Oakland, FL Homes

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  /21

  Est $436,415 Not Listed For Sale

  2261 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,753 Sq Ft
  • Built 2019

  2261 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $254/SF
  • 136 Days On Market

  • Last Sold Price $446,000
  • Mar 13, 2025

  Last Listing Agent tulsi sharma WATSON REALTY CORP
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  /55

  $1,949,000 Open Sat 12PM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 3,862 Sq Ft

  511 Briley Ave, Oakland, FL 34787

  Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space.Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy

  Carolina Dumit CORCORAN PREMIER REALTY

  511 Briley Ave, Oakland, FL 34787
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  /2

  $1,654,248 Sold Apr 14, 2026

  360 Jefferson St, Oakland, FL 34760

  • 4 Beds
  • 4.5 Baths
  • 3,482 Sq Ft
  • Built 2026

  Last Sold Summary

  • $475/SF
  • 0 Days On Market

  Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

  360 Jefferson St, Oakland, FL 34760
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  /2

  Est $1,253,746 Not Listed For Sale

  1112 Hull Island Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,562 Sq Ft
  • Built 2021

  1112 Hull Island Dr, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $357/SF
  • 49 Days On Market

  • Last Sold Price $1,272,000
  • Apr 29, 2025

  Last Listing Agent Kelly Zannini HOMEVEST REALTY
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  /4

  $508,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,083 Sq Ft

  Newbury Plan at Serenade at Ovation - Bungalow, Oakland, FL 34787

  Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

  Dream Finders Homes Builder

  14229 Lanyard Way Unit 36490206, Oakland, FL 34787
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  /2

  $445,999 Sold Mar 23, 2026

  12748 Brodlove Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft
  • Built 2022

  Last Sold Summary

  • $248/SF
  • 30 Days On Market

  Current Estimated Value $444,644

  Last Listing Agent Mayra Rivas Acevedo CASA SOL REALTY LLC

  12748 Brodlove Ln, Oakland, FL 34787
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  /2

  Est $585,841 Not Listed For Sale

  2050 Standing Rock Cir, Oakland, FL 34787

  • 4 Beds
  • 2.5 Baths
  • 2,596 Sq Ft
  • Built 2019

  2050 Standing Rock Cir, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $231/SF
  • 5 Days On Market

  • Last Sold Price $599,000
  • Nov 27, 2024

  Last Listing Agent Scott Swinson, Jr CHARLES RUTENBERG REALTY ORLANDO
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  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, FL 34787
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  /2

  $828,296 Sold Sep 29, 2025

  16146 Point Rock Dr, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 3,225 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 48 Days On Market

  Current Estimated Value $828,000

  Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

  16146 Point Rock Dr, Oakland, FL 34787
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  /2

  Est $462,882 Not Listed For Sale

  14018 Scarlet Aster Aly, Oakland, FL 34787

  • 2 Beds
  • 2.5 Baths
  • 1,785 Sq Ft
  • Built 2024

  14018 Scarlet Aster Aly, Oakland, FL 34787

  Last Sold Summary

  • 1% Above List Price
  • $257/SF
  • 115 Days On Market

  • Last Sold Price $459,175
  • Oct 30, 2024

  Last Listing Agent Abigail Belchick OLYMPUS EXECUTIVE REALTY INC
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  /3

  $548,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  12911 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2

  Dayene Grubert ORLANDO TBI REALTY LLC

  12911 Westhaven Oak Dr, Oakland, FL 34787
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  /2

  $900,000 Sold Jun 25, 2025

  13202 Spring Grove Way, Oakland, FL 34787

  • 4 Beds
  • 4 Baths
  • 2,930 Sq Ft
  • Built 2020

  Last Sold Summary

  • 5% Below List Price
  • $307/SF
  • 54 Days On Market

  Current Estimated Value $893,344

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  13202 Spring Grove Way, Oakland, FL 34787
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  /11

  Est $889,311 Not Listed For Sale

  13259 Tollcross Way, Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,318 Sq Ft
  • Built 2025

  13259 Tollcross Way, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $271/SF
  • 25 Days On Market

  • Last Sold Price $900,000
  • Mar 07, 2025

  Last Listing Agent Dayene Grubert ORLANDO TBI REALTY LLC
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  /3

  $844,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,005 Sq Ft

  12916 Westhaven Oak Dr, Oakland, FL 34787

  Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion Summer 2026- Welcome home to this beautifully designed open-concept residence featuring a sought-after primary suite on the main level. The light-filled two-story foyer creates an impressive first impression and flows seamlessly into spacious living and entertaining areas. Thoughtful layout,

  Dayene Grubert ORLANDO TBI REALTY LLC

  12916 Westhaven Oak Dr, Oakland, FL 34787
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  /2

  $633,000 Sold May 05, 2026

  847 Cura Ct, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Below List Price
  • $211/SF
  • 104 Days On Market

  Current Estimated Value $635,655

  Last Listing Agent Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  847 Cura Ct, Oakland, FL 34787
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  /2

