1,146

Recently Sold Winter Park, FL Homes

Section Image
  • 100 S Virginia Ave Unit 319, Winter Park, FL 32789
    100 S Virginia Ave Unit 319, Winter Park, FL 32789
    /2

    $1,079,000 Sold Sep 05, 2025

    • 2,649 Sq Ft
    • $407/SF
    • 2 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2008

    100 S Virginia Ave Unit 319, Winter Park, FL 32789

    Experience the best of Winter Park living in this distinguished three-bedroom, three-bathroom condominium, located in the secure and sought-after Douglas Grand development—just one block from vibrant Park Avenue. Spanning an impressive 2,649 sq ft on a single level, this third-floor residence blends timeless architectural charm, quality construction, and everyday function. Step inside to an

    Padgett McCormick KELLY PRICE & COMPANY LLC

    100 S Virginia Ave Unit 319, Winter Park, FL 32789
  • 402 Saint Dunstan Way, Winter Park, FL 32792
    402 Saint Dunstan Way, Winter Park, FL 32792
    /2

    $656,402 Sold Sep 05, 2025

    • 1,779 Sq Ft
    • $369/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1964

    402 Saint Dunstan Way, Winter Park, FL 32792

    ACCEPTING BEST AND FINAL OFFERS BY 9AM ON MONDAY, 6/30! Welcome to this beautifully upgraded 3-bedroom, 2-bathroom pool home offering 1,779 square feet of thoughtfully and expertly designed living space, where no detail has been overlooked! Nestled in the highly desirable neighborhood of Winter Park Pines - where the mailman still delivers to your front door - this move-in-ready gem combines

    Amy Turner KELLER WILLIAMS WINTER PARK

    402 Saint Dunstan Way, Winter Park, FL 32792
  • 1767 Meadowgold Ln, Winter Park, FL 32792
    1767 Meadowgold Ln, Winter Park, FL 32792
    /2

    $360,000 Sold Sep 04, 2025

    • 1,368 Sq Ft
    • $263/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    1767 Meadowgold Ln, Winter Park, FL 32792

    Welcome to your new Winter Park home! Located in the highly sought-after community of Autumn Glen, this beautifully maintained property offers peace of mind and modern comfort with a new roof, newer A/C system, updated plumbing, and a remodeled kitchen featuring granite countertops, stainless steel appliances, and a spacious pantry. The L-shaped living and dining area boasts vaulted ceilings,

    Kyle Clark RE/MAX TOWN & COUNTRY REALTY

    1767 Meadowgold Ln, Winter Park, FL 32792
  • 915 Aragon Ave, Winter Park, FL 32789
    915 Aragon Ave, Winter Park, FL 32789
    /2

    $580,000 Sold Sep 04, 2025

    • 1,701 Sq Ft
    • $341/SF
    • 16 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2004

    915 Aragon Ave, Winter Park, FL 32789

    Nestled in a peaceful enclave near Park Avenue in Winter Park, this inviting 3 bedroom, 3 bathroom, 1,701 SF townhome offers classic Florida living with modern comforts. A welcoming entry opens to bamboo wood flooring that flows through the main living areas. The living room and adjacent dining space connect seamlessly to the gorgeous kitchen, featuring 42" wood cabinets, stainless appliances,

    Shelby Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    915 Aragon Ave, Winter Park, FL 32789
  • 618 Blairshire Cir, Winter Park, FL 32792
    618 Blairshire Cir, Winter Park, FL 32792
    /2

    $600,000 Sold Sep 04, 2025

    • 1,876 Sq Ft
    • $320/SF
    • 38 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1964

    618 Blairshire Cir, Winter Park, FL 32792

    First time on the market! This one-owner, 3-bedroom, 3-bathroom single-family pool home offers the perfect blend of classic Florida charm and modern potential. Originally named The Polynesia, the home embraces open Florida living while offering distinct zones for privacy and comfort. A brand-new roof (2025) and 2 New HVAC 2024 , BOTH electrical panels 2025, and Water Heater 2025 provides peace of

