Winter Haven, FL Homes

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  $429,000

  • 4 Beds
  • 3 Baths
  • 2,492 Sq Ft

  144 Beverly Dr, Winter Haven, FL 33884

  Immaculate and updated pool home ideally located in SE Winter Haven just two blocks from Chain of Lakes access. This well-cared for pool residence features a sleek modern appearance with comfortable living spaces and an impressive level of quality updates found throughout. Interior features 4 bedrooms (two master suites), 3 bathrooms, formal dining room and an absolutely stunning kitchen. New

  Christina Loesch KELLER WILLIAMS REALTY SMART 1

  144 Beverly Dr, Winter Haven, FL 33884
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  /25

  $1,295 per month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  320 Spirit Landings Cir, Winter Haven, FL 33880

  Fully furnished 1-bedroom apartment available for immediate occupancy. Rent includes all utilities electric, water, internet, and trash providing a truly hassle-free living experience. Well-maintained unit featuring comfortable furnishings, a functional layout, and abundant natural light. Ideal for professionals, traveling nurses, or anyone seeking a turnkey rental. Conveniently located near

  Laura Medina Ruiz RE/MAX HERITAGE PROFESSIONALS

  320 Spirit Landings Cir, Winter Haven, FL 33880
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  $150,000 Sold Apr 29, 2025

  1810 Woodpointe Dr, Winter Haven, FL 33884

  • Land
  • 0.44 Acre
  • $340,909 per Acre

  Last Sold Summary

  • 1,011 Days On Market

  Current Estimated Value $167,233

  Last Listing Agent John Wood, JR JOHN WOOD REALTY, INC.

  1810 Woodpointe Dr, Winter Haven, FL 33884
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  Est $266,215 Not Listed For Sale

  6130 Grey Heron Dr, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,698 Sq Ft
  • Built 2017

  6130 Grey Heron Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 3% Below List Price
  • $162/SF
  • 75 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Jamar Brown SELL & BUY HOMES REALTY INC
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  /73

  $250,000

  • 2 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  11 Casarena Ct, Winter Haven, FL 33881

  Discover a rare opportunity to own this architecturally distinctive 2-bedroom, 2.5-bath residence located in the gated community of Casarena on the Lakes. This well-designed home offers an impressive blend of indoor and outdoor living spaces. The main level features a formal living room with a fireplace and wet bar, a dining area, a functional kitchen with breakfast bar, a guest half bath, and

  Tim Weisheyer DREAM BUILDERS REALTY

  11 Casarena Ct, Winter Haven, FL 33881
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  /15

  $1,815 per month

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • House for Rent

  171 Southern Breeze Lp, Winter Haven, FL 33880

  From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

  171 Southern Breeze Lp, Winter Haven, FL 33880
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  $352,990 Sold Aug 08, 2025

  3458 Evening Star Dr, Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $186/SF
  • 13 Days On Market

  Current Estimated Value $395,473

  Starlight Homes Sunset Hills

  3458 Evening Star Dr, Winter Haven, FL 33881
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  /16

  Est $226,029 Not Listed For Sale

  108 4th St NE, Winter Haven, FL 33881

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2023

  108 4th St NE, Winter Haven, FL 33881

  Last Sold Summary

  • 10% Below List Price
  • $188/SF
  • 80 Days On Market

  Last Sold Price $252,000

  Last Listing Agent Melissa Witter KELLER WILLIAMS REALTY SMART 1
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  $129,900

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  700 Mirror Terrace NW Unit 505, Winter Haven, FL 33881

  Best view in the building! Welcome to your dream Florida escape at 700 Mirror Terrace NW, a beautifully updated and well-maintained condo in this lively 55+ Spring Lake Towers Community. This stunning unit boasts unparalleled lakefront views on the Chain of Lakes in Winter Haven, offering breathtaking sunrises and sunsets every day. Step inside and discover a spacious living and dining room. The

  Victoria Bollea CHARLES RUTENBERG REALTY INC

  700 Mirror Terrace NW Unit 505, Winter Haven, FL 33881
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  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 1,811 Sq Ft
  • House for Rent

  5465 San Pietro Dr, Winter Haven, FL 33884

  Be the first to live in this brand new 4 bedroom, 2 bath home located in the highly desirable Villa Mar community in Winter Haven. Featuring 1,811 sq ft of thoughtfully designed living space with an open-concept floor plan, this home is perfect for modern family living or entertaining guests. The spacious kitchen showcases contemporary finishes, ample cabinetry, and an island that flows into the

  Veronica Martinez MY REALTY GROUP, LLC.

