15

Winter Park, FL Open Houses

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  • /46

    $1,100,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 3,839 Sq Ft

    2880 Old Castle Dr, Winter Park, FL 32792

    Welcome to this beautifully designed executive pool home with private in-law quarters, nestled on an oversized corner lot in the gated community of Bear Gully Pointe in Winter Park. Thoughtfully crafted with architectural elegance, this residence features timeless details including plantation shutters, crown molding, and hardwood flooring throughout the first floor.Step inside and be

    Agent Photo

    Jennifer King

    CORCORAN PREMIER REALTY

    (321) 517-2794

    2880 Old Castle Dr, Winter Park, FL 32792
  • /29

    $415,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,354 Sq Ft

    259 Blossom Ln, Winter Park, FL 32789

    Charming Winter Park Block Home with Deeded Access to Lake Killarney – Solid, Updated Systems & Priced for Your Personal Touch!Welcome to this well-built 3-bedroom, 2-bath cement block home in one of Winter Park’s most desirable and established neighborhoods. . . . . . Built in 1954 and lovingly cared for over the years, this home offers strong bones, a functional layout, and major system

    Sherrie Wysong LEGACY REALTY & BROKERS LLC

    259 Blossom Ln, Winter Park, FL 32789
  • /77

    $2,900,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 7 Baths
    • 5,416 Sq Ft

    1401 Green Cove Rd, Winter Park, FL 32789

    This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open interior, situated on a spacious corner lot just moments from Park Avenue. From the moment you step into the grand foyer—with its graceful circular staircase, custom tile work, and rich wood floors—it's clear that every detail of this home was crafted with care.The heart of

    Terry Yonker BUCKEYE REALTY LLC

    1401 Green Cove Rd, Winter Park, FL 32789
  • /37

    $950,000 Open Sun 2AM - 4PM

    • 3 Beds
    • 3.5 Baths
    • 2,116 Sq Ft

    1251 Arlington Place, Winter Park, FL 32789

    STUNNING WINTER PARK TOWNHOME - NO HOA, DESIGNER KITCHEN, PRIVATE BACKYARD OASISWelcome to this rare gem in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home WITH NO HOA! From the moment you walk in, you’ll be impressed by 20-FOOT CEILINGS in the foyer and family room, elegant hardwood floors, and OVERSIZED 8.5-FOOT DOORS

    Brad Barnett ANNE ROGERS REALTY GROUP INC

    1251 Arlington Place, Winter Park, FL 32789
  • /44

    $775,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,637 Sq Ft

    2167 Marsh Sedge Ln, Winter Park, FL 32792

    Nestled within the highly sought-after gated community of Hawks Crest in Winter Park, this rare Florentine model by Meritage Homes offers over 2,600 square feet of modern luxury, comfort, and style on a premium, private lot with no rear neighbors. Designed for today's lifestyle, this two-story contemporary masterpiece delivers both peace and elegance in every detail. As you step inside, you’re

    Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

    2167 Marsh Sedge Ln, Winter Park, FL 32792
  • /42

    $410,000 Open Sun 1AM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,603 Sq Ft

    1734 Willa Cir, Winter Park, FL 32792

    Welcome to 1734 Willa Circle. Come check out this beautifully landscaped 3 bedroom 2 bathroom split plan home. Brand new water heater installed 2025. Roof replaced in 2021. Plumbing re-piped in 2014. Master bathroom updated. Ceiling fans and curtains in most rooms. Large screened porch views your peaceful backyard. Quiet neighborhood with no through traffic. Great Tuskawilla area schools.

    Robert Arnold SAND DOLLAR REALTY GROUP INC

    1734 Willa Cir, Winter Park, FL 32792
  • /13

    $495,000 Open Sun 1PM - 3PM

    • Land
    • 0.76 Acre
    • $651,316 per Acre

    2821 Chantilly Ave, Winter Park, FL 32789

    LAKEFRONT! WINTER PARK! 32789! DOMMERICH, MAITLAND, WINTER PARK HIGH! .75 ACRE INCLUDES RIPARIAN RIGHTS OWNERSHIP LAKE VELLA!