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    618 Blairshire Cir, Winter Park, FL 32792
  • 1250 S Denning Dr Unit 108, Winter Park, FL 32789
    1250 S Denning Dr Unit 108, Winter Park, FL 32789
    /2

    $177,000 Sold Sep 04, 2025

    • 658 Sq Ft
    • $269/SF
    • 75 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1967

    1250 S Denning Dr Unit 108, Winter Park, FL 32789

    This move-in-ready, first-floor condo has been completely updated and is ready for its new owner. Enjoy newer flooring, fresh paint, an in unit washer/dryer, and modern fixtures throughout! Located in a well-maintained community with great amenities, including a pool. Conveniently situated in desirable Winter Park, close to shopping, dining, and major roadways. A great opportunity for homeowners

    Cleve Loveland LOVELAND PROPERTIES

    1250 S Denning Dr Unit 108, Winter Park, FL 32789
  • 3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792
    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792
    /2

    $170,000 Sold Sep 04, 2025

    • 840 Sq Ft
    • $202/SF
    • 176 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1990

    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792

    beautiful Condo in of Winter Park.This spacious second-floor unit is filled with natural light from its large windows, creating a bright and inviting atmosphere. The main living areas feature wood laminate tile flooring, while the kitchen showcases sleek granite countertops for a modern touch. Both bathrooms have been stylishly updated with contemporary fixtures and finishes, adding to

    Elenice Pereira WRA BUSINESS & REAL ESTATE

    3651 N Goldenrod Rd Unit 210, Winter Park, FL 32792
  • 171 Cortland Ave, Winter Park, FL 32789
    171 Cortland Ave, Winter Park, FL 32789
    /2

    $1,245,000 Sold Sep 03, 2025

    • 1,683 Sq Ft
    • $740/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1940

    171 Cortland Ave, Winter Park, FL 32789

    Come see this outstanding 15,000 sqft lot surrounded by multi-million dollar homes on one of Winter Parks picturesque tree lined brick streets just a short drive from Park Avenue. This property offers the option of updating and remodeling the existing charming 1,683 sqft 2 bedroom, 2 bath Cottage located on the property or building your dream home in one of the most beautiful residential areas

    Jerry Oller FANNIE HILLMAN & ASSOCIATES

    171 Cortland Ave, Winter Park, FL 32789
  • 3266 Oak Lake Place Unit 140, Winter Park, FL 32792
    3266 Oak Lake Place Unit 140, Winter Park, FL 32792
    /2

    $205,000 Sold Sep 02, 2025

    • 1,031 Sq Ft
    • $199/SF
    • 8 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1984

    3266 Oak Lake Place Unit 140, Winter Park, FL 32792

    Modern Charm in Prime Winter Park Location!Step into this beautiful 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community of Winter Park. Freshly painted with brand-new carpeting throughout, this stylish 1,031 sq. ft. home offers both comfort and flair.Enjoy peace of mind with a new roof installed in 2023 and an updated A/C handler. The exterior is

    Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

    3266 Oak Lake Place Unit 140, Winter Park, FL 32792
  • 1536 Golfside Dr, Winter Park, FL 32792
    1536 Golfside Dr, Winter Park, FL 32792
    /2

    $638,250 Sold Sep 02, 2025

    • 1,888 Sq Ft
    • $338/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    1536 Golfside Dr, Winter Park, FL 32792

    Welcome Home to your charming abode in Winter Park! This courtyard home is cozy, warm and inviting and waiting for you to make it yours. Well maintained, this home is move in ready! Walk into the foyer and you'll be greeted by cherry wood flooring as you step into the living room with high ceilings, beams, and a cozy fireplace. The living room is perfect for family meals, the dining space is

    Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    1536 Golfside Dr, Winter Park, FL 32792
  • 2517 Windward Way, Winter Park, FL 32792
    2517 Windward Way, Winter Park, FL 32792
    /2

    $272,500 Sold Sep 02, 2025

    • 1,070 Sq Ft
    • $255/SF
    • 15 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1975

