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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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$338,700
$1,254/mo
Monthly Payment:
$1,254
Principal & Interest:
$1,254
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $67,740 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,927sq ft $176 / sq ft TWN
Lot Size9,093sq ft Built2014 On Site27days
Open Sun May 31, 2pm-5pm
Brand new, stylish 1,927 sq ft 3 bedroom, 2.5 bath front unit townhome in an established and highly desirable area of Winter Park! Townhome features wood & laminate flooring... more
Brand new, stylish 1,927 sq ft 3 bedroom, 2.5 bath front unit townhome in an established and highly desirable area of Winter Park! Townhome features wood & laminate flooring throughout, downstairs bonus room, downstairs utility room, 2nd floor sun deck/terrace perfect for a Jacuzzi, outside entertaining or observing the night sky, cement patio on 1st floor, 42" high European style kitchen cabinets with granite counter-tops, stainless steel appliances and community green spaces. Enjoy living near Cady Way and Ward Parks, top rated Winter Park schools, Winter Park Hospital, Whole Foods and all of the local venues near Aloma and Lakemont Avenue. Near Rollins, UCF and Full Sail University. *Lot size, parcel ID and legal description subject to change once the 2 units in the building are individually recorded in Orange County. Front unit located on the left of the building. less
Listing Provided Courtesy of Kelly Price & Company Llc
Popularity
We show you every available listing. Here's how
$600,000
$2,222/mo
Monthly Payment:
$2,222
Principal & Interest:
$2,222
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $120,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size1.3acre BuiltN/A On Site27days
Lot size now 1.35 acres. Seller financing an option - Rare opportunity to find 1.35 acres of Olde Florida charm with 100 ft of lake front on Lake Temple - IN Winter Park city... more
Lot size now 1.35 acres. Seller financing an option - Rare opportunity to find 1.35 acres of Olde Florida charm with 100 ft of lake front on Lake Temple - IN Winter Park city limits. Towering oaks, spanish moss and citrus trees dot the property. Value is in the land but a house and separate studio/guest house on property are ready to put your own touches on, or tear down and build your own lake front dream home - the large mouth bass are literally jumping. This is for the buyer who wants seclusion and privacy - you can't even see most of property or house from Temple Dr. Sought after Winter Park schools - Dommerich Elem, Maitland Middle and Winter Park High. Enjoy the best the metro Orlando area has to offer - Central Florida's gem - Winter Park. Your own piece of old Florida charm. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity N/A
$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
4bed 2bath 1,820sq ft $173 / sq ft SFR
Lot Size9,358sq ft Built1964 On Site27days
Come see this beautiful, well cared for 4 Bedroom 2 bath home located in the heart of Kenilworth Shores in Winter Park. This home offers a great split bedroom floor plan,... more
Come see this beautiful, well cared for 4 Bedroom 2 bath home located in the heart of Kenilworth Shores in Winter Park. This home offers a great split bedroom floor plan, spacious living room, separate dining room and a great kitchen & family room combination. The kitchen & all baths have been updated. This home has great curb appeal, newer roof and well water for your landscaping. It's located convenient to great schools, parks, shopping, health care & restaurants with downtown Winter Park only 5 minutes away. less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$212,000
$785/mo
Monthly Payment:
$785
Principal & Interest:
$785
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $42,400 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,261sq ft $168 / sq ft SFR
Lot Size7,613sq ft Built1956 On Site29days
Come home to this beautiful winter park residence that has been totally remodeled. Worry free for years to come with new roof, air conditioner, water heater and newer appliances... more
Come home to this beautiful winter park residence that has been totally remodeled. Worry free for years to come with new roof, air conditioner, water heater and newer appliances with one year home warranty. Bedrooms are bright and spacious with nice size closets. Bonus room/ office has a great view of the lovely newly landscaped backyard. Kitchen boasts new cabinets with adjacent spacious dining and bright living area. Perfect location close to i-4, enjoy the hoping night life and restaurants at winter park village. Trader joes, hillside and more. Ideal starter home. less
Listing Provided Courtesy of La Rosa Realty, Llc
Popularity N/A
$675,000
$2,633/mo
Monthly Payment:
$2,633
Principal & Interest:
$2,500
HOA Dues:
$133
(Based on a 30 year fixed loan at 3.75% with $135,000 down)
Winter Park, FL 32792
Seminole County School District
5bed 5bath 3,956sq ft $171 / sq ft SFR
Lot Size15,356sq ft Built1993 On Site29days
Absolutely stunning executive pool/spa home w/ separate in-law quarters on an oversized corner lot in winter park’s prestigious & gated bear gully pointe! This home is... more
