898 ft
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
2503 VERSAILLES AVENUE
Beautifully updated and offered for the first time, this 2015 David Weekley home sits on a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. This 5-bedroom, 5-bath home features an office, large bonus room, covered lanai with full summer kitchen, an
Living Area:
4026 Sqft.
|
5
Beds,
5
Baths
|
$2,775,000 |
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
Living Area:
3203 Sqft.
|
5
Beds,
5
Baths
|
$1,799,000 |
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
Living Area:
1753 Sqft.
|
3
Beds,
2
Baths
|
$525,000 |
2632 MANDAN TRAIL
Charming traditional ranch located in the desirable “Hills” neighborhood of Winter Park! Step into a welcoming foyer that opens to a spacious floor plan accented by mid-century glass block dividers. The comfortable family room features an entertainment wall, a wood-burning fireplace, and a seaml
Living Area:
2441 Sqft.
|
4
Beds,
3
Baths
|
$799,900 |
2464 DERBYSHIRE ROAD
Auction Property. Welcome to this inviting home offering comfortable living spaces and a thoughtful, functional layout. The residence features practical amenities and well-appointed rooms designed for everyday convenience and relaxation.
This three-bedroom, two-bathroom property in the sought-aft
Living Area:
1860 Sqft.
|
3
Beds,
2
Baths
|
$411,900 |
1421 SUNNYSIDE DRIVE
Welcome to 1421 Sunnyside Drive in Maitland, a beautifully maintained home where timeless design meets modern luxury. This 4-bedroom, 2.5-bath corner lot residence with a pool has a thoughtfully designed indoor and outdoor living space. Its location provides quick access to top-rated schools, boutiq
Living Area:
2116 Sqft.
|
4
Beds,
3
Baths
|
$1,300,000 |
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
Living Area:
1995 Sqft.
|
4
Beds,
3
Baths
|
$679,000 |
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
Living Area:
2676 Sqft.
|
4
Beds,
3
Baths
|
$719,900 |
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
Living Area:
2000 Sqft.
|
4
Beds,
2
Baths
|
$850,000 |
2525 NATIVE COURT
One or more photo(s) has been virtually staged. Welcome Home!Don’t miss this fabulous opportunity to own a beautiful ranch-style home in one of the area’s most sought-after communities! Located on a quiet cul-de-sac, this spacious 2,240 sq ft residence sits on a generous 0.4-acre lot and feature
Living Area:
2240 Sqft.
|
4
Beds,
3
Baths
|
$625,000 |
1885 TEMPLE DRIVE
Update! ALL NEW Black Steel doors installed 11/2025 and windows with low e-dual pane glass to be installed 12/25 ($150k value!). Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Located in highly desirable Lugano Terrace just
Living Area:
3691 Sqft.
|
5
Beds,
4
Baths
|
$2,295,000 |
1401 GREEN COVE ROAD
Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this
Living Area:
5483 Sqft.
|
3
Beds,
7
Baths
|
$2,900,000 |
2412 CHANTILLY AVENUE
Step into a world of modern elegance in this newly completed estate in the heart of Winter Park. Masterfully constructed, this five-bedroom residence with six full and one half baths spans over 4,500 square feet of luxurious design and comfort. From the moment you enter the soaring foyer, light pour
Living Area:
4506 Sqft.
|
5
Beds,
7
Baths
|
$2,350,000 |
2299 VIA TUSCANY
Stunning 4-bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous .40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardwood oak floors, two fireplaces, and a chef’s kitchen offering premium appliances including SubZero
Living Area:
3986 Sqft.
|
4
Beds,
4
Baths
|
$2,345,000 |
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
Living Area:
2162 Sqft.
|
3
Beds,
2
Baths
|
$625,000 |
708 THUNDER TRAIL
Welcome to 708 Thunder Trail in beautiful Maitland, Florida — a stunning 4-bedroom, 2-bath pool home nestled in the sought-after Dommerich neighborhood, with NO HOA! This charming single-story residence perfectly blends mid-century character with modern updates, featuring polished TERRAZZO FLOORS,
Living Area:
1907 Sqft.
|
4
Beds,
2
Baths
|
$635,000 |
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
Living Area:
4144 Sqft.
|
5
Beds,
4
Baths
|
$1,299,000 |
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
Living Area:
6163 Sqft.
|
6
Beds,
6
Baths
|
$2,895,000 |
2514 TUSCARORA TRAIL
Welcome Home to Your Private Lakeside Oasis! ?
