Recently Sold Homes near Winter Park High

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  $192,000 Sold Jul 16, 2025

  • 1,059 Sq Ft
  • $181/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  4878 Tangerine Ave, Winter Park, FL 32792

  WATCH REAL VIDEO & 3D TOUR! Welcome to 4878 Tangerine Ave, a beautifully MOVE IN READY- NEW ROOF - NEW FLOORS- FRESH PAINT updated 2-bedroom, 2-bathroom condo nestled in the serene and highly desirable Wrenwood Condominiums of Winter Park with Community POOL/GYM and ample parking. Yard maintenance, Roof replacement, Trash, and Water are included in the HOA. Step inside and be greeted by

  Arthur Love LA ROSA REALTY ORLANDO LLC

  4878 Tangerine Ave, Winter Park, FL 32792
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• 

  

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  $700,000 Sold Jul 16, 2025

  • 2,098 Sq Ft
  • $334/SF
  • 109 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2012

  1859 Britlyn Alley, Orlando, FL 32814

  Nestled in the highly sought-after heart of Baldwin Park, this exquisite Mediterranean-style townhome offers a peaceful, low-maintenance lifestyle, paired with elegant modern upgrades. A charming trellised brick courtyard leads you to this David Weekley Energy Saver END unit, where every detail has been carefully considered and thoughtfully executed.Built in 2012, this spacious townhome

  Amanda Petruzzello LAKESIDE REALTY WINDERMERE INC

  1859 Britlyn Alley, Orlando, FL 32814
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  $235,000 Sold Jul 15, 2025

  • 1,806 Sq Ft
  • $130/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  9536 Peer Dr, Orlando, FL 32817

  **INVESTOR SPECIAL, CASH ONLY** Great Opportunity for Investor, Landlord or Builder. Great Location. Wonderful neighborhood in a highly demanded area. Large lot .58 acres with private backyard! NO HOA. 1,806 Square Feet total after full remodel. This 3 bedroom 2 bathroom home is ready for your personal touch! Ideal split floor plan. There is an open living room off from the kitchen. All

  Daniel Goodman CHARLES RUTENBERG REALTY ORLANDO

  9536 Peer Dr, Orlando, FL 32817
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  $810,000 Sold Jul 15, 2025

  • 2,090 Sq Ft
  • $388/SF
  • 24 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1966

  2520 Chanute Trail, Maitland, FL 32751

  Come look at this beautifully remodeled pool home in the highly sought-after Dommerich Hills neighborhood in Maitland. The kitchen is a chef's dream, with high-end appliances, plenty of cabinet space, a custom corner seating area, a massive 9 ft center island, and so much more. As you enter through your custom French front doors, you are welcomed by a pleasant seating/reading room that looks into

  Jonathan Maggio KELLER WILLIAMS REALTY AT THE PARKS

  2520 Chanute Trail, Maitland, FL 32751
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  $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
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  $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
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  $50,000 Sold Jul 15, 2025

  • 590 Sq Ft
  • $85/SF
  • 105 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  7309 Daniel Webster Dr Unit D, Winter Park, FL 32792

  Priced to sell! Turnkey Investment Opportunity in Winter Park!Attention investors and savvy buyers—this 1-bedroom, 1-bath condo in the Colonies Condo community is the perfect low-maintenance, high-potential opportunity! With 610 sq. ft. of efficient living space, this unit is ideal for a young professional, student, or tenant looking for affordability in a prime location. Featuring vinyl

  Benjamin Berry EXP REALTY LLC

  7309 Daniel Webster Dr Unit D, Winter Park, FL 32792
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  /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
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  $125,000 Sold Jul 14, 2025

  • 802 Sq Ft
  • $156/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  7344 Swallow Run Unit 7344, Winter Park, FL 32792

  Step into this beautiful 2-bedroom, 2-bathroom condo, freshly painted and filled with natural light throughout. The open-concept floor plan is perfect for entertaining, while the split-bedroom layout ensures added privacy for residents or guests.The primary suite features a walk-in shower, ample storage, and a private en-suite bath. Enjoy serene views of lush green space and located in