  Est $450,155 Not Listed For Sale

  9030 Wading Walk Ln, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Built 2020

  9030 Wading Walk Ln, Oakland, FL 34787

  Last Sold Summary

  • 6% Below List Price
  • $264/SF
  • 23 Days On Market

  • Last Sold Price $479,000
  • Oct 31, 2024

  Last Listing Agent Brooke Barlow REAL ESTATE HOUSE FL INC
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  /35

  $825,000

  • 4 Beds
  • 4 Baths
  • 2,831 Sq Ft

  931 Kylee Aly, Winter Garden, FL 34787

  There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving

  Matt McKee COMPASS FLORIDA LLC

  931 Kylee Aly, Winter Garden, FL 34787
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  /2

  $389,000 Sold Dec 23, 2025

  2218 Gopher Tortoise Terrace, Oakland, FL 34760

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft
  • Built 2020

  Last Sold Summary

  • $264/SF
  • 36 Days On Market

  Last Listing Agent Chelsea Eckert LISA REALTY PARTNERS

  2218 Gopher Tortoise Terrace, Oakland, FL 34760
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  /2

  Est $763,166 Not Listed For Sale

  9517 Emerald Berry Dr, Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft
  • Built 2024

  9517 Emerald Berry Dr, Oakland, FL 34787

  Last Sold Summary

  • 2% Below List Price
  • $266/SF
  • 39 Days On Market

  • Last Sold Price $776,710
  • Oct 14, 2024

  Last Listing Agent William Maltbie MALTBIE REALTY GROUP
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  /42

  $599,000

  • 4 Beds
  • 3.5 Baths
  • 2,743 Sq Ft

  12554 Westhaven Oak Dr, Oakland, FL 34787

  This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

  Adriana PL Franzoi WRA BUSINESS & REAL ESTATE

  12554 Westhaven Oak Dr, Oakland, FL 34787
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  /2

  $2,050,000 Sold Apr 09, 2026

  9008 Morgana Ct, Oakland, FL 34787

  • 5 Beds
  • 5 Baths
  • 4,934 Sq Ft
  • Built 2022

  Last Sold Summary

  • 7% Below List Price
  • $415/SF
  • 76 Days On Market

  Current Estimated Value $2,076,183

  Last Listing Agent Bent Danholm DANHOLM COLLECTION

  9008 Morgana Ct, Oakland, FL 34787
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  /2

  Est $449,495 Not Listed For Sale

  13461 Princess St, Oakland, FL 34787

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2024

  13461 Princess St, Oakland, FL 34787

  Last Sold Summary

  • 2% Above List Price
  • $279/SF
  • 61 Days On Market

  • Last Sold Price $440,000
  • Apr 01, 2025

  Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC
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  /4

  $2,395,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,527 Sq Ft

  1137 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, and a spacious loft across 3,712 square feet of elegantly

  Alexis Anderson REGENCY REAL ESTATE LLC

  1137 Prado Ln, Oakland, FL 34787
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  /2

  $520,000 Sold Aug 29, 2025

  1877 Standing Rock Cir, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft
  • Built 2018

  Last Sold Summary

  • $259/SF
  • 9 Days On Market

  Current Estimated Value $498,739

  Last Listing Agent James Goodyear COMPASS FLORIDA LLC

  1877 Standing Rock Cir, Oakland, FL 34787
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  /2

  Est $1,223,985 Not Listed For Sale

  914 Tilden Oaks Trail, Winter Garden, FL 34787

  • 5 Beds
  • 3.5 Baths
  • 3,803 Sq Ft
  • Built 2022

  914 Tilden Oaks Trail, Winter Garden, FL 34787

  Last Sold Summary

  • 2% Above List Price
  • $316/SF
  • 114 Days On Market

  • Last Sold Price $1,200,000
  • Jan 09, 2025

  Last Listing Agent Matt McKee COMPASS FLORIDA LLC
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  /55

  $2,190,000

  • 5 Beds
  • 4.5 Baths
  • 4,436 Sq Ft

  9014 Morgana Ct, Oakland, FL 34787

  This is more than a house ~ Lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare “water-on-water” moment – breathtaking

  Jennifer Wemert WEMERT GROUP REALTY LLC

  9014 Morgana Ct, Oakland, FL 34787
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  /2

  $645,000 Sold Feb 28, 2026

  2139 Bay Line Rd, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,281 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $283/SF
  • 17 Days On Market

  Current Estimated Value $643,460

  Last Listing Agent Ryan Barnett MARKET CONNECT REALTY LLC

  2139 Bay Line Rd, Oakland, FL 34787
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  /2

  Est $665,004 Not Listed For Sale

  14219 Spring Garden Dr, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,179 Sq Ft
  • Built 2024

  14219 Spring Garden Dr, Oakland, FL 34787

  Last Sold Summary

  • 4% Below List Price
  • $319/SF
  • 48 Days On Market

  • Last Sold Price $695,000
  • Feb 03, 2025

  Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO
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  /60

  $997,000

  • 5 Beds
  • 3.5 Baths
  • 3,910 Sq Ft

  9549 Bolero Rd, Oakland, FL 34787

  The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home water softener, reverse osmosis kitchen

  Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

  9549 Bolero Rd, Oakland, FL 34787
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  /2

  $530,000 Sold Oct 15, 2025

  8001 Sayings Dr, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 2,552 Sq Ft
  • Built 2022

  Last Sold Summary

  • 8% Below List Price
  • $208/SF
  • 66 Days On Market

  Current Estimated Value $527,261

  Last Listing Agent Shanta Navarro KELLER WILLIAMS ADVANTAGE III

  8001 Sayings Dr, Winter Garden, FL 34787
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  /2

  Est $1,223,588 Not Listed For Sale

  15281 Arcadia Bluff Loop, Oakland, FL 34787

  • 5 Beds
  • 4.5 Baths
  • 4,115 Sq Ft
  • Built 2020

  15281 Arcadia Bluff Loop, Oakland, FL 34787

  Last Sold Summary

  • 12% Below List Price
  • $337/SF
  • 80 Days On Market

  • Last Sold Price $1,385,000
  • Nov 12, 2024

  Last Listing Agent Tiago Martins LA ROSA REALTY LLC
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  /41

  $599,990 Pending

  • 5 Beds
  • 4 Baths
  • 3,011 Sq Ft

  2982 Good Vibes Way, Oakland, FL 34787

  Under Construction. The Dylan is all the rage! This stylish two-story home features a first-floor owner’s suite, offering a private retreat with a full bathroom and walk-in closet. An additional bedroom is located near the front of the home, steps from a full bathroom. A spacious and flexible open-concept layout blends the kitchen, living and dining areas, while a nearby flex space provides the

  Ben Goldstein LENNAR REALTY

  2982 Good Vibes Way, Oakland, FL 34787
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  /2

  $850,000 Sold Apr 06, 2026

  501 E Oakland Ave, Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,448 Sq Ft
  • Built 2007

  Last Sold Summary

  • 11% Below List Price
  • $247/SF
  • 104 Days On Market

  Current Estimated Value $867,036

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  501 E Oakland Ave, Winter Garden, FL 34787
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  /9

  Est $416,477 Not Listed For Sale

  10665 Words Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Built 2023

  10665 Words Dr, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $239/SF
  • 26 Days On Market

  • Last Sold Price $418,605
  • Oct 13, 2023

  Last Listing Agent Ben Goldstein LENNAR REALTY
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  /48

  $426,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,636 Sq Ft

  10768 Rhett Butler Aly, Winter Garden, FL 34787

  Designed for modern living, this beautifully maintained 3-bedroom, 2.5-bath townhome is located in the highly desirable Storey Grove community. Built in 2023, this home offers contemporary style, comfort, and convenience in one of the most sought-after areas near Orlando. The first floor features a bright open-concept layout with tile flooring throughout, creating a clean, modern, and

  Emilia Faria KARDOSH REALTY

  10768 Rhett Butler Aly, Winter Garden, FL 34787
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  /2

  $599,200 Sold Sep 25, 2025

  4727 Forest Haven Way, Oakland, FL 34787

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft
  • Built 2025

  Last Sold Summary

  • $310/SF

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  4727 Forest Haven Way, Oakland, FL 34787
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  /2

  Est $429,717 Not Listed For Sale

  6519 Glory Bower Dr, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft
  • Built 2021

  6519 Glory Bower Dr, Oakland, FL 34787

  Last Sold Summary

  • 1% Below List Price
  • $239/SF
  • 10 Days On Market

  • Last Sold Price $435,000
  • Aug 26, 2024

  Last Listing Agent Michael McCourt EPOCH HOMES
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  /22

  $598,000

  • 3 Beds
  • 2 Baths
  • 1,571 Sq Ft

  100 Mather Smith Dr, Oakland, FL 34760

  Nestled in the historic enclave of Oakland, 100 Mather Smith Drive is a premier retreat balancing modern convenience with small-town Florida charm. This meticulously maintained 3-bedroom, 2-bathroom residence sits on a generous quarter-acre corner lot, offering rare privacy with the massive benefit of no annual association fees or HOA oversight. The true crown jewel is the location—you are

  Danny Laniado MARK SPAIN REAL ESTATE

  100 Mather Smith Dr, Oakland, FL 34760
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  /2

  $495,000 Sold Feb 18, 2026

  2755 Bobcat Chase Blvd, Oakland, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 1,822 Sq Ft
  • Built 2020

  Last Sold Summary

  • 7% Below List Price
  • $272/SF
  • 203 Days On Market

  Current Estimated Value $491,729

  Last Listing Agent Tania Matthews KELLER WILLIAMS ELITE PARTNERS III REALTY

  2755 Bobcat Chase Blvd, Oakland, FL 34787
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  /2

  Est $712,655 Not Listed For Sale

  13234 Spring Grove Way, Oakland, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,346 Sq Ft
  • Built 2021

  13234 Spring Grove Way, Oakland, FL 34787

  Last Sold Summary

  • 7% Below List Price
  • $326/SF
  • 18 Days On Market

  • Last Sold Price $765,000
  • Aug 28, 2024

  Last Listing Agent Erica Diaz HOMEVEST REALTY

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