  5465 San Pietro Dr, Winter Haven, FL 33884
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  $340,000 Sold Jul 28, 2025

  741 Canberra Rd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $194/SF
  • 6 Days On Market

  Current Estimated Value $328,738

  Last Listing Agent Julie Matthews JULIE MATTHEWS GROUP LLC

  741 Canberra Rd, Winter Haven, FL 33884
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  Not Listed For Sale

  208 Maple St, Winter Haven, FL 33880

  208 Maple St, Winter Haven, FL 33880

  Last Sold Summary

  • 0 Days On Market

  Last Sold Price $23,000

  Last Listing Agent Mabel Vega Negron LA ROSA REALTY CW PROPERTIES L
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  $329,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,077 Sq Ft

  4422 Blackwell Ave, Lake Wales, FL 33859

  The property is located at 4422 Blackwell Avenue LAKE WALES FL 33859 priced at 329990, the square foot and stories are 2077, 1.The number of bath is 3, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4422 Blackwell Ave, Lake Wales, FL 33859
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  /6

  $1,525 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1407 N Lake Shipp Dr SW, Winter Haven, FL 33880

  rent ready 2/1 in Winter Haven Fl. Home has central heat and air, screened front porch and a 1 car carport with attached utility room. Nice size yard with small shed for you yard tools.

  1407 N Lake Shipp Dr SW, Winter Haven, FL 33880
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  $290,000 Sold Apr 15, 2026

  7010 Summit Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,757 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $165/SF
  • 91 Days On Market

  Current Estimated Value $293,823

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  7010 Summit Cir, Winter Haven, FL 33884
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  Not Listed For Sale

  30 Flamingo Blvd, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1976

  30 Flamingo Blvd, Winter Haven, FL 33880

  Last Sold Summary

  • $81/SF
  • 28 Days On Market

  Last Sold Price $78,000

  Last Listing Agent Ashley Parkinson KELLER WILLIAMS REALTY SMART 1
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  $350,000

  • 5 Beds
  • 2.5 Baths
  • 2,274 Sq Ft

  271 Inman Blvd, Winter Haven, FL 33881

  PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the

  Isabelle Maye BHHS FLORIDA PROPERTIES GROUP

  271 Inman Blvd, Winter Haven, FL 33881
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  /16

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  118 Oak Crest Dr NW, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

  David Small KELLER WILLIAMS REALTY SMART 1

  118 Oak Crest Dr NW, Winter Haven, FL 33881
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  $274,000 Sold Jul 16, 2025

  4163 Pirates Landing, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft
  • Built 1985

  Last Sold Summary

  • 12% Below List Price
  • $142/SF
  • 229 Days On Market

  Current Estimated Value $272,708

  Last Listing Agent April Radermacher CENTURY 21 WATSON & MYERS REALTY

  4163 Pirates Landing, Winter Haven, FL 33884
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  Not Listed For Sale

  235 6th St NW Unit 207, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 857 Sq Ft
  • Built 1982

  235 6th St NW Unit 207, Winter Haven, FL 33881

  Last Sold Summary

  • $176/SF
  • 97 Days On Market

  Last Sold Price $151,000

  Last Listing Agent April Spaulding LPT REALTY, LLC
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  /17

  $315,950 New Construction

  • 4 Beds
  • 2 Baths
  • 1,910 Sq Ft

  5135 Kinsley Dr, Lake Wales, FL 33859

  Discover this must-see Ruby home. Included features: an inviting covered entry; a well-appointed kitchen offering 42 white cabinets, a walk-in pantry and a center island; an elegant dining room; a spacious great room; a lavish primary suite showcasing a generous walk-in closet and a private bath; a laundry and a covered patio. This could be your dream home!

