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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$999,000
$3,701/mo
Monthly Payment:
$3,701
Principal & Interest:
$3,701
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $199,800 down)

543 E Lake Sue Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
4bed 5bath 3,657sq ft $273 / sq ft SFR
Lot Size15,886sq ft Built1986 On Site1days
Four bedroom, four and one-half bath pool home tucked away in Lake Virginia Shores. Full of character, this home features dark, wide-plank wood floors, crown molding, and high... more
Four bedroom, four and one-half bath pool home tucked away in Lake Virginia Shores. Full of character, this home features dark, wide-plank wood floors, crown molding, and high beadboard ceilings. Formal living and dining rooms, an open family room with built-in bookshelves and a fireplace, and a large sunroom help make this home perfect for entertaining. Gourmet kitchen has been beautifully updated and shows like a model with white cabinetry, marble counters, subway tile backsplash, and gas appliances. Downstairs bedroom is perfect for a guest suite. Upstairs are two generously sized bedrooms, each with private en suite, and the Master Bedroom. Master bath is luxurious with marble tile, glass shower, and a claw foot tub. Home office, 3-car garage, circular drive, and a spacious lot are all great features. Motivated sellers and easy to show – call today! less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity N/A
Your search results are current and complete. Learn more
$425,000
$1,574/mo
Monthly Payment:
$1,574
Principal & Interest:
$1,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $85,000 down)

2549 Madeline Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
4bed 4bath 2,506sq ft $170 / sq ft SFR
Lot Size8,405sq ft Built2013 On Site2days
Newer construction on a quiet street ideally located and in an excellent school district. Energy efficient and well designed home built in 2013 has a master suite on the main... more
Newer construction on a quiet street ideally located and in an excellent school district. Energy efficient and well designed home built in 2013 has a master suite on the main floor and three bedrooms plus a bonus room upstairs. Open floor plan and modern design featuring a kitchen with granite countertops, maple cabinets, large pantry, oversized island and stainless steel appliances. Security system, tile floors, transom windows, fenced in yard with covered patio, deck and water feature bring added value to this classic and charming home. less
Listing Provided Courtesy of CORE COMMUNITY REALTY LLC
Popularity
$389,500
$1,443/mo
Monthly Payment:
$1,443
Principal & Interest:
$1,443
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $77,900 down)

1330 Lyndale Boulevard NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
2bed 2bath 1,422sq ft $274 / sq ft SFR
Lot Size10,125sq ft Built1958 On Site2days
Beautiful Winter Park Bungalow located just blocks from downtown Winter Park shops and restaurants. This quaint 2 bedroom 2 bath home is located on a large lot and also offers a... more
Beautiful Winter Park Bungalow located just blocks from downtown Winter Park shops and restaurants. This quaint 2 bedroom 2 bath home is located on a large lot and also offers a large attached air conditioned workshop with a full bath. This property has great potential. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$799,000
$2,960/mo
Monthly Payment:
$2,960
Principal & Interest:
$2,960
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $159,800 down)

2395 Lafayette Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
4bed 5bath 3,961sq ft $202 / sq ft SFR
Lot Size10,536sq ft Built2001 On Site2days
Great Winter Park value! Four bedroom custom pool home on a quiet tree lined street. Almost 4000 sq. ft. Outstanding family home featuring formal living and dining rooms,... more
Great Winter Park value! Four bedroom custom pool home on a quiet tree lined street. Almost 4000 sq. ft. Outstanding family home featuring formal living and dining rooms, study/office with built-ins, downstairs guest suite, large family room, gourmet granite kitchen and breakfast nook, hardwood floors, large indoor laundry, extra large bedrooms and closets, bonus rooms and covered porch overlooking swimming pool and fountains. This home sparkles! Great Dommerich schools. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$305,000
$1,130/mo
Monthly Payment:
$1,130
Principal & Interest:
$1,130
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $61,000 down)

880 N Lakemont Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32792
Orange County School District
3bed 2bath 1,454sq ft $210 / sq ft SFR
Lot Size11,718sq ft Built1958 On Site2days
Value is in the land! The lot size is 69 x 171 (11,718 sf) in Winter Park...Build your dream home here with A rated schools and new construction...Conveniently located close to... more
Value is in the land! The lot size is 69 x 171 (11,718 sf) in Winter Park...Build your dream home here with A rated schools and new construction...Conveniently located close to the YMCA, Park Avenue, Rollins College, Farmers Market, Florida Hospital... less
Listing Provided Courtesy of WINTER PARK LAND CO.
Popularity
$66,000
$505/mo
Monthly Payment:
$505
Principal & Interest:
$244
HOA Dues:
$261
(Based on a 30 year fixed loan at 3.75% with $13,200 down)

