287

Newest Homes for Sale in Winter Park, FL

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  • 2834 Bright Bird Ln, Winter Park, FL 32792
    2834 Bright Bird Ln, Winter Park, FL 32792
    2834 Bright Bird Ln, Winter Park, FL 32792
    /21

    $436,000 Open Sat 10:30AM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    2834 Bright Bird Ln, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome with a one-car garage, located in a newly gated community that offers comfort, style, and convenience. The home features ambient high-hat lighting throughout, creating a warm and modern atmosphere. The spacious kitchen is ideal for everyday living and entertaining, while the open living area is highlighted by a custom accent wood

    Irene Navarro LIFESTYLE INTERNATIONAL REALTY

    2834 Bright Bird Ln, Winter Park, FL 32792
  • 1317 Medinah Ct, Winter Park, FL 32792
    1317 Medinah Ct, Winter Park, FL 32792
    1317 Medinah Ct, Winter Park, FL 32792
    /28

    $778,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,015 Sq Ft

    1317 Medinah Ct, Winter Park, FL 32792

    Fully updated 4 bed/2 bath Winter Park Pines home ready for a new owner! Tucked away at the end of a quiet cul-de-sac, this fully renovated home offers the perfect blend of modern luxury and serene surroundings. The brand new kitchen and bathrooms showcase quartz countertops, elegant gold fixtures, and custom details, complemented by new engineered wood flooring, interior laundry, and new windows

    Zach Mitchell SAND DOLLAR REALTY GROUP INC

    1317 Medinah Ct, Winter Park, FL 32792
  • 1552 Florentino Ln, Winter Park, FL 32792
    1552 Florentino Ln, Winter Park, FL 32792
    1552 Florentino Ln, Winter Park, FL 32792
    /47

    $364,900

    • 3 Beds
    • 2.5 Baths
    • 1,682 Sq Ft

    1552 Florentino Ln, Winter Park, FL 32792

    Welcome to this beautifully upgraded corner townhome located in the desirable gated community of VISTAS AT LAKE HOWELL in Winter Park, Seminole County. This spacious residence offers 1,682 sq ft under air (2,861 sq ft total), built in 2004, with 3 bedrooms and 2.5 baths, and is perfectly positioned on a corner lot for added privacy and natural light. From the moment you enter, you’ll notice the

    Nohora Gomez COLDWELL BANKER RESIDENTIAL RE

    1552 Florentino Ln, Winter Park, FL 32792
  • 690 Osceola Ave Unit 503, Winter Park, FL 32789
    690 Osceola Ave Unit 503, Winter Park, FL 32789
    690 Osceola Ave Unit 503, Winter Park, FL 32789
    /50

    $495,000 Open Sat 12AM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft

    690 Osceola Ave Unit 503, Winter Park, FL 32789

    Welcome to your new lakeside retreat in the heart of Winter Park! This move-in ready fifth-floor residence offers the kind of views that make mornings feel like mini vacations, with stunning vistas of beautiful Lake Virginia greeting you from your spacious family room and sitting area. This thoughtfully designed two-bedroom, two-bathroom condominium spans 1,148 square feet of comfortable living

    Jessica Otero KELLER WILLIAMS REALTY AT THE PARKS

    690 Osceola Ave Unit 503, Winter Park, FL 32789
  • 2432 Barbados Dr, Winter Park, FL 32792
    2432 Barbados Dr, Winter Park, FL 32792
    2432 Barbados Dr, Winter Park, FL 32792
    /34

    $249,000

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

    2432 Barbados Dr, Winter Park, FL 32792

    Welcome to 2432 Barbados Dr, Winter Park! This beautifully updated 2-bedroom, 2-bath home that delivers the perfect blend of comfort, privacy, and that easy Florida lifestyle. From the moment you arrive, you’ll appreciate the peace of mind that comes with a BRAND NEW roof, along with a layout that feels both functional and inviting. Inside, the home offers a bright, open living space that flows

    Agent Photo

    Robert Cozzone

    KOKOMO REALTY LLC

    (321) 467-7900

    2432 Barbados Dr, Winter Park, FL 32792
  • 67 Cypress Ln, Maitland, FL 32751
    67 Cypress Ln, Maitland, FL 32751
    67 Cypress Ln, Maitland, FL 32751
    /43