  Richmond American Homes Builder

  5135 Kinsley Dr, Lake Wales, FL 33859
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  /21

  $1,950 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • House for Rent

  336 Kayden Cove, Winter Haven, FL 33884

  “Se están ACEPTANDO todos los programas de asistencia para la vivienda “Se consideran vales de viviendaEsta encantadora casa de 3 dormitorios y 2 baños está lista para recibirte, con una cocina moderna con una amplia isla y electrodomésticos.Disfruta de un garaje para dos autos en la casa y otros dos en el exterior, un hermoso patio y un total de 1444 pies cuadrados de

  336 Kayden Cove, Winter Haven, FL 33884
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  $415,000 Sold Oct 22, 2025

  731 Avenue A SW, Winter Haven, FL 33880

  • 8 Beds
  • 5 Baths
  • 3,588 Sq Ft
  • Built 1920

  Last Sold Summary

  • 2% Below List Price
  • $116/SF
  • 30 Days On Market

  Current Estimated Value $410,047

  Last Listing Agent Craig Morby SAUNDERS REAL ESTATE, LLC

  731 Avenue A SW, Winter Haven, FL 33880
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  Est $329,680 Not Listed For Sale

  6087 Grey Heron Dr, Winter Haven, FL 33881

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft
  • Built 2017

  6087 Grey Heron Dr, Winter Haven, FL 33881

  Last Sold Summary

  • 2% Below List Price
  • $130/SF
  • 289 Days On Market

  Last Sold Price $338,000

  Last Listing Agent Oscar Medina Garcia LA ROSA REALTY KISSIMMEE
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  /23

  $330,490 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,326 Sq Ft

  Georgia Plan at Peace Creek Reserve - Manor Key Collection, Winter Haven, FL 33884

  This two-story home highlights a modern open layout, seamlessly integrating a first-floor kitchen with a central island, a dining room and a welcoming family room with patio access. On the same level is a private owner's suite with an attached bathroom. Situated upstairs is a versatile loft for additional shared living space and four secondary bedrooms to provide restful retreats to family

  Lennar Builder

  1108 Tyler Loop Unit 36037863, Winter Haven, FL 33884
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  /22

  $2,030 per month

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  2122 Chris Dr, Winter Haven, FL 33884

  Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2122 Chris Dr, Winter Haven, FL 33884
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  $239,000 Sold May 16, 2025

  144 Lowell Rd, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1964

  Last Sold Summary

  • 11% Below List Price
  • $173/SF
  • 49 Days On Market

  Current Estimated Value $235,842

  Last Listing Agent Steven Ray Burnett NUGGET REALTY

  144 Lowell Rd, Winter Haven, FL 33884
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  /25

  Not Listed For Sale

  3000 Thornhill Rd, Winter Haven, FL 33880

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1999

  3000 Thornhill Rd, Winter Haven, FL 33880

  Last Sold Summary

  • $159/SF
  • 50 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Melissa Minck LPT REALTY, LLC
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  /26

  $340,000

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft

  3600 Julius Estates Blvd, Winter Haven, FL 33881

  AMAZING two-story home!!! Located in a BEAUTIFUL LAKEFRONT COMMUNITY! HUGE, fenced corner lot, very nice layout with a FLEX area/room that can be used as a formal Livingroom, office, or den, large master bedroom with a nice bathroom with dual sinks, walk in shower & walk-in closet, laundry room, 2 car garage & so much MORE**Seller may consider buyer's concessions **CALL YOUR AGENT FOR A PRIVATE

  Gladys Falcon LUXURY REAL ESTATE GROUP LLC

  3600 Julius Estates Blvd, Winter Haven, FL 33881
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  /9

  $1,550 total monthly price

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • House for Rent

  5626 Struthers Ct, Winter Haven, FL 33884

  2BR / 1BA Duplex • Washer/Dryer • New A/C • $1,550 • Available April 6Clean and well-maintained 2 bedroom / 1 bathroom duplex located in a quiet Winter Haven neighborhood near US-27 and Legoland.Features:• Washer & dryer included• New central A/C• Tile flooring throughout (no carpet)• Bright, open living space• Large shared yard• 2 parking

