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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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$199,000
$737/mo
Monthly Payment:
$737
Principal & Interest:
$737
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $39,800 down)
Winter Park, FL 32789
N/Asq ft N/A / sq ft LND
Lot Size19,316sq ft BuiltN/A On Site104days
Looking to build your dream home?? Perfect location on this 19,000 sq. ft. corner lot with deeded access to Lake Killarney - one of Winter Park's most private and desirable ski... more
Looking to build your dream home?? Perfect location on this 19,000 sq. ft. corner lot with deeded access to Lake Killarney - one of Winter Park's most private and desirable ski lakes! Beautiful new homes on same street. Conveniently located near I-4, Winter Park Village, in the heart of new development, shopping and dining on Park Ave. *Seller paid over 20k for plans for a 5 bed, 5 bath custom home with 3692 sq. ft. (SEE ATTACHMENTS). less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
Your search results are current and complete. Learn more
$598,900
$2,221/mo
Monthly Payment:
$2,221
Principal & Interest:
$2,218
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $119,780 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,203sq ft $187 / sq ft SFR
Lot Size11,062sq ft Built1967 On Site105days
Wonderful split level family home in desirable Timberlane Shores. Lovingly maintained custom built, one owner home situated on large corner lot. Main level features separate... more
Wonderful split level family home in desirable Timberlane Shores. Lovingly maintained custom built, one owner home situated on large corner lot. Main level features separate living and dining rooms, foyer with slate floor, kitchen with eat-in area. Upstairs has master suite with full bath plus 3 additional bedrooms and 1 extra full bath – all original hardwood floors throughout upstairs bedrooms and stairs to upper bedrooms. Lower level includes a wonderful family/game room which opens onto a lovely screened porch and lush backyard, a spacious additional bedroom suite with full bath and an indoor AC’d workshop room. Roof new 2008, 2 AC water/air systems that both provide AC to entire house – approx 10 years old, replumbed over various stages. All walls and ceilings are imperial plaster, exterior construction is brick + concrete siding block, all exterior wood is redwood. Additional features include plantation shutters, central vacuum, built-ins, crown molding, wide hallways, 2 car attached garage. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$525,000
$2,212/mo
Monthly Payment:
$2,212
Principal & Interest:
$1,945
HOA Dues:
$267
(Based on a 30 year fixed loan at 3.75% with $105,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,354sq ft $223 / sq ft TWN
Lot SizeN/Asq ft Built1989 On Site106days
Open Sun Aug 9, 2pm-4pm
Spacious and bright three bedroom, two and a half bath townhouse in walking distance to Winter Park shopping and dining on the Avenue. It is also a short walk to the community... more
Spacious and bright three bedroom, two and a half bath townhouse in walking distance to Winter Park shopping and dining on the Avenue. It is also a short walk to the community tennis courts and Rollins College. This townhouse features soaring ceilings and expansive windows. There is a stunning floor to ceiling, designer, wood display cabinet in the family room. A warm and cozy fireplace centers the room. The large kitchen features eat-in dining and tall cabinets for optimal storage. There is also a separate dining room or office adjacent to the kitchen. There are two very private patios for outside enjoyment that belong to the townhouse. The community of four townhouses also has its own very private pool in the back with professionally landscaped grounds. Upstairs, you will find an elegant and relaxing master suite with twelve foot high his and her closets, dual vanities, separate tub and shower. Two other bedrooms with a Jack and Jill bath complete the upstairs. This townhouse is one of four, each with a two car garage. Plus, community pool and Winter Park Schools. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$315,000
$1,167/mo
Monthly Payment:
$1,167
Principal & Interest:
$1,167
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,000 down)
Winter Park, FL 32789
Garden Acres Orange County School District
3bed 3bath 1,530sq ft $206 / sq ft SFR
Lot Size12,263sq ft Built1950 On Site107days
This is the perfect opportunity to build a triplex located in Winter Park with easy access to the Park Avenue retail district in one direction and downtown Orlando business... more
This is the perfect opportunity to build a triplex located in Winter Park with easy access to the Park Avenue retail district in one direction and downtown Orlando business district a few minutes in the other direction. The City of Winter Park Zoning on this property will allow for 3 units of approximately 2,250 sf. The existing triplex is currently fully leased with month-to-month tenants. Do not disturb tenants. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$315,000
