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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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$700,000
$2,593/mo
Monthly Payment:
$2,593
Principal & Interest:
$2,593
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $140,000 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 3,158sq ft $222 / sq ft SFR
Lot Size43,280sq ft Built1981 On Site8days
Open Tue Feb 16, 12pm-2pm
Incredible winter park lakefront opportunity!! Ski, fish & play on private lake waunatta! this one acre property has all the bells & whistles: custom front door... more
Incredible winter park lakefront opportunity!! Ski, fish & play on private lake waunatta! this one acre property has all the bells & whistles: custom front door welcomes you to this 2 story contemporary boasting a fabulous master suite with serene views of private lake from balcony, updated bath with soaking tub, huge shower, two walk in closets & additional room perfect for office, nursery or home gym!! The first floor boasts the best open floor plan!! updated kitchen with granite counter & island, wood cabinets & glass tile backsplashes, large family room with stone, wood burning fireplace, formal living room & dining room, plus additional 2 bedrooms & updated guest bath. Step outside to enjoy the sparkling pool, covered patio & deck: perfect for entertaining! Fantastic views of lake waunatta from every room in ths home!! Extras include: 2 car, side entry garage; new flooring throughout; upgraded double paned windows; 2 newer hvac systems; security system; irrigation system. Welcome home!! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
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$511,251
$1,922/mo
Monthly Payment:
$1,922
Principal & Interest:
$1,894
HOA Dues:
$28
(Based on a 30 year fixed loan at 3.75% with $102,250 down)
Winter Park, FL 32792
Seminole County School District
5bed 4bath 3,514sq ft $145 / sq ft SFR
Lot SizeN/Asq ft Built2016 On Site8days
Brand new 2 story home at beautiful Enclave at Aloma community in Winter Park! Close to downtown Winter Park’s charming historical district, residents of Enclave at Aloma... more
Brand new 2 story home at beautiful Enclave at Aloma community in Winter Park! Close to downtown Winter Park’s charming historical district, residents of Enclave at Aloma take pleasure in a town whose admirable gems include gorgeous Rollins College and the Morse Museum of American Art, home to the world’s largest collection of Tiffany glass. Winter Park, an Old Florida resort business titans founded more than a century ago, is full of excellent boutiques and eateries, upscale art galleries, deluxe golf courses, parks, and historic architecture. Enclave at Aloma Park also sits less than one mile from the GreeneWay (SR 417), putting homeowners within reach of Orlando, the international airport, lakes, theme parks, and, of course, the Sunshine State’s world-popular beaches. less
Listing Provided Courtesy of STANDARD PACIFIC OF TAMPA
Popularity
$537,000
$1,989/mo
Monthly Payment:
$1,989
Principal & Interest:
$1,989
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $107,400 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 1,869sq ft $287 / sq ft SFR
Lot Size7,302sq ft Built1940 On Site9days
A must see!! Beautiful florida style bungalow situated on one of the most desired tree lined streets in winter park. 1869 sq feet consists of 4 bedrooms 3 full baths. Two... more
A must see!! Beautiful florida style bungalow situated on one of the most desired tree lined streets in winter park. 1869 sq feet consists of 4 bedrooms 3 full baths. Two bedrooms located downstairs with their own on suite baths. Sun-room just off the kitchen overlooks your gorgeous back yard and large deck with plenty of room to entertain. Conveniently located close to downtown winter park, park ave and rollins college. less
Listing Provided Courtesy of ELEVATE REAL ESTATE BROKERS OF
Popularity
$1,595,000
$6,130/mo
Monthly Payment:
$6,130
Principal & Interest:
$5,909
HOA Dues:
$221
(Based on a 30 year fixed loan at 3.75% with $319,000 down)
Winter Park, FL 32789
Orange County School District
5bed 5bath 4,622sq ft $345 / sq ft SFR
Lot Size17,501sq ft Built2002 On Site9days
This immaculate Cahill home in the prestigious Windsong community has been meticulously maintained with an open floor plan perfect for family living or entertaining. Formal... more
This immaculate Cahill home in the prestigious Windsong community has been meticulously maintained with an open floor plan perfect for family living or entertaining. Formal living room w/ cozy fireplace overlooks the spacious formal dining room. The light & bright family room w/ French doors has wonderful views of the covered lanai & pool. The gourmet eat-in kitchen has stainless appliances, a gas cooktop, double ovens & center island. The downstairs luxurious master retreat features vaulted & hand crafted wood beam ceilings & fabulous wide plank wood floors. The master bath has dual vanities, granite counter tops & a Jacuzzi tub. The 2nd bedroom suite is also on the first floor & perfect for guests, nursery or home office. Upstairs you will find three bedrooms & a large game/media room. The covered lanai w/ summer kitchen overlooks the fenced back yard w/ lush tropical landscape, citrus trees, year round flowering gardens, extensive landscape lighting & a completely remodeled heated pool & spa. Additional amenities include gorgeous wood & travertine floors, custom molding & trim work, built-ins, shutters & window treatment, an entry fountain & 3 car garage. Windsong offers Winter Park chain of lakes access, two community pools, a children’s water park, a recreation building & a scenic pier for fishing. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$350,000
