165

Winter Park, FL 2-Story Homes for Sale

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  • /19

    $179,700

    • 2 Beds
    • 2 Baths
    • 1,003 Sq Ft

    1000 S Semoran Blvd Unit 805, Winter Park, FL 32792

    Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy

    Agent Photo

    Carrie Shawfield

    SHAWFIELD REALTY GROUP

    (321) 334-3379

    1000 S Semoran Blvd Unit 805, Winter Park, FL 32792
  • /41

    $245,000

    • 2 Beds
    • 2 Baths
    • 956 Sq Ft

    2500 Lee Rd Unit 229, Winter Park, FL 32789

    DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    (321) 252-5096

    2500 Lee Rd Unit 229, Winter Park, FL 32789
  • /36

    $269,900

    • 2 Beds
    • 2 Baths
    • 1,495 Sq Ft

    2501 Tahoe Cir Unit 32501, Winter Park, FL 32792

    Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location.The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning

    Agent Photo

    Sarah Doyer

    COLDWELL BANKER REALTY

    (321) 510-4129

    2501 Tahoe Cir Unit 32501, Winter Park, FL 32792
  • /42

    $435,000

    • 3 Beds
    • 3 Baths
    • 2,346 Sq Ft

    2224 Shadowland Loop, Winter Park, FL 32792

    **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (321) 450-7733

    2224 Shadowland Loop, Winter Park, FL 32792
  • /33

    $845,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft

    1090 Wildmeadow Run, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps

    Agent Photo

    Rod Chevalier

    BHHS FLORIDA REALTY

    (321) 468-9784

    1090 Wildmeadow Run, Winter Park, FL 32792
  • /44

    $830,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 3,020 Sq Ft

    1183 Wildmeadow Run, Winter Park, FL 32792

    Welcome to this original-owner residence in The Meadows at Hawk’s Crest, where thoughtful design and exceptional privacy come together—featuring two true primary suites, one on the first floor and one on the second. Set on an oversized fenced homesite along a quiet non-thru street with no neighbor to the east, this beautifully maintained 4-bedroom, 3.5-bath home offers over 3,020 sq.ft. of living

    Agent Photo

    Kara Lushear

    COLDWELL BANKER REALTY

    (321) 621-0024

    1183 Wildmeadow Run, Winter Park, FL 32792
  • /21

    $255,000

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1500 Gay Rd Unit 18A, Winter Park, FL 32789

    REDUCED! Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard and Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has Cabinets matching those in Kitchen and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    (321) 449-7958

    1500 Gay Rd Unit 18A, Winter Park, FL 32789
  • /21

    $264,000

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1500 Gay Rd Unit 24B, Winter Park, FL 32789

    ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    (321) 450-8960

    1500 Gay Rd Unit 24B, Winter Park, FL 32789
  • /33

    $220,000

    • 2 Beds
    • 2 Baths
    • 953 Sq Ft

    225 Lewfield Cir, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (321) 237-3113

    225 Lewfield Cir, Winter Park, FL 32792
  • /40

    $2,650,000 Open Tue 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 4,011 Sq Ft

    1130 Park North Place, Winter Park, FL 32789

    Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The

    Agent Photo

    Jennifer King

    CORCORAN PREMIER REALTY

    (321) 257-9480

    1130 Park North Place, Winter Park, FL 32789
  • /22

    $262,000

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1500 Gay Rd Unit 20D, Winter Park, FL 32789

    LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    (689) 399-5336

    1500 Gay Rd Unit 20D, Winter Park, FL 32789
  • /60

    $574,000

    • 3 Beds
    • 2.5 Baths
    • 1,640 Sq Ft

    5441 Baldwin Park St, Orlando, FL 32814

    Welcome to Baldwin Park - a desirable, centrally-located Community loaded with Amenities! Picture yourself on these tree-line streets enjoying one of three Pools, Clubhouses, Exercise Facility, Parks, Playgrounds, Bike Trails, the Gazebo and Fountain on Lake Baldwin, access to Cady Way Trail and The Town Center with it's shopping and Restaurants. Top-Rated Schools within the Community!Now,