$1,167/mo
Monthly Payment:
$1,167
Principal & Interest:
$1,167
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $63,000 down)
Winter Park, FL 32789
Garden Acres Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size12,263sq ft BuiltN/A On Site107days
This is the perfect opportunity to build a triplex located in Winter Park with easy access to the Park Avenue retail district in one direction and downtown Orlando business... more
This is the perfect opportunity to build a triplex located in Winter Park with easy access to the Park Avenue retail district in one direction and downtown Orlando business district a few minutes in the other direction. The City of Winter Park Zoning on this property will allow for 3 units of approximately 2,250 sf. The existing triplex is currently fully leased with month-to-month tenants. Do not disturb tenants. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity N/A
$189,900
$703/mo
Monthly Payment:
$703
Principal & Interest:
$703
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $37,980 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
2bed 2bath 1,261sq ft $151 / sq ft SFR
Lot Size8,481sq ft Built1955 On Site107days
Location! Location! Location! This Picture Perfect! Move in Ready! Winter Park home is 5 min. to downtown Orlando, minutes to College Park, Winter Park Village, Park Avenue &... more
Location! Location! Location! This Picture Perfect! Move in Ready! Winter Park home is 5 min. to downtown Orlando, minutes to College Park, Winter Park Village, Park Avenue & area hospitals. Completely updated. New Roof, Double Pane Windows, Electric, Plumbing, Kitchen, Bath's and Landscaping. The Gourmet Kitchen is equipped with granite counter tops, a large breakfast bar, title backsplash, designer maple cabinets with wine storage. Brand new Energy Star refrigerator, GE profile range/oven with warming drawer. The hardwood floors are amazing! The 26'x9' tiled Bonus Room is the perfect place for a 3rd bedroom, home office, game room, or movie room. The 2nd bedroom has a built-in cedar closet. It's a must to see! The oversized garage has a 1/2 bath. The front deck with the attached screened porch is the perfect place to unwind. The Roof has a 30 year warranty. Extra attic insulation, & new interior paint. Fenced yard, mature trees and so much more! less
Listing Provided Courtesy of Realty Executives Seminole
Popularity
$1,800,000
$6,668/mo
Monthly Payment:
$6,668
Principal & Interest:
$6,668
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $360,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
N/Asq ft N/A / sq ft LND
Lot Size11.2acre BuiltN/A On Site107days
3 parcels totaling 11+ acres in winter park - 470 feet of road frontage on howell branch road that will offer plenty of exposure in the desirable area. Builders are selling out... more
3 parcels totaling 11+ acres in winter park - 470 feet of road frontage on howell branch road that will offer plenty of exposure in the desirable area. Builders are selling out their communities in less than 6 months and the new san pedro project is only about a mile away ( 900 + new homes ) property could be combined for an equestrian center with live in quarters. This property offers endless possibilities for development and located within minutes of the 417 and downtown winter park..... Call today for more information less
Listing Provided Courtesy of The Titan Group, Inc.
Popularity
$285,000
$1,055/mo
Monthly Payment:
$1,055
Principal & Interest:
$1,055
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $57,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,110sq ft $135 / sq ft SFR
Lot Size21,780sq ft Built1967 On Site108days
Bring your boat, your RV, your utility trailers, No HOA! 4 bedroom 3 bath 2 car garage home situated on 1/2 acre in Winter Park!! This is truly a rare and unique find. Well... more
Bring your boat, your RV, your utility trailers, No HOA! 4 bedroom 3 bath 2 car garage home situated on 1/2 acre in Winter Park!! This is truly a rare and unique find. Well maintained has easy care/allergy free ceramic tile flooring throughout and a practical floorpan, great for entertaining! The property is adjacent to a canal that feeds into Garden Lake for canoeing or paddle boarding. Great shopping, churches schools and restaurants are close by. In addition, it is convenient to the University of Central Florida, Full Sail University, Rollins College, Oviedo Marketplace, and all of the attractions by way of the 417 expressway. Bike/Jogging trails are nearby as well. Whether your destination is Winter Park, Winter Springs, or Oviedo, this home is in the perfect location for you. See it today! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$950,000
$3,519/mo
Monthly Payment:
$3,519
Principal & Interest:
$3,519
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $190,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size22,726sq ft BuiltN/A On Site108days
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York. Walk to... more