    $1,339,000

    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft

    67 Cypress Ln, Maitland, FL 32751

    Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside to discover hardwood floors flowing

    Kelly Price KELLY PRICE & COMPANY LLC

    67 Cypress Ln, Maitland, FL 32751
  • 423 Ololu Dr, Winter Park, FL 32789
    423 Ololu Dr, Winter Park, FL 32789
    423 Ololu Dr, Winter Park, FL 32789
    /51

    $599,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft

    423 Ololu Dr, Winter Park, FL 32789

    Welcome to this distinctive 3-bedroom, 3-bath, two-story residence in Winter Park, offering a rare and versatile layout ideal for multi-generational living, college roommates or those seeking flexible space. Thoughtfully designed with two separate living areas, this home provides privacy, functionality, and room to grow—all just minutes from major highways and the charm of downtown Winter Park.

    Jill Healey KELLER WILLIAMS WINTER PARK

    423 Ololu Dr, Winter Park, FL 32789
  • 1996 Indiana Ave, Winter Park, FL 32789
    1996 Indiana Ave, Winter Park, FL 32789
    1996 Indiana Ave, Winter Park, FL 32789
    /18

    $249,900

    • 2 Beds
    • 1 Bath
    • 818 Sq Ft

    1996 Indiana Ave, Winter Park, FL 32789

    Investor Special – Fixer Upper Opportunity in Winter Park / College Park Area. Rare opportunity to acquire a true fixer-upper in the desirable Winter Park area of College Park. This 2 bedroom, 1 bathroom property needs a full renovation and is being sold as a shell—perfect for investors or builders looking for their next project. Situated on an oversized lot at the end of a quiet dead-end street,

    Mike Rance RE/MAX 200 REALTY

    1996 Indiana Ave, Winter Park, FL 32789
  • 244 Osceola Ct, Winter Park, FL 32789
    244 Osceola Ct, Winter Park, FL 32789
    244 Osceola Ct, Winter Park, FL 32789
    /34

    $1,299,000 Open Sat 2PM - 4PM

    • 4 Beds
    • 2.5 Baths
    • 1,837 Sq Ft

    244 Osceola Ct, Winter Park, FL 32789

    Set in one of Winter Park’s most sought-after locations, this 1940 home delivers something that’s hard to recreate: walkability, character, and flexibility. Just steps from Downtown Winter Park, iconic Park Avenue, and Rollins College, with private access to Lake Osceola, the location alone sets this property apart. The home offers the charm of a historic build without the restrictions of a

    Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    244 Osceola Ct, Winter Park, FL 32789
  • 2231 Nairn Dr, Winter Park, FL 32792
    2231 Nairn Dr, Winter Park, FL 32792
    2231 Nairn Dr, Winter Park, FL 32792
    /19

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,088 Sq Ft

    2231 Nairn Dr, Winter Park, FL 32792

    Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

    David Auerbach PARK TOWN REAL ESTATE LLC

    2231 Nairn Dr, Winter Park, FL 32792
  • 3136 Crown Jewel Ct, Winter Park, FL 32792
    3136 Crown Jewel Ct, Winter Park, FL 32792
    3136 Crown Jewel Ct, Winter Park, FL 32792
    /21

    $329,000

    • 3 Beds
    • 2.5 Baths
    • 1,408 Sq Ft

    3136 Crown Jewel Ct, Winter Park, FL 32792

    UNIQUE OPPORTUNITY TO OWN AN AFFORDABLE TOWNHOME IN THE DESIRABLE WINTER PARK AREA! LOADED WITH LUXURY FEATURES AND DECORATED IN TRENDY EARTH TONES, THIS HOME OFFERS 42 INCH DESIGNER WOOD CABINETRY, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES & FRESH PAINT. NEW LAMINATE FLOORING HAS JUST BEEN INSTALLED & THERE IS NO CARPET IN THIS HOME. ENJOY GENEROUS LIVING SPACES AND ABUNDANT NATURAL LIGHT

    Lana Sabeti REALTY RESOURCE OF CENTRAL FL.

