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| Address | Bed / Bath | Listing Price |
|---|---|---|
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 |
714 DENTON ROAD
Welcome home to this charming 3-bedroom, 3-bathroom single-family residence nestled in the quiet, established neighborhood of Winter Park Estates. Boasting the highly desirable Winter Park school district, this location offers both prestige and tranquility, yet is conveniently located near major roa
Living Area:
1786 Sqft.
|
3
Beds,
3
Baths
|
$449,900 |
801 ELLENDALE DRIVE
Step into this light, bright Mid-Century gem tucked inside Winter Park Estates, one of Winter Park’s most desirable neighborhoods. With top A-rated schools and that classic community feel everyone wants, this is the home you have been waiting for. This solid concrete block 3-bedroom, 2-bath home
Living Area:
1516 Sqft.
|
3
Beds,
2
Baths
|
$395,000 |
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 |
2189 SUSSEX ROAD
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged.
Welcome to your new home at 2189 Sussex Rd, a beautifully home in the Winter Woods community. The primary suite offers its own private balcony that overlooks the pool and spacious backyard. It is a qui
Living Area:
1776 Sqft.
|
4
Beds,
3
Baths
|
$569,990 |
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 |
1605 PURITAN AVENUE
Charming Winter Park block home featuring 3 bedrooms, 2 bathrooms, and a versatile enclosed Florida room—perfect for a home office, playroom, or additional living space. Recently updated with a brand-new roof (June 2025), fresh paint, and remodeled interior, this home is move-in ready. Ideally loc
Living Area:
1285 Sqft.
|
3
Beds,
2
Baths
|
$347,500 |
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 |
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 |
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
|
$2,598,000 |
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 |
2920 ABBEY COURT
Completely Renovated and Move-In Ready! A rare found NO HOA Winter Park POOL home with top rated schools.. This 5-bedroom, 3-bath pool home has been renovated from top to bottom—featuring: NEW ROOF 2025, NEW FLOORING, KITCHEN & BATHS (2025), QUARTZ COUNTER TOPS (2025),FRESH INTERIOR & EXTERIOR PA
Living Area:
2312 Sqft.
|
5
Beds,
3
Baths
|
$650,000 |
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 |
2152 CONIFER AVENUE
This POOL home is amazing in every way and is truly a must see! Original Owner with incredible pride of ownership. Brand NEW Roof, Brand NEW Water Heater, HVAC 2020, entire replumb and newer windows throughout. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location j
Living Area:
1694 Sqft.
|
3
Beds,
2
Baths
|
$460,000 |
1923 LINDEN ROAD
Welcome to 1923 Linden Road, a charming mid-century single-family home nestled in Winter Park’s beloved Tanglewood neighborhood. This beautifully maintained residence offers 2,117 square feet of living space on a generous 0.31-acre lot, blending classic character with modern upgrades.
Step insi
Living Area:
2117 Sqft.
|
4
Beds,
3
Baths
|
$515,000 |
1816 IVY LANE
*More than one of the photos has been virtually staged. DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! SEMINOLE COUNTY TAX DISTRICT BUT WINTER PARK ADDRESS. ZONED TO ALLOW AIRBNB/VRBO SHORT TERM RENTALS (STR)! This is probably the closet you can get to Winter Park (Park Ave) without having
Living Area:
1725 Sqft.
|
4
Beds,
2
Baths
|
$435,500 |
1422 TIERRA CIRCLE
PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent opportunity for qualified Buyers. Welcome to 1422 Tierra Circle, beautifully refreshed immaculate pool home located in the well-established community of Casa Aloma, featuring 4 bedro
Living Area:
1827 Sqft.
|
4
Beds,
2
Baths
|
$499,000 |
1670 CLEMATIS LANE
This stunning home has been completely renovated and is ready for you to move in! Featuring 3 bedrooms, 2 full bathrooms, and a screened-in pool with a spacious deck, it blends modern style with everyday comfort. Inside, you’ll find brand-new waterproof laminate flooring, fresh paint throughout, a
Living Area:
1401 Sqft.
|
3
Beds,
2
Baths
|
$399,900 |
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 |
3319 ELLWOOD COURT
The pool home you’ve been waiting for is here! Welcome to this beautifully renovated 5-bedroom, 3-bathroom home offering 1,546 SF of living space, abundant natural light in every room, a spacious screened porch, a private pool, and a Mother-in-law Suite with its own private entrance—perfect for
Living Area:
1546 Sqft.
|
5
Beds,
3
Baths
|
$480,000 |
1842 PURITAN AVENUE
Modern design, Open concept layout, Sleek quartz counter top, All new appliances, New luxury vinyl plank flooring, New lanai upgrade. This beautiful 4 bedrooms and 2 full bath is situated on a 8,250 square feet lot was newly fenced in 2024 which gives a sense of privacy and spaciousness as you enter
Living Area:
1836 Sqft.
|
4
Beds,
2
Baths
|
$439,000 |
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 |
1914 BONANZA COURT
Welcome to your winter Park retreat!
Step into this beautifully renovated 3 bedroom, 2 bathroom home where modern meets timeless comfort. Designed with an open floor plan, the living space flows seamlessly, making it perfect for both entertaining and everyday living.
The brand new kitchen shin
Living Area:
1727 Sqft.
|
3
Beds,
2
Baths
|
$437,500 |
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 |
1362 TIERRA CIRCLE
Welcome to this unique 4-bedroom ranch-style home in the heart of Winter Park! This residence offers flexibility and comfort for today’s lifestyle. The converted two-car garage has been transformed into an additional bedroom with separate entrance, perfect for guests or an in-law suite. Inside, th
Living Area:
2179 Sqft.
|
4
Beds,
3
Baths
|
$399,000 |
616 ELLENDALE DRIVE
Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living
Living Area:
1405 Sqft.
|
3
Beds,
2
Baths
|
$419,900 |
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 |
5236 LAKE HOWELL ROAD
Experience the best of Winter Park living in this stunning new custom-built pool home situated on a generous .29-acre lot just 1.9 miles from Park Avenue. Designed with a modern aesthetic and built to the highest standards, this 4-bedroom, 3-bath residence is a true showcase of craftsmanship and lux
Living Area:
3710 Sqft.
|
4
Beds,
3
Baths
|
$1,185,000 |
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 |
2708 LION HEART ROAD
$10,00 credit being offered for buyers prepaids and closing costs. Here is a fantastic home in Winter Park Pines, a well-established and sought after community and location in Winter Park! This property is located on a corner lot and has a private pool as well as a two-car garage. This a great way t
Living Area:
1785 Sqft.
|
3
Beds,
2
Baths
|
$525,000 |
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 |
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 |
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 |
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 |
2835 BONGART ROAD
Seller is Motivated, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurf
Living Area:
1880 Sqft.
|
3
Beds,
3
Baths
|
$449,900 |
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 |
701 DENTON ROAD
Motivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Park Estates! Nestled on a quarter-acre lot, step into your private creating memories that last! This exceptional property has been meticulously maintained and enhanced with high-end features, making it a true s
Living Area:
2268 Sqft.
|
3
Beds,
2
Baths
|
$565,000 |
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 |
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 |
2627 AMBERGATE ROAD
Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in!
Investors -- You will love the cash flow upside with this property.
Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more.
You will enjoy en
Living Area:
1805 Sqft.
|
4
Beds,
3
Baths
|
$510,000 |