Recently Sold Winter Park, FL Homes

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  $180,000 Sold Sep 18, 2025

  • 987 Sq Ft
  • $182/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792

  Beautifully updated first-floor condo in the sought-after Four Seasons community. Step inside to a bright, inviting open floor plan with laminate floors, a spacious living room, separate dining area, and a kitchen featuring white cabinetry, granite countertops, and access to the outdoors. The large primary bedroom includes a walk-in closet and updated en suite bath, and the second bedroom is

  peggy amos FANNIE HILLMAN & ASSOCIATES

  200 Saint Andrews Blvd Unit 1901, Winter Park, FL 32792
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  Explore Winter Park

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  $335,000 Sold Sep 17, 2025

  • 1,408 Sq Ft
  • $238/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1987

  3103 Ash Park Loop, Winter Park, FL 32792

  Welcome to Hyde Park, off Howell Branch Road in Seminole County. First time offered. Wonderful two-bedroom, two-bath split plan, with two-car garage and fireplace. The roof has been replaced as well as the air-conditioning unit. Over 1,400 heated square feet, with fabulous large porch (no rear neighbors). This is ready to decorate to your liking! Bring a paintbrush and replace flooring. Tons of

  Pam Hagood Ryan PREMIER SOTHEBY'S INTL. REALTY

  3103 Ash Park Loop, Winter Park, FL 32792
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  /2

  $620,000 Sold Sep 16, 2025

  • 1,156 Sq Ft
  • $536/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  535 N Interlachen Ave Unit 305, Winter Park, FL 32789

  Walk to fun Park Avenue and its restaurants, boutique shops, museums and the historic Winter Park Nine Golf Course from this stylish and fully renovated Winter Park 2/2 condo. With beautiful natural light, hardwood floors and tree- top views, this third floor corner unit offers a luxurious master suite with two closets plus an elegant bath with double sinks, quartz countertops, under cabinet

  A.V. Blalock COLDWELL BANKER RESIDENTIAL RE

  535 N Interlachen Ave Unit 305, Winter Park, FL 32789
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  $343,000 Sold Sep 16, 2025

  • 1,349 Sq Ft
  • $254/SF
  • 61 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1955

  657 Overspin Dr, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyers!** Welcome to your cozy Winter Park retreat! This charming 4-bedroom, 2-bath home blends comfort and convenience in one perfect package. Nestled on a spacious lot with a large backyard—ideal for entertaining, gardening, or playing fetch—this home also features a unique

  Abby Nelson RE/MAX 200 REALTY

  657 Overspin Dr, Winter Park, FL 32789
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  /2

  $1,635,000 Sold Sep 16, 2025

  • 3,248 Sq Ft
  • $503/SF
  • 85 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2015

  2402.5 Temple Dr, Winter Park, FL 32789

  Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 150-foot private drive with gate. Designed with comfortable yet sophisticated living space, this home is perfect for those seeking a serene retreat for both everyday living and entertainment. The heart of the home is the sizable kitchen, boasting a gas stove, high-end

  Steve Schiffer OLDE TOWN BROKERS INC

  2402.5 Temple Dr, Winter Park, FL 32789
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  /2

  $1,950,000 Sold Sep 16, 2025

  • 3,909 Sq Ft
  • $499/SF
  • 170 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2015

  141 Oakwood Way, Winter Park, FL 32789

  Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area. This modern Mediterranean-inspired residence seamlessly blends timeless elegance with contemporary luxury, offering an exceptional living experience with high-end finishes, thoughtfully designed spaces, and unmatched attention to detail. Step inside to whitewashed oak

  Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
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  $825,000 Sold Sep 15, 2025

  • 1,672 Sq Ft
  • $493/SF
  • 27 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1977

  1421 Sunset Dr, Winter Park, FL 32789

  BUYER GOT COLD FEET= YOUR OPPORTUNITY! Welcome to 1421 Sunset Drive – A Turnkey Gem in the Heart of Olde Winter Park!This is a rare opportunity to own a beautifully updated home on one of Olde Winter Park’s most charming, brick-lined, tree-canopied streets. Just steps from serene Lake Knowles and Lake Wilbar, and minutes from the vibrant dining, shopping, and cultural experiences of Park