  Merigan Barton DON HARKINS REALTY LLC

  7344 Swallow Run Unit 7344, Winter Park, FL 32792
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  $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
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  $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
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  $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
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  $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
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  $400,000 Sold Jul 14, 2025

  • 1,387 Sq Ft
  • $288/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  3625 Stonehaven Ct, Orlando, FL 32817

  Seller may consider buyer concessions if made in an offer ~ Whether you are in the market for a MOVE-IN READY first home or looking to invest (LOW HOA!), you will appreciate this single story POOL HOME (with a BRAND NEW POOL PUMP - MAY 2025!) on a spacious lot with over 20K in UPGRADED WINDOWS & DOORS (2024), FRESH INTERIOR & EXTERIOR PAINT (2024), a NEWER ROOF (2021), WATER HEATER (2021) and

  Jennifer Wemert WEMERT GROUP REALTY LLC

  3625 Stonehaven Ct, Orlando, FL 32817
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  $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
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  /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
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  $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
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  $1,100,000 Sold Jul 11, 2025

  • 2,785 Sq Ft
  • $395/SF
  • 14 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2008

  5303 Brady Ln, Orlando, FL 32814

  Welcome to this stunning, beautifully designed 4 bedroom, 3 1/2 bath with office, Baldwin Park home on a corner lot. Prepare to be impressed as you enter from the charming front porch to 2785 SF of bright and inviting space! The open floorplan is perfect for entertaining or spending time with family. The gourmet kitchen is the heart of the home featuring a large center island, granite

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  5303 Brady Ln, Orlando, FL 32814
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  $235,000 Sold Jul 11, 2025

  • 1,228 Sq Ft
  • $191/SF
  • 7 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  2216 Stonington Ave Unit 2216, Orlando, FL 32817

  Welcome Home to this Spacious 2 Bed, 2 and a half Bath Condo! This Home has a great floor plan, in theHighly Desirable Colonial Landings. No Carpets in this entire 2nd story unit. The Interior has newer Paint,Laminate Floors Installed, and Renovated Bathrooms. Features include a Wood Burning Fireplace and aStacked Washer & Dryer. The Community features a Pool, Hot Tub, 2 Tennis

  Shahrin Alam COLDWELL BANKER RESIDENTIAL RE

  2216 Stonington Ave Unit 2216, Orlando, FL 32817
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  $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
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  $349,000 Sold Jul 11, 2025

  • 1,560 Sq Ft
  • $224/SF
  • 116 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1983

  9544 Brimton Dr, Orlando, FL 32817

  BACK ON THE MARKET. BUYER"S FINANCING FELL THROUGH. NO HOA - Welcome to this charming 4-bedroom, 2-bathroom home in the desirable Arbor Bridge community! Boasting 1,560 sq ft of living space, this well-maintained property features a spacious, fenced backyard—perfect for outdoor gatherings, pets, or a peaceful retreat. Inside, you'll find granite countertops and beautiful wood floors.

  Chris Creegan CREEGAN GROUP

  9544 Brimton Dr, Orlando, FL 32817
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  $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
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  $315,000 Sold Jul 10, 2025

  • 1,459 Sq Ft
  • $216/SF
  • 22 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1956

  707 N Solandra Dr, Orlando, FL 32807

  Don't miss this move-in-ready 4 bedroom, 2 bathroom home offering 1,459 sqft of comfortable living in one of Orlando’s most convenient locations. Just off Colonial and Semoran, you’ll enjoy quick access to I-4, Downtown Orlando, Baldwin Park, and Winter Park, plus all the shopping, dining, parks, and amenities those areas offer. Zoned for top-rated public schools in the area. Baldwin Park

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  707 N Solandra Dr, Orlando, FL 32807
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  $390,000 Sold Jul 10, 2025

  • 784 Sq Ft
  • $497/SF
  • 38 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1949

