Winter Park Homes for Sale

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Single Family

1333 CANTERBURY ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
16Picture(s)
1,599Sqft
Charming Bungalow, in Orwin Manor, with front porch says, home sweet home! This home is well maintained and move in ready. Large foyer, with built in bench and lots of windows, is inviting, as you enter this lovely home.
$430,000

Single Family

1901 OGLESBY AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
19Picture(s)
794Sqft
Location, location, location! Check out this bungalow style Winter Park home conveniently located off Fairbanks next to TOP choice restaurants, bars, shopping, and highways! Easy commute to downtown Orlando, College Park, and Park avenue! Live in Orlando's most highly sought after city of Winter Park at a fraction of the cost! Hurry, this property will not last long! One of the best investments yo
$199,000

Townhouse

541 MELROSE AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
1Parking(s)
25Picture(s)
1,801Sqft
You do not want to miss this fabulous townhouse located near downtown Winter Park. The location is superb and is walking distance to many wonderful areas including Rollins College, Lake Virginia, Downtown Winter Park and beautiful Mead Gardens. This property is perfect for a couple downsizing, business professional or a graduate attending college.
$525,000

Single Family

7165 GREEN NEEDLE DRIVE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
2Parking(s)
13Picture(s)
1,210Sqft
>>> MULTIPLE OFFERS HAVE BEEN RECEIVED. SELLER IS REQUESTING 'HIGHEST AND BEST' OFFERS BY 3:00 PM TODAY, TUESDAY, DECEMBER 1ST, 2020.
$225,000

Single Family

459 HENKEL CIRCLE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,532Sqft
Classic and captivating, this renovated character home embodies Winter Park at its best. Built in 1925, but extensively updated, it combines old world charm with many modern amenities. Situated on a large 0.42-acre lot, a short stroll to Park Avenue, and surrounded by multimillion-dollar homes.
$1,450,000

Condominium

102 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
1Parking(s)
25Picture(s)
1,802Sqft
One of the best remodels in the Cloisters. New kitchen and new bathrooms. Wood floors throughout this three bedroom, two and a half bath almost maintenance free condo. Perfect for someone looking for lock and leave capability. Split plan with bright and open rooms and a treetop city view from balcony. Just one block from magnificent Park Avenue shops and restaurants.
$750,000

Single Family

453 FLETCHER PLACE, WINTER PARK, Florida 32789

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,737Sqft
Don't miss out on this one of a kind, well maintained, and updated five bedroom, three and a half bath Winter Park home. This home features hardwood floors, plantation shutters, a brand new 2020 roof and water heater, amongst many other notable traits. The home has recently been renovated with an upstairs addition creating larger bedrooms with new windows and a Jack n' Jill bathroom.
$1,125,000

Single Family

2032 TEMPLE DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,931Sqft
#HomefortheHolidays Picture yourself spending the Holidays of 2020 in this beautiful Winter Park custom home. Move right in and enjoy the gorgeous space with a very flexible floor plan offering 4 bedrooms, plus an extra room downstairs perfect for a home office or amazing customizable home drop zone plus an open upstairs loft.
$949,900

Single Family

640 DUNBLANE DRIVE, WINTER PARK, Florida 32792

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,209Sqft
KENILWORTH SHORES-First time on the market! Real Wood Floors, fireplace, lots of light! This graceful ONE STORY home features three bedrooms, three full bathrooms, and over 2,200 SqFt of living space surrounded by mature landscaping. Feel right at home in the spacious, light-filled family room with vaulted ceilings, french doors, wood burning fireplace, built-ins and skylights.
$460,000

Single Family

2607 LAFAYETTE AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,770Sqft
One or more photo(s) has been virtually staged. Move-in ready, 2018 newer construction home with spacious, open and flexible floorplan in convenient Winter Park location. The interior is light and bright, with clean lines and great flow.
$699,000

Condominium

1250 S DENNING DRIVE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
21Picture(s)
884Sqft
This nicely remodeled 2 bedroom, 2 bath condo is the end unit on the ground floor overlooking the swimming pool. This condo underwent a major remodel about 10 years ago at which time it was stripped down to the wall studs and everything from the drywall in was replaced. The unit was replumbed, the electrical system updated, new AC, a new water heater, and even new windows.
$209,900

Single Family

1707 SARONG PLACE, WINTER PARK, Florida 32792

6Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
3,327Sqft
This stunning home built in 2006 is a MUST SEE! Features included custom-built home entertainment center, stainless steel appliances, granite countertops, plantation shutters, gas and electric heated pool. Call today! This fabulous home looks new on the inside and out. Upgrades are numerous throughout this immaculate house. If you are looking for stunning kitchen, look no more.
$600,000