  Sarah Tomlinson COMPASS FLORIDA LLC

  1421 Sunset Dr, Winter Park, FL 32789
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  /2

  $1,250,000 Sold Sep 15, 2025

  • 2,471 Sq Ft
  • $506/SF
  • 2 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1049 Tuscany Place, Winter Park, FL 32789

  This is a rare opportunity to own a ONE STORY LARKEFRONT home on a HALF-ACRE lot in the highly desirable Via’s of Winter Park. Nestled on a quiet cul-de-sac in Tuscany Place and zoned for top A-rated schools, this beautifully maintained 4-bedroom, 2-bath home offers breathtaking views of Lake Temple from nearly every room. The spacious and light-filled interior features a split bedroom floor plan

  Sarah Tomlinson COMPASS FLORIDA LLC

  1049 Tuscany Place, Winter Park, FL 32789
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  /2

  $110,000 Sold Sep 15, 2025

  • 735 Sq Ft
  • $150/SF
  • 78 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1969

  1000 S Semoran Blvd Unit 415, Winter Park, FL 32792

  NEW AC INSTALLED, PRICE REDUCTION, EXCELLENT INVESTMENT OPPORTUNITY, Great Tenant in place! Spacious Ground-Floor Apartment with Outdoor Terrace Discover this charming and spacious ground-floor apartment, perfect for comfortable living and entertaining. Featuring a private outdoor terrace, this property provides the ideal setting for enjoying fresh air and relaxation without ever needing to climb

  Jhoana Loyo Urrutia LA ROSA REALTY LLC

  1000 S Semoran Blvd Unit 415, Winter Park, FL 32792
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  /2

  $130,000 Sold Sep 15, 2025

  • 753 Sq Ft
  • $173/SF
  • 102 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1973

  4936 Tangerine Ave Unit 4936, Winter Park, FL 32792

  Location! Location! Location! This 1 BEDROOM, 1 BATHROOM, beautifully maintained condo offers an ideal living space and an open floor plan perfect for relaxation. Located just minutes from Full Sail University, the University of Central Florida, supermarkets, dining and more.Residents can enjoy access to the COMMUNITY POOL & CLUBHOUSE. Best of all, it is a one-story unit with no neighbors

  Israel Vinas VINAS DEL MAR REALTY, INC.

  4936 Tangerine Ave Unit 4936, Winter Park, FL 32792
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  /2

  $158,000 Sold Sep 15, 2025

  • 678 Sq Ft
  • $233/SF
  • 206 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1973

  163 Lewfield Cir, Winter Park, FL 32792

  Prime Location! Reduced Price! Motivated Seller – Act Fast!Discover this beautifully renovated first-floor condo in the desirable Stratford community of Winter Park. Featuring a brand-new kitchen, updated bathroom, sleek ceramic tile flooring, and new appliances, this home offers modern living at its finest. With the added bonus of an in-unit washer/dryer, convenience is

  Alexandro Torres Valentin TBO REAL ESTATE PARTNERS INC

  163 Lewfield Cir, Winter Park, FL 32792
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  $200,000 Sold Sep 13, 2025

  • 1,151 Sq Ft
  • $174/SF
  • 131 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792

  HUGE PRICE REDUCTION! We are proud to bring to market this incredibly private END UNIT condo within the Hidden Oaks community. The unit offers three bedrooms (all upstairs), two full bathrooms (upstairs) and one half bathroom (downstairs), two reserved parking spots, upgraded wood-look ceramic tile, upgraded light fixtures, upgraded bathroom mirrors and upgraded fans throughout, upgraded thick

  Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792
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  $385,000 Sold Sep 12, 2025

  • 1,354 Sq Ft
  • $284/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  259 Blossom Ln, Winter Park, FL 32789

  Charming Winter Park Block Home with Deeded Access to Lake Killarney – Solid, Updated Systems & Priced for Your Personal Touch!Welcome to this well-built 3-bedroom, 2-bath cement block home in one of Winter Park’s most desirable and established neighborhoods. . . . . . Built in 1954 and lovingly cared by the same owner for almost 40 years, this home offers strong bones, a functional layout,

  Sherrie Wysong LEGACY REALTY & BROKERS LLC

  259 Blossom Ln, Winter Park, FL 32789
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  $405,000 Sold Sep 12, 2025

  • 1,226 Sq Ft
  • $330/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  5234 Ohio St, Winter Park, FL 32792

