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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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$3,500,000
$12,967/mo
Monthly Payment:
$12,967
Principal & Interest:
$12,967
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $700,000 down)
Winter Park, FL 32789
Windsong Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.4acre BuiltN/A On Site104days
Rare opportunity to build your dream home in the heart of Winter Park. This waterfront property is in the desirable Windsong community and on the Winter Park Chain of Lakes.
Rare opportunity to build your dream home in the heart of Winter Park. This waterfront property is in the desirable Windsong community and on the Winter Park Chain of Lakes. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
We show you every available listing. Here's how
$2,250,000
$8,336/mo
Monthly Payment:
$8,336
Principal & Interest:
$8,336
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $450,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size37,500sq ft BuiltN/A On Site104days
Multifamily development site! 150 x 250 vacant lot, 37,500 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf... more
Multifamily development site! 150 x 250 vacant lot, 37,500 sf. Rarely available "shovel ready" development for 15 townhouses. Approved with variances in place. Total 41,000 sf with a net of 34,000 sf of net saleable air conditioned space. Each unit has a 2 car attached garage and access to outdoor parking for 7+ extra parking spaces. Four 2 story units and eleven 3 story units. Architectural plans available. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$259,900
$962/mo
Monthly Payment:
$962
Principal & Interest:
$962
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $51,980 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,944sq ft $134 / sq ft SFR
Lot Size8,249sq ft Built1958 On Site104days
Quiet Winter Park gem, 4 bedroom 3 bath split plan, with updated kitchens and baths, custom finishes throughout, double master suites, pool with fully fenced large open yard on... more
Quiet Winter Park gem, 4 bedroom 3 bath split plan, with updated kitchens and baths, custom finishes throughout, double master suites, pool with fully fenced large open yard on a dead-end street with NO HOA! This rare find and has been meticulously maintained and offers custom detailing such as crown molding throughout every room in the house, high profile baseboards, chair rail millwork, knock down ceilings, three sets of French doors, there is no carpet in the entire home. The beautifully appointed, generous kitchen is located in the heart of the home and boasts a large peninsula with snack bar, counter height seating complete with extra storage space and cabinets below. There is ample counter space, solid wood cabinets with built in wine rack, tiled backsplash. The large family room opens up into a screened tiled porch from there you step out into the inviting round swimming pool great to relax in on our beautiful Florida days. Pool is surrounded by a spacious paver deck/patio, there is plenty of yard to enjoy the open outdoors! less
Listing Provided Courtesy of EXIT REALTY CENTRAL
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
Orange County School District
3bed 3bath 1,698sq ft $168 / sq ft SFR
Lot Size9,317sq ft Built1959 On Site106days
Beautiful, move-in ready 3 bedroom, 2.5 bath home. Remodeled kitchen includes granite countertops, subway tile backsplash, and stainless steel appliances. Interior features... more
Beautiful, move-in ready 3 bedroom, 2.5 bath home. Remodeled kitchen includes granite countertops, subway tile backsplash, and stainless steel appliances. Interior features include a large family room, eat-in kitchen, oversized utility room, wood burning fireplace, long hallway closet, and original terrazzo floors. Exterior features include gorgeous landscaping and 2 large utility sheds for storage in the backyard. Zoned for A rated Winter Park schools and just minutes from the Downtown Winter Park Historic District. less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$89,900
$626/mo
Monthly Payment:
$626
Principal & Interest:
$333
HOA Dues:
$293
(Based on a 30 year fixed loan at 3.75% with $17,980 down)
Winter Park, FL 32792
Orange County School District
2bed 3bath 1,230sq ft $73 / sq ft CND
Lot Size2.2acre Built1981 On Site106days
Location, location!!Great investment opportunity or first Time home buyers. Cozy,Beautiful 2 bedroom 2,5 bath two story condo !newer than the other buildings in community!close... more