Step into the lifestyle you’ve been dreaming of! This stunning 4-bedroom, 2.5-bath single-family home perfectly blends modern updates with peaceful lakefront living. From the moment you arrive, you’ll feel the warmth and serenity that makes this ho
Living Area:
3000 Sqft.
|
4
Beds,
3
Baths
|
$849,000 |
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
Living Area:
1798 Sqft.
|
3
Beds,
2
Baths
|
$545,000 |
1024 KEWANNEE TRAIL
One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed 2.5 Bath home in sought after Maitland. Tastefully upgraded home on a generous lot, with in ground pool. Great upgraded kitchen with custom cabinets for extra storage complemented with upgraded Stainless Applia
Living Area:
1845 Sqft.
|
4
Beds,
3
Baths
|
$624,000 |
1742 TEMPLE DRIVE
In one of Winter Park’s desirable neighborhoods, this stunning four-bedroom, five-bath modern masterpiece with Control4 automation offers a blend of luxury and function. Designed with sleek lines and open-concept living, the home showcases Italian engineered wood flooring throughout, creating an e
Living Area:
3658 Sqft.
|
4
Beds,
6
Baths
|
$3,600,000 |
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
Living Area:
7278 Sqft.
|
5
Beds,
7
Baths
|
$5,495,000 |
2607 Lafayette Ave
Welcome to 2607 Lafayette Avenue—a stunning custom home in one of Winter Park’s most desirable neighborhoods. This 4-bedroom, 3.5-bath residence features 2,770 SqFt of open living space with a modern kitchen offering quartz countertops, new appliances, shaker cabinets, and a large island. The fi
Living Area:
2770 Sqft.
|
4
Beds,
4
Baths
|
$1,095,000 |
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
Living Area:
7278 Sqft.
|
5
Beds,
7
Baths
|
$5,495,000 |
1807 MAGNOLIA AVENUE
Under Construction. Under construction with estimated completion in March 2026. New construction in the City of Winter Park! This home has been thoughtfully designed, but there is still time to make personalized finish selections if desired. This deep lot is Winter Park's best kept secret, located i
Living Area:
2618 Sqft.
|
5
Beds,
3
Baths
|
$1,201,000 |
1761 LEGION DRIVE
One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned desi
Living Area:
4955 Sqft.
|
5
Beds,
6
Baths
|
$3,399,999 |
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
Living Area:
1579 Sqft.
|
4
Beds,
2
Baths
|
$345,000 |
2607 LAFAYETTE AVENUE
Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless ent
Living Area:
2770 Sqft.
|
4
Beds,
4
Baths
|
$1,095,000 |
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
Living Area:
3474 Sqft.
|
4
Beds,
4
Baths
|
$1,369,950 |
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
Living Area:
1939 Sqft.
|
4
Beds,
3
Baths
|
$529,000 |
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
Living Area:
8174 Sqft.
|
5
Beds,
8
Baths
|
$10,950,000 |
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
Living Area:
1887 Sqft.
|
3
Beds,
2
Baths
|
$975,000 |
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.
Living Area:
1664 Sqft.
|
4
Beds,
2
Baths
|
$424,900 |
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
Living Area:
4814 Sqft.
|
5
Beds,
4
Baths
|
$1,700,000 |
1400 ALABAMA DRIVE
Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is
Living Area:
7916 Sqft.
|
5
Beds,
9
Baths
|
$5,895,000 |
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
Living Area:
4636 Sqft.
|
4
Beds,
5
Baths
|
$6,600,000 |
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
Living Area:
4875 Sqft.
|
4
Beds,
5
Baths
|
$2,499,000 |