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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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$629,000
$2,330/mo
Monthly Payment:
$2,330
Principal & Interest:
$2,330
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $125,800 down)

1236 Via Del Mar NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
3bed 3bath 2,117sq ft $297 / sq ft SFR
Lot Size11,701sq ft Built1958 On Site3days
Available for short or long term lease. Beautifully updated 3 Bedroom 2 1/2 Bath Home in the prestigious tree lined "Vias" of Winter Park. This highly sought after location is... more
Available for short or long term lease. Beautifully updated 3 Bedroom 2 1/2 Bath Home in the prestigious tree lined "Vias" of Winter Park. This highly sought after location is only blocks from the Winter Park Racquet Club, Park Ave and the Interlachen Country Club. With a NEW A/C, NEW electrical, NEW double pane windows with lifetime warranty, NEW mahogany front door, NEW paint inside and out, renovated bathrooms, resurfaced driveway, Brazilian walnut floors, crown moulding and trim that carry out through the over 2100 square foot home. This home is ready for a new owner. The pool was resurfaced and new St Augustine grass was installed. The Kitchen features newly refinished cabinets with granite counter tops and Stainless Steel appliances. The private backyard is bordered by beautiful lush landscaping and surrounds gorgeous pool and cabana. Both the front courtyard and the cabana are pre-wired for sound. This home as a great open floor plan and is perfect for entertaining. Come see what beautiful Winter Park living should feel like. less
Listing Provided Courtesy of Sand Dollar Realty Group Inc
Popularity
We show you every available listing. Here's how
$650,000
$2,408/mo
Monthly Payment:
$2,408
Principal & Interest:
$2,408
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $130,000 down)

1400 S Pennsylvania Avenue NEW Added to the site in the last 3 days

Winter Park, FL 32789
Orange County School District
4bed 3bath 2,258sq ft $288 / sq ft SFR
Lot Size12,745sq ft Built1962 On Site3days
Beautifully Updated Home in Desirable Winter Park. This 4 bedroom, 3 bathroom home is conveniently located to shopping and dining on Park Ave, N. Orange Ave and Hannibal Square.... more
Beautifully Updated Home in Desirable Winter Park. This 4 bedroom, 3 bathroom home is conveniently located to shopping and dining on Park Ave, N. Orange Ave and Hannibal Square. Also nearby is the East End Market. Completely renovated in 2013, this home continues to be enhanced with upgrades like plantation shutters and a suite of Viking appliances which now makes the kitchen a perfect space to channel your inner chef. Granite counters and hardwood cabinetry are hallmarks of the modern and open space. A charming nook provides a wonderful spot for morning coffee and breakfast. The home’s open floor plan with wood flooring and vaulted ceilings make it perfect for family gatherings and entertaining. The Master Suite is large with dual closets and seating area. The Master Bath is a tranquil oasis with soaking tub and glass enclosed shower. A separate Bedroom en suite is perfect for family or guests with its own bathroom. 2 additional bedrooms round out the sleeping quarters. The front and back yards have been professionally landscaped and feature mature plantings, paved walkways, large patio and a calming fountain. The outdoor kitchen is ideal for entertaining with its built in gas grill and stone counters. The inviting fire pit will provide many wonderful evenings with warmth. Surrounded by built in seating this space is the perfect outdoor room for gatherings and conversation. Parking is a breeze for you and your guests. A 2-car garage and circular drive provide ample parking for family and friends. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$177,900
$914/mo
Monthly Payment:
$914
Principal & Interest:
$659
HOA Dues:
$255
(Based on a 30 year fixed loan at 3.75% with $35,580 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,554sq ft $114 / sq ft TWN
Lot Size958sq ft Built2007 On Site5days
This fha approved, townhouse -style condominium, is located in a private gated community and zoned in the sought after winter park school districts. Conveniently located to... more