  5626 Struthers Ct, Winter Haven, FL 33884
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  $377,000 Sold Nov 26, 2025

  522 Alachua Dr, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 2,054 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Below List Price
  • $184/SF
  • 25 Days On Market

  Current Estimated Value $370,730

  Last Listing Agent Christopher Howard DALTON WADE INC

  522 Alachua Dr, Winter Haven, FL 33884
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  Not Listed For Sale

  503 Village Cir SW, Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft
  • Built 1988

  503 Village Cir SW, Winter Haven, FL 33880

  Last Sold Summary

  • $129/SF
  • 40 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Carolyn Christian DALTON WADE INC
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  /43

  $298,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,629 Sq Ft

  141 Browning Cir, Winter Haven, FL 33884

  Private pool living starts here. Welcome to 141 Browning Circle, a well-maintained 2-bedroom, 2-bath home, tucked inside a charming, established neighborhood with no HOA.Designed for true Florida living, you step directly from the home onto a screened porch that opens to your private pool and fenced backyard—creating a seamless indoor-outdoor setting ideal for relaxing or entertaining. The

  Mike Nolen COLDWELL BANKER REALTY

  141 Browning Cir, Winter Haven, FL 33884
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  /27

  $2,220 per month

  • 5 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • House for Rent

  2134 Chris Dr, Winter Haven, FL 33884

  Brand New Two-Story Home for Rent in Winter Haven Welcome to this stunning brand new two-story home located in the heart of Winter Haven, offering the perfect combination of space, style, and convenience. Designed with modern living in mind, this beautiful property is ideal for families or anyone looking for comfort and quality in a prime location. The home features 5 spacious bedrooms, including

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2134 Chris Dr, Winter Haven, FL 33884
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  $265,000 Sold Jun 12, 2025

  118 Browning Cir, Winter Haven, FL 33884

  • 3 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $152/SF
  • 7 Days On Market

  Current Estimated Value $267,532

  Last Listing Agent Ryan Odenweller RE/MAX HERITAGE PROFESSIONALS

  118 Browning Cir, Winter Haven, FL 33884
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  Not Listed For Sale

  6459 Hollyberry Ln NE, Winter Haven, FL 33881

  • 2 Beds
  • 2 Baths
  • 1,012 Sq Ft
  • Built 1987

  6459 Hollyberry Ln NE, Winter Haven, FL 33881

  Last Sold Summary

  • $133/SF
  • 120 Days On Market

  Last Sold Price $134,800

  Last Listing Agent Larry Hilton RE/MAX
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  $320,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,933 Sq Ft

  569 Reggie Rd, Winter Haven, FL 33884

  Under contract-accepting backup offers. Welcome to this beautifully designed two-story, 4 bedroom, 2.5 bathroom home, built in 2024 and located in the desirable Peace Creek Reserve community. This modern residence offers a functional layout, stylish finishes, and a peaceful setting with no rear neighbors. As you enter, you’re greeted by an inviting open floor plan that seamlessly connects the

  John Hubbert, Jr BHHS FLORIDA PROPERTIES GROUP

  569 Reggie Rd, Winter Haven, FL 33884
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  /19

  $1,575 total monthly price

  • 2 Beds
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880

  650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880
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  $218,000 Sold Dec 30, 2025

  1579 Vienna Square Dr, Winter Haven, FL 33884

  • 2 Beds
  • 2 Baths
  • 1,391 Sq Ft
  • Built 2016

  Last Sold Summary

  • 27% Below List Price
  • $157/SF
  • 14 Days On Market

  Current Estimated Value $219,958

  Last Listing Agent Harold Baker KELLER WILLIAMS REALTY SMART 1

  1579 Vienna Square Dr, Winter Haven, FL 33884
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  Est $317,991 Not Listed For Sale

  868 Buccaneer Blvd, Winter Haven, FL 33880

  • 3 Beds
  • 3 Baths
  • 2,190 Sq Ft
  • Built 2013

  868 Buccaneer Blvd, Winter Haven, FL 33880

  Last Sold Summary

  • 3% Above List Price
  • $142/SF
  • 257 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Brandy Duncan COLDWELL BANKER REALTY

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