Location, location!!Great investment opportunity or first Time home buyers. Cozy,Beautiful 2 bedroom 2,5 bath two story condo !newer than the other buildings in community!close to UCF and Full sail university. Living room, kitchen and half bath at downstairs! All Rooms has carpet floor and down stairs has all tile! Community amenities include pool, tennis courts, playground and clubhouse. close to Public transportation,Airport and downtown Orlando!! Easy access to major highways, SR 408, 417 and SR 436.close to Golden road and Colonial.Don't miss this opportunity !! seller is motivated!!just bring your offer!! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$174,900
$647/mo
Monthly Payment:
$647
Principal & Interest:
$647
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $34,980 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 1,389sq ft $126 / sq ft SFR
Lot Size5,858sq ft Built1961 On Site106days
This charming block home features wood and tile flooring with a beautiful color palette throughout the rooms. The galley kitchen features dark wood cabinets and an intricate... more
This charming block home features wood and tile flooring with a beautiful color palette throughout the rooms. The galley kitchen features dark wood cabinets and an intricate light fixture. The window over the sink gives it a homey feel and also lets in plenty of natural light. The large living room has a triple-wide window double doors to the back deck, which wraps around most of the house and ends in a large, uncovered deck in the back yard. Put out some patio furniture and relax in the evenings! It'll feel like home in no time. This is a Fannie Mae HomePath property. less
Listing Provided Courtesy of LEMONTREE REALTY LLC
Popularity
$75,000
$488/mo
Monthly Payment:
$488
Principal & Interest:
$277
HOA Dues:
$211
(Based on a 30 year fixed loan at 3.75% with $15,000 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 749sq ft $100 / sq ft CND
Lot Size3,258sq ft Built1984 On Site107days
Parkview Village Condominiums, where location, convenience and technology come together to create a state-of-the-art home with you in mind. Just minutes away from Full-Sail,... more
Parkview Village Condominiums, where location, convenience and technology come together to create a state-of-the-art home with you in mind. Just minutes away from Full-Sail, Lockheed Martin, Siemens and UCF. Parkview features comfortable living with the extras you deserve. less
Listing Provided Courtesy of CONSORTIUM CAPITAL LLC
Popularity
$749,000
$2,774/mo
Monthly Payment:
$2,774
Principal & Interest:
$2,774
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 3,453sq ft $217 / sq ft SFR
Lot Size18,338sq ft Built1927 On Site108days
Welcome to the Winter Park COMPOUND!! This large property consists of 3 Dwellings! MAIN HOUSE- 4 beds/ 3.5 baths with 2,737sqft. GUEST HOUSE- 1 bed/1 bath home with 782sqft.... more
Welcome to the Winter Park COMPOUND!! This large property consists of 3 Dwellings! MAIN HOUSE- 4 beds/ 3.5 baths with 2,737sqft. GUEST HOUSE- 1 bed/1 bath home with 782sqft. Separate BONUS building with 324sqft. Looking to move your in-laws or have a private office/gym, this compound is for you! The downstairs Master Suite includes a gas fireplace, 2 walk-in closets, a “human car wash” shower, and a bathroom measuring at 18x28 (larger than a 2 car garage). The 2nd bedroom suite downstairs incorporates the updated pool bathroom. The oversized custom spiral staircase leads to a loft & 2 beds/1 bath… kid’s retreat! This unique 1920’s home is like no other with soaring vaulted ceilings, wrapped in glass across the back, and natural wood floors throughout the homes. (not a stitch of carpet on this property!) The Kitchen/Family room combo has 4 glass doors that lead to the outdoor living patio (15x32) with 20 foot ceilings, lounge area, a pool table, and room for dining. This is the ultimate entertainment home! Relax on the "beach" in the salt-water pool or swim in the privacy of the PVC fenced backyard. The GUEST HOUSE is spacious: open living spaces, vaulted ceilings, and a large bedroom & closet…your guests may never leave! There is ample parking in addition to the 2 car garage, wrapped in storage cabinets. The one-way brick street off N. Park Ave is conveniently located to ALL the amenities in the heart of WP and easy access to all major roads. This COMPOUND is for you! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$429,000
$1,589/mo
Monthly Payment:
$1,589
Principal & Interest:
$1,589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $85,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,404sq ft $306 / sq ft SFR
Lot Size10,283sq ft Built1957 On Site108days
