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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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$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 32792
Orange County School District
3bed 2bath 1,919sq ft $164 / sq ft SFR
Lot Size9,344sq ft Built1963 On Site5days
Don't miss out on your chance to own in the desired Brookshire community. This 3/2 ranch home is zoned for "A" schools, close Proximity to Cady Way biking/walking trail,... more
Don't miss out on your chance to own in the desired Brookshire community. This 3/2 ranch home is zoned for "A" schools, close Proximity to Cady Way biking/walking trail, Showalter track and field, and close to downtown Winter Park (Park Ave.) featuring shops, quaint restaurants, churches, Sun Rail and Central Park. . This home also offers a private fenced back yard made to entertain with a pool, hot tub, and covered patio! Call today to schedule a private tour. less
Listing Provided Courtesy of Warner-quinlan Inc
Popularity
Your search results are current and complete. Learn more
$189,000
$700/mo
Monthly Payment:
$700
Principal & Interest:
$700
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $37,800 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,327sq ft $142 / sq ft SFR
Lot Size8,999sq ft Built1960 On Site5days
Light and bright 3 bed/ 1 ½ bath home located in Winter Park Estates. Enjoy the convenience of this WP location close to the hospital, restaurants, shopping and downtown... more
Light and bright 3 bed/ 1 ½ bath home located in Winter Park Estates. Enjoy the convenience of this WP location close to the hospital, restaurants, shopping and downtown Winter Park. Well-maintained home with mature landscaping, large outdoor patio, newer shed and fully fenced large back yard. Kitchen has granite counters, solid wood cabinets, stainless sink and breakfast bar. Dining area opens to the living room. Florida room has expansive view of the back yard and an adjoining office with storage. Improvements include: new tile flooring, bath tub, toilet, sinks and refrigerator. Home was re-plumbed is ’13 and roof and A/C replaced and electrical service upgraded in ’09. Tax roll does not reflect total square footage. Great investment property. Close to the 436 and the 408. Zoned for Lakemont, Maitland Middle and Winter Park High. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$249,000
$922/mo
Monthly Payment:
$922
Principal & Interest:
$922
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $49,800 down)
Winter Park, FL 32789
N/Asq ft N/A / sq ft LND
Lot Size19,316sq ft BuiltN/A On Site5days
Bring Offer! 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... more
Bring Offer! 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
$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
3bed 2bath 1,341sq ft $201 / sq ft SFR
Lot Size13,306sq ft Built1972 On Site5days
Awesome location, conveniently located and tucked away in a quiet neighborhood off aloma and lakemont in winter park. Stroll to whole foods, publix, restaurants and shops.... more
Awesome location, conveniently located and tucked away in a quiet neighborhood off aloma and lakemont in winter park. Stroll to whole foods, publix, restaurants and shops. Minutes to park avenue, winter park hospital, full said and downtown orlando. This charming 3 bedroom, 2 bath plus family room home has an oversized screened room overlooking a large fenced backyard with mature trees which offers a nice canopy from the hot florida sun, plus a double gate and shed for storage and yard can easily accommodate a pool. Just updated with new laminate floors in the living room, dining area, kitchen, ad family room. New carpet in bedrooms. New inside doors and new paint outside, electrical panel just updated. One additional room could be used as a craft room, not included in square footage. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$179,000
$685/mo
Monthly Payment:
$685
Principal & Interest:
$663
HOA Dues:
$22
(Based on a 30 year fixed loan at 3.75% with $35,800 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,367sq ft $131 / sq ft SFR
Lot Size5,336sq ft Built1986 On Site5days
Short Sale. Buyer may need to pay transaction fee - Explained in addendum attached to MLS. Open entry way and kitchen with a pool! Two master suites with walk-in closets both... more
Short Sale. Buyer may need to pay transaction fee - Explained in addendum attached to MLS. Open entry way and kitchen with a pool! Two master suites with walk-in closets both with sliding doors exiting out to the pool/patio. Two full baths and a small office/bonus room. Granite counter tops, two car garage. Bold decorator colors! Fabulous neighborhood with playground, tennis courts, and lake access. Two patios. Beautiful trees and flowering plants. Plantation shutters, corner fireplace, bay window overlooking pool, vaulted ceilings. less
Listing Provided Courtesy of Me Realty, Llc
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
Fairview Shores Orange County School District
6bed 7bath 4,072sq ft $147 / sq ft SFR
Lot Size17,500sq ft Built1935 On Site5days
This newly renovated historic home is on a double lot in the beautiful dubsdread hieghts community. Just steps from the the historic dubsdread golf course and merely minutes... more