    2517 Windward Way, Winter Park, FL 32792

    Welcoming townhome on cul-de-sac with no rear neighbors. Step out ontoyour roomy 16 x 12 screened porch and take in the peaceful views of thetennis courts and green space—it’s the perfect spot to relax with your morningcoffee or unwind after a long day. Inside, you’ll love the bright, open feelthanks to clerestory windows in the living room, freshly painted walls, andbrand-new

    Sheila Mathews COLDWELL BANKER RESIDENTIAL RE

    2517 Windward Way, Winter Park, FL 32792
  • 1117 Park Green Place, Winter Park, FL 32789
    1117 Park Green Place, Winter Park, FL 32789
    /2

    $355,000 Sold Sep 02, 2025

    • 1,235 Sq Ft
    • $287/SF
    • 26 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1992

    1117 Park Green Place, Winter Park, FL 32789

    Charming One-Story Townhome in Prime Winter Park Location!Welcome to this adorable detached 3-bedroom, 2-bath townhome with a spacious 2-car garage, tucked away in the heart of Winter Park (32789). Just minutes from Winter Park Village, Fleming’s, and the boutiques and dining of Park Avenue, this home blends low-maintenance living with unbeatable convenience.Step inside to find a

    Kelly Sue Stonebreaker RE/MAX TOWN & COUNTRY REALTY

    1117 Park Green Place, Winter Park, FL 32789
  • 1733 Harmon Ave, Winter Park, FL 32789
    1733 Harmon Ave, Winter Park, FL 32789
    /2

    $1,595,000 Sold Sep 02, 2025

    • 3,267 Sq Ft
    • $488/SF
    • 27 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2025

    1733 Harmon Ave, Winter Park, FL 32789

    Experience the charm and elegance of Winter Park living in this beautifully designed 5-bedroom, 4.5-bath home offering 3,267 square feet of thoughtfully crafted space.This residence combines timeless architectural character with modern functionality,From the moment you enter, you’re welcomed by warm natural light, the first floor features an office with an open and inviting layout, and

    Jordan Freeland SOUTH REALTY, INC

    1733 Harmon Ave, Winter Park, FL 32789
  • 1764 Mondrian Cir, Winter Park, FL 32789
    1764 Mondrian Cir, Winter Park, FL 32789
    /2

    $920,000 Sold Sep 02, 2025

    • 2,265 Sq Ft
    • $406/SF
    • 9 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2024

    1764 Mondrian Cir, Winter Park, FL 32789

    Act quickly—only three units remain! We are excited to introduce a beautiful, brand-new modern brownstone located in the heart of Winter Park, with access to Lake Killarney. Nestled in an exclusive community of 30 contemporary townhomes, each residence is thoughtfully designed with exquisite finishes, expansive storefront-style windows, and 11-foot ceilings that welcome an abundance of natural

    Brian Teach COLDWELL BANKER RESIDENTIAL RE

    1764 Mondrian Cir, Winter Park, FL 32789
  • 236 N Ranger Blvd, Winter Park, FL 32792
    236 N Ranger Blvd, Winter Park, FL 32792
    /2

    $587,000 Sold Sep 02, 2025

    • 1,844 Sq Ft
    • $318/SF
    • 105 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    236 N Ranger Blvd, Winter Park, FL 32792

    - NO HOA - Welcome to this exquisitely designed and fully remodeled block home! As you enter you step into a stunning open layout featuring a FULLY remodeled kitchen with quartz countertops, real oak soft-close cabinetry, and top-tier appliances—including a wine fridge and an induction cooktop with built-in air fryer/oven combo. On the east wing of the home you will have 3 spacious bedrooms and 2

    Ramses Misel Trillos EXP REALTY LLC

    236 N Ranger Blvd, Winter Park, FL 32792
  • 3306 Fishermans Cove, Winter Park, FL 32792
    3306 Fishermans Cove, Winter Park, FL 32792
    /2

    $468,500 Sold Sep 02, 2025

    • 2,408 Sq Ft
    • $195/SF
    • 97 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    3306 Fishermans Cove, Winter Park, FL 32792

