1,133

Recently Sold Winter Park, FL Homes

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  • 1545 Indiana Ave Unit B, Winter Park, FL 32789
    1545 Indiana Ave Unit B, Winter Park, FL 32789
    /2

    $480,000 Sold Jul 28, 2025

    • 1,598 Sq Ft
    • $300/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2005

    1545 Indiana Ave Unit B, Winter Park, FL 32789

    Tucked away on a quiet street blocks from the cultural heartbeat of Winter Park is this 3-bedroom, 2.5-bath townhouse-style condo that offers a balance of comfort, convenience, and charm. With nearly 1,600 square feet of thoughtful space, the two-story home lives large, featuring an open-concept main floor with high ceilings, ceramic tile throughout, a spacious kitchen with granite counters and

    Ron Murray MAGIC REALTY LLC

    1545 Indiana Ave Unit B, Winter Park, FL 32789
  • 7331 Blue Jacket Place W, Winter Park, FL 32792
    7331 Blue Jacket Place W, Winter Park, FL 32792
    /2

    $389,000 Sold Jul 25, 2025

    • 1,581 Sq Ft
    • $246/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    7331 Blue Jacket Place W, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Incredible Value! Priced to sell below market value—this is your chance to secure a fully upgraded home at a price that won’t last long. Act fast before it's gone!Welcome to this beautifully updated 3-bedroom, 2-bathroom home located in the highly desirable Winter Park community with no HOA! This luxury home sits on a large, fully fenced lot and

    Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

    7331 Blue Jacket Place W, Winter Park, FL 32792
  • 2003 Bentwood Dr, Winter Park, FL 32792
    2003 Bentwood Dr, Winter Park, FL 32792
    /2

    $430,000 Sold Jul 25, 2025

    • 1,675 Sq Ft
    • $257/SF
    • 16 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    2003 Bentwood Dr, Winter Park, FL 32792

    Welcome to this well maintained three bedroom, two bathroom pool home, with a one year old roof in Winter Park! Perfectly designed for comfortable living, this home features a versatile office space, ideal for working from home.Inside, you’ll find an open floor plan with vaulted ceilings, spacious living areas with a cozy fireplace surrounded by built in shelves. This home features a

    Heather Kolin PALMANO GROUP RE BROKERAGE LLC

    2003 Bentwood Dr, Winter Park, FL 32792
  • 490 Shoreview Ave, Winter Park, FL 32789
    490 Shoreview Ave, Winter Park, FL 32789
    /2

    $599,000 Sold Jul 25, 2025

    • 2,266 Sq Ft
    • $264/SF
    • 20 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1935

    490 Shoreview Ave, Winter Park, FL 32789

    Step into timeless elegance with this beautiful 2-story, 3-bed, 2-bath historic home located in one of Winter Park’s most coveted neighborhoods. Built in 1935, this classic residence boasts stunning architectural details throughout—including solid wood floors, 10-inch baseboards, two cozy wood-burning fireplaces, and ornate trim surrounding the windows and doors. The generous living room opens

    Justin Harvey FLORIDA HOME TEAM REALTY LLC

    490 Shoreview Ave, Winter Park, FL 32789
  • 849 Driver Ave, Winter Park, FL 32789
    849 Driver Ave, Winter Park, FL 32789
    /2

    $275,000 Sold Jul 25, 2025

    • 894 Sq Ft
    • $308/SF
    • 54 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1957

    849 Driver Ave, Winter Park, FL 32789

    Great Opportunity in Prime Location! Price adjustment below appraised value.Located just off the Fairbanks Avenue exit from I-4, this charming 2-bedroom, 1-bath fixer-upper sits on a generous 7,000 sq ft lot in a quiet, convenient neighborhood. With original hardwood floors in the living area and bedrooms, this home is full of character and ready for your personal touch. The

    Thor Falk CASTLE & COTTAGE REALTY LLC

    849 Driver Ave, Winter Park, FL 32789
  • 182 N Phelps Ave, Winter Park, FL 32789
    182 N Phelps Ave, Winter Park, FL 32789
    /2

