898 ft
Distance
Cortland Park, Winter Park, FL, USA
Winter Park, Florida, United States
Homes for sale near Cortland Park, Winter Park, FL, USA
| Address | Bed / Bath | Listing Price |
|---|---|---|
1807 YORKSHIRE DRIVE
Under Construction. Location, location, location! Nestled in Winter Park, this home is convenient to the best in shopping, dining and entertainment! The two-story Easterly design hosts four bedrooms, four full bathrooms, one half baths, study and sits on an oversized homesite. The open concept livin
Living Area:
3565 Sqft.
|
4
Beds,
5
Baths
|
$1,450,000 |
1909 EDWIN BOULEVARD
The house is located in great location and features 3 bedrooms, 2 bathrooms. It sits on a corner lot and offers high ceilings throughout.
Living Area:
1355 Sqft.
|
3
Beds,
2
Baths
|
$440,000 |
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 |
1030 N LAKEMONT AVE.
Visit this charming one-story Winter Park home across from the Winter Park YMCA. Enter this adorable single-story home with a comfortable primary suite and two oversized bedrooms. The home boasts a wonderful backyard for outdoor living and a welcoming front porch that welcomes you in. The home has n
Living Area:
1050 Sqft.
|
3
Beds,
2
Baths
|
$425,000 |
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 |
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 |
102 BELL PLACE
One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen
Living Area:
2459 Sqft.
|
4
Beds,
4
Baths
|
$1,499,000 |
525 S LAKEMONT AVENUE
Under Construction. Winter Park Luxury Awaits You!
Welcome to your dream home—a stunning custom-built luxury residence offering the perfect blend of elegance, comfort, and modern design. Featuring 4 spacious bedrooms and 4 beautifully appointed bathrooms, this masterpiece showcases custom cabin
Living Area:
3330 Sqft.
|
4
Beds,
4
Baths
|
$2,350,000 |
2015 SUMMERFIELD ROAD
Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL.
Insid
Living Area:
3024 Sqft.
|
4
Beds,
4
Baths
|
$1,375,000 |
1450 GLENCOE ROAD
Comfort, charm, and LOCATION are KEY for this unique, one-story, KEY West-style pool home with deeded access to Lake Virginia! Nestled on a brick-lined street in the highly sought-after Virginia Heights neighborhood, this location is truly one-of-a-kind, engulfed in the beloved culture and history o
Living Area:
2785 Sqft.
|
4
Beds,
3
Baths
|
$1,625,000 |
1661 PALM AVENUE
Introducing a stunning new custom home by Ellsworth Gallimore and Butler Ridge Development, ideally situated in a prime Winter Park neighborhood. This residence combines timeless elegance with modern luxury, showcasing exceptional design and craftsmanship throughout. The thoughtfully designed home
Living Area:
3570 Sqft.
|
4
Beds,
6
Baths
|
$2,400,000 |
2412 MIDDLETON AVENUE
Gorgeous move in ready or spacious corner lot to build your Dream Home, fully updated 3 bedroom, 2 full bath , corner lot home in a coveted Winter Park neighborhood! The interior is completely renovated throughout, including kitchen with stone countertops, two year old appliances, all new bathrooms
Living Area:
1340 Sqft.
|
3
Beds,
2
Baths
|
$569,000 |
1822 GREENWICH AVENUE
Rare opportunity in the heart of Winter Park! This property sits on a double lot (0.29 acres) — a true rarity in this highly desirable location. The existing 1953 concrete-block home (3 bed / 2 bath) with an attached garage apartment (studio + bath) and shared 2-car carport offers little to no cur
Living Area:
1627 Sqft.
|
3
Beds,
2
Baths
|
$1,199,900 |
132 BURKS CIRCLE
Experience refined living in this completely remodeled single story residence located in the heart of Winter Park. Enjoy luxury living in this impeccably maintained home. This beauty offers three spacious bedrooms and three beautifully appointed baths. Enter the spacious floorplan featuring open li
Living Area:
3022 Sqft.
|
4
Beds,
5
Baths
|
$1,675,000 |
516 HENKEL CIRCLE
This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. Situated on a 1.32 acre lot, the property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local a
Living Area:
4143 Sqft.
|
5
Beds,
6
Baths
|
$3,599,000 |
550 PALMER AVENUE
Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceive
Living Area:
5939 Sqft.
|
5
Beds,
7
Baths
|
$7,200,000 |
633 BALMORAL ROAD
An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area’s private and pristine ski lakes with no public boat ramp, this property offers a rare combination of privacy, location and potential. Set on over a half
Living Area:
2674 Sqft.
|
4
Beds,
3
Baths
|
$1,875,000 |
1861 TAYLOR AVENUE
Built by Meridian Homes in 2023, this newer construction, five-bedroom, five full- and two half-bath residence combines timeless coastal architecture with a fresh, modern sensibility. Designed by Lauren Ayers Interiors, every detail of this home exudes style, sophistication and livable refinement. A
Living Area:
3116 Sqft.
|
5
Beds,
7
Baths
|
$1,925,000 |
428 SELKIRK DRIVE
One or more photo(s) has been virtually staged. Income-Producing Opportunity! Welcome to this versatile Winter Park POOL HOME! At present, this property is split into two separate living quarters with the main house offering 3 bedrooms & 2 bathrooms and the adjoining guest suite offering 1 bedroom &
Living Area:
1782 Sqft.
|
4
Beds,
3
Baths
|
$650,000 |
1581 FOREST AVENUE
Located just steps from Park Avenue, this extraordinary Winter Park residence was fully rebuilt in 2018 by master custom builder Posada Homes. Set on a 0.39-acre lot along one of Winter Park’s most desirable tree-lined streets, the home makes an immediate impression with its elegant architecture a
Living Area:
4683 Sqft.
|
4
Beds,
6
Baths
|
$3,775,000 |
1120 PRESERVE POINT DRIVE
In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely foun
Living Area:
11255 Sqft.
|
7
Beds,
11
Baths
|
$8,950,000 |
457 E NEW ENGLAND AVENUE
Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, set
Living Area:
3847 Sqft.
|
5
Beds,
5
Baths
|
$3,100,000 |
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 |
340 ALBERTA DRIVE
Welcome to 340 Alberta Drive, a beautifully maintained 4-bedroom, 4-bath residence with a new roof installed in 2020. Situated on a spacious .30-acre lot in the heart of Winter Park, this home features an open and functional layout with all the bedrooms on the main floor and a versatile upstairs bon
Living Area:
3226 Sqft.
|
4
Beds,
4
Baths
|
$1,598,000 |
2330 COLDSTREAM DRIVE
Modern luxury meets Winter Park charm — fully renovated 4BR/2BA with $20K seller credit with full price purchase! This beautifully reimagined 4-bedroom, 2-bath home has undergone a complete transformation. Every detail thoughtfully designed and executed. From brand-new plumbing, electrical, and HV
Living Area:
1750 Sqft.
|
4
Beds,
2
Baths
|
$649,900 |
825 PALMER AVENUE
825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly po
Living Area:
3297 Sqft.
|
3
Beds,
3
Baths
|
$1,799,000 |
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 |
250 Cortland Avenue
Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-mainten
Living Area:
2114 Sqft.
|
3
Beds,
2
Baths
|
$950,000 |
1740 ANZLE AVENUE
PROPERTY AS-IS -
DEMO AND NEW-BUILD PLANS APPROVED
*Property with all demo permits and build plans approved ready for a new build*
Nestled in the heart of Winter Park’s coveted 32789 ZIP code, this stunning new possibility offers the epitome of luxury living in one of Central Florida’s mos
Living Area:
1808 Sqft.
|
4
Beds,
3
Baths
|
$580,000 |
1161 VALENCIA AVENUE
Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedro
Living Area:
4181 Sqft.
|
4
Beds,
5
Baths
|
$4,545,000 |
887 GEORGIA AVENUE
Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park
Living Area:
5759 Sqft.
|
6
Beds,
6
Baths
|
$5,900,000 |
208 BREWER AVENUE
Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thoughtfully designed living space. From the moment you arrive, the charm is undeniable—with classic architectural details and a welcoming front porch that set the tone for what’s ins
Living Area:
2173 Sqft.
|
4
Beds,
4
Baths
|
$925,000 |
620 DARCEY DR
New Roof installed July 2025. Preferred lender to offer a credit up to $5k for qualified buyers. Charming brick Winter Park home in the desirable Brookshire Heights neighborhood. Four bedrooms, two baths, over 2,076 square feet of natural sunlight flowing throughout, enclosed back porch and a fully
Living Area:
2076 Sqft.
|
4
Beds,
2
Baths
|
$730,000 |
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 |
617 WORTHINGTON DRIVE
WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivati
Living Area:
3533 Sqft.
|
5
Beds,
5
Baths
|
$1,799,000 |
446 ALBERTA DRIVE
Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar home
Living Area:
3263 Sqft.
|
4
Beds,
3
Baths
|
$1,750,000 |
1112 PRESERVE POINT DRIVE
Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary
Living Area:
6502 Sqft.
|
5
Beds,
6
Baths
|
$8,500,000 |
541 W CANTON AVENUE
Timeless elegance meets boutique craftsmanship at 541 W Canton Avenue—an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Located just steps from Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm
Living Area:
3553 Sqft.
|
4
Beds,
4
Baths
|
$2,935,000 |
1840 BRYAN AVENUE
This custom 2014 built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all that Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophis
Living Area:
3727 Sqft.
|
4
Beds,
4
Baths
|
$1,899,500 |
1399 ALOMA AVENUE
***Price Adjustment *** Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on a private lot in the heart of Winter Park, moments from Rollins College, Park Avenue, and Winter Park Hospital. Just a short walk provides coveted access
Living Area:
1804 Sqft.
|
3
Beds,
2
Baths
|
$665,000 |
1560 WOODLAND AVENUE
You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick-paved street. There are five bedrooms and four and a half bathrooms spread out over 3,800 square feet in this stunning property. Featuring a welcoming pool
Living Area:
3851 Sqft.
|
5
Beds,
5
Baths
|
$1,999,000 |
250 CORTLAND AVENUE
Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-mainten
Living Area:
2114 Sqft.
|
3
Beds,
2
Baths
|
$950,000 |
607 DUNBLANE DRIVE
Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunni
Living Area:
2046 Sqft.
|
4
Beds,
3
Baths
|
$675,000 |
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 |
625 BRECHIN DRIVE
PICTURE PERFECT HOME IN WINTER PARK’S KENILWORTH SHORES! Homes of this quality and preservation hardly come on the market – this immaculately kept, 3-bedroom, 2 bath home offers 1,827 SF and a stunning backyard oasis! Interior offers a spacious living room, dining room, and Florida room. The elo
Living Area:
1827 Sqft.
|
3
Beds,
2
Baths
|
$765,000 |
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 |
