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Recently Sold Winter Park Homes

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  • 311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
    /2

    $362,500 Sold Jul 30, 2025

    • 884 Sq Ft
    • $410/SF
    • 103 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1960

    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789

    Priced to sell!! Motivated Seller. Outstanding structural integrity, no big assessments ahead! Whispering Waters passed its structural integrity inspection and reserves study with flying colors—earning compliments for the quality and care of the buildings. This is a very well-managed community, and the $1,054 monthly HOA covers nearly everything, including electricity! The only exception is cable

    Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
  • 700 Melrose Ave Unit A22, Winter Park, FL 32789
    700 Melrose Ave Unit A22, Winter Park, FL 32789
    /2

    $280,000 Sold Jul 30, 2025

    • 1,074 Sq Ft
    • $261/SF
    • 130 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1964

    700 Melrose Ave Unit A22, Winter Park, FL 32789

    HUGE PRICE CHANGE! Welcome to this beautifully updated second-floor unit, offering a fresh and modern living experience. Featuring brand-new luxury vinyl flooring, new appliances, granite countertops, as well as upgraded fans and light fixtures, this home combines style and comfort. Enjoy breathtaking, floor-to-ceiling pond views from the sunroom, creating the perfect spot to relax and

    Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit A22, 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 1824 Dorris Dr, Orlando, FL 32807
    1824 Dorris Dr, Orlando, FL 32807
    /2

    $350,000 Sold Jul 18, 2025

    • 1,457 Sq Ft
    • $240/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1945

    1824 Dorris Dr, Orlando, FL 32807

    Fully remodeled & move-in ready! This beautifully updated 3-bed Orlando home is packed with upgrades: New roof, New AC, New water heater, brand-new LVP flooring, quartz countertops in a fully remodeled kitchen, new appliances, new bathroom, modern lighting, and fresh interior & exterior paint. This home offers a great amount of natural lighting! Large backyard perfect for entertaining or relaxing

    Shadi Tamimi SET HOMES REALTY LLC

    1824 Dorris Dr, Orlando, FL 32807
  • 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
  • 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
  • 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
  • 186 Scottsdale Square Unit F186, Winter Park, FL 32792
    186 Scottsdale Square Unit F186, Winter Park, FL 32792
    /2

    $82,000 Sold Jul 15, 2025

    • 1,020 Sq Ft
    • $80/SF
    • 0 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1974

    186 Scottsdale Square Unit F186, Winter Park, FL 32792

    Beautiful and well maintained 2 bedroom 2 bath condo. Located close to Full sail University. Stainless Steel appliances. New A/C February 2024. Condo was recently remodeled in October 2023 (all new kitchen - cabinets and appliances, new floors, new vanities in the bathrooms, new light fixtures. Easy access to major roads and highways. Beautiful outdoor area, playground, and pool.

    John Harbuck FANNIE HILLMAN & ASSOCIATES

    186 Scottsdale Square Unit F186, Winter Park, FL 32792
  • 1077 Minnesota Ave, Winter Park, FL 32789
    1077 Minnesota Ave, Winter Park, FL 32789
    /2

    $1,335,000 Sold Jul 15, 2025

    • 3,046 Sq Ft
    • $438/SF
    • 75 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2025

    1077 Minnesota Ave, Winter Park, FL 32789

    Under Construction. New Construction in the Heart of Winter Park by Nautilus Homes - Introducing an exceptional opportunity to own a brand-new luxury residence by award-winning builder Nautilus Homes, ideally situated between Orlando Avenue and Orange Avenue—just moments from Winter Park’s renowned shops, dining, and cultural attractions.This thoughtfully designed 4-bedroom, 4-bath estate

    Jake Johnson SHORES REAL ESTATE

    1077 Minnesota Ave, Winter Park, FL 32789
  • 1750 Winchester Dr, Winter Park, FL 32789
    1750 Winchester Dr, Winter Park, FL 32789
    /2

    $1,400,000 Sold Jul 15, 2025

    • 2,637 Sq Ft
    • $531/SF
    • 91 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1960