$1,327/mo
Monthly Payment:
$1,327
Principal & Interest:
$1,296
HOA Dues:
$31
(Based on a 30 year fixed loan at 3.75% with $70,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 2bath 2,266sq ft $154 / sq ft SFR
Lot Size10,762sq ft Built1982 On Site9days
Stunning 4 bedroom 2 bath Winter Park remodel. New flooring though out including modern 20" porcelain tile and 12 mm 6" plank laminate in all four bedrooms. 3 bedrooms have... more
Stunning 4 bedroom 2 bath Winter Park remodel. New flooring though out including modern 20" porcelain tile and 12 mm 6" plank laminate in all four bedrooms. 3 bedrooms have automatic blinds. Energy Star stainless steel appliances in kitchen with upgraded granite and tumbled travertine tile on back splash. Kitchen has upgraded solid wood cabinets with updated stainless pulls and soft close drawers and doors. Under cabinet lighting and accented Edison lighting over island in kitchen and dinette. Master bathroom has large white porcelain floor tile with walk in shower newly redone with floor to ceiling Crema Marfil marble and glass enclosure. Great room boasts a vaulted ceiling with 2 ceiling fans. Plenty of closet space. Gorgeous matured hardy Florida landscaping. Large fenced back yard. less
Listing Provided Courtesy of KELLER WILLIAMS HERITAGE RLTY
Popularity
$210,000
$799/mo
Monthly Payment:
$799
Principal & Interest:
$778
HOA Dues:
$21
(Based on a 30 year fixed loan at 3.75% with $42,000 down)
Winter Park, FL 32792
Goldenrod Orange County School District
3bed 2bath 1,689sq ft $124 / sq ft SFR
Lot Size12,702sq ft Built1977 On Site9days
Short sale. 3 bed 2 bath 2 car garage. Great neighborhood. Total square feet 2,277 Info on listing is believed accurate but not guaranteed.
Short sale. 3 bed 2 bath 2 car garage. Great neighborhood. Total square feet 2,277 Info on listing is believed accurate but not guaranteed. less
Listing Provided Courtesy of AMERICAN REALTY EXPERTS INC
Popularity
$204,000
$755/mo
Monthly Payment:
$755
Principal & Interest:
$755
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $40,800 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,713sq ft $119 / sq ft SFR
Lot Size8,158sq ft Built1981 On Site9days
This beautiful single family home is located in a prime location with high quality “A” rated schools. This home has many recent upgrades including carpet, air... more
This beautiful single family home is located in a prime location with high quality “A” rated schools. This home has many recent upgrades including carpet, air conditioner, paint, hot water heater, garbage disposal, shower tiles, and back porch remodeled. less
Listing Provided Courtesy of LISTSMART
Popularity
$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)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,683sq ft $386 / sq ft SFR
Lot Size7,161sq ft Built2004 On Site9days
Rare opportunity to live in this fantastic "Walk to Park Ave" home just two blocks from Winter Parks stunning dining and artistic hub. The Mediterranean inspired... more
Rare opportunity to live in this fantastic "Walk to Park Ave" home just two blocks from Winter Parks stunning dining and artistic hub. The Mediterranean inspired residence that boasts 3 bedrooms and 3 full bathrooms welcomes you with Brazilian wood floors, plantation shutters, and high vaulted 10’ ceilings. The open floor plan includes a gourmet kitchen with designer cabinetry, granite counter tops and stainless steel appliances. The main floor offers a full bathroom with a separate “pool entrance", a sprawling living and dining room that also features two sets of French doors that lead you to the outside lanai, summer kitchen and fantastic cocktail pool. There is also an additional 238SqFt of air conditioned space above the garage that is currently being used as a 4th bedroom. The spacious master suite presents a large walk in closet, dual vanities, a spa tub and over sized steam shower. Along with the balcony off of the front of the house, the upstairs also offers french doors in both the master suite and second bedroom; both leading to the intimate screened in joint balcony over looking the private backyard oasis. Additional amenities include a brick paver driveway with motorized remote gated entry leading to the two-car garage, energy efficient A/C system with 3 zones, complete security system with 3 cameras and recording capability, crown molding and baseboards and surround sound speakers in master, master porch, lanai and first floor. less