Welcome 1701 Magnolia Ave in Olde Winter Park! Cute 3/2 on a LARGE 75 x 137 lot on a beautiful tree lined and cobble stoned street. Buy now, build later, you will be surrounded... more
Welcome 1701 Magnolia Ave in Olde Winter Park! Cute 3/2 on a LARGE 75 x 137 lot on a beautiful tree lined and cobble stoned street. Buy now, build later, you will be surrounded by all the conveniences that this location offers! less
Listing Provided Courtesy of CHARLES RUTENBERG REALTY
Popularity
$269,900
$999/mo
Monthly Payment:
$999
Principal & Interest:
$999
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $53,980 down)
Winter Park, FL 32792
Orange County School District
5bed 2bath 1,514sq ft $178 / sq ft SFR
Lot Size9,252sq ft Built1963 On Site108days
Welcome Home! This charming 5 bedroom 2 bath home with a converted garage is truly the definition of a move in ready home! As you arrive at the community you will see just how... more
Welcome Home! This charming 5 bedroom 2 bath home with a converted garage is truly the definition of a move in ready home! As you arrive at the community you will see just how nice this is. From the very second you arrive you will see mature landscaping, well maintained exterior elevations and so much more. Once you arrive at the home you will be welcomed by the newly upgraded landscaping, large oak tree and a 2 car driveway. The large front and fenced rear yard is a must see! As you make your way into the home you will be excited to see the front entry screen room, formal entry and a storage closet. As you start your tour you will see an open plan, An abundance of Terrazzo flooring and a bright an airy home. The large living room featuring a fireplace is great for those cold winter nights. Sit back and relax as the fire burns. The living room is open to the kitchen and dining room. This is the perfect layout for entertaining! The large kitchen with window features plenty of cabinets for storage and lots of counter space for the chef in the household. As you continue the tour you will see the large Florida Room perfect for relaxing after a long day! The large guest rooms are sure to please all your overnight guests. Don't forget to go out in the back and see the large fenced in yard. This is a must see! The storage shed in the back is great for extra storage. This is a move in ready home! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$499,900
$1,852/mo
Monthly Payment:
$1,852
Principal & Interest:
$1,852
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,980 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 2,192sq ft $228 / sq ft SFR
Lot Size15,256sq ft Built1969 On Site109days
***Click the virtual tour icon above to watch drone and video footage!!!***This large, open floor plan has been renovated beautifully with a new kitchen, stainless appliances... more
***Click the virtual tour icon above to watch drone and video footage!!!***This large, open floor plan has been renovated beautifully with a new kitchen, stainless appliances and granite tops. There is extensive wood flooring and a large study with French doors. The kitchen opens to a large great room with wood burning fireplace. There is a large, screen porch with new tile floors right off the great room. The spacious master has a double vanity with a jetted shower system and a large walk in. This home has so many features you just don't find in a home of this era. The large, private lot is completely fenced with mature landscaping and plenty of room to roam. There is a separate utility shed as well as a 2 car garage so storage will never be an issue. Come see this one today before its gone! less
Listing Provided Courtesy of COLEDEV REAL ESTATE LLC
Popularity
$819,500
$3,036/mo
Monthly Payment:
$3,036
Principal & Interest:
$3,036
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $163,900 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,201sq ft $256 / sq ft SFR
Lot Size13,544sq ft Built2000 On Site111days
Winter Park Exclusive home built in 2000 with "Old Winter Park" charm! Drive up and expect to be impressed with the circular driveway and exterior features of this home! Upon... more
Winter Park Exclusive home built in 2000 with "Old Winter Park" charm! Drive up and expect to be impressed with the circular driveway and exterior features of this home! Upon entering the home the foyer greets you with volume ceilings as it overlooks the formal living and dining room with the amazing staircase that leads to two bedrooms and a bath, off of the formal area is the fabulous master bedroom featuring his and her closets, French doors, spa like entry to bath. The family room is light and bright off of the kitchen. The other two bedrooms and bath are located on the other side of the home! Floor plan has a 3 way split for privacy! This home is equipped with Hardwood floors in main areas and Plantation shutters through out. The back yard is large enough for a Large pool! Location is just minutes from Park Ave., close to shopping, restaurants, hospitals and highways! This home is located near the chain of lakes, walk to lake and launch kayaks or paddle boards! A must see home! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$512,000