This fha approved, townhouse -style condominium, is located in a private gated community and zoned in the sought after winter park school districts. Conveniently located to baldwin park, whole foods, florida hospital, downtown orlando, downtown winter park. Easy access to 408, i-4, 417 and airport. Close proximity to full sail university, rollins college, and ucf. The kitchen boasts 42' wooden cabinets and corian counter tops with pantry closet and is open to the dining and living room areas; cathedral ceilings and tile throughout. Screened in porch w/ sliding glass doors off main living area on 1st level. Clean and well cared for home. Master bedroom suite is spacious and has dual vanity sinks, stand up shower, linen closet, and large walk in closet. There is space for a small office/ play area in the upstairs loft. 2 bedrooms and bath upstairs. Stack-able washer in "laundry closet" located upstairs next to large linen closet. Extra storage under the staircase and 1 car garage. Community features playground, putting green, fountain, 24 hr security gate, and 'doggie play area". less
Listing Provided Courtesy of Re/max Town Centre
Popularity
$379,000
$1,404/mo
Monthly Payment:
$1,404
Principal & Interest:
$1,404
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,800 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 2,141sq ft $177 / sq ft SFR
Lot Size10,889sq ft Built1972 On Site5days
This completely renovated 4 bedroom home in the highly desired Winter Park school district is a must-see. 4 bedrooms, 2,5 baths, gorgeous kitchen and hard wood floor through-out... more
This completely renovated 4 bedroom home in the highly desired Winter Park school district is a must-see. 4 bedrooms, 2,5 baths, gorgeous kitchen and hard wood floor through-out makes this a rare find in this well established neighborhood. Entry to home is through charming atrium area. Large living room with Kitchen overlooking the family room. French doors open up onto a 25x10 screened in tiled porch. Huge backyard and a hall bath planned for a pool. Walk in closets in 2 bedrooms and an over-sized garage. Mature landscaping with large oaks and located on a quiet cul-de-sac. less
Listing Provided Courtesy of H & R Properties Of Central Fl
Popularity
$299,900
$1,111/mo
Monthly Payment:
$1,111
Principal & Interest:
$1,111
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,980 down)
Winter Park, FL 32792
Baldwin Park Orange County School District
3bed 2bath 1,400sq ft $214 / sq ft SFR
Lot Size10,803sq ft Built1959 On Site6days
When the ordinary is not enough, imagine yourself at a unique retreat. This beautiful Winter Park home is well maintained with a gorgoues pool surrounded by lush greenery. Just... more
When the ordinary is not enough, imagine yourself at a unique retreat. This beautiful Winter Park home is well maintained with a gorgoues pool surrounded by lush greenery. Just minutes away from shopping / dining, area parks and A+ rated school districts this is a great buy. Close to downtown Orlando and major highways. This home was originally built as a 4/2, but was remodeled while converting 2 rooms into one grand room. This home has a mother in law suite which can be utilized as a rental unit. A rarity of this particular area 2 car attached garage with pool is amazing.... request a special showing to view this lovely home before its gone... less
Listing Provided Courtesy of Re/max Executive Group
Popularity
$259,000
$959/mo
Monthly Payment:
$959
Principal & Interest:
$959
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $51,800 down)
Winter Park, FL 32792
Orange County School District
2bed 4bath 1,318sq ft $197 / sq ft SFR
Lot Size9,362sq ft Built1964 On Site6days
Cute pool home in Winter Park is up for grab! Welcome home with open parking space on a circular drive way. This 2/2 open floor plan, with a pool view thorough the windows give... more
Cute pool home in Winter Park is up for grab! Welcome home with open parking space on a circular drive way. This 2/2 open floor plan, with a pool view thorough the windows give you the relaxation feeling as you walk in. Travertine design floor, and beautiful granite counter top in the kitchen and baths. Kitchen and baths just recently updated. Ready for your personal touch to call it home. Won't last! less
Listing Provided Courtesy of Keller Williams Advantage Iii
Popularity
$499,000
$1,848/mo
Monthly Payment:
$1,848
Principal & Interest:
$1,848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,079sq ft $162 / sq ft SFR
Lot Size9,066sq ft Built1959 On Site6days
Fantastic Family Home! 5 bedrooms, 2 car garage. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well. Crown molding thru... more
Fantastic Family Home! 5 bedrooms, 2 car garage. Beautiful kitchen with stainless steel appliances and granite counter tops. Bathrooms are updated as well. Crown molding thru out. Wonderful real wood flooring. Master upstairs has an additional space being used as an office. Back yard is private and has plenty of room for a pool if buyer needed. Winter Park Schools! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$499,000
$1,848/mo
Monthly Payment:
$1,848
Principal & Interest:
$1,848