332 Scottsdale Square #332 NEW Added to the site in the last 3 days

Winter Park, FL 32792
Orange County School District
2bed 2bath 1,020sq ft $65 / sq ft CND
Lot Size8,519sq ft Built1974 On Site2days
This spacious 2nd floor 2 bedroom 2 full bathroom condo features a large living room / dining area with newly installed laminate floors, multiple large closets, private balcony,... more
This spacious 2nd floor 2 bedroom 2 full bathroom condo features a large living room / dining area with newly installed laminate floors, multiple large closets, private balcony, washer and dryer closet, master bedroom with private bathroom. Condo is located near Full Sail University, UCF, major roads, transportation, shopping and just a few minutes to downtown Orlando and downtown Winter Park. Air conditioner is fairly new, and electrical panel was replaced in 2015. Washer and Dryer and living room furniture featured are included. less
Listing Provided Courtesy of RENCHER REALTY GROUP
Popularity
$72,500
$268/mo
Monthly Payment:
$268
Principal & Interest:
$268
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $14,500 down)

1000 S Semoran Boulevard #115 NEW Added to the site in the last 3 days

Winter Park, FL 32792
Orange County School District
2bed 2bath 1,003sq ft $72 / sq ft CND
Lot Size6.0acre Built1969 On Site2days
Charming Winter Park 2/2 condo with updated kitchen cabinets, fresh paint, all tiled floors and newer bathroom vanities. WASHER AND DRYER included for your convenience and is... more
Charming Winter Park 2/2 condo with updated kitchen cabinets, fresh paint, all tiled floors and newer bathroom vanities. WASHER AND DRYER included for your convenience and is located in the new screened enclosure on the back patio. Large living/dining room area with plenty of room to spread out to eat and watch TV. GROUND floor, END unit makes it feel like you have your very own space with room outside to enjoy the beautiful weather. For the younger members of the household – 2015-2016 top rated Winter Park schools to include Brookshire Elementary, Glenridge Middle and Winter Park High School! For the older members you are minutes from Full Sail University, UCF, Valencia and Rollins College. For work and play enjoy a short drive to OIA, convenient shopping and dining with nearby Baldwin Park and Park Avenue. Great INVESTMENT property with CURRENT TENANT!!!!!! less
Listing Provided Courtesy of BHHS FLORIDA REALTY
Popularity
$3,450,000
$12,781/mo
Monthly Payment:
$12,781
Principal & Interest:
$12,781
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $690,000 down)

1420 Via Tuscany NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
5bed 8bath 8,658sq ft $398 / sq ft SFR
Lot Size33,140sq ft Built2010 On Site2days
Magnificent Winter Park Estate in The Vias. Reminiscent of homes on the Costa del Sol, this unique home has four en suite bedrooms, three half baths, a 6-car garage, a casita... more
Magnificent Winter Park Estate in The Vias. Reminiscent of homes on the Costa del Sol, this unique home has four en suite bedrooms, three half baths, a 6-car garage, a casita with one en suite bedroom, two fireplaces and luxurious resort-style amenities. Particular attention was paid to the design and craftsmanship throughout the home. The sense of the Costa del Sol begins at the gated entry with ironwork details in the Spanish tradition. Beyond the gate, the courtyard pool provides a formal order to a picturesque composition by organizing the buildings and spaces around it. Daily life focuses on an open kitchen/family room on the main floor. Exquisite marble floors, mosaic tile ceiling, large island and professional grade gas stove make up the gourmet kitchen that opens onto the family room, butler/pantry area, and breakfast space with French doors to the courtyard. East-facing windows in the living and formal dining rooms capture soft morning light, creating a gallery for fine art and collectibles. Ground floor master suite in the projecting wing of the home is complimented by a library/study, dressing area, and a grand master bath complete with breakfast bar, expansive closets, and crystal light fixtures. Each wing of the home opens onto or overlooks the courtyard, which is a visual focus as well a serene setting. Second floor media room has built-in audio-visual equipment and an oversized projection screen. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$225,000
$855/mo
Monthly Payment:
$855
Principal & Interest:
$833
HOA Dues:
$22
(Based on a 30 year fixed loan at 3.75% with $45,000 down)