    MULTIPLE OFFERS HAVE BEEN RECEIVED. PLEASE SUBMIT BEST AND FINAL BY 12:00PM TOMORROW, TUESDAY, JULY 22nd. Beautiful home is the sought-after community of Pelican Bay in Winter Park. Pelican Bay only has 48 homes in the community and has a small HOA of $500 a year. This 3- bedroom, 2-bathroom pool home is full of charm, warmth, and love, and ready to move-in. Located on a corner lot as you enter

    Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

    3306 Fishermans Cove, Winter Park, FL 32792
  • 2209 Fairglenn Way, Winter Park, FL 32792
    2209 Fairglenn Way, Winter Park, FL 32792
    /2

    $435,000 Sold Aug 31, 2025

    • 2,027 Sq Ft
    • $215/SF
    • 54 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1986

    2209 Fairglenn Way, Winter Park, FL 32792

    **New roof will be installed prior to closing**Located in the sought-after Quail Run community, this 4-bedroom, 2-bathroom home offers over 2,000 sq ft of comfortable living space on an oversized lot.The heart of the home is the large kitchen, complete with two sinks—perfect for extra prep and easy cleanup. Just off the kitchen, enjoy a spacious screened-in patio, ideal for

    Benjamin Benami HIVE REALTY LLC

    2209 Fairglenn Way, Winter Park, FL 32792
  • 443 Beloit Ave, Winter Park, FL 32789
    443 Beloit Ave, Winter Park, FL 32789
    /2

    $1,740,000 Sold Aug 29, 2025

    • 2,964 Sq Ft
    • $587/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1983

    443 Beloit Ave, Winter Park, FL 32789

    Welcome to the timeless charm of Beloit Avenue, one of Winter Park’s most desired streets. This classic and elegant 3-bedroom, 2.5-bath residence offers nearly 3,000 square feet of thoughtfully designed living all on one level. Just two blocks from Park Avenue and a short stroll to the Winter Park Golf Course, the location is truly unmatched.Inside, high ceilings, detailed crown molding,

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    443 Beloit Ave, Winter Park, FL 32789
  • 7642 Glenmoor Ln, Winter Park, FL 32792
    7642 Glenmoor Ln, Winter Park, FL 32792
    /2

    $310,000 Sold Aug 29, 2025

    • 1,217 Sq Ft
    • $255/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1984

    7642 Glenmoor Ln, Winter Park, FL 32792

    ***MULTIPLE OFFERS...SELLER CALLING FOR HIGHEST AND BEST BY SUNDAY, AUGUST 17TH AT 12PM***INVESTOR SPECIAL OR FIRST-TIME BUYER OPPORTUNITY!Bring your vision and a little TLC to unlock the full potential of this charming 2-bedroom, 2-bathroom home on an OVERSIZED .27-acre lot with NO HOA fees. Whether you’re looking to renovate and resell, rent for income, or create your own dream home, this

    Pam Grabenhorst THE WILKINS WAY LLC

    7642 Glenmoor Ln, Winter Park, FL 32792
  • 1871 Staunton Ave, Winter Park, FL 32789
    1871 Staunton Ave, Winter Park, FL 32789
    /2

    $425,000 Sold Aug 29, 2025

    • Land
    • 0.32 Acre
    • $1,328,125 per Acre
    • 3 Days On Market

    1871 Staunton Ave, Winter Park, FL 32789

    A Double Lot Near Lake Killarney! This bungalow nestled on a generous 0.32-acre lot—one of the largest in the neighborhood—just one block from scenic Lake Killarney is perfect for something NEW. With a spacious backyard, mature landscaping, and even a shuffleboard court, this property offers a rare opportunity to create your very own backyard retreat. There's room to add a pool, a pickleball

    Greg Staker WATSON REALTY CORP.