    $3,450,000 Sold Jul 25, 2025

    • 4,812 Sq Ft
    • $717/SF
    • 61 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 2025

    182 N Phelps Ave, Winter Park, FL 32789

    Welcome to a stunning new home positioned near Windsong and the AdventHealth Hospital. This extraordinary property boasts 4,812 square feet under AC. The stately manner is thoughtfully designed with four commodious bedrooms and five full-size bathrooms. Additionally, it features an expansive three-car garage complemented by an impressively constructed circular paver driveway. The first floor

    Marcio Tannus LA ROSA REALTY HORIZONS LLC

    182 N Phelps Ave, Winter Park, FL 32789
  • 2138 Whitehall Dr, Winter Park, FL 32792
    2138 Whitehall Dr, Winter Park, FL 32792
    /2

    $500,000 Sold Jul 25, 2025

    • 1,752 Sq Ft
    • $285/SF
    • 63 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1964

    2138 Whitehall Dr, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Welcome to this well-maintained home in the desirable Kenilworth Shores Neighborhood of Winter Park. The three-bedroom, two-bath home has just over 1,750 square feet and has lots of extra storage. Wonderful floorplan with large living room, dining room, and separate family room with wood-burning fireplace. Updates include BRAND-NEW Roof (4/2025),

    Angela McCloskey KELLER WILLIAMS REALTY AT THE PARKS

    2138 Whitehall Dr, Winter Park, FL 32792
  • 1430 Hyde Park Dr, Winter Park, FL 32792
    1430 Hyde Park Dr, Winter Park, FL 32792
    /2

    $425,000 Sold Jul 25, 2025

    • 1,947 Sq Ft
    • $218/SF
    • 83 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1987

    1430 Hyde Park Dr, Winter Park, FL 32792

    Step inside and be ready to see an AMAZING LAKE VIEW from this SPLIT plan, 2 bedroom 2 bath BEAUTIFUL home. NEW LUXURY VINYL PLANK flooring throughout the entire home. NEW paint and NEW baseboards inside. The family room has a FIREPLACE, and a separate dining room adjacent to it. Kitchen features NEW STAINLESS STEEL APPLIANCES and beautiful lake views from the breakfast nook. The HUGE

    Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

    1430 Hyde Park Dr, Winter Park, FL 32792
  • 274 N Ranger Blvd, Winter Park, FL 32792
    274 N Ranger Blvd, Winter Park, FL 32792
    /2

    $520,000 Sold Jul 25, 2025

    • 1,420 Sq Ft
    • $366/SF
    • 309 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    274 N Ranger Blvd, Winter Park, FL 32792

    Welcome to your fully renovated home located in the highly sought-after Winter Park Pines Golf Course Community. This beautiful open floor plan residence offers a fresh and modern living experience, perfect for both relaxation and entertaining. Inside you'll find brand-new flooring throughout, along with fully upgraded bathrooms that include stylish new vanities and custom tile work. The kitchen

    Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

    274 N Ranger Blvd, Winter Park, FL 32792
  • 5240 N Lake Burkett Ln, Winter Park, FL 32792
    5240 N Lake Burkett Ln, Winter Park, FL 32792
    /2

    $436,000 Sold Jul 24, 2025

    • 2,290 Sq Ft
    • $190/SF
    • 224 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    5240 N Lake Burkett Ln, Winter Park, FL 32792

    Seller is offering up to $3,000 in concessions. Welcome to 5240 North Lake Burkett Lane, a classic 4 bedroom, 2.5 bathroom home, located in beautiful Winter Park! The open floor plan and high ceilings offer a bright, airy feel. At the center of the home is a large kitchen, connecting the dining, living, and family rooms. The primary suite is conveniently located on the first floor for

    Ashley Harper COLDWELL BANKER REALTY

    5240 N Lake Burkett Ln, Winter Park, FL 32792
  • 4029 Cool Water Ct Unit 2, Winter Park, FL 32792
    4029 Cool Water Ct Unit 2, Winter Park, FL 32792
    /2