  Tropical Vibes + Total Privacy in Winter Park! A rare find, indeed!! Tucked away at the very end of a quiet cul-de-sac, this charming block construction home offers the ultimate in peaceful vibes, comfort, and Florida living. Built in 1973, this one-story gem offers timeless durability with the added benefit of modern comfort and unmatched privacy. Set on a beautifully landscaped,

  Emily Nickley MARKET CONNECT REALTY LLC

  5234 Ohio St, Winter Park, FL 32792
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  $655,000 Sold Sep 12, 2025

  • 1,704 Sq Ft
  • $384/SF
  • 23 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  1640 Cypress Point Ln, Winter Park, FL 32792

  Welcome to 1640 Cypress Point – a home like no other in Winter Park. This beautifully maintained 3-bedroom, 2-bathroom home offers 1,704 sq. ft. overlooking a serene spring-fed pond and the Winter Park Pines Golf Course. Nestled on a quiet street with a cul-de-sac, this property combines privacy, natural beauty, and convenience in one exceptional location. As you walk up to the front door, you’ll

  Amy Turner KELLER WILLIAMS WINTER PARK

  1640 Cypress Point Ln, Winter Park, FL 32792
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  /2

  $434,000 Sold Sep 12, 2025

  • 1,556 Sq Ft
  • $279/SF
  • 55 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1978

  1122 Washington Ave Unit 7, Winter Park, FL 32789

  Welcome to 1122 Washington Avenue – a delightful 2-bedroom, 2.5-bath townhome located in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue, Rollins College, the Winter Park Tennis Center, and the brand-new Seven Oaks Park, this home offers the perfect blend of lifestyle and location.This area is undergoing tremendous transformation, especially along the

  Raul Veitia BELMONT REALTY

  1122 Washington Ave Unit 7, Winter Park, FL 32789
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  $1,555,000 Sold Sep 12, 2025

  • 3,971 Sq Ft
  • $392/SF
  • 146 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1990

  817 Antonette Ave, Winter Park, FL 32789

  Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality and charm. This thoughtfully designed home boasts detailed moldings and millwork, wood floors, high ceilings, and beautiful oversized windows throughout. A grand foyer leads to a central gallery with an atrium and a custom-designed bannister, while a unique glass ceiling allows

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  817 Antonette Ave, Winter Park, FL 32789
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  /2

  $365,000 Sold Sep 11, 2025

  • 1,278 Sq Ft
  • $286/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  2008 Nottingdale Ln, Winter Park, FL 32792

  Nestled in the highly desirable Winter Park, Florida, 2008 Nottingdale Lane presents a meticulously updated and move-in-ready single-family home. This delightful residence offers 3 bedrooms and 2 bathrooms within a comfortable 1,278 square feet of living space, all without the encumbrance of a Homeowners Association (HOA). Situated on a generous 0.24-acre lot, the property boasts a fully fenced

  Robert Bretz, PA EXP REALTY LLC

  2008 Nottingdale Ln, Winter Park, FL 32792
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  /2

  $1,785,000 Sold Sep 11, 2025

  • 2,907 Sq Ft
  • $614/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1953

  1640 Mayfield Ave, Winter Park, FL 32789

  This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered

  Beverly Brown RE/MAX PRIME PROPERTIES

  1640 Mayfield Ave, Winter Park, FL 32789
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  $410,000 Sold Sep 11, 2025

  • 1,907 Sq Ft
  • $215/SF
  • 109 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2023

  2949 Clever Ln, Winter Park, FL 32792

  Welcome to this stunning former model townhome built in 2023, ideally located in the highly sought-after gated community of Grayson Square in Winter Park, Florida. This beautifully designed residence offers a blend of modern finishes and functional layout, with the first floor featuring a completely open floor plan bathed in natural light. The spacious kitchen boasts quartz countertops, upgraded

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  2949 Clever Ln, Winter Park, FL 32792
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  /2

  $265,000 Sold Sep 11, 2025

  • 1,036 Sq Ft
  • $256/SF
  • 116 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1982

  3310 Royal St, Winter Park, FL 32792

  Welcome to 3310 Royal Street – a beautifully maintained mid-century gem nestled in one of Winter Park’s most desirable neighborhoods. This 2-bedroom, 1 and a half bath home offers the perfect blend of timeless charm and modern updates, ideal for families, professionals, or anyone looking to enjoy the Winter Park lifestyle.Step inside to discover an open-concept layout filled with natural