    3136 Crown Jewel Ct, Winter Park, FL 32792
  • 1655 Tremont Ln, Winter Park, FL 32792
    1655 Tremont Ln, Winter Park, FL 32792
    1655 Tremont Ln, Winter Park, FL 32792
    /21

    $385,000 Open Sat 10AM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft

    1655 Tremont Ln, Winter Park, FL 32792

    Modern upgrades meet peaceful lakeside living with NO REAR NEIGHBOR. Freshly painted inside and out, this refreshed home is move in ready and checks all the boxes. The modern kitchen features granite countertops, stainless steel appliances, custom pull out shelving, and plenty of counter space for cooking, coffee bars, and hosting friends. A charming atrium adds natural light and a unique

    Frankie Register THE WILKINS WAY LLC

    1655 Tremont Ln, Winter Park, FL 32792
  • 1378 Chilean Ln, Winter Park, FL 32792
    1378 Chilean Ln, Winter Park, FL 32792
    1378 Chilean Ln, Winter Park, FL 32792
    /53

    $379,990

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft

    1378 Chilean Ln, Winter Park, FL 32792

    Stunning Newly Remodeled Move-In Ready Home!Property Highlights:• 3 Bedrooms | 2 Bathrooms – Both bathrooms fully modernized with contemporary fixtures, sleek tile work, and high-end finishes• Brand-New Flooring Throughout – Fresh, durable, and stylish flooring for a clean, modern look• Gourmet Kitchen with Quartz Countertops – Gorgeous new quartz surfaces, updated cabinetry, and

    Constantin Florean FUTURE HOME REALTY INC

    1378 Chilean Ln, Winter Park, FL 32792
  • 850 Juanita Rael, Winter Park, FL 32789
    850 Juanita Rael, Winter Park, FL 32789
    850 Juanita Rael, Winter Park, FL 32789
    /50

    $1,425,000

    • 4 Beds
    • 3 Baths
    • 2,306 Sq Ft

    850 Juanita Rael, Winter Park, FL 32789

    Location, location, location. Sought after location on the North end of Park Avenue. Avoid the traffic in and out of Downtown Winter Park while being minutes away from everything on the Avenue. One of the very few single level homes of this quality in Winter Park 32789.Single story ranch on a lovely, private, large corner lot. 2306 heated and cooled square feet. Primary bedroom en-suite with

    Brad Grosberg PHIL KEAN REAL ESTATE LLC

    850 Juanita Rael, Winter Park, FL 32789
  • 230 Strathy Ln, Winter Park, FL 32792
    230 Strathy Ln, Winter Park, FL 32792
    230 Strathy Ln, Winter Park, FL 32792
    /12

    $499,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    230 Strathy Ln, Winter Park, FL 32792

    Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

    David Auerbach PARK TOWN REAL ESTATE LLC

    230 Strathy Ln, Winter Park, FL 32792
  • 1523 Miller Ave, Winter Park, FL 32789
    1523 Miller Ave, Winter Park, FL 32789
    1523 Miller Ave, Winter Park, FL 32789
    /6

    $1,550,000 New Construction

    • 5 Beds
    • 4 Baths
    • 3,164 Sq Ft

    1523 Miller Ave, Winter Park, FL 32789

    Under Construction. UNDER CONSTRUCTION. This 3,164 sq ft new construction home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area

    Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

    1523 Miller Ave, Winter Park, FL 32789
  • 3060 George Mason Ave Unit 10, Winter Park, FL 32792
    3060 George Mason Ave Unit 10, Winter Park, FL 32792
    3060 George Mason Ave Unit 10, Winter Park, FL 32792
    /13

    $89,500

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    3060 George Mason Ave Unit 10, Winter Park, FL 32792

    GREAT INVESTMENT OPPORTUNITY! Seller is motivated! Completely remodeled and move-in ready, this beautiful 1-bedroom, 1-bathroom condo in Winter Park offers the perfect blend of comfort, convenience, and value. Located just 11 minutes from Orlando International Airport and close to UCF, Full Sail University, shopping malls, restaurants, major highways, and popular theme parks, this home is ideal

    John Silva JOHN SILVA REALTY & ASSOCIATES

    3060 George Mason Ave Unit 10, Winter Park, FL 32792
  • 958 Dupont Ave, Winter Park, FL 32789
    958 Dupont Ave, Winter Park, FL 32789
    958 Dupont Ave, Winter Park, FL 32789
    /27

    $381,000

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    958 Dupont Ave, Winter Park, FL 32789

    Welcome to 958 Dupont Ave, a home that exudes charm and functionality. The kitchen is a chef's dream, boasting all stainless steel appliances that add a sleek, modern touch. Step outside to a spacious, fenced-in backyard, perfect for privacy and outdoor activities. Enjoy leisurely afternoons or entertain on the covered patio, a delightful extension of the living space. A storage shed provides