1459 E Brookshire Court NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,673sq ft $134 / sq ft SFR
Lot Size8,760sq ft Built1987 On Site2days
This immaculate 3bd, 2bth winter park pool home on a cul-de-sac is priced to sell! Completely move in ready, this must see home boasts beautiful hardwood floors and ceramic tile... more
This immaculate 3bd, 2bth winter park pool home on a cul-de-sac is priced to sell! Completely move in ready, this must see home boasts beautiful hardwood floors and ceramic tile throughout, a wood burning fireplace within a spacious living room complete with gorgeous vaulted ceilings, an eat-in kitchen large enough to accommodate the whole family, large bedrooms, and tons of storage. The home has energy efficient argon windows, was re-plumbed within the last 5 years, the ac is 2 years old with a 10 year warranty, and has a transferable indoor alarm system for its new owners! Located in a quiet neighborhood with very little traffic at the back of the hyde park development with plenty of privacy beyond the sparkling screened pool and patio. Schools are conveniently within a 5-10 min ride as well as publix, the fresh market, parks, and access to major roads and highways. less
Listing Provided Courtesy of KELLER WILLIAMS AT THE PARKS
Popularity
$169,900
$1,009/mo
Monthly Payment:
$1,009
Principal & Interest:
$629
HOA Dues:
$380
(Based on a 30 year fixed loan at 3.75% with $33,980 down)

700 Melrose Avenue #230 NEW Added to the site in the last 3 days

Winter Park, FL 32789
2bed 2bath 1,074sq ft $158 / sq ft CND
Lot Size5,050sq ft Built1964 On Site2days
This property is ideal for a primary residence or a second home. Winter Park Gardens is a quiet, clean, and exceptionally well maintained condominium in a... more
This property is ideal for a primary residence or a second home. Winter Park Gardens is a quiet, clean, and exceptionally well maintained condominium in a desirable Winter Park location within walking and biking distance to many amenities including Park Avenue, Rollins College and Orlando's Loch Haven Park, Cady Way and Orlando's urban bike trail. Adjacent to tennis courts and Mead Gardens park. Convenient to downtown Winter Park, Orlando, and Maitland; and a short drive to Publix, Trader Joe's, Fresh Market and Whole Foods Market. The unit has brand-new carpet in the master; laminate floors in the living room, foyer, kitchen, and bonus room; and kitchen counter-tops, tile back-splash, sink, stove, dishwasher and microwave. Plenty of closets with a view of the beautifully landscaped common areas and pool. The building has two handicap accessible ramps and two recently refurbished elevators. less
Listing Provided Courtesy of JACK KELLER INC
Popularity
$319,500
$1,183/mo
Monthly Payment:
$1,183
Principal & Interest:
$1,183
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,900 down)

1210 Oaks Boulevard NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
2bed 1bath 986sq ft $324 / sq ft SFR
Lot Size7,398sq ft Built1955 On Site2days
Fantastic corner lot in a hot new construction area walking distance to downtown Winter Park and soon, to the new 40,000 sf Whole Foods on 17-92. House is being sold AS-IS but... more
Fantastic corner lot in a hot new construction area walking distance to downtown Winter Park and soon, to the new 40,000 sf Whole Foods on 17-92. House is being sold AS-IS but has an excellent rental history. 3,181 max FAR with a 30' front setback, per the city of Winter Park. less
Listing Provided Courtesy of RE/MAX TOWN CENTRE
Popularity
$139,000
$514/mo
Monthly Payment:
$514
Principal & Interest:
$514
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $27,800 down)

5010 Ferncrest Drive NEW Added to the site in the last 3 days

Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,534sq ft $91 / sq ft SFR
Lot Size12,480sq ft Built1969 On Site3days
Multiple offer situation. Submit highest and best offer with proof of funds by monday, 2/8 at noon. winter park 4 bedroom home for under $140k and being sold... more
Multiple offer situation. Submit highest and best offer with proof of funds by monday, 2/8 at noon. winter park 4 bedroom home for under $140k and being sold with an appraisal! Sold as is. Investors special. Corner, over sized lot with beautiful mature landscaping. Tax records indicate 3 bedrooms but it is in fact a 4 bedroom, + a converted garage that can be converted back or used as another family room. Separate parking pad, carport with storage and shed behind the house and accessible from citrus ave. **appraisal attached in supplements and is for informational purposes only. ** cash only - special needs trust less
Listing Provided Courtesy of KELLER WILLIAMS CLASSIC REALTY
Popularity
$230,000
$855/mo
Monthly Payment:
$855
Principal & Interest:
$852
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $46,000 down)