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $99,800 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,582sq ft $193 / sq ft SFR
Lot Size5,910sq ft Built2005 On Site6days
This charming bungalow is located just two blocks from Rollins College and Park Avenue! As you enter the beautiful French doors from the covered porch, you are welcomed with... more
This charming bungalow is located just two blocks from Rollins College and Park Avenue! As you enter the beautiful French doors from the covered porch, you are welcomed with gorgeous hardwood floors, beautiful crown molding, and plantation shutters throughout this four bedroom, two and one half bath house. The kitchen features custom cabinetry, granite countertops, a breakfast bar, and stainless steel appliances. As you are cooking in the kitchen, you will look out at the living area that features a cozy wood-burning fireplace. The master suite is located on the first floor and has a large bathroom with a garden tub, dual sinks, and walk-in shower. Walking up the hardwood steps to the second floor, you enter into the generous bonus room. The three bedrooms upstairs all have large closets and lots of natural light that come through the plantation shutters. The upstairs bathroom is huge and has two vanities on either side with a separate area for the shower/tub. This is a beautiful home and a must see! Everything from the hardwood floors to the paint color to the carpet and kitchen are tastefully done and will fit with any décor style. Come see this lovely Winter Park home today! less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
$170,000
$629/mo
Monthly Payment:
$629
Principal & Interest:
$629
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $34,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,763sq ft $96 / sq ft SFR
Lot Size14,040sq ft Built1956 On Site6days
Great opportunity to invest! House needs some TLC. Home features split floor plan with 3 bedrooms, 2 bath, kitchen, family room and formal living room. Spacious master bedroom... more
Great opportunity to invest! House needs some TLC. Home features split floor plan with 3 bedrooms, 2 bath, kitchen, family room and formal living room. Spacious master bedroom with master bath. Huge backyard with lots of potential enough space to build a pool. Don't wait! Show it today! less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity
$77,900
$360/mo
Monthly Payment:
$360
Principal & Interest:
$288
HOA Dues:
$72
(Based on a 30 year fixed loan at 3.75% with $15,580 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,284sq ft $61 / sq ft TWN
Lot Size3,048sq ft Built1979 On Site7days
Interior unit in Windward Square offers the same gated courtyard entry featured throughout this terrific community. Step inside to a truly unique layout that includes a large... more
Interior unit in Windward Square offers the same gated courtyard entry featured throughout this terrific community. Step inside to a truly unique layout that includes a large kitchen/dining combo w/all appliances, laundry closet, and a gorgeous Zen pond and brick walls opening up to the sky! Home also features a large living room, enclosed porch, small backyard, and split-planned bedrooms that include 2 bedrooms and a shared bathroom off of the living room and a master suite w/full, handicap modified bathroom off of the kitchen area. Loads of amenities including shuffleboard, picnic/BBQ areas, and a community pool are offered in this community. It's all about location with this unit. Live within minutes of local public schools, Full Sail University, and tons of restaurants and shops. Plus, this is a very easy drive to UCF and Seminole State! Why pay high room and board when you can own! less
Listing Provided Courtesy of 100% Real Estate, Inc
Popularity
$194,900
$722/mo
Monthly Payment:
$722
Principal & Interest:
$722
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $38,980 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
4bed 2bath 1,717sq ft $114 / sq ft SFR
Lot Size8,919sq ft Built1974 On Site7days
What an amazing location in Winter Park . This amazing pool home features 4 bedrooms, 2 baths, a split floor plan, separate dining room, living room and family room with a... more
What an amazing location in Winter Park . This amazing pool home features 4 bedrooms, 2 baths, a split floor plan, separate dining room, living room and family room with a spacious kitchen in the middle of the home. The Master Bedroom has is own private over sized bathroom area. In addition the kitchen overlooks the large screened porch and the huge pool. The back yard is completely fenced and is very private. The home has a large 2 car garage and has plenty of parking. This amazing home is zoned for great Seminole County Schools. less