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York. Walk to the shops of Park Avenue and the Winter Park Farmers Market. The value of this property is in the land but, for the Mid-Century Modern enthusiast, the land comes with a free “60’s-classic” house. Of course the house is included “as is” but it features an 18’x40’ air conditioned atrium, polished terrazzo floors, oversized 2 car garage, and a charming mother-in-law suite. Restore this Mid-Century gem or build a new gem on this wonderful corner lot that sits high on Park Avenue with more than 150 feet of frontage! less
Listing Provided Courtesy of Anne Rogers Realty Group Inc
Popularity N/A
$950,000
$3,519/mo
Monthly Payment:
$3,519
Principal & Interest:
$3,519
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $190,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,610sq ft $364 / sq ft SFR
Lot Size22,726sq ft Built1961 On Site108days
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York. Walk to... more
Rare opportunity to own a lot of this size on Park Avenue (.52 acre parcel). All the prestige of a Park Avenue address with the convenience of a driveway on New York. Walk to the shops of Park Avenue and the Winter Park Farmers Market. The value of this property is in the land but, for the Mid-Century Modern enthusiast, the land comes with a free “60’s-classic” house. Of course the house is included “as is” but it features an 18’x40’ air conditioned atrium, polished terrazzo floors, oversized 2 car garage, and a charming mother-in-law suite. Restore this Mid-Century gem or build a new gem on this wonderful corner lot that sits high on Park Avenue with more than 150 feet of frontage! less
Listing Provided Courtesy of Anne Rogers Realty Group Inc
Popularity
$150,000
$555/mo
Monthly Payment:
$555
Principal & Interest:
$555
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $30,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,449sq ft $104 / sq ft SFR
Lot Size11,200sq ft Built1958 On Site108days
*****investor alert.....Investor alert.....Calling all investors!!!!!!!****** this property has great potential. Seller offers one year financing. Close to everything! Only a... more
*****investor alert.....Investor alert.....Calling all investors!!!!!!!****** this property has great potential. Seller offers one year financing. Close to everything! Only a short commute to shopping, entertainment and dining. Minutes away from i-4 makes traveling to anywhere easy. less
Listing Provided Courtesy of Carrington Real Estateservices
Popularity
$689,500
$2,557/mo
Monthly Payment:
$2,557
Principal & Interest:
$2,554
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $137,900 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 3bath 1,824sq ft $378 / sq ft SFR
Lot Size9,278sq ft Built1935 On Site109days
REDUCED!!! Historic registered home in desirable Virginia Heights Neighborhood. Beautiful lush/mature landscaping covers the entire property from front to back. This home was... more
REDUCED!!! Historic registered home in desirable Virginia Heights Neighborhood. Beautiful lush/mature landscaping covers the entire property from front to back. This home was featured in "Southern Living Magazine" in the August 2005 Edition. The 1920's craftsmanship shows and home packed with charm. The main house offers 2 bedroom 2 bath with finished attic that can be used as a 3rd bedroom or bonus room. The basement area can be used for extra storage, etc. Exquisite appointments include crown moldings, plantation shutters, hardwood floors, gas burning fireplace, and Florida room with slate flooring. New roof and AC installed 2014. The brick paved driveway leads to covered parking area. The detached guest house offerers a kitchenette and full bathroom. Enjoy the screened patio area that overlooks the gorgeous saltwater pool. Walk to deeded Lake Virginia, Chain of Lakes access. This home is a true beauty. Completely updated while preserving the feel of the yesteryear. less
Listing Provided Courtesy of Beck Realty Llc
Popularity
$715,000
$2,649/mo
Monthly Payment:
$2,649
Principal & Interest:
$2,649
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $143,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,800sq ft $255 / sq ft SFR
Lot Size10,455sq ft Built1967 On Site110days
Located on a quiet Cul-de-Sac, this unique completely renovated modern sanctuary offers both form & function. Designed by architect Alan Berman, no detail has been overlooked.... more