    1750 Winchester Dr, Winter Park, FL 32789

    Welcome to this masterfully renovated Winter Park residence, where modern luxury meets timeless comfort in coveted Timberlane Shores. The heart of this home is a chef's dream kitchen, featuring a professional WOLF range, custom two-tone cabinetry in rich wood and sophisticated navy blue, and premium stone countertops that extend to a generous entertainment island. Gleaming terrazzo floors flow

    Michael Ford FANNIE HILLMAN & ASSOCIATES

    1750 Winchester Dr, Winter Park, FL 32789
  • 795 W Canton Ave, Winter Park, FL 32789
    795 W Canton Ave, Winter Park, FL 32789
    /2

    $1,050,000 Sold Jul 14, 2025

    • 2,374 Sq Ft
    • $442/SF
    • 23 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2017

    795 W Canton Ave, Winter Park, FL 32789

    Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and Winter Park Village, this stunning modern Craftsman by David Weekley Homes perfectly blends luxury, comfort, and convenience.The thoughtfully designed floor plan features a downstairs primary suite, rich hardwood flooring, and sliding barn doors opening to a versatile

    Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

    795 W Canton Ave, Winter Park, FL 32789
  • 1795 Greenwich Ave, Winter Park, FL 32789
    1795 Greenwich Ave, Winter Park, FL 32789
    /2

    $2,435,000 Sold Jul 14, 2025

    • 3,852 Sq Ft
    • $632/SF
    • 31 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2019

    1795 Greenwich Ave, Winter Park, FL 32789

    Welcome to a one-of-a-kind, custom-designed residence offering the perfect blend of modern sophistication, thoughtful functionality, and resort-style amenities. Designed by Origins Residential Design and meticulously constructed by Native Homes, this 5-bedroom, 5.5-bathroom showplace is located in one of Winter Park’s most sought-after neighborhoods—just minutes from Park Avenue, Baldwin Park,

    Jennifer Sloan KELLY PRICE & COMPANY LLC

    1795 Greenwich Ave, Winter Park, FL 32789
  • 1139 Fairway Dr, Winter Park, FL 32792
    1139 Fairway Dr, Winter Park, FL 32792
    /2

    $705,000 Sold Jul 14, 2025

    • 2,385 Sq Ft
    • $296/SF
    • 57 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1979

    1139 Fairway Dr, Winter Park, FL 32792

    NEW LOWER PRICE 6/3/25, OWNER WANTS OFFERS. NO HOA. Fabulous RENOVATED home in the heart of Winter Park, where timeless charm meets tranquil Winter Park Pines golf course living. Nestled on a lush, manicured lot right on the 9th fairway, this expansive REMODELLED OPEN AND AIRY SPLIT-plan residence offers a SPLIT PLAN WITH 4 generously sized bedrooms, 2 full baths, and FABULOUS FLEX SPACE that

    Gale Milgrim KELLER WILLIAMS WINTER PARK

    1139 Fairway Dr, Winter Park, FL 32792
  • 1394 Stewart St, Winter Park, FL 32789
    1394 Stewart St, Winter Park, FL 32789
    /2

    $1,942,000 Sold Jul 14, 2025

    • 3,907 Sq Ft
    • $497/SF
    • 50 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1961

    1394 Stewart St, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Five-bedroom, 3900+ sq ft pool home with 3 car garage on a large corner lot in the sought -after Park Grove neighborhood near Lake Maitland and Park Avenue. Great Room consists of a Family Room area with a wood-burning fireplace and tray ceilings and a Sun Room area with bay windows and french doors overlooking the pool deck. Kitchen

    Richard Vaughn REALTY ONE GROUP INSPIRATION

    1394 Stewart St, Winter Park, FL 32789
  • 1518 Coletta Dr, Orlando, FL 32807
    1518 Coletta Dr, Orlando, FL 32807
    /2

    $350,000 Sold Jul 14, 2025

    • 1,276 Sq Ft
    • $274/SF
    • 92 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1925