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    (407) 904-4080

    5441 Baldwin Park St, Orlando, FL 32814
  • /5

    $1,825,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 3,655 Sq Ft

    2305 Coldstream Dr, Winter Park, FL 32792

    Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and entertaining alike. All bedrooms are

    Agent Photo

    Jennifer King

    CORCORAN PREMIER REALTY

    (321) 490-4786

    2305 Coldstream Dr, Winter Park, FL 32792
  • /71

    $699,900

    • 4 Beds
    • 3 Baths
    • 2,702 Sq Ft

    3114 Heartleaf Place, Winter Park, FL 32792

    Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

    Nadia Kurakin CHAMPION HOMES

    3114 Heartleaf Place, Winter Park, FL 32792
  • /94

    $4,195,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,665 Sq Ft

    2020 Via Tuscany, Winter Park, FL 32789

    PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5

    Mauro Costa CORCORAN PREMIER REALTY

    2020 Via Tuscany, Winter Park, FL 32789
  • /26

    $285,000

    • 2 Beds
    • 2.5 Baths
    • 1,495 Sq Ft

    2401 Sun Valley Cir, Winter Park, FL 32792

    Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and

    Jamie Vanosdol EXP REALTY LLC

    2401 Sun Valley Cir, Winter Park, FL 32792
  • /44

    $850,000

    • 4 Beds
    • 3.5 Baths
    • 3,020 Sq Ft

    1287 Verdant Glade Place, Winter Park, FL 32792

    This beautiful home is in the gated Hawk's Crest community of Winter Park. Built in 2020, the spacious layout gives everyone plenty of room to spread out featuring NO CARPET and a LARGE SCREENED LANAI. The open floor plan is perfect for everyday living and entertaining, with a beautiful kitchen that flows into the main living area and plenty of natural light throughout the home. The primary suite

    Megan Hedrick Mark Spain Real Estate

    1287 Verdant Glade Place, Winter Park, FL 32792
  • /84

    $2,850,000 Open Fri 4PM - 6PM

    • 4 Beds
    • 6 Baths
    • 4,356 Sq Ft

    1529 Holts Grove Cir, Winter Park, FL 32789

    Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by

    Kristin Vogt PLLC KGV REALTY GROUP

    1529 Holts Grove Cir, Winter Park, FL 32789
  • /38

    $1,795,000

    • 3 Beds
    • 3.5 Baths
    • 2,399 Sq Ft

    621 Huntington Ave, Winter Park, FL 32789

    Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors,

    Noelle LeBlanc OLDE TOWN BROKERS INC

    621 Huntington Ave, Winter Park, FL 32789
  • /56

    $2,850,000

    • 5 Beds
    • 5.5 Baths
    • 4,389 Sq Ft

    1300 Mayfield Ave, Winter Park, FL 32789

    Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately 1⁄2-acre corner lot and has been enhanced with thoughtful improvements, delivering a rare combination of modern functionality, Old World charm, and a fabulous lifestyle. Notable updates include newer HVAC systems (2020 and 2025), a tankless gas water heater, a fully renovated laundry room with new

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1300 Mayfield Ave, Winter Park, FL 32789
  • /66

    $3,250,000

    • 5 Beds
    • 4.5 Baths
    • 5,243 Sq Ft

    141 Glenridge Way, Winter Park, FL 32789

    Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive

    Mary Colton FANNIE HILLMAN & ASSOCIATES

    141 Glenridge Way, Winter Park, FL 32789
  • /30

    $257,000

    • 2 Beds
    • 2.5 Baths
    • 959 Sq Ft

    Unlisted Address

    One or more photo(s) has been virtually staged. Welcome to one of the most affordable opportunities to own in the highly sought-after Winter Park High School district. This well-maintained community is tucked into a beautiful setting and is extremely convenient to everything that makes Winter Park one of Central Florida's top lifestyle destinations. This end-unit two bedroom / two-and-a-half bath

    Mike Derenthal DERENTHAL REALTY

    Unlisted Address
  • /40

    $1,630,000

    • 3 Beds
    • 3.5 Baths
    • 3,174 Sq Ft

    101 S New York Ave Unit 302, Winter Park, FL 32789

    Discover unparalleled luxury at The Douglas Grand, a distinguished location just a stone’s throw from Park Ave in Downtown Winter Park. This expansive 2-Story unit boasts 3,174 sq/ft of living space with your private elevator. From the moment you step inside, you’ll be captivated by the exquisite craftmanship and modern comforts that define this exceptional residence. This stunning condo boast

