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| Address | Bed / Bath | Listing Price |
|---|---|---|
1600 PALMER AVENUE
Discover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story residence in sought-after Winter Park. Offered at $1,200,000, this stunning home seamlessly blends modern luxury with thoughtful design.
The heart of this home features a customized chef's kitchen with top-of-the-l
Living Area:
2550 Sqft.
|
3
Beds,
3
Baths
|
$1,200,000 |
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 |
1985 JAPONICA ROAD
One or more photo(s) has been virtually staged. One or more photos were edited virtually. Welcome to 1985 Japonica Rd—your newly reimagined Winter Park retreat! This beautifully updated 4-bedroom, 2-bath home offers a perfect blend of contemporary design, comfort, and smart living. Featuring a NEW
Living Area:
2096 Sqft.
|
4
Beds,
2
Baths
|
$659,900 |
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
|
$430,000 |
1205 MAYFIELD AVENUE
One or more photo(s) has been virtually staged. This beautiful two-story residence is located in the highly desired Temple Heights neighborhood in the heart of Winter Park. Situated on an expansive double lot, this well-maintained home offers over 3,900 sq ft of heated living space and features 5 be
Living Area:
3948 Sqft.
|
5
Beds,
4
Baths
|
$2,490,000 |
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 |
1630 CHESTNUT AVENUE
Discover a fresh take on modern living in one of Winter Park's most admired neighborhoods - the "Tree Streets." This custom three-story LunDev home marries modern minimalism with subtle Dutch Colonial influences, creating a distinctive and inviting retreat. The carefully curated neutral palette sets
Living Area:
3164 Sqft.
|
3
Beds,
5
Baths
|
$1,750,000 |
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 |
1885 TEMPLE DRIVE
Update! ALL NEW Black Steel doors installed 11/2025 and windows with low e-dual pane glass to be installed ($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 steps
Living Area:
3691 Sqft.
|
5
Beds,
4
Baths
|
$2,295,000 |
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 |
2666 DERBYSHIRE ROAD
RENOVATIONS OF THE HIGHEST STANDARD!! Sunshine State Home’s experienced design team continues to exceed the expectations of today’s discerning Buyer’s. The renovation of this classic Mid-Century Maitland home brings delightful charm within a highly sought after NON-HOA neighborhood of Indian
Living Area:
1887 Sqft.
|
3
Beds,
2
Baths
|
$585,000 |
2632 DERBYSHIRE ROAD
**2025 ROOF** | **POOL HOME** Start your new life to one of Orlando's most prestigious suburbs! Located in the heart of Maitland and zoned for great schools! This 4 bedroom, 2 bath home is a sanctuary for a growing family or to start yours. In this stunning home comfort meets timeless charm. Outside
Living Area:
1770 Sqft.
|
4
Beds,
2
Baths
|
$555,000 |
1816 IVY LANE
NEW REDUCED PRICE BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property h
Living Area:
1725 Sqft.
|
4
Beds,
2
Baths
|
$435,000 |
1540 PALM AVENUE
Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright,
Living Area:
3423 Sqft.
|
5
Beds,
4
Baths
|
$1,999,000 |
1920 CARRIGAN AVENUE
Welcome home to 1920 Carrigan Avenue! Located in the highly desirable Winter Park section of Seminole County, this beautifully updated 3-bedroom, 2-bathroom home sits on an oversized 0.22-acre lot with mature trees and no HOA. Inside, you’ll find a modern and inviting space featuring remodeled bat
Living Area:
1242 Sqft.
|
3
Beds,
2
Baths
|
$315,000 |
702 VIA BELLA
Welcome to 702 Via Bella, an impressive 2025 English cottage estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom,
Living Area:
3720 Sqft.
|
4
Beds,
6
Baths
|
$4,250,000 |
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 |
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 |
736 FOREST GLEN COURT
One or more photo(s) has been virtually staged. New Price - Motivated Seller!! Welcome to this beautifully maintained 4-bedroom, 2-bathroom pool home nestled in the heart of Maitland, within sought-after Seminole County. Offering over 1,600 square feet of bright and open living space, this home is d
Living Area:
1647 Sqft.
|
4
Beds,
2
Baths
|
$479,899 |
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 |
1710 ONECO AVENUE
Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5-bedroom, 4.5-bathroom home with bonus room that offers a perfect blend of comfort, and functionality. This exceptiona
Living Area:
3174 Sqft.
|
5
Beds,
5
Baths
|
$1,895,000 |
1150 VIA SALERNO
In the heart of Winter Park’s coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Designed and developed by Steve and Jodie Warrick Konold of Scout & Co., the 3,850 sf layout offers 4 bedrooms &
Living Area:
3850 Sqft.
|
4
Beds,
6
Baths
|
$4,750,000 |
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 |
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 |
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 |
1660 PALMER AVENUE
New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps arou
Living Area:
6406 Sqft.
|
5
Beds,
7
Baths
|
$4,950,000 |
1660 WALNUT AVENUE
Under Construction. Elegant and modern new construction home perfectly situated in beautiful Winter Park. Scheduled for completion in December 2025, this brand new construction home offers a perfect blend of luxury, comfort, and contemporary design. With 4 spacious bedrooms, 3.5 beautifully appointe
Living Area:
2172 Sqft.
|
4
Beds,
4
Baths
|
$1,759,000 |
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 |