    Karen Albright OPENDOOR BROKERAGE LLC

    958 Dupont Ave, Winter Park, FL 32789
  • 4190 Bear Gully Rd, Winter Park, FL 32792
    4190 Bear Gully Rd, Winter Park, FL 32792
    4190 Bear Gully Rd, Winter Park, FL 32792
    /30

    $540,000

    • 4 Beds
    • 2.5 Baths
    • 2,058 Sq Ft

    4190 Bear Gully Rd, Winter Park, FL 32792

    Spacious Winter Park home on over a half acre with no rear neighbors!. In Bear Gully Forest community and has over 2,000 s/f- with a Living Room, Dining Room, Eat-in Kitchen and more. The home's fully-equipped kitchen has excellent cabinet space and appliances that include a stove, microwave, and dishwasher. An inside laundry room has a washer/dryer combination for your convenience. Bedroom with

    Craig Swetnam ADVANCE REALTY & MANAGEMENT LLC

    4190 Bear Gully Rd, Winter Park, FL 32792
  • 2500 Lee Rd Unit 237, Winter Park, FL 32789
    2500 Lee Rd Unit 237, Winter Park, FL 32789
    2500 Lee Rd Unit 237, Winter Park, FL 32789
    /23

    $169,000

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft

    2500 Lee Rd Unit 237, Winter Park, FL 32789

    Welcome to lakeside living! This cozy one-bedroom, one-bathroom condo offers a blend of amenities and convenience. This perfectly located condominium has low HOA FEES and has no assessment fees! Enjoy your days fishing, boating, or hanging out by the pool overlooking gorgeous Lake Killarney, a 240 acre spring-fed lake! Cherish living on the shores of Lake Killarney, complete with coveted dock

    Lydia Cassaro LPT REALTY LLC (DB)

    2500 Lee Rd Unit 237, Winter Park, FL 32789
  • 1816 Meadowgold Ln, Winter Park, FL 32792
    1816 Meadowgold Ln, Winter Park, FL 32792
    1816 Meadowgold Ln, Winter Park, FL 32792
    /47

    $459,000

    • 3 Beds
    • 2.5 Baths
    • 1,546 Sq Ft

    1816 Meadowgold Ln, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Location is Everything.If you want the best home in the best location look no further. This three bedroom two and half bathroom home is located in the much desired Autumn Glen community. The home is perfect and has a very flexible floorplan with the 3rd bedroom currently configured as a loft with a closet for the work from home person and can be

    Kyle Clark RE/MAX TOWN & COUNTRY REALTY

    1816 Meadowgold Ln, Winter Park, FL 32792
  • 311 E Morse Blvd Unit 2-5, Winter Park, FL 32789
    311 E Morse Blvd Unit 2-5, Winter Park, FL 32789
    311 E Morse Blvd Unit 2-5, Winter Park, FL 32789
    /32

    $2,100,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    311 E Morse Blvd Unit 2-5, Winter Park, FL 32789

    Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and

    Megan Cross FANNIE HILLMAN & ASSOCIATES

    311 E Morse Blvd Unit 2-5, Winter Park, FL 32789
  • 860 N Denning Dr, Winter Park, FL 32789
    860 N Denning Dr, Winter Park, FL 32789
    860 N Denning Dr, Winter Park, FL 32789
    /48

    $749,900

    • 3 Beds
    • 2.5 Baths
    • 1,290 Sq Ft

    860 N Denning Dr, Winter Park, FL 32789

    NEW CONSTRUCTION–QUALITY | WALKABLE WINTER PARK | FULL SMART HOME This is not a renovation—this is a complete architectural transformation. Taken down to the studs and roofline, expanded, and rebuilt with intention, this custom luxury residence is ideally located just steps from Winter Park Village and minutes from iconic Park Avenue, offering a truly walkable, car-optional lifestyle. The home

    LaDarrius Sanders OUTLET REALTY

    860 N Denning Dr, Winter Park, FL 32789
  • 2232 Shadowland Loop, Winter Park, FL 32792
    2232 Shadowland Loop, Winter Park, FL 32792
    2232 Shadowland Loop, Winter Park, FL 32792
    /12