    Julie Scott COLDWELL BANKER REALTY

    101 S New York Ave Unit 302, Winter Park, FL 32789
  • /44

    $845,000

    • 5 Beds
    • 3.5 Baths
    • 3,188 Sq Ft

    2175 Marsh Sedge Ln, Winter Park, FL 32792

    Beautifully designed and impeccably maintained, this light-filled home offers the perfect blend of modern comfort and timeless style. Featuring an open and airy layout, the home is highlighted by abundant natural light, neutral designer finishes, and thoughtfully curated living spaces throughout. The bright and inviting living area flows seamlessly, creating the ideal space for both everyday

    Liz Jones ORANGE SLICE PROPERTIES

    2175 Marsh Sedge Ln, Winter Park, FL 32792
  • /28

    $825,000

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft

    1131 Wildmeadow Run, Winter Park, FL 32792

    Taylor Morrison, Anastasia Model, 4 bdrm 3.5 baths on premium lot overlooking pond in the Meadows at Hawk's Crest. Large, spacious open floor plan with 20'+ ceilings, plantation shutters and builtins. Gourmet kitchen with pantry opens to dining area overlooking the great room. Master suite downstairs, laundry room, and half bath. Upstairs 3 bedrooms and 2 baths including an additional primary

    Joann Beck BECK REALTY LLC

    1131 Wildmeadow Run, Winter Park, FL 32792
  • /39

    $1,690,000

    • 4 Beds
    • 3.5 Baths
    • 3,048 Sq Ft

    1570 Palmer Ave, Winter Park, FL 32789

    Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functionality. Designed for both everyday living and entertaining, the home features an open and inviting floor plan filled with natural light and high-end finishes throughout. The gourmet kitchen is equipped with granite countertops,

    David Auerbach PARK TOWN REAL ESTATE LLC

    1570 Palmer Ave, Winter Park, FL 32789
  • /2

    $120,000

    • 2 Beds
    • 1 Bath

    1695 Lee Rd Unit B204, Winter Park, FL 32789

    2 bedroom, 2 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. Unit is long-term tenant occupied, offering immediate rental income for an investor buyer. Interior is in original condition and presents an excellent opportunity for updates and value enhancement. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village,

    Mauricio Toro MTRE GROUPE LLC

    1695 Lee Rd Unit B204, Winter Park, FL 32789
  • /46

    $1,899,500

    • 4 Beds
    • 3.5 Baths
    • 3,727 Sq Ft

    1840 Bryan Ave, Winter Park, FL 32789

    This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all 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 sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    1840 Bryan Ave, Winter Park, FL 32789
  • /47

    $1,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,249 Sq Ft

    1750 Carollee Ln, Winter Park, FL 32789

    Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. In one of Winter Park’s established neighborhoods, residents enjoy access to top-rated schools, tree-lined streets, and proximity to Park Avenue’s renowned dining and shopping, as well as the area’s scenic Chain of Lakes. Originally built in 2012, this four-bedroom, 3.5-bath home offers over 3,200 square feet of thoughtfully

    Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

    1750 Carollee Ln, Winter Park, FL 32789
  • /51

    $1,450,000

    • 4 Beds
    • 3.5 Baths
    • 3,223 Sq Ft

    1649 Harmon Ave, Winter Park, FL 32789

    Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    1649 Harmon Ave, Winter Park, FL 32789
  • /45

    $300,000

    • 3 Beds
    • 1.5 Baths
    • 1,332 Sq Ft

    7796 Fernbrook Way, Winter Park, FL 32792

    New listing in Winter Park! On a quiet cul-de-sac in Seminole County just off Howell Branch Road, this inviting townhouse offers comfort, flexibility and convenience in a desirable location. Inside, you’ll find a bright, spacious living room with large windows, a cozy dining nook adjacent to the kitchen with extensive cabinets, and a flexible first-floor third bedroom used as an office/gym that

    Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

    7796 Fernbrook Way, Winter Park, FL 32792
  • /33

    $875,000

    • 4 Beds
    • 3 Baths
    • 2,509 Sq Ft

    668 Overspin Dr, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional

    Kris Kennedy COMPASS FLORIDA LLC

    668 Overspin Dr, Winter Park, FL 32789
  • /23

    $700,000

    • 3 Beds
    • 2.5 Baths
    • 2,150 Sq Ft

    661 Selkirk Dr, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Welcome to the highly sought-after Kenilworth Shores community, a neighborhood loved for its charm, strong sense of community, and convenient Winter Park lifestyle. From the moment you walk through the front door, the home offers a warm and welcoming flow with a thoughtfully designed split layout. The spacious living room to the left creates the

    David Miller KELLER WILLIAMS HERITAGE REALTY

    661 Selkirk Dr, Winter Park, FL 32792
  • /35

    $165,000

    • 2 Beds
    • 2.5 Baths
    • 1,090 Sq Ft

    3027 Aaron Burr Ave Unit 1, Winter Park, FL 32792

    Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathrooms, this home has been thoughtfully upgraded from top to bottom. The first floor showcases elegant marble-look tile flooring, creating a sleek and durable living space ideal for both relaxing and entertaining. Upstairs, you’ll

    Rosa Rodriguez STIRLING INTERNATIONAL REAL ES

    3027 Aaron Burr Ave Unit 1, Winter Park, FL 32792
  • /34

    $165,000

    • 2 Beds
    • 2.5 Baths
    • 1,108 Sq Ft

    7300 Daniel Webster Dr Unit 7, Winter Park, FL 32792

    Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor

    Rosa Rodriguez STIRLING INTERNATIONAL REAL ES

    7300 Daniel Webster Dr Unit 7, Winter Park, FL 32792
  • /39

    $185,000

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792

    Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor corner-unit condo in Winter Park, offering comfort, convenience, and peace of mind, with major updates completed in 2026. These upgrades were specifically implemented to enhance the property's aesthetic appeal and energy efficiency.The exterior updates include replacing all windows with single-hung, double-pane, low-E

    REZA Shirzad ANNE ROGERS REALTY GROUP INC

    3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792
  • /28

    $170,000

    • 1 Bed
    • 1 Bath
    • 793 Sq Ft

    200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792

    Beautifully maintained condo in a prime Winter Park location! This bright and inviting unit has been exceptionally well cared for and shows true pride of ownership. The interior is spotless, featuring a clean, modern feel with comfortable living spaces that make it easy to feel right at home. Enjoy a well-designed layout with plenty of natural light and a welcoming atmosphere throughout. The

    Reinaldo Roman ROMAN'S PRO REALTY LLC

    200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792
  • /42

    $1,795,000

    • 4 Beds
    • 4 Baths
    • 2,807 Sq Ft

    1903 N Park Ave, Winter Park, FL 32789

    Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home

    Chris Creegan CREEGAN GROUP

    1903 N Park Ave, Winter Park, FL 32789
  • /25

    $580,000

    • 3 Beds
    • 2.5 Baths
    • 1,818 Sq Ft

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789

    Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s

    Courtney Dietch ALL REAL ESTATE & INVESTMENTS

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789
  • /27

    $99,000

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft

    278 Scottsdale Square Unit 278, Winter Park, FL 32792

    Welcome to 278 Scottsdale Square in Winter Park, a well-maintained 2-bedroom, 2-bathroom condominium offering over 1,000 square feet of comfortable living space in a highly convenient location. This second-story unit features wood-like laminate flooring throughout, creating a clean and cohesive look that is both stylish and easy to maintain. The home has been carefully cared for and kept in

    Chris Creegan CREEGAN GROUP

    278 Scottsdale Square Unit 278, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 5

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$481,250
Median Single Family Sale Price
$600,000
Median Townhouse Sale Price
$457,000
Median 2 Bedroom Sale Price
$205,000
Median 1 Bedroom Sale Price
$154,000
Average Price Per Sq Ft
$370
Number of Homes for Sale
309
Last 12 months Home Sales
1,024
Months of Supply
3.60
Median List Price
$533,950
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
2%
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