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    2821 Chantilly Ave, Winter Park, FL 32789
  • /23

    $265,000 Open House 8/24

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft

    7707 Country Place Unit 4, Winter Park, FL 32792

    Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

    Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

    7707 Country Place Unit 4, Winter Park, FL 32792
  • /29

    $369,000 Open Sat 1PM - 4PM

    • 2 Beds
    • 1 Bath
    • 1,028 Sq Ft

    1516 Pinewood Dr, Winter Park, FL 32789

    PINEWOOD SUB N/9 LOT 12 BLK AWell-maintained, modest 2-1 home in College Park with carport, deck, and porch. Home materials include laminate and tile flooring, granite kitchen countertops, energy efficient windows, vinyl siding, and metal roof. All appliances included (washer, dryer, refrigerator, dishwasher, oven/stove with range hood, microwave). Also includes backyard garden, working

    Matt Buttner LIST NOW REALTY, LLC

    1516 Pinewood Dr, Winter Park, FL 32789
  • /51

    $799,000 Open Sun 1PM - 4PM

    • 2 Beds
    • 2 Baths
    • 1,143 Sq Ft

    100 S Interlachen Ave Unit 204, Winter Park, FL 32789

    Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious,

    Lois Rawson COLDWELL BANKER RESIDENTIAL RE

    100 S Interlachen Ave Unit 204, Winter Park, FL 32789
  • /47

    $725,000 Open House 8/16

    • 5 Beds
    • 3.5 Baths
    • 3,568 Sq Ft

    7895 Pleasant Pine Cir, Winter Park, FL 32792

    Seller Motivated! Bring any and all offers.Welcome to Your Dream Home in Enclave at Aloma, Winter Park!Step into this stunningly maintained 5-bedroom, 3.5-bathroom residence located in the highly sought-after gated community of Enclave at Aloma. Perfectly positioned with no rear neighbors, this home offers ultimate privacy and tranquility.As you enter, you’ll immediately

    Yvette Hoover ALL REAL ESTATE & INVESTMENTS

    7895 Pleasant Pine Cir, Winter Park, FL 32792
  • /26

    $207,990 Open Sat 10AM - 12PM

    • 2 Beds
    • 1.5 Baths
    • 1,393 Sq Ft

    7466 Canford Ct Unit 25, Winter Park, FL 32792

    MOTIVATED SELLER. Welcome to this cozy and well-maintained condo with a townhome feel nestled in the desirable community of Winter Park. Offering 1,393 square feet of comfortable living space, this 2-bedroom, 1.5-bathroom home features an open-concept layout that creates a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly together, enhanced by Vinyl wood flooring

    Joseph Sipp KELLER WILLIAMS WINTER PARK

    7466 Canford Ct Unit 25, Winter Park, FL 32792
  • /18

    $325,000 Open Sat 12PM - 2PM

    • 1 Bed
    • 1 Bath
    • 823 Sq Ft

    1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789

    $25,000 below appraised value! Walk to Park Ave!! Sip coffee or tea overlooking lush Mead Gardens from your private deck. Unwind beneath vaulted ceilings and skylights, and enjoy life just moments from Rollins College and the vibrant shops and restaurants of Park Avenue. This spacious one-bedroom, one-bath gem features a stylishly updated kitchen with sleek stone counters and a sophisticated tile

    Michelle Richardson KELLER WILLIAMS CLASSIC

    1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789
  • /38

    $245,000 Open Sat 12PM - 3PM

    • 1 Bed
    • 1 Bath
    • 787 Sq Ft

    700 Melrose Ave Unit L23, Winter Park, FL 32789

    Welcome to your serene retreat in the highly desirable Winter Park Gardens community. This beautifully renovated second-floor 1-bedroom, 1-bathroom condo offers an exceptional living experience with modern upgrades and a prime location less than a mile from Park Avenue and Orlando Avenue. Step inside to discover luxury vinyl flooring throughout the entry, living space, and kitchen, complemented

    Elena Sanchez BALDWIN PARK REALTY LLC

    700 Melrose Ave Unit L23, Winter Park, FL 32789
  • /90

    $2,750,000 Open Sat 1PM - 3PM

    • 8 Beds
    • 6 Baths
    • 7,000 Sq Ft

    1860 Via Contessa, Winter Park, FL 32789

    Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Vias neighborhood, offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcoming atmosphere. Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

    Sylvester Harding SIERRA REALTY GROUP LLC

    1860 Via Contessa, Winter Park, FL 32789

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$469,190
Median Single Family Sale Price
$830,000
Median Townhouse Sale Price
$775,000
Median 2 Bedroom Sale Price
$170,000
Median 1 Bedroom Sale Price
$149,000
Average Price Per Sq Ft
$342
Number of Homes for Sale
29
Last 12 months Home Sales
176
Months of Supply
2.00
Median List Price
$634,950
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
5%
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