    $429,000

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft

    2232 Shadowland Loop, Winter Park, FL 32792

    Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood in winter park. The townhouse has perfect layout when you walk into the house, beautiful tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and

    He Gao U S GLORY REALTY

    2232 Shadowland Loop, Winter Park, FL 32792
  • 731 Bongart Rd, Winter Park, FL 32792
    731 Bongart Rd, Winter Park, FL 32792
    731 Bongart Rd, Winter Park, FL 32792
    /28

    $570,000

    • 4 Beds
    • 3 Baths
    • 1,526 Sq Ft

    731 Bongart Rd, Winter Park, FL 32792

    Experience luxury living in this stunning, remodeled single-family home located in the heart of Winter Park. This spectacular residence features four spacious bedrooms and three modern bathrooms, boasting sleek laminate flooring throughout. The chef-inspired kitchen comes fully equipped with premium stainless steel appliances, while the massive backyard and sparkling pool provide an ideal setting

    Maria Gomez Arevalo MY REALTY GROUP, LLC.

    731 Bongart Rd, Winter Park, FL 32792
  • 1630 Gulfview Dr Unit 423, Maitland, FL 32751
    1630 Gulfview Dr Unit 423, Maitland, FL 32751
    1630 Gulfview Dr Unit 423, Maitland, FL 32751
    /32

    $239,000

    • 3 Beds
    • 3 Baths
    • 1,328 Sq Ft

    1630 Gulfview Dr Unit 423, Maitland, FL 32751

    WOW WOW WOW PRICE TO SELL!! SELLER MOTIVATED !! Fully Remodeled 3 Bed 3 Bathrooms. *** One bedroom and full bathroom downstairs, 2 Bed and 2 Bath Upstairs. *** Completely Remodeled** Some flooring needs to be adjusted in one bedroom upstairs and stairs*** Newer Roof & Attic Insulation *** New Windows *** Remodeled Kitchen and Bathrooms** Patio Courtyard Carolina Mountain Stone *** Turn-key

    Denise San Miguel REALTY LYNK INC

    1630 Gulfview Dr Unit 423, Maitland, FL 32751
  • 2002 Indiana Ave, Winter Park, FL 32789
    2002 Indiana Ave, Winter Park, FL 32789
    2002 Indiana Ave, Winter Park, FL 32789
    /8

    $358,000

    • Land
    • 0.16 Acre
    • $2,237,500 per Acre

    2002 Indiana Ave, Winter Park, FL 32789

    Great buildable lot centrally located close to I-4 for easy access. Currently zoned R-2 for multifamily housing 2+ units possible. Please consult the zoning and planning Dept. for info and guidelines for building. The lot has single family homes on both sides of it and faces a retention pond area across the street. Front half of the lot is cleared. Back half of the lot is wooded. Paved road

    David Nicholson DAWN REALTY

    2002 Indiana Ave, Winter Park, FL 32789
  • 1280 Gladiolas Dr, Winter Park, FL 32792
    1280 Gladiolas Dr, Winter Park, FL 32792
    1280 Gladiolas Dr, Winter Park, FL 32792
    /4

    $499,500

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    1280 Gladiolas Dr, Winter Park, FL 32792

    Welcome to this beautifully updated 3-bedroom, 2-bath home with a screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting layout is perfect for everyday living and entertaining, and the

    Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

    1280 Gladiolas Dr, Winter Park, FL 32792
  • 637 N Park Ave, Winter Park, FL 32789
    637 N Park Ave, Winter Park, FL 32789
    637 N Park Ave, Winter Park, FL 32789
    /86

    $3,895,000

    • 3 Beds
    • 5 Baths
    • 4,237 Sq Ft

    637 N Park Ave, Winter Park, FL 32789

    A refined, custom brownstone with an exclusive Park Avenue address, offering an unparalleled Winter Park lifestyle enhanced by the finest designer selections throughout. The timeless brick elevation and expansive windows evoke the charm of a favorite city street while preserving the tranquility of this sought-after setting. This three-story townhouse offers 4,237 square feet of thoughtfully

    Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

    637 N Park Ave, Winter Park, FL 32789
  • 1673 Mayfield Ave, Winter Park, FL 32789
    1673 Mayfield Ave, Winter Park, FL 32789
    1673 Mayfield Ave, Winter Park, FL 32789
    /44

