park Chain is the context; the shoreline of Lake Minnehaha is the setting. A three-story, columned home opens with an honest, crafted tone: new low-profile concrete tile roof, operable cypress shutters with hand-forged hardware, Chippendale balustrades, and a beveled front door offering a
MAITLAND, FL
Living Area: 6163 Sqft.
6 Beds, 6 Baths
$2,895,000
Picture of 1231 SIDCUP ROAD
1231 SIDCUP ROAD
Prepare to be captivated by this fully renovated gem located in the highly sought after English Estates neighborhood. Offering 1,798 square feet of meticulously designed living space, this three bedroom, two bathroom home blends timeless charm with modern luxury. Every inch has been thoughtfully upd
MAITLAND, FL
Living Area: 1798 Sqft.
3 Beds, 2 Baths
$540,000
Picture of 601 ORANOLE ROAD
601 ORANOLE ROAD
Welcome to Your Family's Next Chapter in Beautiful Maitland! Nestled in one of Maitland's most sought-after neighborhoods, this fully renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and timeless charm, ideal for families ready to make new memories. From the moment
MAITLAND, FL
Living Area: 1950 Sqft.
3 Beds, 2 Baths
$399,900
Picture of 2211 Azalea Pl
2211 Azalea Pl
Luxurious waterfront estate in one of Winter Park’s most prestigious neighborhoods, offering 7,278 SF of elegant living with direct canal access to Lake Maitland. This 5-bedroom, 6.5-bath home features all en-suite bedrooms, including two on the main floor, a gourmet kitchen with Viking appliances
Winter Park, FL
Living Area: 7278 Sqft.
5 Beds, 7 Baths
$5,495,000
Picture of 2211 AZALEA PLACE
2211 AZALEA PLACE
Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence
WINTER PARK, FL
Living Area: 7278 Sqft.
5 Beds, 7 Baths
$5,495,000
Picture of 249 SPARTAN DRIVE
249 SPARTAN DRIVE
Discover Your Perfect Maitland Retreat! Tucked away on a quiet dead-end street, this delightful 4-bedroom home offers the perfect blend of comfort, space, and convenience—with no HOA to worry about! Sitting on an oversized .24-acre lot, there's room to create the outdoor paradise you’ve always
MAITLAND, FL
Living Area: 1579 Sqft.
4 Beds, 2 Baths
$345,000
Picture of 822 GLEN ARDEN WAY
822 GLEN ARDEN WAY
ENJOY YOUR OWN PRIVATE POOL—PERFECT FOR OUTDOOR RELAXATION AND ENTERTAINING! This fully renovated 3-bedroom, 2-bath residence offers stylish living with high-end finishes throughout. The updated kitchen features stone countertops, brand-new cabinetry, and stainless steel appliances—all designed
ALTAMONTE SPRINGS, FL
Living Area: 1852 Sqft.
3 Beds, 2 Baths
$524,900
Picture of 952 MOSS LANE
952 MOSS LANE
Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creat
WINTER PARK, FL
Living Area: 3474 Sqft.
4 Beds, 4 Baths
$1,369,950
Picture of 1695 E HORATIO AVENUE
1695 E HORATIO AVENUE
Great Location, this home is located on Community of Dommerich Estates, Maitland, Florida, No HOA, Top Rated Shools, less than 1 mile to Lake Minnehaha and approximately 2.6 miles to Lake Maitland, and less than 1 mile to John Langdon Park, John Hudson Park, and Kings Row Park. House is just revita
MAITLAND, FL
Living Area: 1939 Sqft.
4 Beds, 3 Baths
$529,000
Picture of 1640 E ADAMS DRIVE
1640 E ADAMS DRIVE
Behind private gates along the shores of Lake Maitland, this elegant Mizner-style Mediterranean estate offers an extraordinary opportunity to own a timeless lakefront masterpiece on the Winter Park Chain of Lakes. Encompassing approximately two acres of meticulously manicured grounds framed by soari
MAITLAND, FL
Living Area: 8174 Sqft.
5 Beds, 8 Baths
$10,950,000
Picture of 913 MOSS LANE
913 MOSS LANE
***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL – A 2023 Masterpiece Awaits! Step into luxury living at 913 Moss Lane, a breathtakingly renovated 3-bedroom, 2-bath haven in th
WINTER PARK, FL
Living Area: 1887 Sqft.
3 Beds, 2 Baths
$975,000
Picture of 1913 POINSETTA LANE
1913 POINSETTA LANE
Motivated Seller! Stunningly Renovated 4-Bedroom Home in Prime Maitland Seize this rare opportunity! The seller is motivated and ready to make a deal. Ideally located just 0.5 miles from English Estates Elementary and minutes from Kewannee Park, dining, shopping, scenic trails, I-4, and the airport.
MAITLAND, FL
Living Area: 1664 Sqft.
4 Beds, 2 Baths
$424,900
Picture of 255 W GEORGE AVENUE
255 W GEORGE AVENUE
Experience the blend of timeless elegance and modern luxury in this Maitland estate a block away from Lake Sybelia. Completely renovated in 2007, every detail of this home exudes sophistication. A spacious paver driveway leads to a two-car garage, framed by lush tropical landscaping, decorative ston
MAITLAND, FL
Living Area: 4814 Sqft.
5 Beds, 4 Baths
$1,700,000
Picture of 140 E FAITH TERRACE
140 E FAITH TERRACE
NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2025 - Seperate detached GUEST HOUSE offering built-in monthly income potential. Previously rented under market value at $900/month, the guesthouse is currently vacant and ready for a new tenant, a private space for
MAITLAND, FL
Living Area: 2748 Sqft.
4 Beds, 3 Baths
$525,000
Picture of 2661 VIA TUSCANY
2661 VIA TUSCANY
CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMS Introducing a Unique, Stunning Modern Home A groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ce
WINTER PARK, FL
Living Area: 4636 Sqft.
4 Beds, 5 Baths
$6,600,000
Picture of 2550 VENETIAN WAY
2550 VENETIAN WAY
"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Park, accessing the Maitland/Winter Park CHAIN OF LAKES! This custom modern/contemporary 2008 build, d
WINTER PARK, FL
Living Area: 4875 Sqft.
4 Beds, 5 Baths
$2,499,000