$1,896/mo
Monthly Payment:
$1,896
Principal & Interest:
$1,896
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $102,400 down)
Winter Park, FL 32789
Virginia Heights Orange County School District
3bed 3bath 2,406sq ft $213 / sq ft TWN
Lot Size6,408sq ft Built1999 On Site112days
Great 3 bedroom, 2 1/2 bathroom town home That feels like a private home in desirable Winter Park. As you enter the home you are welcomed into the foyer which leads to a bright... more
Great 3 bedroom, 2 1/2 bathroom town home That feels like a private home in desirable Winter Park. As you enter the home you are welcomed into the foyer which leads to a bright and open floor plan. The dining area is open to the kitchen as well as the spacious living room. The bright kitchen features wood cabinets, an island, breakfast bar, solid surface counter tops and eat in space. Off the kitchen is a side patio great for grilling. The living room has wood floors, crown molding and tons of space along with an electric fireplace, and two doors leading to the outdoor patio area and beautiful backyard. The ground floor master suite also has French doors that open to the backyard patio. The back patio is covered by a trellis and it opens to the backyard. The Master suite has new carpet, a large walk in closet, his and hers separate sinks and vanities, a large soaking tub and a private potty room with a large separate shower. Heading to the second floor, the stairs lead to a bonus loft area and two generous sized bedrooms with large closets and a Jack and Jill bath. All new carpet upstairs. Two HVAC units within the last two years... Two blocks from beautiful Lake Virginia and walking trails of Rollins College; one block from Mead Gardens (back entrance); close to Winter Park shopping. This home is a must see!! There is a transferable termite bond. less
Listing Provided Courtesy of SUTTON & SUTTON REALTY, INC.
Popularity
$69,900
$592/mo
Monthly Payment:
$592
Principal & Interest:
$258
HOA Dues:
$334
(Based on a 30 year fixed loan at 3.75% with $13,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,300sq ft $54 / sq ft CND
Lot Size8,617sq ft Built1974 On Site112days
Beautiful home in Winter Park! Fantastic location close to very good schools and major highways! She possesses vaulted ceilings and split floor plan making it extremely... more
Beautiful home in Winter Park! Fantastic location close to very good schools and major highways! She possesses vaulted ceilings and split floor plan making it extremely inviting. Our home has always been maintained with love and care. The community features 2 pools, a playground and tennis courts. less
Listing Provided Courtesy of FLATFEE.COM
Popularity
$749,000
$2,774/mo
Monthly Payment:
$2,774
Principal & Interest:
$2,774
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $149,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 3,339sq ft $224 / sq ft SFR
Lot Size14,913sq ft Built1930 On Site115days
Charming older home with many updates. Beautiful creekside setting close to Rollins College and downtown Winter Park. Spacious and light with recent exterior paint. Each of the... more
Charming older home with many updates. Beautiful creekside setting close to Rollins College and downtown Winter Park. Spacious and light with recent exterior paint. Each of the three bathrooms has been totally renovated. The master suite has a balcony, fireplace, an expanded bath, an ENORMOUS closet (16x11) with built-ins and an additional storage/hobby space. This home has wood floors, two fireplaces, lots of windows to let the sunlight in. Newer stainless appliances in large kitchen. Covered outdoor dining/entertaining area with wall mounted flat screen. deeded access to Lake Virginia with pedestrian dock at college point. Survey and recent building inspection available. A wonderful opportunity to enjoy a winter park lifestyle. less
Listing Provided Courtesy of OVERSTREET REAL ESTATE INC
Popularity
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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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Data last updated: Tuesday, February 9, 2016 at 7:57 PM. Properties in listings may have been sold or may no longer be available.