    $525,000 Sold Jul 23, 2025

    • 2,733 Sq Ft
    • $192/SF
    • 104 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1979

    4029 Cool Water Ct Unit 2, Winter Park, FL 32792

    Welcome Home! This spacious 5-bedroom, 3-bathroom home nestled in highly sought-after Winter Park. This home offers a versatile layout, oversized lot, and limitless potential to make it your own. Priced below market value based on square footage. Upgraded features include a NEW ROOF, flooring, updated plumbing, epoxy garage flooring, modern light fixtures, ceiling fans, freshly painted interior &

    Cedrick Williams MAGNUS REALTY GROUP LLC

    4029 Cool Water Ct Unit 2, Winter Park, FL 32792
  • 700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
    700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
    /2

    $330,000 Sold Jul 23, 2025

    • 1,074 Sq Ft
    • $307/SF
    • 303 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1964

    700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789

    PRICE IMPROVEMENT – Best buy in Winter Park..........Motivated Sellers! CLICK ON VIRTUAL TOUR to get an overview of the complex.Step into this beautifully updated 2-bedroom, 2-bath condo located in the highly desirable Winter Park Gardens community. This move-in-ready unit has been thoughtfully upgraded with modern features, including brand-new plumbing, a tankless water heater,

    Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
  • 1945 Bering Ave, Winter Park, FL 32789
    1945 Bering Ave, Winter Park, FL 32789
    /2

    $439,900 Sold Jul 22, 2025

    • 1,576 Sq Ft
    • $279/SF
    • 6 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1958

    1945 Bering Ave, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. ***BUY THIS HOME WITH AN FHA INTEREST RATE OF 5.375% WHEN USING THE SELLER'S PREFERRED LENDER*** You will fall in love with this mid-century Winter Park home across from Lake Bell in charming Lake Bell Terrace. This home offers 3 Bedrooms, 1 spa-like bathroom, and an en-suite half bath, a family room, living room, dining room, and a laundry room.

    Carmen Gonzalez, Pa HORIZON WEST REALTY

    1945 Bering Ave, Winter Park, FL 32789
  • 1624 Little Wren Ln, Winter Park, FL 32792
    1624 Little Wren Ln, Winter Park, FL 32792
    /2

    $450,000 Sold Jul 22, 2025

    • 2,308 Sq Ft
    • $195/SF
    • 23 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2019

    1624 Little Wren Ln, Winter Park, FL 32792

    Welcome to Hawks Crest – where modern living meets convenience and comfort. Built in 2019, this beautifully upgraded 3-bedroom, 2.5-bath townhome offers the perfect blend of style, function, and low-maintenance living—ready for you to move right in. From the moment you arrive, you’ll be charmed by the paver driveway and walkway framed by lush landscaping, leading to a bold, eye-catching front

    Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

    1624 Little Wren Ln, Winter Park, FL 32792
  • 1821 Windsor Dr, Winter Park, FL 32789
    1821 Windsor Dr, Winter Park, FL 32789
    /2

    $995,000 Sold Jul 22, 2025

    • 2,188 Sq Ft
    • $455/SF
    • 25 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2017

    1821 Windsor Dr, Winter Park, FL 32789

    WELCOME to 1821 WINDSOR DR in WINTER PARK, FLORIDA! This is a ONCE IN A LIFETIME OPPORTUNITY to own this BEAUTIFUL CUSTOM-BUILT MASTERPIECE of a HOME in ONE OF THE MOST DESIRED LOCATIONS in TOWN! When you buy this Home, you aren’t just purchasing a NEWLY BUILT CUSTOM HOME FULL OF LUXURIOUS UPGRADES and ARCHITECTURAL FEATURES; you are also buying into the LIFESTYLE that others DREAM OF LIVING in

    Chris Creegan CREEGAN GROUP

    1821 Windsor Dr, Winter Park, FL 32789
  • 940 Lincoln Cir, Winter Park, FL 32789
    940 Lincoln Cir, Winter Park, FL 32789
    /2