  2312 Vivada St, Orlando, FL 32803

  FOR SALE ONLY-NOT FOR RENT***BUILDER & INVESTOR SPECIAL-CASH OR REHAB LOAN ONLY***Incredible opportunity to build your dream home in the highly sought after Orlando neighborhood of Colonialtown North. This charming bungalow is situated on a nearly quarter acre lot and is short uber ride away from everything downtown has to offer. Catch a play at the Dr.Phillips Center for the performing arts,

  Christina Rordam FLORIDA REALTY INVESTMENTS

  2312 Vivada St, Orlando, FL 32803
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  $277,000 Sold Jul 10, 2025

  • 988 Sq Ft
  • $280/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1985

  9526 Turkey Oak Bend, Orlando, FL 32817

  Searching for a 3 bed, 2 bath home without pesky HOA fees AND situated on a beautiful, tranquil POND LOT that's just under a quarter of an acre? Look no further! Arbor Ridge West is a well maintained and centrally located community that you will be proud to call home. The living room, dining area and kitchen are all open and make entertaining a breeze. You will love the enormous screened

  Virginia Werneken FUTURE HOME REALTY INC

  9526 Turkey Oak Bend, Orlando, FL 32817
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  $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
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  $985,000 Sold Jul 10, 2025

  • 2,249 Sq Ft
  • $438/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2006

  4094 Oak St, Orlando, FL 32814

  Welcome to this stunning residence in the heart of Baldwin Park, a blend of classic elegance and contemporary sophistication. From the moment you arrive, the stately front porch invites you to slow down and savor a leisurely morning coffee. Go inside and be greeted by a thoughtful floor plan highlighted by soaring ceilings and tall, elegant doors that bathe the interior in natural sunlight. The

  Lynda Miller PREMIER SOTHEBYS INT'L REALTY

  4094 Oak St, Orlando, FL 32814
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  $239,000 Sold Jul 10, 2025

  • 816 Sq Ft
  • $293/SF
  • 115 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1969

  1140 S Orlando Ave Unit J6, Maitland, FL 32751

  PRICE IMPROVEMENT...Lakefront Condo in Maitland’s Jupiter Building – First-Floor Unit with access to Scenic Lake Views.Welcome to lakefront living in the desirable Lake Maitland Terrace community! This beautifully maintained first-floor, 2-bedroom, 1.5-bath condo in the Jupiter Building offers the perfect blend of comfort, convenience, and lifestyle. The updated kitchen features maple

  Miriam Furey EXP REALTY LLC

  1140 S Orlando Ave Unit J6, Maitland, FL 32751
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  $390,000 Sold Jul 09, 2025

  • 2,436 Sq Ft
  • $160/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1983

  3917 Lake Mira Dr, Orlando, FL 32817

  Opportunity Knocks! Discover the possibilities in this spacious 4-bed, 2-bath home situated on an oversized corner cul-de-sac lot in a highly sought-after, established neighborhood zoned for A-rated Winter Park schools! Priced below appraisal, this is an investor's dream or a fantastic chance to live in and update to your personal style. Built in 1983, it boasts an ideal split plan with tile

  Alin Zdroba PROPERTIO

  3917 Lake Mira Dr, Orlando, FL 32817
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  $367,500 Sold Jul 09, 2025

  • 1,454 Sq Ft
  • $253/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1986

  9833 Tattersall Ave, Orlando, FL 32817

  Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller's preferred lender. Ask for details.Welcome to this delightful 3-bedroom, 2-bathroom home nestled in the heart of East Orlando. This residence boasts FRESH INTERIOR PAINT and BRAND NEW FLOORING, offering a warm and inviting atmosphere. The spacious living and dining areas provide ample room for

  Kathryn West EXP REALTY LLC

  9833 Tattersall Ave, Orlando, FL 32817
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  /2

  $645,000 Sold Jul 09, 2025

  • 2,910 Sq Ft
  • $222/SF
  • 6 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1979