Residential

502 South Lakemont Avenue, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
24Picture(s)
1,218Sqft
Centrally located in the beautiful neighborhood of Winter Park, this amazing one story home features 3 bedrooms, 2 baths and 2 car garage with new standing showers. Recently renovated with a beautiful peninsula kitchen. Bonus room can be used many different ways such as a formal dinning area or converted into a home office. Everything is updated and upgraded.
$2,350

Single Family

2324 RANDALL ROAD, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,151Sqft
Welcome home to the charm of Winter Park. This executive pool home is situated in the perfect location with NO HOA, convenient to Lake Sue, Parks, World Class Shopping, and Fine Dining. This Smart stunning Contemporary home is meticulously crafted and makes extensive use of windows allowing natural light to flow through the open living spaces.
$1,770,000

Condominium

291 SCOTTSDALE SQUARE, WINTER PARK, Florida 32792

1Bedroom(s)
1Bathroom(s)
12Picture(s)
785Sqft
LOCATION, LOCATION !!!! Perfect for your primary residence or as an investment. FIRST FLOOR. Easy access to Full Sail University. UCF, 408,417 Barry Law School. HOA includes water and sewer. Appliances included, new A/C. Close to Fashion Square Mall, Shopping Center and Restaurants in the area.
$94,000

Condominium

1163 WASHINGTON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,263Sqft
One or more photo(s) has been virtually staged. You won't believe this chic and cozy 2/2 condo with a 1 car garage in Winter park. Walk to Park Ave, Rollins College, Meads Garden or play a few sets at the Winter Park Tennis club. Step back in time and marvel unique Winter Park with its cobble stone streets and many beautiful homes from all time periods.
$359,000

Single Family

1410 ARBOR PARK DRIVE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
1,160Sqft
Located in the Heart of Winter Park this bungalow type home is located 10 minutes from Downtown Park Ave., its' restaurants and unique shops, the Winter Park Golf course, and a 5 mins. walk from the Winter Park YMCA and the local children's favorite Phelps Park.
$317,800

Condominium

315 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,806Sqft
One or more photo(s) has been virtually staged. Winter Park’s “Luxury Condo Corridor,” featuring VILLA SIENA is just steps away from famed Park Ave with award winning restaurants, cafés, boutiques, and Rollins College and is directly across the street from the Alfond Inn. This 3 bed, 3.
$1,525,000

Single Family

1849 LOCH BERRY ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,490Sqft
MOVE IN TODAY! This charming, updated 3/2 Winter Park home features 1,490 sq.ft. of living space, a split floor plan, crown molding, two-car garage with AC and an epoxy coated flooring, a deck ideal for entertaining, shed for storage, a PVC fenced yard with room to park an RV or boat on a beautifully landscaped, large corner lot.
$469,000

Condominium

1140 WASHINGTON AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,069Sqft
Fabulous opportunity in the very desirable Winter Park! Location can't be beat! This unique condo with over 2000 SF living space is nestled on a tree and brick-lined street, features a 3 bedroom 2.5 bath townhome with open kitchen/family room concept with wood burning fireplace and beautiful natural light from ceiling to floor windows.
$354,000

Condominium

162 SCOTTSDALE SQUARE, WINTER PARK, Florida 32792

1Bedroom(s)
1Bathroom(s)
15Picture(s)
756Sqft
2nd Floor Condo features 1 bedroom, 1 bathroom with living room/dining room combo. Kitchen features all major appliances. Bedroom is large with lots of storage. Sliding glass door leads out to your back porch with extra storage. Perfect home for first-time home buyer or investor.
$79,000

Single Family

1035 N KENTUCKY AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,983Sqft
** HOLIDAY BONUS! $15,000 Buyer incentive with accepted offer ** Location and style, this Winter Park POOL home has it all. 1035 N. Kentucky is a transitional modern, newer construction home set among other new, luxury homes on a charming brick street with a lovely view of Lake Midget. From the cozy front porch to the stunning interior, this gorgeous home will impress.
$1,295,000

Single Family

2760 SALISBURY BOULEVARD, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
4Picture(s)
888Sqft
This home will not be on the market very long, this home is located in a very nice neighborhood in Winter Park, Fl within minutes from I-4. So bring your best offers.
$175,900

Condominium

186 SCOTTSDALE SQUARE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
18Picture(s)
1,020Sqft
This is a beautiful and well maintained 2 bedroom 2 bath condo just waiting for the right family to enjoy all of the amenities that it has to offer. Located close to Full Sail University. Freshly painted throughout and the kitchen sports stainless steel appliances with an open style.
$95,000