This newly renovated historic home is on a double lot in the beautiful dubsdread hieghts community. Just steps from the the historic dubsdread golf course and merely minutes from the art district of winter park and downtown Orlando. This custom home was renovated in 2015 on a lot size of 125 x 140. A detached 652 s/f 1 bed/1 bath home is included in sq. footage. The 2+car garage has also been converted into an 1 bed one bath efficiency as well which is includes in the sq footage calculations. 3 lots on both sides of this home are also for sale. realtor only remarks. Custom designed cathedral ceilings in the Family/Great Room will be the talking point of your guests when they visit your new residence. This home has 2 fireplaces in the main house. The following renovations were completed within the last year; travertine flooring, refinished solid oak hardwood flooring, All new cabinets and granite countertops in the kitchen and bathrooms, New Irrigation system, New paved driveway, New exterior paint, and new interior paint in all rooms. The garage conversion/in law suite features a kitchen and 1 bath. The separate guest house features new cabinets in the kitchen and bathroom, and a fireplace. The main house is around 2900sq ft 4bed 4.1/2 bath. the garage conversion and the guest house are both 1/1 and are each aroun 600sq ft. less
Listing Provided Courtesy of Homefirst Realty
Popularity
$3,100,000
$11,485/mo
Monthly Payment:
$11,485
Principal & Interest:
$11,485
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $620,000 down)
Winter Park, FL 32789
Orange County School District
5bed 8bath 7,988sq ft $388 / sq ft SFR
Lot Size28,577sq ft Built1996 On Site5days
Park Ave Mediterranean 3 story estate just steps to dining, shopping & golf. Privately gated with immaculate landscaping, fruit trees, koi pond, fountain and screen enclosed... more
Park Ave Mediterranean 3 story estate just steps to dining, shopping & golf. Privately gated with immaculate landscaping, fruit trees, koi pond, fountain and screen enclosed pool area with summer kitchen and auto awning. Inside you'll find 5 bedrooms, 7.5 baths, elevator, finished basement and gorgeous features throughout including solid oak hardwood floors with decorative inlays, French solid wood doors, wrought iron fixtures and continuous archways. The dramatic foyer opens into a formal living area complete with French doors leading to lanai. A formal dining room is perfectly situated near the butler's pantry and a gourmet chef's kitchen with built-in shelves and office, commercial 6 burner gas range, 2 Sub-Zero refrigeration systems in wall cabinetry, 6 refrigerator drawers, double full size Thermador ovens, stainless steel appliances, granite counter tops and an ample walk-in pantry. Plenty of counter seating next to the breakfast nook and a spacious family room with vaulted ceiling, built-ins, wet-bar and fireplace. The 1st of 2 master suites is just beyond the well-appointed office with cherry built-ins and fireplace. Both masters feature fireplaces, xtra lrg walk-in closets & cedar closets, double sinks, and separate showers/garden tubs. The 2nd master is upstairs along with 2 bedrooms with private baths, a fully furnished media room and separate loft as well as a separate guest suite above the 3 garage. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$260,000
$963/mo
Monthly Payment:
$963
Principal & Interest:
$963
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $52,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,302sq ft $200 / sq ft SFR
Lot Size5,805sq ft Built1949 On Site5days
Beautiful Bungalow located in the center of town. Great entry level home in The desirable Winter Park area. Close to everything I-4 , 17-92 , Florida Hospital ,... more
Beautiful Bungalow located in the center of town. Great entry level home in The desirable Winter Park area. Close to everything I-4 , 17-92 , Florida Hospital , Downtown Orlando , Lake Highland . less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$685,000
$2,540/mo
Monthly Payment:
$2,540
Principal & Interest:
$2,537
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $137,000 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,203sq ft $214 / sq ft SFR
Lot Size11,062sq ft Built1967 On Site6days
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 featured include plantation shutters, central vacuum, built-ins, crown molding, wide hallways, 2 car attached garage. 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
3bed 3bath 2,678sq ft $186 / sq ft SFR
Lot Size8,087sq ft Built1950 On Site6days
Orwin Manor, midcentury home, transformed in 2007 with a spacious and open concept! 3 bedrooms, 2 ½ baths with an OFFICE provides everyone their space to work, play or... more
Orwin Manor, midcentury home, transformed in 2007 with a spacious and open concept! 3 bedrooms, 2 ½ baths with an OFFICE provides everyone their space to work, play or rest. Beautiful wood floors welcome you as you enter creating a warm and inviting atmosphere. Formal dining room is perfect for hosting those special holiday meals and the fabulous kitchen with granite countertops, large breakfast bar, SS appliances, gas range, double ovens, wine and beverage coolers will no doubt be the place where everyone gathers! During the winter, enjoy the wood burning fireplace from the kitchen or couch with French doors going out to the salt water pool and heated spa. The downstairs office is tucked away off the dining room, 2 bedrooms, 1 ½ baths downstairs with an incredible Master Bedroom and Bath upstairs. The master suite has a walk in closet with ample storage, dual head shower and Jacuzzi tub. Natural gas line supply for the kitchen cooktop, pool spa, tankless water heater and piped for a BBQ grill in the future. The covered patio allows you to enjoy the outdoors year round with artificial turf under the playset for easy care and maintenance. Winter Park’s Orwin Manor is without a doubt the most centrally located neighborhood in Orlando and why it’s so popular. It is not an exaggeration that you are 10 minutes from Park Avenue, College Park, Thornton Park, Downtown Orlando, I-4, Ivanhoe Village, Winter Park Village, Trader Joe’s and Florida Hospital. Don’t pass on this home – you won’t be disappointed! less