  Kevin Schudel BUY IT INC

  3310 Royal St, Winter Park, FL 32792
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  $240,000 Sold Sep 10, 2025

  • 1,173 Sq Ft
  • $205/SF
  • 41 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  2480 Tahoe Cir, Winter Park, FL 32792

  Seminole County and Winter Park! Centrally located on the border of Orange County, this well-established community of Cedarwood Village is conveniently located to beautiful Park Ave and all of the greater Orlando suburbs, locations and attractions. This well maintained single story cinderblock stucco has amble skylight natural light, open kitchen to family room, soaring vaulted ceilings and

  Michael Wood UNITED REAL ESTATE PREFERRED

  2480 Tahoe Cir, Winter Park, FL 32792
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  /2

  $25,000 Sold Sep 09, 2025

  • Land
  • 0.2 Acre
  • $125,000 per Acre

  • 10 Days On Market

  1964 Bering Ave, Winter Park, FL 32789

  There is a light pole easement. This lot is not buildable and is only good for non structural uses that are comparable with duke energy requirements. Please conduct your own due diligence before making an offer.

  Clarence Fields LUXURY & BEACH REALTY INC

  1964 Bering Ave, Winter Park, FL 32789
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  /2

  $2,200,000 Sold Sep 09, 2025

  • 3,155 Sq Ft
  • $697/SF
  • 2 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1954

  1554 Lake Knowles Cir, Winter Park, FL 32789

  Exuding timeless charm and Southern elegance, this gorgeous Charleston-style residence sits on a large lot overlooking the tranquil waters of Lake Knowles. Framed by a picturesque brick street lined with beautiful homes, the property boasts striking curb appeal, a 32-foot second-story porch with breathtaking sunset views, and classic architectural details that invite you in at every turn. A

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1554 Lake Knowles Cir, Winter Park, FL 32789
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  /2

  $100,000 Sold Sep 09, 2025

  • 1,036 Sq Ft
  • $97/SF
  • 38 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792

  What an opportunity !! A 2 bedroom 2 bath Condo located in Winter Park. Fantastic opportunity-priced to sell! 2 bedroom, 2 bath condo in The Colonies ready for new owner. Light and bright First floor unit features Eat-kitchen, tile floors throughout - no carpet! French doors with built-in blinds lead to spacious balcony. Both bedrooms have large Walk-In closets! *Inside laundry *A/C 2017 -

  Pedro Ramos ROCKER'S REAL ESTATE, LLC

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
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  /2

  $351,000 Sold Sep 09, 2025

  • 1,678 Sq Ft
  • $209/SF
  • 147 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1977

  1041 Manchester Cir, Winter Park, FL 32792

  Incredible Winter Park Location!This spacious 4-bedroom, 2-bathroom pool home is situated in a highly desirable area, offering plenty of room for the whole family. The large covered and screened lanai is perfect for enjoying the outdoors year-round, while the oversized garage provides ample space for storage and parking. With a split floor plan, this home is designed to offer privacy and

  Robert Paulson COLDWELL BANKER RESIDENTIAL RE

  1041 Manchester Cir, Winter Park, FL 32792
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  /2

  $837,500 Sold Sep 08, 2025

  • 1,305 Sq Ft
  • $642/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  200 Carolina Ave Unit 201, Winter Park, FL 32789

  A unique opportunity to own this Winter Park luxury corner condominium unit in the gated Park West community. Resting on the corner of New York Avenue and Carolina, with direct second-floor balcony views of Central Park and Park Avenue, and proximity to the quintessential Winter Park experience. Designed by nationally renowned Soco Interiors, a turnkey opportunity that adds ease to the

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  200 Carolina Ave Unit 201, Winter Park, FL 32789
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  $175,000 Sold Sep 08, 2025

  • 1,018 Sq Ft
  • $172/SF
  • 165 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792

  Move in ready with 30K in renovations! Welcome to this inviting first-floor condo, designed with an open concept floor plan that seamlessly blends comfort and style. The expansive family room provides a generous space for family gatherings and entertaining, with abundant natural light flowing through large windows and a screened-in porch. This condo features two generously sized bedrooms and two

  Dean D Nikolic PMI PROPERTY ALLIANCE

  2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792
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  /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
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  /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
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  /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
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  /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
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  /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
• 

  /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
• 

  /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
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  /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
• 

  /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
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  /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
• 

  /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
• 

  /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

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