    1871 Staunton Ave, Winter Park, FL 32789
  • 2739 Amsden Rd, Winter Park, FL 32792
    2739 Amsden Rd, Winter Park, FL 32792
    /2

    $510,000 Sold Aug 29, 2025

    • 1,877 Sq Ft
    • $272/SF
    • 6 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1959

    2739 Amsden Rd, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Multiple offers received - please submit HIGHEST & BEST by THURSDAY, JULY 17th at 5:00 PM. Welcome to the most gorgeous waterfront property in Winter Park for UNDER $500,000! This charming 4 bedroom, 3 bath home is situated on a third of an acre with a stunning pool and water features overlooking a serene water view. The backyard truly must be seen

    D'Anne Mica FANNIE HILLMAN & ASSOCIATES

    2739 Amsden Rd, Winter Park, FL 32792
  • 1840 Biscayne Dr, Winter Park, FL 32789
    1840 Biscayne Dr, Winter Park, FL 32789
    /2

    $940,000 Sold Aug 29, 2025

    • 2,646 Sq Ft
    • $355/SF
    • 17 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2024

    1840 Biscayne Dr, Winter Park, FL 32789

    Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom Homes—and it’s ready for its very first owner. Set in a prime Winter Park location, this two-story home offers clean lines, high-end finishes, and a layout that fits real life.With just over 2,600 square feet under air, the home features 4 bedrooms and 3 full bathrooms.

    Jennifer King CORCORAN PREMIER REALTY

    1840 Biscayne Dr, Winter Park, FL 32789
  • 1355 Hibiscus Ave, Winter Park, FL 32789
    1355 Hibiscus Ave, Winter Park, FL 32789
    /2

    $1,800,000 Sold Aug 29, 2025

    • 4,155 Sq Ft
    • $433/SF
    • 32 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2006

    1355 Hibiscus Ave, Winter Park, FL 32789

    Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-family home offering over 4,100 SF of living space. Ideally located on a tree-lined street with Winter Park’s signature brick roads, this home sits in one of the area’s most sought-after neighborhoods. Just minutes from the Winter Park Racquet Club in the Vias, Park Avenue shops and dining, YMCA, top hospitals, and

    Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

    1355 Hibiscus Ave, Winter Park, FL 32789
  • 1050 Reading Ct, Winter Park, FL 32792
    1050 Reading Ct, Winter Park, FL 32792
    /2

    $349,000 Sold Aug 29, 2025

    • 1,637 Sq Ft
    • $213/SF
    • 52 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1983

    1050 Reading Ct, Winter Park, FL 32792

    Great investment opportunity in the prime location of Winter Park, Florida. Ideal for a growing family or investor. Well established neighborhood of Howell Estates, 3 bedroom, 2 full bathrooms, 1,637 square feet of living area with just over a quarter of an acre. Split plan bedrooms for added privacy. Exterior of the home is concrete block and stucco. The eat-in-kitchen and large family room

    Carmen Vazquez REALTY TECH INC

    1050 Reading Ct, Winter Park, FL 32792
  • 3011 Temple Trail, Winter Park, FL 32789
    3011 Temple Trail, Winter Park, FL 32789
    /2

    $900,000 Sold Aug 29, 2025

    • 2,406 Sq Ft
    • $374/SF
    • 83 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1965

    3011 Temple Trail, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to this exceptional –FULLY UPGRADED / POOL HOME– in the highly sought-after Dommerich Estates, where timeless style meets modern design on a spacious .31 ACRE CONSERVATION LOT with serene WOODED VIEWS! Major updates set this home apart; enjoy year round outdoor living with a large

    Jennifer Wemert WEMERT GROUP REALTY LLC

    3011 Temple Trail, Winter Park, FL 32789
  • 1250 S Denning Dr Unit 111, Winter Park, FL 32789
    1250 S Denning Dr Unit 111, Winter Park, FL 32789
    /2

    $259,000 Sold Aug 29, 2025

    • 908 Sq Ft
    • $285/SF
    • 76 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1967

    1250 S Denning Dr Unit 111, Winter Park, FL 32789

    LOCATION LOCATION!! Now is your chance to own this STUNNING NEWLY RENOVATED 2 bed / 2 full bath FIRST FLOOR condo in the highly desirable MEAD GARDEN COMMUNITY within WALKING/BIKING DISTANCE to Rollins College and the Park Ave Area! This unit was recently renovated to include it's own DEDICATED LAUNDRY CLOSET! (2024) WASHER/DRYER COMBO INCLUDED! NEW ROOF (2022) NEW WATER HEATER (2024) This