    $2,495,000 Sold Jul 22, 2025

    • 3,551 Sq Ft
    • $703/SF
    • 47 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1995

    940 Lincoln Cir, Winter Park, FL 32789

    Now offered at $2,495,000—an outstanding value for a thoughtfully designed pool home on a spacious lot in Winter Park’s most sought after neighborhoods. Located in the heart of the “Golden Triangle”—the core residential district just a short walk from Park Avenue’s world-class shopping and dining—940 Lincoln Circle is a beautifully renovated West Indies/Key West-style home that blends

    Padgett McCormick KELLY PRICE & COMPANY LLC

    940 Lincoln Cir, Winter Park, FL 32789
  • 3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792
    3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792
    /2

    $198,000 Sold Jul 21, 2025

    • 1,031 Sq Ft
    • $192/SF
    • 11 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1983

    3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792

    Welcome to this beautifully updated 2-bedroom, 2.5-bath condo in the heart of Winter Park! Featuring ceramic tile and laminate wood flooring throughout, this home offers a modern feel with upgraded kitchen finishes, refreshed lighting, ceiling fans, and recently updated sinks, toilets, and flooring. The spacious layout provides comfort and convenience, with both bedrooms offering en-suite

    Brandon Feng KELLER WILLIAMS WINTER PARK

    3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792
  • 1261 Burning Tree Ln, Winter Park, FL 32792
    1261 Burning Tree Ln, Winter Park, FL 32792
    /2

    $806,000 Sold Jul 21, 2025

    • 2,223 Sq Ft
    • $363/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1979

    1261 Burning Tree Ln, Winter Park, FL 32792

    Impeccably Redesigned Pool Home in Coveted Winter Park NeighborhoodWelcome to 1261 Burning Tree Lane, a beautifully updated 4-bedroom, 2-bathroom pool home located in the highly sought-after Greenview at Winter Pines subdivision. Tucked beneath a canopy of mature oak trees and surrounded by manicured landscaping, this architect-owned residence combines timeless design with thoughtful

    Adrienne Kane KELLER WILLIAMS RLTY FL. PARTN

    1261 Burning Tree Ln, Winter Park, FL 32792
  • 208 Scottsdale Square, Winter Park, FL 32792
    208 Scottsdale Square, Winter Park, FL 32792
    /2

    $86,000 Sold Jul 21, 2025

    • 1,085 Sq Ft
    • $79/SF
    • 19 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1974

    208 Scottsdale Square, Winter Park, FL 32792

    Welcome to this beautifully updated 2-story condo located in the heart of Winter Park, just minutes from UCF, Full Sail University, major highways, shopping, and dining. Nestled on the second level, this inviting home offers a functional layout with 2 spacious bedrooms and a full bathroom upstairs, plus a convenient half bathroom on the main floor.Step inside to find stylish luxury vinyl

    Jackie Criswell RE/MAX TOWN & COUNTRY REALTY

    208 Scottsdale Square, Winter Park, FL 32792
  • 1730 Oneco Ave, Winter Park, FL 32789
    1730 Oneco Ave, Winter Park, FL 32789
    /2

    $705,000 Sold Jul 21, 2025

    • 1,408 Sq Ft
    • $501/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1967

    1730 Oneco Ave, Winter Park, FL 32789

    Vintage house with close proximity to Park Avenue surronded by newely constructed homes on a scenic brick street. A creative designer would find this vintage house a great project with a newly constructed roof to save the time. This winter park corner lot is highly sought after for its location and its potential.