Absolutely stunning executive pool/spa home w/ separate in-law quarters on an oversized corner lot in winter park’s prestigious & gated bear gully pointe! This home is laden w/ impressive architectural features & upgrades: plantation shutters, crown molding & hardwood floors! From the moment you enter, you’ll love the mesmerizing view of the fabulous pool/lanai, the soaring ceilings, circular-style staircase & bright, open floor plan! Ideal layout features a downstairs master bedrm & an adjacent bedrm. Upstairs are two more bedrms, two baths & a loft. The in-law suite is accessed on the other side of the pool, w/ its own bath/living area. All living areas overlook the expansive screened/covered lanai & htd pool/spa w/ multiple sets of sliding glass doors. The impressive kitchen is the heart of the home & perfect for entertaining w/ granite & corian counters, ss appliances, island, gas cooktop, double ovens, counter bar, butler’s pantry & desk, oversized walk-in pantry & a breakfast nook! Oversized master overlooks pool/lanai & features its own sitting area & a 16x13 bath w/ garden tub, rimless shower & a 14x10 organizer closet! Large laundry rm w/ w/d included; spacious 3-car side entry garage features an epoxy finish; gas water heater; circular front driveway, extended side driveway, upgraded landscaping. Fantastic community w/ its own tennis cts & playground. Conveniently located 2 minutes from trinity prep; 3 minutes to the 417; 10 minutes to downtown winter park/park ave, 15 min to the airport or ucf. less
Listing Provided Courtesy of Keller Williams Advantage Rlty
Popularity
$2,450,000
$9,077/mo
Monthly Payment:
$9,077
Principal & Interest:
$9,077
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $490,000 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size41,874sq ft BuiltN/A On Site30days
Premier oversized lakefront lot in A+ prime location on Lake Mailtand - largest lake on the 6-lake chain... This lot orients well for a gated entrance and privacy to set home... more
Premier oversized lakefront lot in A+ prime location on Lake Mailtand - largest lake on the 6-lake chain... This lot orients well for a gated entrance and privacy to set home back away from the street... Enjoy picturesque long sunset views from this .96 acre Lake Maitland property. A park like setting surrounded by lush landscaping and mature Oak trees & Cypress tress... Quiet, secluded neighborhood in the heart of the Via's off Via Tuscany... conveninet to the WPRC (Winter Park Racquet Club) and ICC (Interlachen Country Club)... Build your dream lakefront estate on this wonderful proeprty cleared and ready for new constuction! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$309,000
$1,144/mo
Monthly Payment:
$1,144
Principal & Interest:
$1,144
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $61,800 down)
Winter Park, FL 32792
Orange County School District
3bed 2bath 1,588sq ft $195 / sq ft SFR
Lot Size8,240sq ft Built1959 On Site30days
Open Sat May 23, 11am-1pm
Darling updated 3 bed 2 bath in great location -- walk to Lakemont Elementary, YMCA, Florida Hospital WP, Ward Park, shopping & dining. Neat as a pin! Hardwood floors, big open... more
Darling updated 3 bed 2 bath in great location -- walk to Lakemont Elementary, YMCA, Florida Hospital WP, Ward Park, shopping & dining. Neat as a pin! Hardwood floors, big open kitchen with eat in and Study/office area. Sunny big bedrooms, updated bathrooms and good closets. Large, fenced back yard with open patio, pretty trees and landscape. One car garage, utility & workshop area, great storage. Pack your bags and move right in! Don't miss this gem. less
Listing Provided Courtesy of Keller Williams Winter Park
Popularity N/A
$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 Site30days
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 N/A
$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 Site30days
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 N/A
$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 Site30days
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
$569,000
$2,108/mo
Monthly Payment:
$2,108
Principal & Interest:
$2,108
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $113,800 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
6bed 7bath 4,072sq ft $140 / sq ft SFR
Lot Size17,500sq ft Built1935 On Site30days
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 Site30days
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
$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 Site31days
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
$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 Site32days
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
$385,000
$1,447/mo
Monthly Payment:
$1,447
Principal & Interest:
$1,426
HOA Dues:
$21
(Based on a 30 year fixed loan at 3.75% with $77,000 down)
Winter Park, FL 32792
Seminole County School District
5bed 4bath 3,046sq ft $126 / sq ft SFR
Lot Size15,188sq ft Built1989 On Site32days
Renovated home with a pool on a spacious lot (over a 1/3 acre) in a quiet neighborhood…You'll love this home! Numerous upgrades include: Professionally landscaped front... more
Renovated home with a pool on a spacious lot (over a 1/3 acre) in a quiet neighborhood…You'll love this home! Numerous upgrades include: Professionally landscaped front yard. High-end hardwood floors throughout the first floor living area and office. Gorgeous custom kitchen includes 42” maple cabinets, granite countertop, stainless steel appliances, and ceramic tile flooring. Spectacular master bathroom boasts of new shower & tub, dual sinks with maple cabinets & granite countertops and new fixtures. New carpet in the bedrooms and living room. Fresh interior paint. New architectural shingled roof installed in 2013 is still under warranty. Entire house was re-piped this year. Big backyard with separate basketball Ct. Excellent schools! Conveniently located near shops, restaurants and 417. less
Listing Provided Courtesy of Re/max Innovation
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 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: Saturday, May 23, 2015 at 6:04 AM