  4030 Cool Water Ct, Winter Park, FL 32792

  Welcome to 4030 Cool Water Ct! Nestled in the highly desirable Lake Waunatta Woods neighborhood, this spacious Winter Park Pool home is zoned for top-rated schools, including Winter Park High School and Lakemont Elementary School. With a new roof installed in 2022, this 5-bedroom, 3-bath home offers peace of mind along with undeniable charm. Situated on an oversized lot surrounded by mature trees

  Chris Creegan CREEGAN GROUP

  4030 Cool Water Ct, Winter Park, FL 32792
• 

  /2

  $1,092,000 Sold Jul 09, 2025

  • 2,258 Sq Ft
  • $484/SF
  • 79 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  8616 Port Said St, Orlando, FL 32817

  Enjoy the best of lakefront living in this fully renovated 4-bedroom, 2.5-bath home located in the highly desirable and A+ rated Winter Park school district. Set on a peaceful residential street, this home features nearly $300K in upgrades in 2022, blending modern luxury with outdoor adventure.Step into an open-concept floor plan filled with natural light, showcasing a gourmet kitchen

  Rob Sassos SIMPLICITY: A RE BROKERAGE CO

  8616 Port Said St, Orlando, FL 32817
• 

  /2

  $350,000 Sold Jul 09, 2025

  • 1,552 Sq Ft
  • $226/SF
  • 252 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  7819 Puritan Rd, Orlando, FL 32807

  Back on Market! Great opportunity to own this wonderful 3 Bed 2 Bath home close to UCF and zoned for Winter Park High School. The home features ceramic tile flooring in all interior areas except the bedrooms, Stainless Steel Appliances and an Electrical Panel. Exterior features include all brick house, cozy covered and screened rear porch and a large back yard. Location is great, close to

  Esteban Clavell, PA LPT REALTY, LLC

  7819 Puritan Rd, Orlando, FL 32807
• 

  /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
• 

  /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
• 

  /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
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  /2

  $3,200,000 Sold Jul 08, 2025

  • 4,790 Sq Ft
  • $668/SF
  • 188 Days On Market

  • 5 Beds
  • 8 Baths
  • Built 2024

  1948 Rowena Ave, Orlando, FL 32803

  Welcome Home! This Modern Coastal new construction from FG Schaub Custom Homes is a 4,790-SF masterpiece complete with 5 bedrooms, an office, 5 full bathrooms, 3 half bathrooms, and so much more! No expense was spared on the quality and meticulous design of this stunning, new construction, two-story residence, boasting unwavering attention to detail and only the finest features and finishes

  Laura Earl CORCORAN PREMIER REALTY

  1948 Rowena Ave, Orlando, FL 32803
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  /2

  $519,180 Sold Jul 08, 2025

  • 2,205 Sq Ft
  • $235/SF
  • 201 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  2518 Sweetwater Trail, Winter Park, FL 32789

  Welcome home! This beautiful 4-bed, 2-bath pool home boasts a spacious 2,205 square feet of living space with a fantastic floor plan in Winter Park. Along with a new roof and water heater this home is ready for years of memories to come. A cozy entry foyer greets you at the front door and provides access to the secondary bedrooms, formal dining room, and well-lit family room enhanced by its

  Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  2518 Sweetwater Trail, Winter Park, FL 32789
• 

  /2

  $2,100,000 Sold Jul 07, 2025

  • 3,182 Sq Ft
  • $660/SF
  • 36 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1926

  104 Cortland Ave, Winter Park, FL 32789

  Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  104 Cortland Ave, Winter Park, FL 32789
• 

  /2

  $1,050,000 Sold Jul 07, 2025

  • 3,377 Sq Ft
  • $311/SF
  • 9 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1964

  2923 Cove Trail, Winter Park, FL 32789

  A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today’s discerning buyer. REIMAGINED in 2011 this

  Robin Delaney KELLER WILLIAMS ADVANTAGE III

  2923 Cove Trail, Winter Park, FL 32789

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