1904 Natalen Road NEW Added to the site in the last 3 days

Winter Park, FL 32792
Orange County School District
3bed 2bath 1,400sq ft $164 / sq ft SFR
Lot Size11,206sq ft Built1957 On Site3days
Excellent value on this traditional styled Winter Park home. Step inside to large open living and dining space. Notice the beautiful parquet flooring throughout the common... more
Excellent value on this traditional styled Winter Park home. Step inside to large open living and dining space. Notice the beautiful parquet flooring throughout the common areas! Formal dining space is adjacent to the galley kitchen. Kitchen has the perfect amount of cabinet and counter space. All appliances included! Spacious family room in rear of home with a “wall of windows” that make the home bright. Master suite off the family room. You will appreciate the updated secondary bath. Corner lot with large, fenced yard and utility shed. Oversized carport with additional storage and laundry facilities. No HOA! Good location – short drive to Baldwin Park and SR 436. Come make this classic home your own! less
Listing Provided Courtesy of KELLER WILLIAMS CLASSIC REALTY
Popularity
$700,000
$2,593/mo
Monthly Payment:
$2,593
Principal & Interest:
$2,593
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $140,000 down)

7801 Georgeann Street NEW Added to the site in the last 3 days

Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 3,158sq ft $222 / sq ft SFR
Lot Size43,280sq ft Built1981 On Site3days
Incredible winter park lakefront opportunity!! Ski, fish & play on private lake waunatta! this one acre property has all the bells & whistles: custom front door... more
Incredible winter park lakefront opportunity!! Ski, fish & play on private lake waunatta! this one acre property has all the bells & whistles: custom front door welcomes you to this 2 story contemporary boasting a fabulous master suite with serene views of private lake from balcony, updated bath with soaking tub, huge shower, two walk in closets & additional room perfect for office, nursery or home gym!! The first floor boasts the best open floor plan!! updated kitchen with granite counter & island, wood cabinets & glass tile backsplashes, large family room with stone, wood burning fireplace, formal living room & dining room, plus additional 2 bedrooms & updated guest bath. Step outside to enjoy the sparkling pool, covered patio & deck: perfect for entertaining! Fantastic views of lake waunatta from every room in ths home!! Extras include: 2 car, side entry garage; new flooring throughout; upgraded double paned windows; 2 newer hvac systems; security system; irrigation system. Welcome home!! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$511,251
$1,922/mo
Monthly Payment:
$1,922
Principal & Interest:
$1,894
HOA Dues:
$28
(Based on a 30 year fixed loan at 3.75% with $102,250 down)

7937 Pleasant Pine Circle NEW Added to the site in the last 3 days

Winter Park, FL 32792
Seminole County School District
5bed 4bath 3,514sq ft $145 / sq ft SFR
Lot SizeN/Asq ft Built2016 On Site3days
Brand new 2 story home at beautiful Enclave at Aloma community in Winter Park! Close to downtown Winter Park’s charming historical district, residents of Enclave at Aloma... more
Brand new 2 story home at beautiful Enclave at Aloma community in Winter Park! Close to downtown Winter Park’s charming historical district, residents of Enclave at Aloma take pleasure in a town whose admirable gems include gorgeous Rollins College and the Morse Museum of American Art, home to the world’s largest collection of Tiffany glass. Winter Park, an Old Florida resort business titans founded more than a century ago, is full of excellent boutiques and eateries, upscale art galleries, deluxe golf courses, parks, and historic architecture. Enclave at Aloma Park also sits less than one mile from the GreeneWay (SR 417), putting homeowners within reach of Orlando, the international airport, lakes, theme parks, and, of course, the Sunshine State’s world-popular beaches. less
Listing Provided Courtesy of STANDARD PACIFIC OF TAMPA
Popularity
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Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
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Data last updated: Friday, February 5, 2016 at 2:28 PM. Properties in listings may have been sold or may no longer be available.