    John Tremblay THE TEAM REAL ESTATE GROUP INC

    1730 Oneco Ave, Winter Park, FL 32789
  • 2832 Buccaneer Dr, Winter Park, FL 32792
    2832 Buccaneer Dr, Winter Park, FL 32792
    /2

    $472,000 Sold Jul 21, 2025

    • 1,736 Sq Ft
    • $272/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    2832 Buccaneer Dr, Winter Park, FL 32792

    Nestled in one of Winter Park’s peaceful neighborhoods with *NO HOA*, this meticulously upgraded 3 bedrooms, 2 bath pool home plus 2 versatile bonus rooms, perfectly blends modern comfort, sustainable living, and timeless charm. With two vacant city-owned lots directly to the west, the property enjoys uninterrupted golden sunset views that fill the home with natural light. The exterior showcases

    Virginia Silberstein ORLANDO EXPERT REALTY LLC

    2832 Buccaneer Dr, Winter Park, FL 32792
  • 1690 Palm Ave, Winter Park, FL 32789
    1690 Palm Ave, Winter Park, FL 32789
    /2

    $2,495,000 Sold Jul 21, 2025

    • 3,967 Sq Ft
    • $629/SF
    • 56 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2020

    1690 Palm Ave, Winter Park, FL 32789

    This Fabulous transitional 5 bedroom pool home is perfect for family living & entertaining & just minutes from downtown Winter Park's shopping, entertainment & dining on Park Avenue. Floor plan is ideal w/ 2 bedroom suites downstairs plus office/flex space. Meticulously constructed by Austin Homes, modern & traditional elements blend together w/ its open layout & clean lines. Main floor features

    Daniel Robinson HOUWZER INC

    1690 Palm Ave, Winter Park, FL 32789
  • 2855 Lion Heart Rd, Winter Park, FL 32792
    2855 Lion Heart Rd, Winter Park, FL 32792
    /2

    $620,000 Sold Jul 21, 2025

    • 1,727 Sq Ft
    • $359/SF
    • 62 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    2855 Lion Heart Rd, Winter Park, FL 32792

    Welcome to 2855 Lion Heart Dr, Winter Park — a beautifully remodeled home that seamlessly combines modern comfort with an unbeatable location. This move-in ready residence features a brand-new kitchen with smart stainless steel appliances, completely updated bathrooms, new luxury flooring throughout, and an open-concept layout perfect for entertaining. Major upgrades include a new roof (2025) and

    Kevin Henao LA ROSA REALTY LLC

    2855 Lion Heart Rd, Winter Park, FL 32792
  • 1541 Florentino Ln, Winter Park, FL 32792
    1541 Florentino Ln, Winter Park, FL 32792
    /2

    $350,000 Sold Jul 21, 2025

    • 1,682 Sq Ft
    • $208/SF
    • 70 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2004

    1541 Florentino Ln, Winter Park, FL 32792

    MOTIVATED SELLER! Beautifully maintained Townhome in desirable gated community of Vistas at Lake Howell. This spacious 3 bedroom 2 and 1 half bath home is ready for its new owner. With new carpet, paint and appliances it's in move-in condition. Large kitchen overlooks the expansive dinning living room combination with sliding doors leading out to the screened-in patio. Upstairs you will find the

    Jeffrey Friedman FANNIE HILLMAN & ASSOCIATES

    1541 Florentino Ln, Winter Park, FL 32792
  • 1911 Stonehurst Rd, Winter Park, FL 32789
    1911 Stonehurst Rd, Winter Park, FL 32789
    /2

    $2,910,000 Sold Jul 21, 2025

    • 5,097 Sq Ft
    • $571/SF
    • 82 Days On Market
    • 4 Beds
    • 6 Baths
    • Built 2001

    1911 Stonehurst Rd, Winter Park, FL 32789

    Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle.The red brick facade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    1911 Stonehurst Rd, Winter Park, FL 32789
  • 1129 Golfside Dr, Winter Park, FL 32792
    1129 Golfside Dr, Winter Park, FL 32792
    /2

    $689,500 Sold Jul 19, 2025

    • 1,750 Sq Ft
    • $394/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    1129 Golfside Dr, Winter Park, FL 32792

