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Looking for delicious cookies in Winter Park, Florida? Check out Crumbl Cookies! This popular retail bakery offers a variety of tasty treats that are sure to satisfy your sweet tooth. With a focus on quality and flavor, Crumbl Cookies is a must-visit destination for cookie lovers in Winter Park.
| Address | Bed / Bath | Listing Price |
|---|---|---|
875 W LYMAN AVENUE
Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice
Living Area:
760 Sqft.
|
2
Beds,
2
Baths
|
$475,000 |
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 |
870 CARVER STREET
Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-s
Living Area:
1875 Sqft.
|
3
Beds,
3
Baths
|
$975,000 |
1033 HAMLET DRIVE
This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels,
Living Area:
1146 Sqft.
|
3
Beds,
2
Baths
|
$350,000 |
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 |
2612 ROXBURY ROAD
SELLER MOTIVATED!! CONTRIBUTING $10,000 FLEX CASH!!! Potential of an extra one percent for closing costs, just ask your agent!!
A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open
Living Area:
2472 Sqft.
|
5
Beds,
3
Baths
|
$800,000 |
1150 KENWOOD AVENUE
Nestled in the heart of Winter Park, this exquisite 3-bedroom, 2.5-bath residence offers 2,557 square feet of beautifully designed living space along with a spacious 2-car garage. Situated on a charming, tree-lined brick street just minutes from Park Avenue, the home’s first level includes a welco
Living Area:
2557 Sqft.
|
3
Beds,
3
Baths
|
$1,190,000 |
607 ELLEN DRIVE
Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural
Living Area:
2812 Sqft.
|
4
Beds,
5
Baths
|
$1,630,000 |
1655 SUNNYSIDE DRIVE
Welcome to 1655 Sunnyside Drive, a beautifully charming home nestled on a picturesque corner lot in the heart of Maitland. Set on classic brick-lined roads, this 3-bedroom, 2-bathroom residence offers 1,418 square feet of thoughtfully designed living space filled with character and warmth. From the
Living Area:
1418 Sqft.
|
3
Beds,
2
Baths
|
$699,000 |
259 BLOSSOM LANE
No HOA! Fully Renovated Home with Deeded Lake Access to Lake Killarney in Prime Winter Park Location! Welcome to this move-in ready gem nestled in one of Winter Park’s most coveted neighborhoods. This solid concrete block home has been thoughtfully updated with timeless finishes, featuring a brand
Living Area:
1354 Sqft.
|
3
Beds,
2
Baths
|
$499,000 |
1007 EARLY AVENUE
Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bathroom home. Thoughtfully maintained, this home combines character with modern comfort. Step inside to find inviting living spaces and enjoy peace of mind with a roof replaced in 2019. The spacious backyard is p
Living Area:
1721 Sqft.
|
3
Beds,
2
Baths
|
$425,000 |
1302 RAINTREE PLACE
An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue.
A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with el
Living Area:
4738 Sqft.
|
5
Beds,
6
Baths
|
$5,300,000 |
1510 MILLER AVENUE
Under Construction. New Construction – Modern Luxury Meets Urban Living at Winter Park's Newest Neighborhood, Winter Park Grove!
Step into the future of refined living with this stunning new construction pool home, situated in the vibrant heart of Winter Park. Just minutes from the eclectic energ
Living Area:
3252 Sqft.
|
5
Beds,
5
Baths
|
$1,634,900 |
1540 MILLER AVENUE
Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community!
This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shop
Living Area:
2984 Sqft.
|
4
Beds,
4
Baths
|
$1,399,900 |
183 ORANGE PLACE
This exquisite attached single family home blends contemporary elegance with unbeatable convenience in a truly coveted Maitland address. Just a stroll from Maitland Preparatory School and mere minutes from the vibrant heart of Downtown Winter Park, this residence offers the best of both worlds. From
Living Area:
2014 Sqft.
|
3
Beds,
4
Baths
|
$845,000 |
2001 LAKE DRIVE
Nestled on a quiet cul-de-sac in the heart of Winter Park, this canal-front residence offers the perfect balance of elegance and lifestyle. With direct access to Lake Killarney, the home invites days filled with boating, fishing, and entertaining poolside. Offering a total of 4,798 heated square fee
Living Area:
4798 Sqft.
|
5
Beds,
4
Baths
|
$2,165,000 |
1875 STAUNTON AVENUE
Welcome to this newer single-family home tucked away in the Karolina On Killarney section of Winter Park. Situated on a generously sized .16 acre lot with no HOA, this property offers both privacy and optimal convenience. Enjoy hopping over to Park Avenue for shopping and restaurants or to the weekl
Living Area:
2036 Sqft.
|
4
Beds,
3
Baths
|
$560,000 |
1525 GRANVILLE DRIVE
Under Construction. Just steps from the boutiques and fine dining of Park Avenue, this brand-new bespoke estate by acclaimed builder Vimaro Homes delivers a rare combination of architectural sophistication and thoughtful design. Perfectly positioned on an oversized 0.34-acre lot, the residence encom
Living Area:
5211 Sqft.
|
5
Beds,
6
Baths
|
$4,750,000 |
1166 OAKS BOULEVARD
HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxur
Living Area:
2860 Sqft.
|
4
Beds,
4
Baths
|
$1,649,999 |
720 W WEBSTER AVENUE
Discover the charm of Winter Park living in this beautifully maintained 1950s home, where convenience and comfort meet modern updates. Just minutes from Park Avenue and Winter Park Village, this 3-bedroom, 2-bath residence offers a lifestyle surrounded by boutique shopping, dining, and cultural expe
Living Area:
1356 Sqft.
|
3
Beds,
2
Baths
|
$575,000 |
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 |
Lot #21 KAROLINA AVE
Pre-Construction. To be built. Step into a life where charm meets convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath, 2,662 sq. ft. home is situated on a 6,748 sq. ft. lot and is a thoughtfully designed masterpiece, blending elegant country charm with the comfort and functio
Living Area:
2662 Sqft.
|
4
Beds,
4
Baths
|
$916,050 |
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 |
1074 HAMLET DRIVE
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer
Living Area:
1076 Sqft.
|
3
Beds,
2
Baths
|
$308,000 |
501 LAKEVIEW AVENUE
Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the ma
Living Area:
3253 Sqft.
|
4
Beds,
5
Baths
|
$1,390,000 |
525 LAKEVIEW AVENUE
Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-su
Living Area:
3253 Sqft.
|
4
Beds,
5
Baths
|
$1,390,000 |
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 |
922 N PENNSYLVANIA AVENUE
Experience timeless elegance and modern sophistication in this stunning 3 bedroom, 4 bath Mediterranean home, ideally situated on the 4th hole of the beautifully maintained Winter Park 9-hole golf course. Nestled on a 75 x 100 lot, this 3,440 sq ft residence was extensively renovated in 2017. From t
Living Area:
3440 Sqft.
|
3
Beds,
4
Baths
|
$2,175,000 |
1018 TURNER ROAD
Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat l
Living Area:
2237 Sqft.
|
3
Beds,
2
Baths
|
$835,000 |
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 |
720 N PENNSYLVANIA AVENUE
Nestled in one of Winter Park’s most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern elegance with everyday comfort. From the moment you step inside, you'll be captivated by the sleek, contemporary finishes, recessed lighting, and stylish fixtures that enhance ever
Living Area:
1115 Sqft.
|
3
Beds,
2
Baths
|
$550,000 |
726 N PENNSYLVANIA AVENUE
Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of modern elegance and prime location. The gourmet kitchen boasts 42” black cabinets, granite countertops, a decorative backsplash, and stainless steel appliances, making it a stunning focal point of the home. The op
Living Area:
1167 Sqft.
|
3
Beds,
2
Baths
|
$695,000 |
726/720 N PENNSYLVANIA AVENUE
Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms an
Living Area:
2284 Sqft.
|
6
Beds,
4
Baths
|
$1,215,000 |
1451 LYNDALE BOULEVARD
**Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor!
Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home,
Living Area:
3853 Sqft.
|
6
Beds,
4
Baths
|
$1,999,993 |