Single Family

1681 WALNUT AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,499Sqft
This adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods. Located on a shady, brick street surrounded by upscale houses, this home features an attractive kitchen opening into a family room with a fireplace and separate dining room.
$489,000

Single Family

1901 PALMER AVENUE, WINTER PARK, Florida 32792

3Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
1,165Sqft
You don't want to miss this Absolutely Adorable, Charming Home Situated on an Oversized Corner Lot. There are no rear neighbors on the backside of this property and Features a Creek running behind. This 3 Bedroom/ 1 Bath, Pool Home has 1,165sq.ft. and has been Beautifully Updated.
$365,000

Single Family

2829 BONGART ROAD, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,680Sqft
Charming 3 bedroom, 2 bathroom, single-family pool home located in the community of Winter Park Estates. This home features a living room with a brick fireplace and a dining room with tiled floors. The kitchen boasts butcher block countertops, decorative backsplash, appliances, plenty of overhead cabinet space, and an eat-in kitchen nook with a window seat.
$310,900

Single Family

2725 SCARLET ROAD, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,649Sqft
Welcome home to this GORGEOUS Winter Park Pines open floor plan beauty that backs up to the lovely Cady Way Trail! This recently updated home features finishes and features that are SO HARD TO FIND in this price range in one of Central Florida's most sought after school districts.
$369,000

Single Family

1766 MILLER AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
1Parking(s)
23Picture(s)
929Sqft
Charming 2 bedroom with recently refinished beautiful oak floors, new windows ( they were permitted so they comply with new hurricane standards). Kitchen has new cabinets and solid surface counters. This property is zoned R-2, lot size is 50X140. Convenient location in between Winter Park and Ivanhoe Village perfect for Advent Health employees.
$269,750

Single Family

433 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

10Bedroom(s)
14Bathroom(s)
4Parking(s)
25Picture(s)
8,325Sqft
A unique offering to say the least. Originally built in 1920, the woodwork highlights the best of lost skills retained in the massive renovation done in 2009. Sitting on over 1/2 acre this home is a short walk to park Ave and city hall. The library with an office highlights the skills of the craftsman society.
$4,200,000

Single Family

947 ARAGON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
2Parking(s)
13Picture(s)
1,184Sqft
In a very desirable Winter Park area a cute renovated 1925 cottage with fenced back yard. Two bedrooms with original hardwood floor one bathroom with tiles and a full size bath. High ceiling. Large living room with hardwood floor and fire place. A large dining room with hardwood floor. Big open kitchen with tile floor, stainless steel appliances and granite kitchen counter. larger utility room.
$375,000

Lots And Land

1740 OAKHURST AVENUE, WINTER PARK, Florida 32789

5Picture(s)
0.23Acre
Located in Winter Park, close to schools, restaurants and shopping.
$424,900

Single Family

1740 OAKHURST AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
1Bathroom(s)
12Picture(s)
1,269Sqft
Located in Winter Park, close to schools, restaurants and shopping.
$424,900

Single Family

995 LINCOLN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,636Sqft
Truly exquisite, 1940’s character home in the Heart of Winter Park. Located just one block from Park Avenue, this quintessential Winter Park residence is the ideal place to call home. Completely renovated, the three bedroom, three and one-half bath pool home features an expansive, single-story interior layout with large gathering rooms built for entertaining.
$2,300,000

Single Family

1576 WILLIAMS DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,948Sqft
What a location! This home is situated on a large corner lot in Park Grove, one of Winter Parks most desirable neighborhoods! Enjoy your weekends walking/biking to either the Winter Park or Maitland Farmers market. It is close to many fabulous options for restaurants and retail. It also offers easy access to I-4 for working downtown Orlando or visiting the attractions.
$715,000

Lots And Land

1576 WILLIAMS DRIVE, WINTER PARK, Florida 32789

25Picture(s)
0.37Acre
What a location! This home is situated on a large corner lot in Park Grove, one of Winter Parks most desirable neighborhoods! Enjoy your weekends walking/biking to either the Winter Park or Maitland Farmers market. It is close to many fabulous options for restaurants and retail. It also offers easy access to I-4 for working downtown Orlando or visiting the attractions.
$715,000