    Nestled on an idyllic tree-lined street, this charming 3-bedroom, 2-bathroom POOL HOME offers the Winter Park Lifestyle you've been dreaming of! Step inside to discover a beautifully appointed kitchen featuring granite countertops and NEW STAINLESS STEEL APPLIANCES. The light and bright formal dining room flows seamlessly into the spacious family room, complete with vaulted ceilings and a cozy

    Tess Muccigrosso RE/MAX 200 REALTY

    1129 Golfside Dr, Winter Park, FL 32792
  • 130 Lewfield Cir Unit 130, Winter Park, FL 32792
    130 Lewfield Cir Unit 130, Winter Park, FL 32792
    /2

    $142,000 Sold Jul 18, 2025

    • 678 Sq Ft
    • $209/SF
    • 64 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1973

    130 Lewfield Cir Unit 130, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Welcome Home! Step into effortless style and convenience with this beautifully updated second floor condo located in the sought after Stratford community of Winter Park. With thoughtful upgrades throughout including a modern kitchen with new appliances, and luxury vinyl and tile flooring, this home is move-in ready and full of charm. Enjoy the

    Renee Kumar LA ROSA REALTY LLC

    130 Lewfield Cir Unit 130, Winter Park, FL 32792
  • 100 S Interlachen Ave Unit 304, Winter Park, FL 32789
    100 S Interlachen Ave Unit 304, Winter Park, FL 32789
    /2

    $900,000 Sold Jul 18, 2025

    • 2,286 Sq Ft
    • $394/SF
    • 63 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1971

    100 S Interlachen Ave Unit 304, Winter Park, FL 32789

    Indulge in serene lakefront living from the comfort of two private balconies, each offering views of both the pool and the lake. This expansive, combined residence boasts the most generous square footage of any single unit within The Cloisters. Thoughtfully connected by an interior passthrough, it presents an ideal layout for elegant multi-generational living.Each wing of the home features

    Greg Vazzana FANNIE HILLMAN & ASSOCIATES

    100 S Interlachen Ave Unit 304, Winter Park, FL 32789
  • 1000 Howell Branch Rd, Winter Park, FL 32789
    1000 Howell Branch Rd, Winter Park, FL 32789
    /2

    $755,000 Sold Jul 18, 2025

    • Land
    • 0.55 Acre
    • $1,372,727 per Acre
    • 241 Days On Market

    1000 Howell Branch Rd, Winter Park, FL 32789

    Welcome home to 1000 Howell Branch Road, a canal front private oasis. This recently cleared lot is located on an oversized half acre+ lot with a recently dredged fresh water canal frontage, with easy access to Lake Maitland/Winter Park Chain of lakes. Hurry, it’s currently the only vacant lot available on the Chain of lakes. The private backyard is backed up to more than 2 acres of conservation

    Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1000 Howell Branch Rd, Winter Park, FL 32789
  • 5334 Cypress Dr, Winter Park, FL 32792
    5334 Cypress Dr, Winter Park, FL 32792
    /2

    $420,000 Sold Jul 17, 2025

    • 1,734 Sq Ft
    • $242/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1976

    5334 Cypress Dr, Winter Park, FL 32792

    Meticulously maintained 4-bedroom, 2-bath concrete block home in desirable Winter Park, lovingly cared for by the same owners for 37 years. Upgrades include a remodeled kitchen, updated master and guest baths, double-pane windows, and re-piping (2014). HVAC and electrical panels replaced in 2016. Roof, screen porch, and patio updated in 2022. Enjoy the beautifully landscaped backyard with St.

    Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

    5334 Cypress Dr, Winter Park, FL 32792
  • 1387 Sawgrass Ct, Winter Park, FL 32792
    1387 Sawgrass Ct, Winter Park, FL 32792
    /2

    $550,000 Sold Jul 17, 2025

    • 1,867 Sq Ft
    • $295/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1979

    1387 Sawgrass Ct, Winter Park, FL 32792

    Tucked away on a peaceful cul-de-sac, 1387 Sawgrass Court welcomes you home. This pristine, 1867 sq ft, single-story residence stands out with its distinctive and mature landscaping, perfectly nestled within a tree-lined, golf-front community. Located on a serene pond along the 15th hole of Winter Park Pines Golf Course (WP18), it offers a retreat with no rear neighbors- ideal for quiet

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    1387 Sawgrass Ct, Winter Park, FL 32792
  • 463 Warrenton Rd Unit 463, Winter Park, FL 32792
    463 Warrenton Rd Unit 463, Winter Park, FL 32792
    /2

    $270,000 Sold Jul 17, 2025

    • 1,043 Sq Ft
    • $259/SF
    • 20 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1986

    463 Warrenton Rd Unit 463, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Multiple Offers Received. Please present highest and best by 3pm on June 30th. Immaculate and move-in ready, this beautifully maintained 2 bed/2 bath one-story condo in sought after Winter Park Pines offers comfort, style and convenience. Step through your front courtyard, perfect for enjoying morning coffee and into a spacious great room featuring

    Jenny Lake FANNIE HILLMAN & ASSOCIATES

    463 Warrenton Rd Unit 463, Winter Park, FL 32792
  • 609 Langholm Dr, Winter Park, FL 32789
    609 Langholm Dr, Winter Park, FL 32789
    /2

    $916,000 Sold Jul 17, 2025

    • 1,981 Sq Ft
    • $462/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1960

    609 Langholm Dr, Winter Park, FL 32789

    Nestled in the heart of Winter Park in one of the area’s most sought-after neighborhoods, this professionally designed and fully renovated 3-bedroom, 2.5-bathroom home offers luxurious living with timeless modern style.Step inside to an open-concept layout featuring a gourmet kitchen outfitted with custom cabinetry, stunning quartz countertops, GE Cafe appliances, a Thermador drawer-style

    Jason Shore JMO REAL ESTATE GROUP

    609 Langholm Dr, Winter Park, FL 32789
  • 5436 Tangerine Ave, Winter Park, FL 32792
    5436 Tangerine Ave, Winter Park, FL 32792
    /2

    $415,000 Sold Jul 17, 2025

    • 1,996 Sq Ft
    • $208/SF
    • 22 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1977

    5436 Tangerine Ave, Winter Park, FL 32792

    Beautiful 4-Bedroom, 2-Bath Home in Winter Park (32792) — No HOA!Enter through your double front doors into a thoughtfully updated, move-in ready home. You're welcomed by a charming entry nook with a bench and hooks—perfect for organizing shoes, backpacks, and daily essentials.The formal living and dining rooms offer flexible space for entertaining or can easily be converted into a

    Amy Phillips CALL IT CLOSED INTL REALTY

    5436 Tangerine Ave, Winter Park, FL 32792
  • 5575 Garden Grove Cir, Winter Park, FL 32792
    5575 Garden Grove Cir, Winter Park, FL 32792
    /2

    $415,000 Sold Jul 17, 2025

    • 1,414 Sq Ft
    • $293/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    5575 Garden Grove Cir, Winter Park, FL 32792

    Charming 3-Bedroom, 2-Bathroom Home with Pool in the Heart of Winter ParkNestled in the desirable Park Avenue area of Winter Park, this beautiful single-family home offers the perfect blend of comfort and convenience. Enjoy easy access to the vibrant downtown Winter Park, known for its charming boutiques, cafes, and cultural attractions.This home features 3 spacious bedrooms and 2

    Torey Eisenman BENCHMARK REAL ESTATE GRP INC

    5575 Garden Grove Cir, Winter Park, FL 32792
  • 1670 Clematis Ln, Winter Park, FL 32792
    1670 Clematis Ln, Winter Park, FL 32792
    /2

    $286,000 Sold Jul 17, 2025

    • 1,401 Sq Ft
    • $204/SF
    • 16 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1962

    1670 Clematis Ln, Winter Park, FL 32792

    Location, Location, Location! Don’t miss this fantastic opportunity in highly desirable Winter Park—a beautiful 3-bedroom, 2-bath home with a heated pool! Recent Upgrades Include: Pool resurfaced (2023), Electrical panel replaced (2023), New roof and AC (2021), New water heater, Fully fenced backyard for privacy and convenience. While the home boasts major mechanical updates, the price reflects

    Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

    1670 Clematis Ln, Winter Park, FL 32792
  • 2159 Marsh Sedge Ln, Winter Park, FL 32792
    2159 Marsh Sedge Ln, Winter Park, FL 32792
    /2

    $760,000 Sold Jul 17, 2025

    • 2,192 Sq Ft
    • $347/SF
    • 42 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2019

    2159 Marsh Sedge Ln, Winter Park, FL 32792

    JUST LISTED - FANTASTIC WINTER PARK CONSERVATION LOT HOME LOCATED IN THE HEART OF THE PRESERVE AT HAWKS CREST!– 2159 Marsh Sedge Lane, Winter Park – Stunning Hawk’s Crest Residence – Offered at $789,000! Highly desirable, single-story residence in Winter Park’s newest gated community. This is the Pomelo model built by Meritage Homes. An absolutely stunning, immaculate, "betterthan new

    Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

    2159 Marsh Sedge Ln, Winter Park, FL 32792
  • 2309 Sun Valley Cir, Winter Park, FL 32792
    2309 Sun Valley Cir, Winter Park, FL 32792
    /2

    $252,500 Sold Jul 17, 2025

    • 1,669 Sq Ft
    • $151/SF
    • 65 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    2309 Sun Valley Cir, Winter Park, FL 32792

    Welcome to the largest floor plan in the community! This beautifully maintained 2 bedroom, 2 bathroom condo offers a fresh coat of interior paint and a thoughtfully designed layout perfect for comfortable living and entertaining.The main floor features two spacious bedrooms and an open-concept living and dining area, while the upstairs boasts a generous loft—ideal for a third bedroom,

    Kristin Vogt CENTURY 21 INTEGRA

    2309 Sun Valley Cir, Winter Park, FL 32792
  • 3520 Wilde Ave, Winter Park, FL 32792
    3520 Wilde Ave, Winter Park, FL 32792
    /2

    $310,000 Sold Jul 17, 2025

    • Land
    • 1.01 Acres
    • $306,931 per Acre
    • 94 Days On Market

    3520 Wilde Ave, Winter Park, FL 32792

    Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just over an acre, lot in coveted Winter Park. Nestled on the end of a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level

    Gwendolen Flynn COLDWELL BANKER RESIDENTIAL RE

    3520 Wilde Ave, Winter Park, FL 32792
  • 2823 Cady Way, Winter Park, FL 32792
    2823 Cady Way, Winter Park, FL 32792
    /2

    $439,000 Sold Jul 17, 2025

    • 1,688 Sq Ft
    • $260/SF
    • 137 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1965

    2823 Cady Way, Winter Park, FL 32792

    Gorgeous new flooring throughout the home!!New roof 2020! New water heater 2025. Beautiful Winter Park 4 Bedroom/ 2 Bath home in the sought-after Winter Park Pines neighborhood! This lovely residence has a beautiful split floorplan with lots of natural light! This home offers both a separate family room and living room to provide ample space to entertain or enjoy a relaxing evening with the

    Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

    2823 Cady Way, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 18

Florida Winter Park

Recently Sold Real Estate & Homes 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 $810,569.
What is the average time to sell a house in Winter Park, FL?
The houses for sale in Winter Park, FL spend an average of 95 days on the market.
What is the number of active homes for sale in Winter Park, FL?
There are 29 active homes for sale in Winter Park, FL.
How many homes have sold over the last 12 months in Winter Park, FL?
174 homes have sold in Winter Park, FL over the last 12 months.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 95 days on the market compared to the national average of 70 days. The median sale price for homes in Winter Park, FL over the last 12 months is $450,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$450,000
Median Single Family Sale Price
$810,000
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
$339
Number of Homes for Sale
29
Last 12 months Home Sales
174
Months of Supply
2.00
Median List Price
$630,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
1%
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