Listing Provided Courtesy of REGAL R.E. PROFESSIONALS LLC
Popularity
$61,900
$458/mo
Monthly Payment:
$458
Principal & Interest:
$229
HOA Dues:
$229
(Based on a 30 year fixed loan at 3.75% with $12,380 down)
Winter Park, FL 32792
Seminole County School District
1bed 1bath 678sq ft $91 / sq ft CND
Lot SizeN/Asq ft Built1973 On Site9days
If you want to be in the middle of everything - shopping, dining, schools, bus lines - then look no further! This spacious, well-maintained unit in the Stratford Condominium... more
If you want to be in the middle of everything - shopping, dining, schools, bus lines - then look no further! This spacious, well-maintained unit in the Stratford Condominium offers a rare opportunity to own a condo with a view of the community pool right outside the back door! Lounge on the covered patio, and enjoy the view of the pool at the same time! Additional amenities include tennis courts, clubhouse and workout facility. This condo is centrally located to UCF, Full Sail, Rollins College, Downtown Winter Park, and is minutes from the 417. Thirty minutes to downtown Orlando and the airport. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$180,000
$1,046/mo
Monthly Payment:
$1,046
Principal & Interest:
$666
HOA Dues:
$380
(Based on a 30 year fixed loan at 3.75% with $36,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,174sq ft $153 / sq ft CND
Lot Size6,717sq ft Built1964 On Site10days
Lovely 2 bedroom 2 bath condo in a 55+ community. This well maintained unit has an inviting enclosed porch with an eastern exposure looking out over the lush landscaping of... more
Lovely 2 bedroom 2 bath condo in a 55+ community. This well maintained unit has an inviting enclosed porch with an eastern exposure looking out over the lush landscaping of Winter Park Gardens. Beautifully decorated unit with wood laminate flooring in living area and kitchen, tile in foyer, tile in sun room and carpet in bedrooms. Features include a closet equipped with a built in desk and shelves, separate coat closet, linen closet, separate storage closet, ceilings fans throughout with lovely window treatments. Location is prime, close to Park Ave and WP Village. Quiet, easy "lock and leave" condo in the heart of Winter Park. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$1,895,000
$7,187/mo
Monthly Payment:
$7,187
Principal & Interest:
$7,020
HOA Dues:
$167
(Based on a 30 year fixed loan at 3.75% with $379,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,395sq ft $351 / sq ft SFR
Lot Size18,930sq ft Built2004 On Site10days
Sophisticated executive home in prestigious vias. This stately 2 story residence with magnificent balconies is situated on a .44 acre lot in a secluded cul-de-sac with privacy... more
Sophisticated executive home in prestigious vias. This stately 2 story residence with magnificent balconies is situated on a .44 acre lot in a secluded cul-de-sac with privacy brick wall. Custom built in 2004 with impressive room sizes throughout! Gracious front porch and 27x8 foyer with hardwood floors & soaring ceilings invite you into the formal rooms & through to serene lanai, pool, hot tub & manicured backyard garden. Gourmet kitchen complete with butler's pantry, huge 16x6 walk in pantry, island + breakfast bar and cozy 12x11 breakfast nook. Family room with custom built-ins plus delightful game room with wet bar creates a perfect place to entertain. Amazing downstairs master suite boasts a renovated bath, his & her 20x6 closets, dressing area plus 13x8 office, massage room or nursery. Upstairs you will find 3 large en suite bedrooms plus additional flex room for home gym, upstairs family room or 5th bedroom, + 2 balconies for relaxation. Extras include: 3 car detached garage, plantation shutters, gas fireplaces in living room & game room, 3 new hvac units, generator & deeded lake access to the winter park chain of lakes!! Welcome home! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$375,000
$1,389/mo
Monthly Payment:
$1,389
Principal & Interest:
$1,389
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $75,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,662sq ft $226 / sq ft SFR
Lot Size7,500sq ft Built1998 On Site10days
Move-in ready 3 bedroom, 2 bath home in Hannibal Square of Downtown Winter Park! Built in 1998 and renovated in 2015, this charming bungalow has been lovingly maintained and... more
Move-in ready 3 bedroom, 2 bath home in Hannibal Square of Downtown Winter Park! Built in 1998 and renovated in 2015, this charming bungalow has been lovingly maintained and renewed. Brand new wood floors throughout, new baseboards, new window treatments, new stainless steel appliances, new bathrooms, new lighting and much more! This home has a large indoor laundry room that can double as a pantry/storage room, and a one-car attached garage. New privacy fenced backyard with new shed - wired for electric. New landscaping with Empire Zoysia grass and new irrigation system on well. Live in one of Winter Park's most sought-after neighborhoods due to its walkability score to the restaurants and retail stores of Park Avenue and Hannibal Square, Rollins College, the Winter Park Farmer's Market, the SunRail station and Central Park. You can even walk to Hillstone's and Trader Joe's. Live the quaint Winter Park urban lifestyle with privacy and no HOA. Located across the street from Martin Luther King Jr. Park. See attachments for the entire list of improvements. less