Listing Provided Courtesy of Watson Realty Corp
Popularity
$68,500
$473/mo
Monthly Payment:
$473
Principal & Interest:
$253
HOA Dues:
$220
(Based on a 30 year fixed loan at 3.75% with $13,700 down)
Winter Park, FL 32792
Orange County School District
1bed 1bath 749sq ft $91 / sq ft CND
Lot Size3,258sq ft Built1984 On Site6days
Nice 2nd floor unit at Parkview Village. Parkview Village is located within walking distance to Full Sail University, restaurants and bus line. UCF is only 6 miles away. Easy... more
Nice 2nd floor unit at Parkview Village. Parkview Village is located within walking distance to Full Sail University, restaurants and bus line. UCF is only 6 miles away. Easy access to shopping, downtown Orlando and major highways. Unit has cherry wood floor through out. Upgrade bathroom and kitchen. Stainless steel appliances. Great investment opportunity! less
Listing Provided Courtesy of Central Florida Realty Experts
Popularity
$299,000
$1,107/mo
Monthly Payment:
$1,107
Principal & Interest:
$1,107
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,491sq ft $201 / sq ft SFR
Lot Size9,501sq ft Built1955 On Site6days
Updated Pool Home with LOCATION, LOCATION, LOCATION! This 3 bedroom 2 bath home has beautiful hard wood flooring, screened in back patio and a huge pool! Rarely available and... more
Updated Pool Home with LOCATION, LOCATION, LOCATION! This 3 bedroom 2 bath home has beautiful hard wood flooring, screened in back patio and a huge pool! Rarely available and only a few blocks from Winter Park High School and minutes to the Cady Way Bike Trail. The master bath remodel was just completed. Don't wait to see this one!! ** Pre-view this Saturday 4/25 from 1-3 pm** less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$249,900
$928/mo
Monthly Payment:
$928
Principal & Interest:
$925
HOA Dues:
$3
(Based on a 30 year fixed loan at 3.75% with $49,980 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,604sq ft $156 / sq ft SFR
Lot Size7,978sq ft Built1963 On Site7days
Beautifully updated 3 bedroom 2 bath charming home in desirable Winter Park Pines neighborhood!!! Gorgeous mature oak trees greet you as you approach from a lovely, tree-lined... more
Beautifully updated 3 bedroom 2 bath charming home in desirable Winter Park Pines neighborhood!!! Gorgeous mature oak trees greet you as you approach from a lovely, tree-lined street. A welcoming foyer and reading nook flow into an airy, open living space, formal dining area and eat-in kitchen with newer stainless steel appliances. Through the new French doors you will find a garden patio where you can relax by the fruit trees and enjoy a private, fully fenced backyard. Wonderful community of Winter Park Pines offers excellent schools and community events and is minutes from the golf course, YMCA, WP Hospital, Rollins College, and Downtown Winter Park! Welcome Home!!! less
Listing Provided Courtesy of Chamberlain Realty Llc
Popularity
$175,000
$648/mo
Monthly Payment:
$648
Principal & Interest:
$648
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $35,000 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,663sq ft $105 / sq ft SFR
Lot Size11,700sq ft Built1957 On Site7days
Short Sale. Great home for first time buyer. Located in the desired winter park area and on a corner lot. Upon entering the home you walk into your foyer, to the right is the... more
Short Sale. Great home for first time buyer. Located in the desired winter park area and on a corner lot. Upon entering the home you walk into your foyer, to the right is the kitchen, and walking strait ahead you reach the living room. The bedrooms are on your left, while past the living room is the florida room and your separate dining area. Walking thru your dining area you reach your laundry room with side door entry to the covered carport. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$144,900
$554/mo
Monthly Payment:
$554
Principal & Interest:
$536
HOA Dues:
$18
(Based on a 30 year fixed loan at 3.75% with $28,980 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,298sq ft $112 / sq ft SFR
Lot Size4,538sq ft Built1989 On Site7days
Don't miss a great opportunity in Bridgewater just off of Howell Branch Rd. This 3 bedroom 2 bath home is nestled in a small enclave community with a great community setting,... more
Don't miss a great opportunity in Bridgewater just off of Howell Branch Rd. This 3 bedroom 2 bath home is nestled in a small enclave community with a great community setting, The home features a great double door car garage and a split layout. Make this home really shine and schedule your showing today! This a Fannie Mae Homepath property less
Listing Provided Courtesy of Smith Realty 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
Content provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid Florida Regional MLS 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 MLS. 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 MLS. 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 MLS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited.

Copyright 2015 Mid Florida Regional MLS. All rights reserved.

Data last updated: Monday, April 27, 2015 at 10:30 PM