Listing Provided Courtesy of Real Living Good Neighbor Rlty
Popularity
$234,900
$909/mo
Monthly Payment:
$909
Principal & Interest:
$870
HOA Dues:
$39
(Based on a 30 year fixed loan at 3.75% with $46,980 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 1,840sq ft $128 / sq ft SFR
Lot Size6,410sq ft Built1985 On Site7days
Short sale. Walk the kids to school, play in the park, enjoy the tennis courts or fish off the dock on serene lake florence. Country lane is a friendly neighborhood in the heart... more
Short sale. Walk the kids to school, play in the park, enjoy the tennis courts or fish off the dock on serene lake florence. Country lane is a friendly neighborhood in the heart of east winter park. This well-maintained 2 story home has 4 beds/2.5baths with updated kitchen and baths. Beautiful wrought iron railings makes the entry open and elegant. New laminate flooring in the living, dining, and up the stairs. Tiled screened porch leads to tropical backyard, gazebo for entertaining and a cute shed that can be used as a play house. Sprinkler system is on a well and timer. Ac is under warranty until 2017. Come look at your new home..... less
Listing Provided Courtesy of Charles Rutenberg Realty
Popularity
$205,000
$759/mo
Monthly Payment:
$759
Principal & Interest:
$759
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $41,000 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,650sq ft $124 / sq ft SFR
Lot Size18,896sq ft Built1970 On Site8days
Freshly painted inside and out, this Winter Park pool home also features brand new laminate and carpet. Need room for your cars, bikes, or toys? Look no further! This propety... more
Freshly painted inside and out, this Winter Park pool home also features brand new laminate and carpet. Need room for your cars, bikes, or toys? Look no further! This propety includes a 30x30 corregated metal garage with concrete floor...all on an oversized lot. The architectual shingled roof was replaced in 2013. The great room includes a sitting area with wood burning fireplace. The master bedroom has a huge (approx 15x10) walk in closet with skylight. Conveniently located near UCF, Full Sail, and Winter Park shopping, restaurants and entertainment. Visit soon and make this unique home your own! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$2,195,000
$11,722/mo
Monthly Payment:
$11,722
Principal & Interest:
$8,132
HOA Dues:
$3,590
(Based on a 30 year fixed loan at 3.75% with $439,000 down)
Winter Park, FL 32789
Orange County School District
3bed 5bath 4,090sq ft $537 / sq ft CND
Lot SizeN/Asq ft Built2005 On Site9days
Downtown Winter Park premier luxury condominium building… adjacent to new Alfond Inn hotel, walk to Park Ave and Rollins College… This is arguably the best located... more
Downtown Winter Park premier luxury condominium building… adjacent to new Alfond Inn hotel, walk to Park Ave and Rollins College… This is arguably the best located unit in the building on the West end with sunset and downtown Winter Park & Orlando views plus Interlachen Ave, Alfond Inn, Rollins College & tree top views … The most desired "A" (end) unit in the building. Exquisitely finished, hardwood floors in main living areas, wetbar and kitchen/gathering room, custom oversized island kitchen with solid wood cabinets, a fireplace & additional cabinets unique to this unit, extensive crown, tall base moldings & built-ins throughout , completely redesigned master-suite w/ oversized closets and separate his/her baths, enlarged custom designed laundry room… open bright floor plan with lots of great windows/doors to enjoy panoramic views and multiple terraces… split bedroom plan with large, lavish private master retreat... 2 premium assigned parking spaces & a potential 3rd parking space for discussion with contract... This luxurious building offers wonderful amenities including great entertaining rooms, 24/7 security, on site manager & staff for complete concierge services and lifestyle to enjoy downtown Winter Park living at its best!! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$599,000
$2,219/mo
Monthly Payment:
$2,219
Principal & Interest:
$2,219
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $119,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size16,140sq ft BuiltN/A On Site9days
Large corner lot in park grove - 16,138
Large corner lot in park grove - 16,138 less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity N/A
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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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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, July 28, 2015 at 7:58 PM. Properties in listings may have been sold or may no longer be available.