Listing Provided Courtesy of PHIL KEAN REAL ESTATE LLC
Popularity
$459,000
$1,717/mo
Monthly Payment:
$1,717
Principal & Interest:
$1,700
HOA Dues:
$17
(Based on a 30 year fixed loan at 3.75% with $91,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,990sq ft $231 / sq ft SFR
Lot Size13,007sq ft Built1973 On Site10days
Quail Hollow 3 bedroom, 2 bath pool home plus an additional spare room that can easily be made into a fourth bedroom on an over-sized interior lot! This well designed home... more
Quail Hollow 3 bedroom, 2 bath pool home plus an additional spare room that can easily be made into a fourth bedroom on an over-sized interior lot! This well designed home features an inside utility room, living room, kitchen nook, dining room and a family room with a wood burning fireplace. The Master bedroom with an updated bathroom overlooks the pool and has two walk in closets; one of which has a window and is currently being used as an office. The spacious backyard is fenced in and also includes a utility shed. The home also features numerous upgrades such as new plumbing (2015), new electrical circuit breaker and outlets throughout (2013), newly painted interior & exterior, new flooring, new windows, resurfaced pool with a new pool filter and variable speed pool pump. Enjoy living in an ideal location near many community happenings! The home is a short walking distance to East End Market, Corrine area shops, Baldwin Park, Windsong and a quick bike ride to Park Avenue. Quail Hollow is about 8 minutes to Rollins College and 15-20 minutes to UCF. Quail Hollow neighborhood has an active community association with a low yearly non-mandatory HOA. The neighborhood hosts events such as pizza parties for Halloween, firework cul-de-sac gatherings for the 4th of July and holiday events. The home is zoned for A+ rated schools and offers a wonderful Winter Park in-town experience while keeping the tranquility and peace of an established neighborhood. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$695,000
$2,574/mo
Monthly Payment:
$2,574
Principal & Interest:
$2,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,495sq ft $279 / sq ft SFR
Lot Size5,250sq ft Built2014 On Site13days
Better than new! Luxury custom home located in the heart of winter park. This custom one of a kind home is the second of three beautiful custom homes all side by side with... more
Better than new! Luxury custom home located in the heart of winter park. This custom one of a kind home is the second of three beautiful custom homes all side by side with direct views of lake midget. Everything was finished with high end materials and in a contemporary style. This homes features: wood floors, granite counter tops,10 foot ceilings, 8 foot doors, gas fireplace and range, stainless appliances, crown molding, california custom closets, architectural shingle roof, upgraded tile, upgraded lighting and plumbing fixtures, and more. This home is also green conscious with duel zone a/c, tank less hot water systems and upgraded r40 attic insulation and foamed block walls. All windows are finished with powered and remote controlled custom roller shades including blackout shades in master bedroom. Master bathroom has a soaking tub and separate rainfall spa shower. 1080 hd camera adt pulse security system with sensors on all doors and windows controlled via mobile app. New landscaping, completely fenced in backyard with sprinkler system. When you are not enjoying the views from your amazing master suite's balconies, you can walk to orange ave and park ave for shopping or dining. Don't wait show it today! less
Listing Provided Courtesy of ARROWSMITH REALTY INC
Popularity
$245,000
$1,272/mo
Monthly Payment:
$1,272
Principal & Interest:
$907
HOA Dues:
$365
(Based on a 30 year fixed loan at 3.75% with $49,000 down)
Winter Park, FL 32789
Orange County School District
2bed 1bath 798sq ft $307 / sq ft CND
Lot SizeN/Asq ft Built1981 On Site13days
Two blocks to Winter Park Village, plus only 4 blocks to famous Park Avenue and Hannibal Square. Updated 2 bedroom/1 bathroom condo. Upgrades include: Hardwood floors, granite... more
Two blocks to Winter Park Village, plus only 4 blocks to famous Park Avenue and Hannibal Square. Updated 2 bedroom/1 bathroom condo. Upgrades include: Hardwood floors, granite countertops, plantation shutters, tile and so much more. Master bedroom has a nice walk in closet, too! Great LOCATION, easy living, lock and leave convenience. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
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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: Wednesday, February 10, 2016 at 2:30 PM. Properties in listings may have been sold or may no longer be available.