Located on a quiet Cul-de-Sac, this unique completely renovated modern sanctuary offers both form & function. Designed by architect Alan Berman, no detail has been overlooked. This rare home offers four spacious beds, three fully remodeled baths, a remodeled kitchen, new house systems (irrigation, filtration, lighting, electrical), a pool, private courtyard & multiple living spaces. Natural elements of sunlight, air & garden views add to this home’s welcoming environment. The light, bright & open kitchen remodeled in 2010 offers clean lines & ergonomic spaces inspired by modern, eco-friendly European design. The kitchen was engineered w/ rigorous attention to detail, including top-of-the-line appliances (Electolux, Miele) & a sense of function & flow. With quartz countertops, Italian tile, wine & beverage refrigerators & well-lighted environmentally friendly work stations, this kitchen provides an elegant blend of luxury & ease. The home’s clean lines & open, airy feel continue into the living space, the centerpiece of which is an authentically mid-century modern sunken fireplace w/ built-in seating. The living room features soaring ceilings & new floating beechwood floors. Floor-to-ceiling windows & glass doors bring together the indoor & outdoor, offering direct access to the courtyard w/ its mature trees & resurfaced pool. Convenient location is minutes to downtown Winter Park, Orlando, Orlando International Airport, UCF, I-4, 417 as well as local shops & restaurants. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$1,375,000
$5,094/mo
Monthly Payment:
$5,094
Principal & Interest:
$5,094
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $275,000 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 2,218sq ft $620 / sq ft SFR
Lot Size1.7acre Built1953 On Site111days
This is beautiful lakefront property across the street from Lake Baldwin Park in the City of Winter Park. It is 1.74 acres, could be subdivided into smaller lots, is zoned R-2... more
This is beautiful lakefront property across the street from Lake Baldwin Park in the City of Winter Park. It is 1.74 acres, could be subdivided into smaller lots, is zoned R-2 which allows up to 10 units per acre, and has direct frontage on private Lake Spier and Lake Compton. There is approximately 175 feet of frontage on S Lakemont Ave, with additional access on the west side from Lake Spier Drive. It may be possible to change the street address of the property to Lake Spier Drive, 32789. The house is being sold "AS IS". Ideally located just a short walk to downtown Baldwin Park and great Winter Park schools. less
Listing Provided Courtesy of Brad Gustafson, Realtor
Popularity
$429,000
$1,689/mo
Monthly Payment:
$1,689
Principal & Interest:
$1,589
HOA Dues:
$100
(Based on a 30 year fixed loan at 3.75% with $85,800 down)
Winter Park, FL 32792
4bed 4bath 2,842sq ft $151 / sq ft SFR
Lot Size10,889sq ft Built2015 On Site111days
Basically brand new home, The Inverness Model features Upgrades galore! Gated Sanctuary at Aloma in Winter Park. Extremely Energy Efficient!! This home welcomes you with warm... more
Basically brand new home, The Inverness Model features Upgrades galore! Gated Sanctuary at Aloma in Winter Park. Extremely Energy Efficient!! This home welcomes you with warm hardwood floors throughout. Formal Living and Dining Rooms separate. Top of the line Stainless Steel appliances. Large Over sized Quartz Counter Tops, Upgraded Cabinets with under-mount and interior lighting. Flex Space can be used as Office/Den/Playroom area. Large Master Bedroom, Master Bath features oversized upgraded Shower with Rainfall shower & Dual shower heads and built in bench. His and her Vanities, bidet. Triple Sliders lead to the Large, Covered Screen Porch. Convenient location to Aloma and the 417. 25 minutes to downtown Orlando. Great Schools & more! Call today for your private showing. less
Listing Provided Courtesy of Bhhs Florida Realty
Popularity
17 18 19 20 21 22 23 24 25 ... 30
ZipRealty helps you find current homes for sale in Winter Park, FL. We show up to 30% more MLS listings than other websites, including new homes for sale, condos for sale, townhomes for sale, foreclosed homes for sale and land for sale. Set up your unique Winter Park real estate search criteria to see results that match what you're looking for. Explore maps, photos, schools and more to get an idea of what your life would be like in a new neighborhood. Find a local Winter Park real estate agent to work with by reading realtor reviews left by buyers and sellers like you. If you want to know what your home is worth, you can instantly view home values for any address by visiting our Seller Center. If you're planning to sell your home, you can also see how much similar homes are selling for in Winter Park to get an idea of how to price your home.
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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The information being provided by Mid-Florida Regional Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid-Florida Regional Multiple Listing Service. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid-Florida Regional Multiple Listing Service. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

The accuracy of all information, regardless of source, including but not limited to open house information, square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by Mid-Florida Regional Multiple Listing Service and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

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Data last updated: Tuesday, August 4, 2015 at 8:11 PM. Properties in listings may have been sold or may no longer be available.