    1518 Coletta Dr, Orlando, FL 32807

    Located in one of Orlando’s most strategic areas, 1518 Coletta Drive is a beautifully fully renovated single-family home that blends traditional charm with modern conveniences. Featuring 3 bedrooms and 3 bathrooms, this home offers 1,276 sqft of well-designed living space, ensuring both comfort and functionality.The primary bedroom includes a walk-in closet, while the inviting front porch and

    Andres Ospina Rivera LPT REALTY, LLC

    1518 Coletta Dr, Orlando, FL 32807
  • 541 Virginia Dr, Winter Park, FL 32789
    541 Virginia Dr, Winter Park, FL 32789
    /2

    $5,400,000 Sold Jul 14, 2025

    • 4,725 Sq Ft
    • $1143/SF
    • 152 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2008

    541 Virginia Dr, Winter Park, FL 32789

    *Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home.Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers

    Keith Moore HOMEVEST REALTY

    541 Virginia Dr, Winter Park, FL 32789
  • 151 N Orlando Ave Unit 131, Winter Park, FL 32789
    151 N Orlando Ave Unit 131, Winter Park, FL 32789
    /2

    $385,000 Sold Jul 12, 2025

    • 1,000 Sq Ft
    • $385/SF
    • 355 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1960

    151 N Orlando Ave Unit 131, Winter Park, FL 32789

    FULL LAKE FRONT VIEW, ONE OUT OF 6 UNITS WITH BEST VIEW IN LAKE KILLARNEY CONDO! Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability).

    Adriana Montes MBA ? FLORIDA DREAMS REALTY GRP INC

    151 N Orlando Ave Unit 131, Winter Park, FL 32789
  • 2809 Sanbina St, Winter Park, FL 32789
    2809 Sanbina St, Winter Park, FL 32789
    /2

    $420,000 Sold Jul 11, 2025

    • 1,140 Sq Ft
    • $368/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1961

    2809 Sanbina St, Winter Park, FL 32789

    Beautifully Updated 3 Bedroom, 2 Bath Pool Home in Desirable Winter Park! Welcome to your dream home! This spacious one story gem features 3 bedrooms, 2 full baths, and a private POOL, perfect for enjoying Florida living year round. Step inside to find brand NEW LUXURY VINYL PLANK flooring and FRESH INTERIOR PAINT throughout, giving the home a modern and move-in ready feel. The open layout offers

    Harry Kazarian STRONG FOUNDATION REALTY LLC

    2809 Sanbina St, Winter Park, FL 32789
  • 624 Dunraven Dr, Winter Park, FL 32792
    624 Dunraven Dr, Winter Park, FL 32792
    /2

    $618,900 Sold Jul 11, 2025

    • 1,762 Sq Ft
    • $351/SF
    • 65 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    624 Dunraven Dr, Winter Park, FL 32792

    Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the sought-after Kenilworth Shores neighborhood of Winter Park. Featuring an open-concept layout, the home is anchored by a modern kitchen with an island, stainless steel appliances, granite countertops, and stylishly renovated bathrooms. Enjoy cozy evenings by the fireplace or relax in the spacious,

    Brian Rotenberger COMPASS FLORIDA LLC

    624 Dunraven Dr, Winter Park, FL 32792
  • 1511 Chestnut Ave, Winter Park, FL 32789
    1511 Chestnut Ave, Winter Park, FL 32789
    /2

    $675,000 Sold Jul 10, 2025

    • 1,275 Sq Ft
    • $529/SF
    • 1 Day On Market
    • 2 Beds
    • 2 Baths
    • Built 1960

    1511 Chestnut Ave, Winter Park, FL 32789

    Attention builders and investors! Here’s your chance to own a prime property in the coveted Tree Streets of Winter Park, one of Central Florida’s most desirable neighborhoods. Whether you’re looking for immediate rental income or planning to build your dream home in the future, this opportunity is not to be missed!Tucked away just minutes from Phelps Park, the Winter Park YMCA, Lake

    Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

    1511 Chestnut Ave, Winter Park, FL 32789
  • 309 Park Ct N, Winter Park, FL 32789
    309 Park Ct N, Winter Park, FL 32789
    /2

    $1,115,000 Sold Jul 10, 2025

    • 3,096 Sq Ft
    • $360/SF
    • 50 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1968

    309 Park Ct N, Winter Park, FL 32789

    Endless Potential in the Heart of Park North!Just steps from the charm and energy of Winter Park’s Park Avenue—where boutique cafes, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await—this rare Park North gem offers the ultimate opportunity to create your dream home.Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF)

    Mary Colton FANNIE HILLMAN & ASSOCIATES

    309 Park Ct N, Winter Park, FL 32789
  • 835 Antonette Ave, Winter Park, FL 32789
    835 Antonette Ave, Winter Park, FL 32789
    /2

    $1,175,000 Sold Jul 08, 2025

    • 1,867 Sq Ft
    • $629/SF
    • 7 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1925

    835 Antonette Ave, Winter Park, FL 32789

    Charming 1925 Craftsman with Spanish-Style Guest Apartment in Winter Park's College Quarter.Nestled in the heart of the historic College Quarter, this beautifully preserved 1925 Craftsman home offers timeless character, modern livability, and a rare bonus: a separate Spanish/Moorish-style garage apartment with its own unique architectural flair.The main house features 3 bedrooms, 2

    Alexis Davis FANNIE HILLMAN & ASSOCIATES

    835 Antonette Ave, Winter Park, FL 32789
  • 1665 Temple Dr, Winter Park, FL 32789
    1665 Temple Dr, Winter Park, FL 32789
    /2

    $1,825,000 Sold Jul 08, 2025

    • 3,830 Sq Ft
    • $477/SF
    • 10 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2007

    1665 Temple Dr, Winter Park, FL 32789

    A rare gem in the heart of the Vias – Nestled in one of Winter Park’s most sought-after neighborhoods, this beautifully designed home is the epitome of comfort, luxury, and convenience. Located just minutes from Park Avenue, top-rated schools, and the best dining and shopping in Central Florida, this property offers an unbeatable lifestyle in a truly prime location.Inside, the home

    Brandon Geers COMPASS FLORIDA LLC

    1665 Temple Dr, Winter Park, FL 32789
  • 2536 Brookshire Ave, Winter Park, FL 32792
    2536 Brookshire Ave, Winter Park, FL 32792
    /2

    $1,275,000 Sold Jul 08, 2025

    • 3,140 Sq Ft
    • $406/SF
    • 83 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2018

    2536 Brookshire Ave, Winter Park, FL 32792

    Welcome to 2536 Brookshire Ave, a spacious 4-bedroom, 3.5-bath modern farmhouse located in the heart of Winter Park. The open floor plan enhances connectivity throughout, with a first-floor primary suite featuring generous his and her closets. Designer lighting and plumbing fixtures, custom interior paint, 8-foot doors, and wood-like tile floors create a cohesive design.Enjoy additional

    Richard Palmano PALMANO GROUP RE BROKERAGE LLC

    2536 Brookshire Ave, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 16

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Recently Sold Real Estate & Homes in Winter Park, Winter Park

Learn more about living in Winter Park

Frequently Asked Questions

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 83 days on the market.
What is the number of active homes for sale in Winter Park, FL?
There are 57 active homes for sale in Winter Park, FL.
Is Winter Park, FL a good neighborhood?
Winter Park, FL is a highly rated neighborhood receiving 4.4 stars from it's current and former residents.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 83 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 $364,994, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$364,994
Median Single Family Sale Price
$385,000
Median Townhouse Sale Price
$376,250
Median 2 Bedroom Sale Price
$390,000
Median 1 Bedroom Sale Price
$565,000
Average Price Per Sq Ft
$234
Number of Homes for Sale
57
Last 12 months Home Sales
471
Months of Supply
1.50
Median List Price
$393,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
1%
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