    $1,195,000 Open Sun 1PM - 4PM

    • 4 Beds
    • 4 Baths
    • 2,540 Sq Ft

    1673 Mayfield Ave, Winter Park, FL 32789

    In the heart of Winter Park, this extensively renovated modern farmhouse offers exceptional value for the location. A circular drive and inviting front porch welcome you into light-filled living spaces enhanced by all-new energy-efficient windows, custom millwork and designer finishes throughout. The functional layout includes a first-floor guest suite, additional well-appointed bedrooms and

    Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

    1673 Mayfield Ave, Winter Park, FL 32789
  • 1340 Blue Stem Ln, Winter Park, FL 32792
    1340 Blue Stem Ln, Winter Park, FL 32792
    1340 Blue Stem Ln, Winter Park, FL 32792
    /48

    $740,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,587 Sq Ft

    1340 Blue Stem Ln, Winter Park, FL 32792

    Welcome to Hawk’s Crest, one of Winter Park’s most desirable gated communities. Set on a larger lot with peaceful pond views, this beautifully maintained two-story home combines comfort, style, and gorgeous upgrades in a light-filled, open floor plan designed for everyday living. A pavered driveway and walkway create an inviting arrival and lead into a bright interior with soaring ceilings and

    Beth Hobart MAINFRAME REAL ESTATE

    1340 Blue Stem Ln, Winter Park, FL 32792
  • 1920 Woodcrest Dr Unit 9, Winter Park, FL 32792
    1920 Woodcrest Dr Unit 9, Winter Park, FL 32792
    1920 Woodcrest Dr Unit 9, Winter Park, FL 32792
    /27

    $229,000

    • 2 Beds
    • 2 Baths
    • 1,010 Sq Ft

    1920 Woodcrest Dr Unit 9, Winter Park, FL 32792

    Opportunity property in the heart of Winter Park. Welcome to 1920 Woodcrest Drive, Unit 9, a 2 bedroom, 2 bathroom condo that has been fully gutted and is ready for a buyer with vision. This is a true blank canvas for a discerning owner occupant who wants to curate a space to their personal taste, or an investor seeking a value add renovation in a highly desirable area. Minutes from Baldwin Park

    David Hijar OLYMPUS EXECUTIVE REALTY INC

    1920 Woodcrest Dr Unit 9, Winter Park, FL 32792
  • 1841 Harland Park Dr, Winter Park, FL 32789
    1841 Harland Park Dr, Winter Park, FL 32789
    1841 Harland Park Dr, Winter Park, FL 32789
    /28

    $1,999,000

    • 4 Beds
    • 3.5 Baths
    • 3,470 Sq Ft

    1841 Harland Park Dr, Winter Park, FL 32789

    Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete with a double-door entry for added

    Shanon Luiz SELECTIVE REALTY GROUP LLC

    1841 Harland Park Dr, Winter Park, FL 32789
  • 1816 Azalea Ave, Winter Park, FL 32789
    1816 Azalea Ave, Winter Park, FL 32789
    1816 Azalea Ave, Winter Park, FL 32789
    /26

    $369,900

    • 3 Beds
    • 2 Baths
    • 1,584 Sq Ft

    1816 Azalea Ave, Winter Park, FL 32789

    OFFER ACCEPTED - AWAIT SIGNED CONTRACT TO PEND - Welcome to this classic ranch home offering 3 bedrooms, 2 baths, and a wonderfully livable floor plan designed for everyday comfort, work-from-home flexibility, and easy entertaining. With 1,584 sqft of living space this home lives large and offers generous room sizes, plenty of storage, and a layout that simply makes sense. From the big front

    Shaunda Hall GENSTONE REALTY

    1816 Azalea Ave, Winter Park, FL 32789
  • 5473 Bracken Ct, Winter Park, FL 32792
    5473 Bracken Ct, Winter Park, FL 32792
    5473 Bracken Ct, Winter Park, FL 32792
    /27

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,178 Sq Ft

    5473 Bracken Ct, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open and architectural focal point. The functional layout includes a

    David Fraser KELLER WILLIAMS ADVANTAGE III

    5473 Bracken Ct, Winter Park, FL 32792
  • 1518 Pinewood Dr, Winter Park, FL 32789
    1518 Pinewood Dr, Winter Park, FL 32789
    1518 Pinewood Dr, Winter Park, FL 32789
    /29

    $489,900

    • 3 Beds
    • 2 Baths
    • 1,197 Sq Ft

    1518 Pinewood Dr, Winter Park, FL 32789

    Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility.

    Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

    1518 Pinewood Dr, Winter Park, FL 32789
  • 7426 Wynnewood Square Unit 195, Winter Park, FL 32792
    7426 Wynnewood Square Unit 195, Winter Park, FL 32792
    7426 Wynnewood Square Unit 195, Winter Park, FL 32792
    /17

    $185,000

    • 3 Beds
    • 2 Baths
    • 1,117 Sq Ft

    7426 Wynnewood Square Unit 195, Winter Park, FL 32792

    Excellent opportunity to acquire a 3-bedroom, 2-bath first-floor end-unit condo offering approximately 1,117 sq ft in a well-established community. The unit features a functional layout and a highly desirable location near UCF, Full Sail University, Valencia College, and major shopping and dining. Priced to sell, this property is ideal for investors seeking a light-to-moderate rehab with strong

    Qing Lin SPRINGHILL PROPERTIES LLC

    7426 Wynnewood Square Unit 195, Winter Park, FL 32792
  • 2500 Lee Rd Unit 222, Winter Park, FL 32789
    2500 Lee Rd Unit 222, Winter Park, FL 32789
    2500 Lee Rd Unit 222, Winter Park, FL 32789
    /25

    $199,000

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft

    2500 Lee Rd Unit 222, Winter Park, FL 32789

    Welcome to your next chapter of lakeside living! This charming one-bedroom, one-bathroom condo offers a perfect blend of tranquility and convenience in the heart of Winter Park. Step inside to discover a thoughtfully designed space where comfort meets style. The open-concept living area welcomes you with beautiful engineered wood floors, creating a seamless flow between the living room and

    Christine Bouchard HOMESMART

    2500 Lee Rd Unit 222, Winter Park, FL 32789
  • 3601 Midiron Dr, Winter Park, FL 32789
    3601 Midiron Dr, Winter Park, FL 32789
    3601 Midiron Dr, Winter Park, FL 32789
    /7

    $499,000

    • Land
    • 0.21 Acre
    • $2,376,190 per Acre

    3601 Midiron Dr, Winter Park, FL 32789

    Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a

    Juliana Usquiano EMPIRE NETWORK REALTY

    3601 Midiron Dr, Winter Park, FL 32789
  • 731 Midget Dr, Winter Park, FL 32789
    731 Midget Dr, Winter Park, FL 32789
    731 Midget Dr, Winter Park, FL 32789
    /7

    $940,000

    • Land
    • 0.19 Acre
    • $4,947,368 per Acre

    731 Midget Dr, Winter Park, FL 32789

    Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and

    Juliana Usquiano EMPIRE NETWORK REALTY

    731 Midget Dr, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 8

Florida Orange County Winter Park

Newest Listings for Sale in Winter Park, FL

Frequently Asked Questions

What is the average home price in Winter Park, FL?
Homes for sale in Winter Park, FL have an average home price of $966,950.
How many homes have sold over the last 12 months in Winter Park, FL?
1,043 homes have sold in Winter Park, FL over the last 12 months.
What are the most popular zip codes in Winter Park, FL?
The most popular zip codes in Winter Park, FL include 32789, 32751, 32792, 32803 and 32814.
How much do you need to make to afford a house in Winter Park?
The median home price in Winter Park is $539,000. If you put a 20% down payment of $107,800 and had a 30-year fixed mortgage with an interest rate of 6.16%, your estimated principal and interest payment would be $2,630 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $113K a year to afford the median home price in Winter Park. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winter Park, FL?
Winter Park, FL has highly rated public and private schools. Some of the best schools in Winter Park based on Niche Grades are Lake Highland Preparatory School, Park Maitland School and Trinity Preparatory School. Browse all the schools in Winter Park, FL to learn more.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 64 days on the market compared to the national average of 53 days. The median sale price for homes in Winter Park, FL over the last 12 months is $493,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$493,000
Median Single Family Sale Price
$600,000
Median Townhouse Sale Price
$459,500
Median 2 Bedroom Sale Price
$220,000
Median 1 Bedroom Sale Price
$154,500
Average Price Per Sq Ft
$372
Number of Homes for Sale
258
Last 12 months Home Sales
1,043
Months of Supply
3.00
Median List Price
$539,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
4%
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