Single Family

1301 MAYFIELD AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,722Sqft
Don't miss out on this beautiful home located in a prime, tree-lined Winter Park neighborhood. A short walk from downtown Winter Park, Kraft Azalea Gardens on Lake Maitland, and Phelps Park, this 3722 square foot home features Brazilian cherry hardwood floors and crown molding throughout. A large entry foyer opens into a gorgeous open kitchen with all stainless appliances.
$995,500

Single Family

1750 EDWIN BOULEVARD, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,108Sqft
Beautifully custom built two story modern home offers five bedrooms, four and a half baths, circular driveway with two car side entry garage, and an amazing outdoor living and entertaining area. The interior design elements leave you wanting for nothing more, with eleven foot soaring ceilings with modern LED-backlit detail and endless natural light.
$1,495,000

Single Family

1727 OAKHURST AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,283Sqft
Brand New Listing in the Heart of Winter Park! Welcome to this stunning 4 bedroom, 3.5 bath David Weekley home built with traditional elegance in mind. Located on a quiet street, within walking distance to A-rated Lakemont Elementary, this beautifully appointed home features an open layout with lots of room for entertainment and every day living.
$1,025,000

Condominium

100 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,271Sqft
The wait is over. Sophisticated, light, bright, open and updated Spacious two bedroom/two bath at the Cloisters in Downtown Winter Park. Open kitchen with large island, Carrera marble counters and beautiful white cabinetry. Spacious living/dining area with gorgeous wood floors offers wonderful views of Lake Osceola and serene grounds. Sun room has windows on three sides.
$495,000

Condominium

315 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
2Parking(s)
20Picture(s)
1,605Sqft
STUNNING WINTER PARK two bedroom condo oriented in the most private section of the Jewel of Winter Park! Villa Siena is located 2 blocks off Park Avenue and is directly across from the chic Alfond Inn.
$965,000

Condominium

104 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
21Picture(s)
1,283Sqft
Ideal location in the heart of downtown Winter Park. Approximately 2 blocks from Park Avenue which is renowned for shopping & dining. Orlando International Airport can be reached from the downtown Sun Rail Station. Unit 313 features updated baths & kitchen. Brazilian hardwood floors, crown molding, plantation shutters throughout. Washer and dryer in the unit.
$480,000

Single Family

1830 GIPSON GREEN LN, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
6,444Sqft
Luxury and elegance abound in this private, gated Winter Park Chain of Lakes estate, nestled on almost an acre at the end of a secluded cul-de-sac, with elevated views of beautiful Lake Maitland. Remodeled by award-winning interior designer, Betsy Godfrey, and designed with entertaining in mind, the rooms are large, timeless and sophisticated.
$4,195,000

Condominium

1913 WOODCREST DRIVE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
25Picture(s)
987Sqft
Do not miss out on your opportunity to own this charming Winter Park renovated 2 bedroom 2 bathroom second floor condo ! This unit has been loved and it shows, enjoy countless upgrades from an airy kitchen with soft close cabinets, stainless steel appliances, master walk in closet, and a spa like master bathroom!! Unit also equipped with smart features including smart canned lighting in living roo
$199,900

Single Family

2835 ROUEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
21Picture(s)
1,914Sqft
You don't want to miss out on this Winter Park home! 3 bedrooms, 2 baths plus an office sitting on almost 1/4 acre in the 32789 zip code.
$395,000

Single Family

5048 N WOODCREST DRIVE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
1Parking(s)
20Picture(s)
1,362Sqft
Beautifully renovated Winter Park turn key home ready for you. 3 Bedroom and 2 Bath home with out homeowner's Association. Home shows like new and has BRAND NEW ROOF, New flooring, New solid wood cabinets kitchen with granite countertop and Stainless steel appliances. Crown molding throughout. AC system and refrigerator to be replaced soon.
$308,000

Single Family

1000 Anchorage Court, WINTER PARK, Florida 32789

6Bedroom(s)
7Bathroom(s)
25Picture(s)
7,336Sqft
Location, Location, Location! This Stunning Estate Home in Winter Park's famed "Golden Triangle" is TRUE walking distance to Park Ave. Attention to every detail, this home provides the perfect "Old World" backdrop for your personal furnishing style - from Traditional to European to Modern. This home perfectly balances luxurious space with warm and inviting finishes.
$1,988,000

Single Family

501 DUNRAVEN DRIVE, WINTER PARK, Florida 32792

5Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,024Sqft
Pre-Construction. To be built. Expect to be impressed with this stunning brand new construction home in the beautiful neighborhood of Kenilworth Shores in the Winter Park Pines. This beautiful home features 5 bedrooms/3 full baths, a sparkling saltwater pool w/water features, an inside laundry room, and a two-car front loading garage.
$890,000
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