Active

$440,000

299 Winwood Dr, Lebanon, TN 37087

3beds

1,838sqft

$2,577/mo

Get pre-qualified

Single Family Residence, Residential

Built in 1968

0.6 Acres Lot

$-- Zestimate^®

$239/sqft

$-- HOA

What's special

Discover the perfect combination of comfort, space, and convenience in this beautifully updated 3-bedroom, 2-bath, one-level home situated on a spacious .60-acre corner lot. With two separate living areas, there’s plenty of room for entertaining, relaxing, or creating a flexible space to fit your lifestyle. All three bedrooms feature walk-in closets, offering exceptional storage throughout the home. The private primary suite includes a spacious walk-in closet and an en-suite bathroom with a tub/shower combination, creating a comfortable retreat. Step outside to enjoy the screened-in patio overlooking the generous backyard. The outdoor storage shed, along with the dryer, will convey with the property. Conveniently located in the heart of town, you'll enjoy quick access to restaurants, shopping, hospitals, and everyday amenities while still having the space and privacy. This well-maintained home is ready for its next owner. Don't miss your opportunity to make it yours!

1 day

156

12

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2
Main level bedrooms: 3

Bedroom 1

Features: Suite
Level: Suite

Bedroom 2

Features: Walk-In Closet(s)
Level: Walk-In Closet(s)

Bedroom 3

Features: Walk-In Closet(s)
Level: Walk-In Closet(s)

Primary bathroom

Features: Primary Bedroom
Level: Primary Bedroom

Den

Features: Separate
Level: Separate

Kitchen

Features: Eat-in Kitchen
Level: Eat-in Kitchen

Living room

Features: Great Room
Level: Great Room

Heating

Central, Electric, Natural Gas

Cooling

Ceiling Fan(s), Central Air

Appliances

Included: Built-In Electric Oven, Cooktop, Dishwasher, Dryer, Microwave

Features

Ceiling Fan(s), Redecorated, Walk-In Closet(s)
Flooring: Luxury Vinyl, Tile
Basement: Crawl Space,None
Number of fireplaces: 1

Interior area

Total structure area: 1,838
Total interior livable area: 1,838 sqft
Finished area above ground: 1,838

Property

Parking

Total spaces: 1
Parking features: Garage Faces Rear, Asphalt, Driveway
Attached garage spaces: 1
Has uncovered spaces: Yes

Features

Levels: One
Stories: 1
Patio & porch: Porch, Covered, Patio, Screened

Lot

Size: 0.6 Acres
Dimensions: 135.3 x 200

Details

Additional structures: Storage
Parcel number: 069E C 03000 000
Special conditions: Standard

Construction

Type & style

Home type: SingleFamily
Property subtype: Single Family Residence, Residential

Materials

Brick, Vinyl Siding
Roof: Asphalt

Condition

New construction: No
Year built: 1968

Utilities & green energy

Sewer: Public Sewer
Water: Public
Utilities for property: Electricity Available, Natural Gas Available, Water Available

Community & HOA

Community

Subdivision: Blair Lane 2

HOA

Has HOA: No

Location

Region: Lebanon

Financial & listing details

Price per square foot: $239/sqft
Tax assessed value: $251,300
Annual tax amount: $1,817
Date on market: 7/23/2026
Electric utility on property: Yes

Estimated market value

Not available

Estimated sales range

Not available

Price history

Date	Event	Price
7/24/2026	Listed for sale	$440,000+29.4%$239/sqft
Source: RealTracs MLS as distributed by MLS GRID #3304560 Report a problem
10/21/2021	Sold	$340,000-4.2%$185/sqft
Source: RealTracs MLS as distributed by MLS GRID #2282927 Report a problem
9/8/2021	Pending sale	$355,000$193/sqft
Source: RealTracs MLS as distributed by MLS GRID #2282927 Report a problem
8/18/2021	Listed for sale	$355,000+4.9%$193/sqft
Source: RealTracs MLS as distributed by MLS GRID #2282927 Report a problem
7/28/2021	Sold	$338,400+35.9%$184/sqft
Source: Public Record Report a problem
6/11/2019	Sold	$249,000$135/sqft
Source: RealTracs MLS as distributed by MLS GRID #2028019 Report a problem
5/2/2019	Price change	$249,000-0.4%$135/sqft
Source: Benchmark Realty, LLC #2028019 Report a problem
4/8/2019	Listed for sale	$250,000-1.2%$136/sqft
Source: Benchmark Realty, LLC #2028019 Report a problem
6/1/2018	Listing removed	$253,000$138/sqft
Source: Blackwell Realty and Auction #1909637 Report a problem
5/5/2018	Price change	$253,000-2.3%$138/sqft
Source: Blackwell Realty and Auction #1909637 Report a problem
4/4/2018	Price change	$259,000-2.3%$141/sqft
Source: Blackwell Realty and Auction #1909637 Report a problem
3/12/2018	Listed for sale	$265,000+42.5%$144/sqft
Source: Blackwell Realty and Auction #1909637 Report a problem
1/4/2016	Sold	$186,000-2.1%$101/sqft
Source: Public Record Report a problem
10/20/2015	Listed for sale	$189,900$103/sqft
Source: West Main Realty and Auction #1678232 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$1,817	$62,825
2024	$1,817	$62,825
2023	$1,817	$62,825
2022	$1,817	$62,825
2021	--	$62,825 +56%
2020	$1,514 +49.2%	$40,275
2019	$1,014 -28.2%	$40,275
2018	$1,413 +0%	$40,275
2017	$1,413 +20.9%	$40,275
2016	$1,169 -20%	$40,275
2015	$1,461 +9.7%	$40,275 +9.7%
2014	$1,332	$36,716
2013	$1,332 +9.6%	$36,716
2012	$1,215 +2.3%	$36,716
2011	$1,188	$36,716
2010	--	$36,716 -13.2%
2009	$1,336	$42,313
2008	$1,336 +23.7%	$42,313 +11.6%
2007	$1,081 -12%	$37,914
2006	$1,228	$37,914
2005	$1,228 -15.6%	$37,914
2003	$1,456 +21.2%	$37,914 +21.2%
2002	$1,201	$31,270
2001	--	$31,270 -75%
2000	--	$125,079

Find assessor info on the county website

Monthly payment

Est. payment

Payment breakdown

Explore the cost of this home by adjusting the details. Changes won't be saved.

Principal & interest
$1,547
Mortgage insurance
$0
Property taxes
$170
Home insurance
$105
HOA fees
$0
Utilities
Not included

All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.

HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.

Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.

See how much you could borrow to make a competitive offer.

Get pre-qualified

Climate risks

Neighborhood: 37087

Getting around

25 / 100

Car-Dependent

34 / 100

Somewhat Bikeable

Nearby schools

GreatSchools rating

6/10
Castle Heights Elementary School
Grades: PK-5Distance: 2.4 mi
6/10
Winfree Bryant Middle School
Grades: 6-8Distance: 1.1 mi

Schools provided by the listing agent

Elementary: Castle Heights Elementary
Middle: Winfree Bryant Middle School
High: Lebanon High School

Source: RealTracs MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.