    Alayna Phillips EXP REALTY LLC

    1250 S Denning Dr Unit 111, Winter Park, FL 32789
  • 7602 Glenmoor Ln, Winter Park, FL 32792
    7602 Glenmoor Ln, Winter Park, FL 32792
    /2

    $380,000 Sold Aug 29, 2025

    • 1,687 Sq Ft
    • $225/SF
    • 126 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    7602 Glenmoor Ln, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom single-family home in the heart of Winter Park, FL! Featuring a newer roof and AC, this home offers comfort and peace of mind.Step inside to find freshly painted interiors and a layout designed for both relaxation and entertaining. The formal living room boasts a cozy wood-burning fireplace, while the separate dining room sits

    Uzi Husain KELLER WILLIAMS REALTY AT THE PARKS

    7602 Glenmoor Ln, Winter Park, FL 32792
  • 1021 Mare Bello Dr, Winter Park, FL 32792
    1021 Mare Bello Dr, Winter Park, FL 32792
    /2

    $370,000 Sold Aug 29, 2025

    • 1,730 Sq Ft
    • $214/SF
    • 151 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1965

    1021 Mare Bello Dr, Winter Park, FL 32792

    NEW ROOF coming soon! A great Single-Family Home in Winter Park HS district. Check out this beautiful freshly painted interior and exterior single story 3 bedroom 2 1/2 bath home with bonus room and all new LVP flooring throughout. When you walk in the front door turn left to enter the Great Room that includes the open concept kitchen, dining and family rooms. The kitchen includes all appliances

    Lori Hutchinson THE WILKINS WAY LLC

    1021 Mare Bello Dr, Winter Park, FL 32792
  • 1500 Gay Rd Unit 7A, Winter Park, FL 32789
    1500 Gay Rd Unit 7A, Winter Park, FL 32789
    /2

    $230,000 Sold Aug 29, 2025

    • 1,026 Sq Ft
    • $224/SF
    • 205 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1972

    1500 Gay Rd Unit 7A, Winter Park, FL 32789

    NEW WINDOWS AND SLIDING GLASS DOOR JUST INSTALLED!!! Discover unparalleled comfort in this stunning 2-bed, 2-bath Condominium, nestled in the sought-after Winter Park community with frontage on Lake Killarney. Immerse yourself in luxury with a sparkling community pool and a host of recent upgrades that include upgraded flooring, kitchen cabinets, counter-tops, bathrooms, and more. Positioned on

    Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

    1500 Gay Rd Unit 7A, Winter Park, FL 32789
  • 541 London Rd, Winter Park, FL 32792
    541 London Rd, Winter Park, FL 32792
    /2

    $468,000 Sold Aug 28, 2025

    • 1,899 Sq Ft
    • $246/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    541 London Rd, Winter Park, FL 32792

    Mid-Century Modern vibes in this spacious 3 bedroom, 2 bathroom home with an innovative courtyard design that offers scenic views of the expansive lot from almost every room. The house is nestled under a canopy of mature trees on one of the largest lots in Winter Park Pines. Kitchen and baths are original but recent updates include: ROOF 2019, HVAC 2017, REPLUMBED 2009, GARAGE DOOR REPLACED,

    Christopher Bauman REVEL REALTY LLC

    541 London Rd, Winter Park, FL 32792
  • 1500 Mizell Ave, Winter Park, FL 32789
    1500 Mizell Ave, Winter Park, FL 32789
    /2

    $1,300,000 Sold Aug 28, 2025

    • 2,303 Sq Ft
    • $564/SF
    • 2 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1957

    1500 Mizell Ave, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. An extraordinary opportunity to own a beautifully renovated home on a prestigious tree-lined street in Winter Park’s 32789. Set on a desirable 13,500 square foot (90 × 150) lot with no HOA and bordering the prestigious Windsong community, this prime property offers the freedom to live comfortably now, expand over time, or build new. This 4-bedroom,

    Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

    1500 Mizell Ave, Winter Park, FL 32789
  • 1610 Chestnut Ave, Winter Park, FL 32789
    1610 Chestnut Ave, Winter Park, FL 32789
    /2

    $980,000 Sold Aug 28, 2025

    • 2,140 Sq Ft
    • $458/SF
    • 20 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1974

    1610 Chestnut Ave, Winter Park, FL 32789

    Nestled in the desirable Tree Streets of Winter Park, this stunning Mid-Century Modern residence offers timeless style, thoughtful updates, and effortless indoor-outdoor living. With over 2,100 square feet of beautifully designed space, this 3-bedroom, 2.5-bath home delivers modern functionality with elegant character—just minutes from the heart of Park Avenue.Inside, you'll find an open

    Derek Kammerer THE AGENCY ORLANDO

    1610 Chestnut Ave, Winter Park, FL 32789
  • 2151 Conifer Ave, Winter Park, FL 32792
    2151 Conifer Ave, Winter Park, FL 32792
    /2

    $450,000 Sold Aug 28, 2025

    • 1,806 Sq Ft
    • $249/SF
    • 32 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    2151 Conifer Ave, Winter Park, FL 32792

    This POOL home is amazing in every way and is truly a must see! Original Owner with pride of ownership. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location just minutes to everything. This residence boasts an array of desirable features. Three bedrooms and two full baths with oversized primary bedroom. As you enter through the new, striking front door and

    Denise Korrey KORR REALTY CORP

    2151 Conifer Ave, Winter Park, FL 32792
  • 2426 Windward Way, Winter Park, FL 32792
    2426 Windward Way, Winter Park, FL 32792
    /2

    $270,000 Sold Aug 28, 2025

    • 932 Sq Ft
    • $290/SF
    • 50 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1976

    2426 Windward Way, Winter Park, FL 32792

    Nestled in the heart of the highly desirable Windward Square community, this beautifully maintained home offers the perfect blend of comfort, style, and convenience. Step inside from the tranquil front patio and be welcomed by a surprisingly spacious open floor plan that instantly feels like home.The kitchen shines with newer appliances, granite countertops and beautiful upgraded cabinetry.

    Kim Coburn RE/MAX TOWN & COUNTRY REALTY

    2426 Windward Way, Winter Park, FL 32792
  • 233 Hampden Place, Winter Park, FL 32789
    233 Hampden Place, Winter Park, FL 32789
    /2

    $1,110,000 Sold Aug 26, 2025

    • 2,813 Sq Ft
    • $395/SF
    • 7 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1980

    233 Hampden Place, Winter Park, FL 32789

    Vintage original 5-Bed, 3-Bath pool home with new roof on an estate-size lot adorned with mature landscaping and breathtaking views that overlook a natural wooded area in desirable Virginia Heights. This fabulous property could have a full renovation to make best use of the existing home, or the 16,000+ square foot lot offers the perfect opportunity to build the new home of your dreams and

    Frank Ferrell FERRELL REALTY, INC.

    233 Hampden Place, Winter Park, FL 32789
  • 2358 Sun Valley Cir, Winter Park, FL 32792
    2358 Sun Valley Cir, Winter Park, FL 32792
    /2

    $272,500 Sold Aug 26, 2025

    • 1,295 Sq Ft
    • $210/SF
    • 24 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1984

    2358 Sun Valley Cir, Winter Park, FL 32792

    Welcome to the established and well-maintained community of Cedarwood Village, located in highly desirable Winter Park! TREE-LINED STREETS lead you to this completely REMODELED single-story, 2-bedroom, 2-bath BLOCK-CONSTRUCTED condominium offering nearly 1,300 square feet of interior living space, plus an enclosed SUNROOM for year-round enjoyment. As you enter the foyer, you’ll immediately

    Natalie Kauffman KELLER WILLIAMS CLASSIC

    2358 Sun Valley Cir, Winter Park, FL 32792
  • 3430 Arbutus Ln, Winter Park, FL 32792
    3430 Arbutus Ln, Winter Park, FL 32792
    /2

    $368,000 Sold Aug 26, 2025

    • 1,674 Sq Ft
    • $220/SF
    • 40 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1960

    3430 Arbutus Ln, Winter Park, FL 32792

    Charming Winter Park Pool Home with Mother-In-Law Suite. Welcome to your own slice of paradise in the heart of Winter Park! This beautifully maintained 4-bedroom, 3-bathroom home offers the perfect blend of comfort, functionality, and Florida living. The main home features 3 spacious bedrooms and 2 full bathrooms, with a bright and open layout that’s ideal for both everyday living and

    Monica Bouyouris URBAN NEST CLUB INC

    3430 Arbutus Ln, Winter Park, FL 32792
  • 2812 Mulford Ave, Winter Park, FL 32789
    2812 Mulford Ave, Winter Park, FL 32789
    /2

    $610,000 Sold Aug 25, 2025

    • 1,627 Sq Ft
    • $375/SF
    • 162 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1953

    2812 Mulford Ave, Winter Park, FL 32789

    Welcome to 2812 Mulford Avenue. This updated 3 bedroom and 2 bath home is located perfectly in Winter Park. Walking distance to East End Market, close to Rollins College, steps from Baldwin Park, 1 mile from Mills 50 area, and close to Mead Gardens, Leu Gardens and Loch Haven Park. The neighborhood is quiet with low traffic, oversized lots, and NO HOA, yet surrounded by amazing schools, local

    Haley Young SYNCHRONICITY REAL ESTATE SOLUTIONS

    2812 Mulford Ave, Winter Park, FL 32789
  • 7682 Glenmoor Ln, Winter Park, FL 32792
    7682 Glenmoor Ln, Winter Park, FL 32792
    /2

    $530,000 Sold Aug 22, 2025

    • 2,254 Sq Ft
    • $235/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    7682 Glenmoor Ln, Winter Park, FL 32792

    Welcome to 7682 Glenmoor Lane – Located in the established community of Glenmoor, zoned for Winter Park HS, Maitland Middle and Lakemont Elementary.This beautifully renovated Winter Park gem is situated on a generous 0.26-acre lot, this stunning single-family home blends timeless style with modern updates throughout.Step inside to discover custom tile flooring, solid wood cabinetry in

    Bob Holston, Jr HOLSTON PROPERTIES & DEV., INC

    7682 Glenmoor Ln, Winter Park, FL 32792
  • 1422 Via Sangro Place, Winter Park, FL 32792
    1422 Via Sangro Place, Winter Park, FL 32792
    /2

    $1,295,000 Sold Aug 22, 2025

    • 4,161 Sq Ft
    • $311/SF
    • 8 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 2015

    1422 Via Sangro Place, Winter Park, FL 32792

    Welcome to your WATERFRONT dream home in the prestigious Lakeside Estates, a private gated community situated on Garden Lake. Highly desirable cul-de-sac location and short stroll to the playground. The Kerrville model home is designed for stylish, easy living and offers an open floor plan with high-end finishes throughout. Impress your family and friends with the inviting foyer, 20+ ceilings,

    Jennifer Sloan KELLY PRICE & COMPANY LLC

    1422 Via Sangro Place, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 18

Florida Orange County 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 $946,293.
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 63 days on the market.
What is the number of active homes for sale in Winter Park, FL?
There are 321 active homes for sale in Winter Park, FL.
How many homes have sold over the last 12 months in Winter Park, FL?
1,032 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 63 days on the market compared to the national average of 52 days. The median sale price for homes in Winter Park, FL over the last 12 months is $480,000, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$600,000
Median Townhouse Sale Price
$468,200
Median 2 Bedroom Sale Price
$220,000
Median 1 Bedroom Sale Price
$155,000
Average Price Per Sq Ft
$367
Number of Homes for Sale
321
Last 12 months Home Sales
1,032
Months of Supply
3.70
Median List Price
$524,950
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group